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Home / Blog / Clothing and Style

How to Dress Well In Your 40s and 50s (and Beyond)

Published on September 10, 2022 by Brock McGoff · Clothing and Style, Popular May contain affiliate links (what's this?)

If you’re an over 40 years old male and want to dress better than most 20-somethings, this post is for you!

Cardigan under field jacket
@ericrnycstyle aging like top shelf whiskey 😉

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First off, a disclaimer: despite “old man style” being in the title of this post, being over 40 doesn’t mean you’re old.

Also, being an older guy doesn’t mean you have to dress a certain way.

The way you dress is influenced by your lifestyle. What kind of work do you do? Do you follow a specific dress code on a daily basis?

So it wouldn’t make sense to say “men over 40 should dress like this…” and “men under 40 should dress like that…”.

But for most older men, age does play a role in personal style. You don’t want people to think you’re trying to look younger.

This is even more complicated for older guys with non-average builds (like shorter guys). One of the big issues you run into is the difficulty of finding clothes that fit.

Unfortunately, many brands that really focus on fit are targeted at younger men – or even teenagers.

H&M Instagram feed example
A sample of H&M’s Instagram feed (and overall aesthetic)

For example, brands like Zara, H&M and ASOS tend to carry fitted clothing in smaller sizes. But are these brands really appropriate for men over 40?

If you’re an older gent and want to wear “younger” clothing, that’s totally fine! But if you want to dress in a more traditionally “age appropriate” way, this post will help.

First off, here’s a quick list of specific things to avoid, assuming you don’t want people to think you’re trying to look younger:

  • Distressed jeans (any kind of tears, fading or stains)
  • Graphic tees
  • Sandals or flip flops
  • Baseball caps (at least worn backward)
  • Clothes with large logos or obvious branding
  • Hooded sweatshirts
  • Denim shorts
  • Basketball sneakers / tennis shoes
  • Overly trendy hairstyles
  • Tight fitting clothes
  • Baggy clothing

Come to think of it, most men should avoid most of the things on that list. But some things (like super distressed jeans) are especially inappropriate for older, more mature gentlemen.

For example, look at Robert Downey Jr., who is 5’8″ and 57 years old (at the time of writing). He likes to wear sneakers with suits, which could be an attempt to look young and hip.

But it has the exact opposite effect, making it look like he’s trying to be something he’s not.

 

View this post on Instagram

 

A post shared by Robert Downey Jr. Official (@robertdowneyjr)

It’s like when a little boy wears a suit and tie. It just emphasizes how young and small he is.

So what should you wear? To figure that out, let’s look at six examples of men in their 40s, 50s and 60s (and older) who are doing it right.

Example #1: George Stephanopoulos

George is a well known television personality, and he understands how to dress the part.

When he’s working, George often wears suits (which are likely custom, or at least tailored for a better fit).

 

View this post on Instagram

 

A post shared by Ali Wentworth (@therealaliwentworth)

George’s style is safe, sharp and age appropriate. It comes off as self-aware but effortless, and he’s a great example of how older gents can dress.

His casual game is on point too. I really like his layered, smart casual outfit above.

Example #2: Ralph Lauren

Ralph Lauren is one of the most famous fashion designers of all time. He’s 82 years old at the time of writing, and he happens to be a shorter guy at just 5’6″.

Ralph loves classic American prep style, so you’ll often see him in dark suits, blue blazers and worn in jeans.

 

View this post on Instagram

 

A post shared by Ralph Lauren Style (@ralph.lauren.style)

He doesn’t shy away from double-breasted jackets or light colors – two style choices that short men are often told to avoid.

Lauren also prefers classic silhouettes (i.e. straight leg pants), and he’s a great example of older gents wearing blue instead of grey for a more youthful look (more on that below).

Example #3: Daymond John

Daymond John, founder of FUBU and my personal favorite shark, knows a lot about fashion and business.

His style stems from hip hop culture, but these days you’ll usually find him wearing impeccably tailored suits.

 

View this post on Instagram

 

A post shared by Daymond John (@thesharkdaymond)

One thing I really admire about Daymond’s style is his attention to detail. For example, even when slim ties and small knots (like the four in hand) were all the rage, he bucked those trends.

Instead, Daymond wears wider ties (and lapels) and uses bulkier knots (like the half Windsor), which compliment his broad neck and chest.

This is a great example of ignoring a trend that younger men may be tempted to get on board with, especially when it doesn’t suit your body type.

It’s these small, seemingly insignificant choices that can take your style from good to great.

Example #4: Scott Schuman

Also known as The Sartorialist, Scott Schuman is the fashion photographer that made street style photography so widely popular.

He’s been documenting real style “in the wild” on the streets of NYC and around the world on his blog for years, and he’s become pretty famous for his work.

 

View this post on Instagram

 

A post shared by Scott Schuman (@thesartorialist)

But his own style is pretty remarkable too, which is dually impressive since he stands well below average height (probably somewhere in the 5’3″ to 5’5″ range).

Scott’s style is mature and understated. His color palette is simple and relatively neutral, and his clothes fit properly. What else do you need?

Example #5: Nick Wooster

Last, but definitely not least, let’s look at fashion industry legend Nick Wooster.

Here’s a man who has deep knowledge and understanding of menswear. He knows all of the rules, and he loves to break them.

Wooster is constantly pushing the envelope with his style. Even his more traditional getups are characterized by one or two bold elements.

