A Man’s Guide to Dressing Well in His 40s and 50s ( Men over 40)

If you’re a man over 40 who wants to dress better than most 20-somethings, this post is for you!

First and foremost, despite the moniker “old guy style,” being over 40 does not imply you’re old. Also, just because you’re an older guy doesn’t mean you have to dress a specific way. First and foremost, despite the moniker “old guy style,” being over 40 does not imply you’re old. Also, just because you’re an older guy doesn’t mean you have to dress a specific way.

Your lifestyle influences how you dress. What kind of work do you do? Do you have a daily dress code? As a result, saying “guys over 40 should dress like this…” and “men under 40 should dress like that…” makes no sense.

This is considerably more difficult for older men who are not of typical build (like shorter guys). One of the major challenges you have is the difficulty in obtaining clothes that fit.

Unfortunately, many companies that emphasize fit are aimed at younger guys – or even teenagers.

Brands such as Zara, H&M, and ASOS, for example, sell fitting apparel in smaller sizes. But are these brands truly acceptable for guys over 40?

It’s very OK for an older gentleman to dress in “younger” attire! This post, on the other hand, will assist you with dressing in a more traditionally “age appropriate” manner.

To begin, here’s a quick list of particular things to avoid if you don’t want people to think you’re attempting 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

Most of the things on that list should be avoided by most men. But some things, like jeans with a lot of holes in them, are not appropriate for older, more mature men.

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

But it looks like he’s trying to be someone he’s not, which is the opposite of what he wanted.

It’s like a little boy putting on a suit and tie. It just shows how small and young he is.

How should you dress? Let’s look at six men in their 40s, 50s, 60s, and older who are doing things right to find out. Go with Teeanime for all your doubts!

#1: GEORGE STEPHANOPOULOS

George is a well-known TV personality who knows how to dress for the job.

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

George’s style is safe, stylish, and right for his age. It looks like he knows what he’s doing but doesn’t try too hard, and he’s a great example of how older men can dress.

Even in his free time, he plays well. I really like his layering and smart-casual style.

#2: RALPH LAUREN

Ralph Lauren is one of the world’s most well-known fashion designers. He’s 82 years old at the time of writing, and he’s a shorter guy at 5’6′′.

Ralph is a fan of classic American prep style, thus he frequently wears dark suits, blue blazers, and worn-in trousers.

He doesn’t shy away from double-breasted jackets or bright colors, both of which are frequently advised against for short guys.

Lauren also favors classic styles (such as straight leg jeans), and he’s an excellent illustration of an elderly gentleman wearing blue instead of grey for a more youthful appearance (more on that below).

#3: DAYMOND JOHN

Daymond John, the founder of FUBU and my personal favorite shark, is well-versed in both fashion and business.

His style is influenced by hip hop culture, although now days you’ll see him wearing perfectly cut suits.

One aspect of Daymond’s style that I love is his attention to detail. For example, he defied fashion by wearing slender ties and little knots (such as the four in hand).

Daymond instead favors bigger ties (and lapels) and bulkier knots (such as the half Windsor), which complement his broad neck and chest.

This is an excellent example of avoiding a fad that younger guys may be tempted to adopt, especially if it does not suit your body shape.

These seemingly inconsequential adjustments may elevate your look from excellent to spectacular.

#4: SCOTT SCHUMAN

Scott Schuman, also known as The Sartorialist, is a fashion photographer who popularized street style photography.

For years, he’s been recording true style “in the wild” on the streets of NYC and around the world on his blog, and he’s become rather famous for it.

But his personal style is rather outstanding as well, which is doubly surprising given his short stature (possibly between 5’3′′ and 5’5′′).

Scott has a mature and understated aesthetic. His color scheme is straightforward and generally neutral, and his clothes are well-fitting. What else do you require?

#5: NICK WOOSTER

Last but not least, let’s take a look at fashion industry great Nick Wooster.

This is a man with extensive expertise and understanding of menswear. He knows all of the rules and enjoys breaking them.

Wooster’s style is always pushing the envelope. Even his more conservative ensembles feature one or two striking touches.

Here’s the thing: I’m not suggesting you dress like Nick Wooster.

I just wanted to mention him since he exemplifies having fun and expressing yourself through your clothing.

He’s over the age of 60. He dresses the part sometimes, and sometimes not, and that’s what I like about him.

Style is fundamentally personal, so do anything you want with it!

EXPERT STYLE ADVICE FROM OLDER GUYS

I asked three of the best-dressed men over 40 I know for their best advice for older men who want to look good.

This is what they said:

JOHN GALFANO

Wearing dark solid hues is, in my opinion, the single most effective style tip for most guys.

Wearing dark solids has various advantages. To begin, most dark solids complement each other effectively in an outfit.

Second, mixing shirts and pants becomes more easier because you don’t have to think about which half of the design to wear (trousers or shirt).

Third, dark colors make you appear slimmer and trimmer. Light colors reflect light and have a bulking effect that might make you appear larger than you are.

The opposite effect is produced by darks.

Finally, confidently wearing dark colors might make you appear more mysterious and expensive – truly!

Consider your favorite James Bond (