 

View this post on Instagram

 

A post shared by Nickelson Wooster (@nickwooster)

Here’s the thing: I’m not saying you should try to dress like Nick Wooster.

I just wanted to include him because he’s a great example of having fun and expressing yourself with what you wear.

He’s over 60 years old. Sometimes he dresses the part, and sometimes he doesn’t, and that’s what I love about him.

Style is inherently personal, so make sure to do what you want with it!

Expert Style Advice from Older Guys

I reached out to three of the most stylish males over 40 I know to get their top tips for older guys who want to dress sharp.

Here’s what they had to say:

John Galfano

Follow John: 40 Over Fashion

In my opinion, the singular style tip that works universally for most guys is to wear dark solid colors.

There are several benefits to wearing dark solids. Firstly, most dark solids work well together when they’re paired up in an outfit.

Wear mostly dark colors

Second, mixing shirts with pants becomes a lot easier because you don’t have to worry about which half to wear a pattern (trousers or shirt).

Dark colors patterned shirt

Third, dark colors are in fact slimming making you appear more trim. Light colors reflect light and have a bulking effect that can give the illusion that you’re bigger than you actually are.

Darks have the opposite effect.

Dark colors slimming effect

Finally, wearing dark colors with confidence can make you look more mysterious and more expensive – seriously!

Visualize your favorite James Bond (for me it’s Daniel Craig). He looks like a badass wearing black, and the costume designers know this, so they put him in darks a lot for the movie.

He’s supposed to look mysterious and expensive, which wouldn’t be the case in a light tan suit or a loud pattern shirt.

Now, I’m not saying you should wear all black all the time, but try to experiment with dark blues, dark browns, dark burgundy and black.

Red and burgundy jacket

If you like patterns like I do, go for subtle, small prints or patterns that are close in color. For example, a dark navy shirt with slightly lighter navy patterns vs. a dark navy shirt with lots of white stripes.

If you want a place to shop, I suggest looking at Nordstrom and Banana Republic for age-appropriate clothing.

Bret Hoffer

Follow Bret: Silverfox Collective

I want to give all of my fellow mature, studly gents a valuable style tip which will boost your confidence and prevent you from looking like your grandfather.

Bret Hoffer

You’ve likely heard or read it somewhere before but I’m here to remind you in 2020:

When wearing denim, leave the running sneakers at home. Stop wearing actual trainers with jeans.

It just isn’t attractive, and they’re not a fashion statement unless you’re a streetwear guy. And to be honest, none of us in our late 40’s and 50’s should be attempting a streetwear look.

Instead, get yourself a few nice pairs and colors of casual sneakers, one in plain white and another in black. It’s that simple!

Bret Hoffer

Bret Hoffer

Black and white minimal sneakers

That’s all you need to step up your footwear game when you aren’t wearing dress shoes.

Jeff Morgan

Follow Jeff: The Style OG

My style advice for guys over 40 would be to invest in high quality, classic essentials like a navy blazer, dark wash denim and brogues – while remaining aware of current trends.

Jeff Morgan Style OG

You should not chase trends, but you should be in the know. Adopting the subtle fluctuations of silhouettes, colors and small details will have you looking well-seasoned and in season.

Jeff Morgan

Two of my favorite brands for men over 40 are Uniqlo (great for clothing basics) and Beckett Simonon (high quality, essential footwear with a timeless aesthetic, without designer prices).

How to Look Younger (as a Man)

There are a few subtle things you can do to add a youthful touch to your look – without being blatant about it.

#1: Wear Blue

First off, you can wear navy or blue instead of charcoal or grey. This especially applies to suits.

Blue is appropriate for any age, but it’s a decidedly younger color than grey (see Ralph Lauren above).

#2: Pops of Color

You can add small “pops” of color to your outfit. They can be subtle or bold (like Nick Wooster’s yellow shoes).

Either way, you’re showing people that you’re not just a boring old man.

#3: Accessorize

Feel free to go wild with accessories. Get a trendy new pair of glasses from Warby Parker. Add some funky ties and colorful socks to your collection (but avoid “novelty” socks).

This is one area where you can get away with less traditional choices.

#4: Groom Better (or Different)

Been clean shaven for a while? Try the scruffy look. Had a beard for the past few years? Shave it all off!

If you’re hair is still healthy, grow it out. If it’s been long for a long time, get a clean, modern haircut.

And make sure to take care of your face. Use moisturizer with SPF and anti-aging cream. Trim those eyebrows, nostrils and ears.

#5: Trim the Fat

While clothing fit is extremely subject to trend, slimmer silhouettes have been in style for years and probably aren’t going anywhere, at least not anytime soon.

This is great because it’s a very flattering look on most guys, including men over 40 and over 50 years old.

So be sure to get your clothes tailored: shirts taken in, pants hemmed, sleeves shortened. Trim the fat out of your garments for a younger, leaner look.

Clothing Brands for 40 Year Old Men (and Older)

There are many clothing brands for men over 40, 50 and beyond.

In fact, most mainstream menswear brands cater to this demographic because, well, older guys have more money.

You’ll want to avoid brands that are unapologetically aimed at younger males, including fast fashion brands like H&M, Zara and Pacsun.

Instead, try sticking with men’s clothing brands that emphasize a more timeless aesthetic and middle-of-the-road fit.

Specifically, here are the best clothing brands for 40+ year old men:

  • J.Crew
  • Ralph Lauren
  • Banana Republic
  • Bonobos
  • Ash & Erie (for shorter guys)
  • L.L.Bean
  • Buck Mason
  • Taylor Stitch
  • Suitsupply
  • Huckberry
  • Reiss
  • Hugo Boss
  • Billy Reid
  • Barbour
  • Charles Tyrwhitt
  • Spier & Mackay
  • Brooks Brothers
  • James Perse

Any of the above brands will work for men over 40. It just depends on your budget and aesthetic.

But you can’t go wrong with the menswear brands listed above.

Questions About How to Dress In Your 40s

Here are answers to some of the most frequently asked questions about dressing well as an older man:

Should men over 40 wear jeans?

Yes, men over 40 can and should wear jeans. Just make sure they’re slim-straight and tapered (not skinny or relaxed) and don’t have any rips or overt distressing.

Should a 40 year old man wear skinny jeans?

40+ year old men should avoid skinny jeans, unless they have very skinny legs. Instead, wear slim tapered jeans that aren’t skin tight.

What should a 40 year old man wear to a nightclub?

Always check the dress code of whatever club you’re going to. In general, slim dark wash jeans or slim chinos with a casual button down shirt work well for a nightclub. Wear minimalist leather sneakers or Chelsea boots, and complete your outfit with a nice watch, necklace and/or bracelet.

Can a 50 year old man wear a hoodie?

A 50 year old man can wear a hoodie, but outside of the gym or doing yard work, I wouldn’t recommend it. Instead of a hoodie, wear a simple sweatshirt, wool sweater, cardigan or overshirt.

How should a 50 year old man dress casually?

A 50+ year old man should dress casually in slim-straight jeans or chinos, solid color tees, polos or untucked button up shirts, and tasteful outerwear (like a Harrington jacket, leather jacket or bomber). For shoes, keep it simple with leather boots, casual loafers, or plain leather or suede sneakers.

Should older guys wear leather jackets?

Yes, older guys look great in leather jacket! Just make sure they’re the right size. Leather jackets should be pretty fitted. Nothing says “grandpa style” like a leather jacket that’s 1-2 sizes too large 👴🏼

Clothing and Style, Popular older men, over 40

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About Brock McGoff

The Modest Man founder, Brock is an aspiring minimalist who enjoys working out, spending time with his family, discovering new brands and creating great content.

Background: Brock McGoff has a bachelor's degree in psychology and a professional background in digital marketing. He believes that men's fashion is just one facet of self-improvement, and he started The Modest Man to help regular guys feel more confident by improving their appearance.

An east coast native, Brock currently lives in Arizona with his wife and daughter. When he's not working, he spends time with family, training BJJ, reading/listening to books and podcasts, and unsuccessfully trying to decide which movie to stream.

Expertise: Brock has built a men's lifestyle YouTube channel with over 400k subscribers. He's also worked as the creative marketing manager in a men's apparel startup. Brock has been quoted in, mentioned by or featured in publications like Esquire, Huff Post, Men's Health, WWD and Forbes.

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  1. Full Facial inc. says

    September 27, 2023 at 3:44 pm

    Shave beard off ? You’ve got to be kidding ! Maybe you are one of those weirdos that shave their armpits! Women love them….at least my kind of woman does….and they don’t shave their armpits either.

    Reply
  2. Scott says

    September 24, 2023 at 5:58 pm

    I. 62 look 52 don’t like clothes with big logos is cowboy boots good to wear as dressed up or do I need casual shoes

    Reply
  3. Lee says

    August 28, 2023 at 9:06 am

    I’m 5’6″ and in mid 40’s but look a lot younger. Should I still go with these suggestions for dressing in my 40’s or try something slightly different?

    Reply
  4. Dave says

    August 10, 2023 at 6:34 pm

    Looking for the classic linen white/cream colored sport jacket. Have pics of those!

    Reply
  5. Chris Y. says

    August 4, 2023 at 8:53 am

    You list H&M, Zara and similar retailers as being inappropriate stores for mature gentlemen and provide a list of places that you consider suitable.

    I cannot shop at many of the places you list because they don’t carry items that fit me. That is why I will buy a pair of jeans at H&M because I can find my size (28/30) and I don’t have to pay a ridiculous price.

    Reply
  6. ChrisB58 says

    July 30, 2023 at 8:44 pm

    I find it “interesting” that many came here to criticize your accomplished focus on men in their 40’s and 50’s, yet they won’t share their own talented blog giving you an example of what a more accomplished and refined article would look like… 😉

    To all the “critics” here, let’s see your ideas and let us have our opinions towards your discovery…. That’s what I thought!

    Ok, now onto my comment to Brock….. I think you’re onto something. Here’s the problem with today’s 40’s to 50’s man… He isn’t “yesterday’s 40 or 50 year old! I know that first hand. I’m a grandfather of 11 grandkids, at only 58 years old, but I look about 39 to 41. In fact, when I walk around with my oldest son who’s 37, his friends think I’m his older brother.

    It’s very hard to be a “professional” and keep a certain image, while also attempting to not look like you’re a perverted old man chasing younger skirt, or the older female who wears styles that are twenty something and it just looks terrible! It’s very hard to be in your 40’s and 50’s these days and find that perfect balance.

    In fact, I’d say that based on the criticism received here by so many comments, that “validates” my point! You have to find that perfect pocket between style and class without clashing with the mainstream judges that no doubt draw conclusions faster than the old west quick guns…..

    I “LOVE” the article you have here, it’s a great jump into a category I think many are not brave enough to face. I look forward to your future articles. Forget the critics, keep’em coming!

    Reply
  7. James says

    July 22, 2023 at 6:38 pm

    Utter nonsense. Older men can wear what they want A lot of things that young men wear older men where wearing first.

    Reply
    • Ryan Hallstrom says

      July 26, 2023 at 11:59 am

      Hey James! Of course older men can wear what they want. This article just has a few tips from the pov of the author.

      Reply
      • Ryan says

        August 4, 2023 at 9:16 am

        Whilst i agree with alot of your points, ive always seen fashion as your own personal style regardless of age, but age plays a part on how you put that style together.

        For example, if you have your own style and just don’t blindly follow trends, why change that because you are a little older?

        I disagree with your point of Downey JR though, he’s always dressed with his own style and owns it, but i do agree there’s nothing sadder than an overweight 50 year old that buys the brightest pair of Jordan’s they can find in an attempt to be cool, but if you’ve always been into that style and it fits your lifestyle, why change to brogues and chinos.

        I guess what i’m trying to say is, if everyone dressed the same as they age, then it wouldn’t make clothing as fun and personal as it can be.

        Reply
  8. John says

    May 25, 2023 at 2:00 pm

    You need Belstaff clothing in that list. Mint classy clothing for the discerning Gent’s.

    Reply
    • Ryan Hallstrom says

      June 6, 2023 at 1:03 pm

      Good call, John! One of my friends has a Belstaff waxed jacket and it’s pretty great quality.

      Reply
  9. Michael says

    May 7, 2023 at 7:28 am

    With regards to fast fashion UNIQLO is certainly an option. They are certainly positioning themselves to cater for the older demographic as evidenced by a long term contract with, now retired, Roger Federer. The denim, chinos and polos and roll neck tops, usually in navy, are in my wardrobe.

    Reply
  10. Mark says

    April 11, 2023 at 5:23 pm

    Older man either get bonny slim with chicken legs, or get fat. When they go to the gym and get bigger because they add muscle to the fat hence the old man look. Get slim and ripped and you’ll look younger, your posture will improve and you will fill clothes same as a young man, hence you will look good in them. Those gentleman pictured above are overweight and too tight clothed. Don’t develop pecs, go for the thigs. For arms prefer definition over size, like a normal younger man that don’t go to the gym but do sports. I’m only state the obvious, if your physique is good all clothes work. The other thing to watch is your gait, if you lean forward or drag your feet you will look old no matter what your face complexion. And in the subject of gyms, don’t compete with the other old farts trying to show they are as strong as young men, concentrate on your body, set your goals and work towards them.

    Reply
    • Kd says

      May 6, 2023 at 8:26 am

      Well say

      Reply
    • ChrisB58 says

      July 30, 2023 at 8:59 pm

      I agree in some aspects of your comment. But like most things, we can worry so much about a concentrated area that we become too critical on a particular subject… For an example, you said, “don’t worry about bigger pecs or arms”. That’s not always true. Some older men have muscular thighs and their chests have all but caved in…. But like you said, which is very true, if you’re an older guy with a natural “V-Shape” and bird legs, and you only enhance your chest and arms, you’re going to look very odd…

      The point is, “Everything In Moderation/Balance”… Focus on the areas of your body that “need size” while “defining” the areas that don’t”… 🙂

      I also liked what you said about the men who walk with a hunch or drag their feet. I’ve seen some men who are more fit than a 20 something year old athlete and they walk with the “old man hunch over” syndrome. It’s very self-defeating, and it does effect your overall mental state as well as your back’s health.

      I disagree with you saying the men above are “overweight”. That’s not a true statement. I think this is an area where you’ve let your own “preferences” take control and didn’t allow there to be a range of body shape that’s acceptable….

      I’ve seen some men who just don’t have the body or the face for a oversized muscular body, and some men who have a puny body with a bull-sized melon and the face of a gladiator…. What I believe is every man needs to look in the mirror and SEE himself in accordance to what he should be.

      Head Size Matters! If you have a small head and large body, you’re going to look weird! Just facts! And vice versa! Big head and puny body, not good. There’s a proportionate Range that balances the head, torso and thigh/leg area. Finding that “balance” will make you look GREAT! Emphasizing one to a point where it’s out of proportion with the other 2 and you’re just going to look bad. Period!

      Knowing how to shape your body to meet that balance that is just right for YOU, means you take the time to study, observe, be TRUTHFUL with yourself, and then set a goal… Best of luck men! In today’s world, Men are being attacked from all sides and more than ever we have to be “ambassadors” for each other. Keep It Real, But Keep It Up To Par!

      Reply
    • Jerry says

      August 29, 2023 at 1:07 pm

      Very well put. As a matter of fact, I copied what you wrote and put it in my notes.

      Reply
    • Scott says

      September 24, 2023 at 6:01 pm

      I’m 62 do dumbbells at home don’t want to loose all muscle I look 50 do crunches ,need to loose 28 lbs

      Reply
  11. Brandon D. says

    February 21, 2023 at 4:42 pm

    Reading this and was a bit surprised Peter Manning NY is no longer in the list of brands. I like their style and some items for really well and not as expensive as Ash & Erie. Mostly classic styles for all the basics.

    Reply
    • Brock McGoff says

      March 1, 2023 at 3:46 pm

      I haven’t worn much PM stuff over the past couple years. Anecdotally, I’ve heard mixed things about their quality/customer service since ownership changed.

      I do wear Ash & Erie pieces pretty regularly, although most of my wardrobe is made up of non-specialty brands (which tend to be a bit more stylish IMO).

      Reply
      • ChrisB58 says

        July 30, 2023 at 9:04 pm

        I agree Brock! One of the most “best compliments” a person can get is when you mix non-specialty brands and someone issues you a compliment on your selection and tries to guess the brand and/or the amount you paid…. 🙂

        “Uniqueness” has its place, and most mix and matches that compliment your own style usually wins the day… 😉

        Reply
  12. Jason says

    January 27, 2023 at 6:11 pm

    I think the whole “trying to look younger” thing is grossly misrepresented. I’m 45, have always loved music and skateboarding. It’s who I am. So wearing my Ramones shirt and Vans is childish? Some of these outfits you present as being appropriate just look “stiff” and pretty dorky. So to all the men who read this and think, “Huh, I wear lots of those things on the Do Not List, I wouldn’t worry about it. At all.

    Reply
    • Aaron says

      June 1, 2023 at 12:48 pm

      Tony Hawk loves skateboarding as well, but he looks old wearing jeans that are to long, clumpy skateboarding shoes and baggy shirts. Makes him look like he’s try to keep being a kid. Tony, you made it, you’re successful spend a little money and dress a little better.

      Reply
  13. Sam R says

    January 19, 2023 at 2:58 am

    First off, here’s a quick list of specific things to avoid, assuming you don’t want people to think you’re trying to look younger:

    Distressed jeans (any kind of tears, fading or stains)

    Next

    *Picture of Ralph Lauren in distressed jeans

    Reply
    • Brock McGoff says

      January 19, 2023 at 10:15 pm

      A perfect example of knowing the rules, then breaking them in a way that works.

      Reply
  14. Pedro says

    January 2, 2023 at 9:19 pm

    Great information.i have an excuse to buy a leather jacket

    Reply
  15. Peter Crawford says

    December 20, 2022 at 6:41 pm

    I am 73 years young ,still working as a medical device designer,I am often asked …truly how old are you really ,even the cops challenged my age ,until
    Proof was provided, I totally agree with your visual observation dress accordingly,.! Men and Women world wide spend a $$$$ fortune on fashion ,but cannot buy
    “ Style” Thanking you excellent overview .!

    Reply
  16. 40 UK M says

    November 25, 2022 at 1:42 am

    Horrible, wear what you want, how you want.

    This is clearly written for a certain person with a certain income who has a certain need to look a certain way.

    Look in the mirror and if you feel comfortable then wear it. Do not let anyone tell you how you should look.

    Reply
    • Atheisticgod says

      August 13, 2023 at 12:34 am

      It’s true, wear what you feel comfortable in BUT don’t be surprised if you’re not taken seriously, get that date you wanted/promotion etc…act like a child be treated like a child, it’s painfully obvious that you are here to get advice, please take it as such and move along. Can’t wait to see you in your bedazzled Tupac T-shirt, plaid boxers, 2x to big mark echo jeans and leopard print Jordan’s showing up to the office- or maybe a tie died shirt, 1x to big belted Levi’s and a pair of toms.
      Cheers

      Reply
  17. Joe says

    November 19, 2022 at 11:52 am

    Love the grey and black shoes on Bret…what brand are they?

    Reply
  18. BR77 says

    April 28, 2022 at 1:36 pm

    Comments from 2017 and article timestamp keeps being updated throughout the years!

    Reply
    • Brock says

      April 28, 2022 at 1:58 pm

      We update articles at least once a year, so the date you see at the top of the article shows the last time it was updated.

      Reply
  19. Mike Cagle says

    March 3, 2022 at 1:53 pm

    I really enjoyed this article, and learned a lot about appropriate wardrobe choices for the older gentleman. I normally wear khakis and a Polo to work so that is what I am most comfortable going out in. But I don’t necessarily always want to dress like I just came from work, I’d like to wear something that will invoke the reaction “D@#n, he looks good!” But as a bulkier six foot man (trying to lessen the bulk) I don’t always look right in the more popular “normal” styles. But this article definitely helps, I do however agree with topic above that there is really no emphasis on warmer climate areas or summertime choices. Thank you for your time

    Reply
    • Bruce says

      November 21, 2022 at 11:22 am

      A gréât article. I have to agree to most issues, except skinny’s- I’m average-tall, 146, 5.10, most slim can look slouchy. I do wear skinny’s with blazers, proper coats, and must look like a million because I have comments regularly. 68, guessed around 50. My source for all wool V-neck sweaters, wool jackets, suit, French-cuffs, formal wear, blazers is Charles Tyrwhitt- London. Dress well- you’re worth it!

      Reply
  20. That Tim says

    January 19, 2022 at 10:31 am

    Sadly like nearly all other mens fashion articles, this is only for people that live in the artic north. Nothing shown as an example works for a southern man or a man that lives where it averages 80-90F most of the year. I would be a pile of sweat in everything shown as an example.

    Please can we get articles for hot weather?

    Reply
    • Jigul says

      May 7, 2022 at 8:18 pm

      Agree show us some fashion for 50-60s men located in hot climates

      Reply
    • Karl R says

      August 4, 2022 at 7:52 am

      Hot weather ideas…

      Pants:
      Chino shorts, linen shorts, linen pants.

      Shirts:
      Polo shirt, short-sleeve shirt, long-sleeve linen shirt w/ sleeves rolled up.

      Shoes (with no-show socks):
      Loafers, boat shoes, driving moccasins.

      Sunglasses:
      Aviators, clubmasters, wayfarers.

      Hat:
      Panama hat.

      You can combine any of the items above, and the outfit will work well. Mostly wear light colors, and you have the option to wear brighter colors than you would in the cooler months.

      Reply
    • Nes says

      September 20, 2022 at 2:02 pm

      Same here. I live in southern California, where our winters are still high 60’s low 70’s. I’d love to wear outfits like these, but at times is not feasible. Even right now mid-September through mid-October we’ll be hovering in low 80º weather.

      I have a different issue for a different thread, I’ll be 41 soon but look 28. It’s actually annoying, but different conversation for a different day.

      Reply
  21. Malachy notime says

    January 5, 2022 at 6:44 am

    I really enjoy this your encouragement about dressing at 40’s and above. I love dressing iam above but the color is what iam emphasizing on putting on black signify a mourning mood. Though putting on white cap balance the normal dressing mood I really enjoy you guys thanks so much. Ride on !’,,,,,,,

    Reply
    • A Non-Emus says

      August 31, 2023 at 2:06 am

      Ralph Lauren’s jeans clearly ripped and distressed in that photo.

      Reply
  22. Mike G says

    November 13, 2021 at 1:33 pm

    First, thanks for not taking a condescending tone with regard to older men’s fashion. That’s so often the case elsewhere and can be so off putting. Your reasonable and sensible recommendations fall right in line with the direction I’m taking.

    I’m retired and in my 70s and have recently become a successful fine artist with my work showing at museums and galleries across the country. I have a full head of beautiful gray hair and keep it styled in what I call “strategic disarray,” a little messy on purpose. Not too sprayed-in-place. I want to dress with a little flare and style that befits a more “artsy” sort, but I’m not interested in looking clownish or like I’m in desperate need to look young. That ship has sailed. I am able to get away with western wear at some of my museum shows because I’m known for western art, but that’s only when special events call for it. Otherwise, I prefer a more widely-accepted style for everyday.

    My first big fashion NO occurred several years ago with backwards baseball caps. Unless I’m rolling paint on a ceiling, you’d never catch me wearing one that way. To me it looks too desperate at any age. Graphic T-shirts are now my go-to only when I want to wipe a brush on it in the studio. The ball caps went in a box a while back. Now I’m fond of newsboy caps in summer and winter weights and fabric and in winter, have a couple of fedoras. I think I can pull them off.

    Sandals? I’m in the hot steaming south. Losing them isn’t going to happen when I’m just beating around, no matter how lousy these old feet look now.

    Articles/videos like yours give me a little more confidence that what I’m doing is right. Work in progress.

    Reply
  23. Realist says

    June 13, 2021 at 2:41 am

    Unrealistic to use celebrities as examples what the everyday guy should wear. How many of us have stylists, personal trainers and deep pockets?

    Also all these “How to dress when you are more mature” articles are very myopic and unrealistic. Do you really expect an everyday guy to wear a sport coat, or suit to go on a weekend excursion to CostCo or Home Depot?

    How about something more realistic like Harrington jackets, V-neck sweaters, golf and polos, bomber jackets with chinos or non-blue jeans with casual shoes or boots. That’s far more realistic for a mature man to dress outside of work than wearing a blue blazer and tie to take the wife and kids to Applebee’s.

    Maybe these such articles should be aimed to celebrities because very few tips apply to most men’s circumstances. Not all of us have a gala event like the Grammys or Oscars to attend.

    Reply
    • Steve says

      December 29, 2021 at 11:56 am

      Damn!!! This is spot on!

      Reply
      • Gary Humphries says

        September 20, 2022 at 1:51 pm

        I absolutely agree, and everything recommended is over priced for a lot of everyday men.

        Reply
    • henrik says

      July 11, 2023 at 8:25 am

      you should look at mark twain a true artist you will get some ideas from him

      Reply
  24. Scott says

    May 22, 2021 at 11:04 pm

    This is hilarious. I’m sure George S doesn’t always look like a slob! Ralph L is a time travel to the 80s. Wooster is exactly what the problem is with Robert D. Thank you for the laugh.

    Reply
  25. Rick says

    May 16, 2021 at 12:30 pm

    George Stephanopoulos was 40 during the Clinton administration. Come on now.

    Reply
  26. Jack says

    April 30, 2021 at 12:21 pm

    This…kind of looks like the opposite of “modest”. Most of these pictures seem like how-tos on looking pretentious and unapproachable. Also, I’ve been looking at a lot of these articles–do any of you live in a place where it’s hot most of the year. “No t-shirts” can be akin to “enjoy your heatstroke”.

    Reply
  27. GLENN T. FIORE says

    February 28, 2021 at 1:10 pm

    I’m 5’7.5″ 70 years old and I don’t wear sneakers . When you looking at someone like Howie Long for example on NFL Sunday your looking at this face while he is talking and you can see his feet because of his sneakers just looks like he has no class (to me) on how he looks. Another thing I did not do, is wear a striped tie and a striped shirt the Tucker Carson look . His overwhelming amounts of strips are going in a hundred different directions. Not a class act when it comes to his dress. for me, penny loafer with tassels is my choose with jeans
    Harris Tweed jacket .

    Reply
  28. Corey says

    November 2, 2020 at 1:33 am

    Simplicity is key ~ with that being said men’s fashion needs to step up . All of these looks are homogenous and too Jcrew.

    Reply
    • FashionNonExpert says

      May 28, 2021 at 11:07 pm

      Agree. I would suggest looking at older men’s fashion in Europe or Asia (Tokyo). These examples are 99% of men walking around in the US. Spend a buck and look quality.

      Reply
  29. James says

    July 23, 2020 at 2:55 am

    Hi… I’m a 40 year old English man living in Uganda, Africa. I’m 14 stone and 5ft 10… so a bit of a belly. I am also a farther of a 2 year old and a teacher. As such I am always on my feet and often covered in paint or mess of somesort.

    Could you advise some style tips for hotter climates. It’s almost always too hot for jeans and often too hot for chinos.

    I do sweat pretty easily but not that bad.

    Given these weather conditions I often wear sandals or trainers and shorts and round neck or v neck tshirts.

    I know I need to update my style but when I research my findings are always for cooler climates.

    Thanks in advance for any tips you can offer.

    J

    Reply
    • That Tim says

      January 19, 2022 at 10:34 am

      This right here. It seems every single mens fashion article is for NYC mid winter.

      Reply
  30. colin sherwood says

    July 11, 2020 at 9:43 am

    im 48, im eccentric, and have worn all sorts of things, after losing parents , its easy to go into a slump, and i became unfit, i allways dressed well been tall and thin…but in the next 2 years, i want to ditch the hooded tops, the cowboy hats, the beads and coats that feel like a carpet…you give some great advice here..and it will be wonderful to get fit and smarten up the style and actually dress my age..instead of trying to look like the latest stallion from the gym.

    Reply
  31. Tim Hayashi says

    February 7, 2020 at 1:37 am

    Brock, I love about 99.9% of your posts, pictures and advice, and you have truly been inspirational to all 5’6” of me but I have to disagree with you on a couple of “Avoids”.
    First, I’ve been in the apparel business for over 40 years and have sold everything from suits to boardshorts. I’ve spent the last 33 years in the Surfwear industry and currently work for several of the top brands.
    If you live in coastal areas like So. Cal, Florida or Hawaii, sandals are perfectly acceptable, as long as they are worn at appropriate times and they’re not 99cent rubber slippers. Nice leather sandals are a great casual look and are a staple of warm climate areas. I”m not saying that wearing them when going out to a nice dinner or date is cool, but as the saying goes, “if the shoe fits” the occasion, sandals can be worn with style.
    Second, I believe that hooded sweatshirts, in light weight solids and textured fabrics are totally appropriate for me over 50. I avoid big and baggy hoodies and do not wear anything with bold logo, but a nice fitted solid hoodie can be a great layering piece. Another one of my favorite fashion inspirational gurus, John Galfano agrees in this recent video he released. https://youtu.be/pQJFl7sETso
    John totally rocks a hoodie.
    I agree 100% with you with the rest of your list especially distressed denim, baseball hats worn backwards, denim shorts and baggy clothing.
    My mantra is, “You don’t always have to “Dress for success”. Sometimes you just need to dress successfully™️. You, John and a few other influencers do a fantastic job of explaining this and I have the deepest respect for you.

    Reply
  32. John Galfano says

    January 23, 2020 at 12:42 pm

    Thanks for including me in this article Brock!

    Reply
  33. Barry Hellespont says

    November 26, 2019 at 1:28 am

    Irrelevant information for soulless, style-less, sheep.

    Reply
    • Brock says

      November 26, 2019 at 9:41 am

      And what exactly does that make you, Barry?

      Reply
    • Alabel says

      September 12, 2022 at 1:29 pm

      So. Did you read the entire article? You soulless soul 🙂

      Reply
  34. A-Z Formal [email protected] says

    January 23, 2019 at 5:07 am

    Thanks Brock – thoughtful stuff I Really Like it.

    Reply
  35. Chenzo Wilson says

    December 5, 2018 at 6:06 pm

    Daymond earrings are awful. They ruin his whole look. Sorry but no guy past his late 20s should be wearing the diamond stud earrings or any earrings for that matter. Just tacky past a certain age no matter how much wealth you have.

    Reply
  36. Ben Neki says

    July 11, 2018 at 4:29 am

    Fashion rules? Bunkum!

    Reply
  37. Ted says

    December 30, 2017 at 1:04 pm

    48 and 5’10”- I’ve donated about 6 tall kitchen garbage bags of baggy jeans and t-shirts in the last 2 months and replaced it, in large part, following the new found rules I learned from TMM, GG, and to an extent RMRS. Rafael has a lot of clout and great production value and detail but pushes fashion to a dandy state. Antonio has his strong points particularly in his info-graphics, but it is hard to get past the high pressure salesman side of him. A few things I like about TMM is that, even at 5’10.75″ I still wouldn’t mind looking taller. And who DOESN’T want to come across as more confident? Arrogant A-holes, maybe? So the main thrust of the site is on point with a LOT broader audience than it was originally intended. I like that no other site is more upfront about “these are the fashion rules, feel free to break them (once you know them)”. I like the overall style projected. Sharp, smart, stylish, but not over the top, and not pushy.

    Reply
  38. Yusri says

    December 29, 2017 at 11:46 pm

    No to distressed jeans and you yet showed Ralph rocking a pair at 77 years of age. And Nick Wooster’s photos practically yelling ‘bollocks!’ to your style tips. And you ended your article with a message rightfully contradicting your own ‘advice’.

    As a 48-year old, this is probably one reason I don’t take style tips from younger guys. They don’t always know what they are talking about. Style is personal. Whatever you choose to wear, own the look but be mindful of the social context. The latter says you’re clued in, not clueless. If you’re not comfortable wearing ‘someone else’s looks’ it will become obvious to everyone else that you’re simply trying too hard.

    Reply
  39. Joe Judge says

    November 29, 2017 at 1:55 pm

    You say to ditch the baseball cap, but replace it with what? I’m bald and need a hat. I like old fashioned brim hats like guys work in the 50s and 60s, but nowdays you look contrived. Knit caps make you look like a bum… or teen. Suggestions?

    Reply
    • Gary Humphries says

      November 29, 2017 at 2:31 pm

      I would just go with the baseball cap or the old brim style you love to wear,personally i would go with what makes you happy, i’m 51 and wear baseball caps all the time and i don’t think age should matter as to what type of hat you wear.

      Reply
    • Gary Humphries says

      November 29, 2017 at 2:32 pm

      I wear knit caps to simply keep my head warm.

      Reply
      • Chris Rothschild says

        March 18, 2018 at 11:52 pm

        Function over form=old age.

        Reply
        • Gary Humphries says

          March 20, 2018 at 4:30 pm

          Chris those are my sentiments exactly, even tho it may not be be hip or fashionable!! All about function and comfort!!

          Reply
    • henrik says

      July 11, 2023 at 8:33 am

      try pap nun nice hats

      Reply
  40. Ante says

    June 15, 2017 at 11:06 pm

    I am 52. 6″2′. 96 kg. Gray haired. I do not try to pretend that I’m younger then my age but I do not agree that older guys shouldn’t wear T-shirts. Recently I couldn’t resist to purchase original and unique design “Poet and Rider” by Silver Gang. The head turner. I think that men should choose their wardrobe in accordance with “feel good” factor. Some fashion gurus are biased. The same T-shirt on Nick Wooster will be declared “top pick” or “ultimate fashion”.

    Reply
    • GARY says

      June 16, 2017 at 9:17 pm

      I completely agree on this although some tee shirts should be worn by our younger counterparts!!

      Reply
  41. Larry Lacy says

    March 18, 2017 at 8:10 am

    I am 56 and 5’5 tall. My style leads towards dress and casually dressed with various colors that can accentuate my wear. This article is spot on. Also I am going to purchase some shirts that one can wear untucked.

    Reply
  42. Gary Humphries says

    March 16, 2017 at 6:31 pm

    50 Years old and 5’6″ Tall. What is a good style if you like to tuck your shirts in most of the time? Brock very nice article and have you ever thought about doing a video on this? How about segments for those over 40 or 50 on a regular basis?

    Reply
  43. lou says

    March 12, 2017 at 12:36 am

    why is 40 old?

    Reply
    • J says

      March 8, 2021 at 3:29 pm

      It’s not old. However if you haven’t kept up with trends and you’ve
      neglected your body and your look it can look old!

      Reply
  44. Paul Sterry says

    March 1, 2017 at 7:41 pm

    54 and 5ft 4″ Just get on with it, be happy. Just make sure it fits properly.

    Reply
  45. Frank Gadson says

    March 1, 2017 at 6:56 am

    Enjoyed the article great advice as a man of 62 years short in stature I wholeheartedly agree with he tips you suggest…however I think one needs to tread lightly in the areas of “pop of color” or “accessorizing” the wrong color or accessory can just simply destroy an entire look thanks for the article!

    Reply
    • J says

      March 8, 2021 at 3:27 pm

      I think it all depends on how old you actually look!
      If you look 15 years younger, then wear for that.
      However, once over 50 – it doesn’t matter if you’re
      15 years younger looking, you’re still following the
      grown-up rules. Nothing is going to put you in your
      20s again.

      Reply
  46. Simon Miles says

    March 1, 2017 at 4:09 am

    I’m enjoying my clothes now (in my forties) more than at any other time of my life. I love the ease, comfort and understated elegance of these simple, classic styles. It’s a look that can come across a bit stuffy and staid on a young man, but on an older man just works. I’m also now at the stage in my life when I can afford to invest in decent quality and fit (including alterations as required). Getting the right fit is always challenging, but with so many more options on line these days (and blogs like this one) it’s a lot easier than it used to be. Great article.

    Reply
    • henrik says

      July 11, 2023 at 8:34 am

      self edge

      Reply
  47. Tom says

    February 28, 2017 at 1:42 pm

    Basically a dress shirt in every instance, with maybe a polo shirt thrown into the mix here or there.

    Reply
  48. Frank says

    February 28, 2017 at 11:01 am

    If you wear a jacket with jeans tennis shoes are okay but if you wear a jacket dress pants and a black T-shirt or Pollo shirt, black shoes with black or grey is the manly way

    Reply
    • Matthew H Phillips says

      September 11, 2021 at 11:18 pm

      im a fan of color. alot of ur wardrobe is personality. if u own it ur good. being confident and comfortable in ur clothes is more important than the label
      ur wearing. if ur clean and well groomed and happy i wear chuck taylors or vans and own it.

      Reply

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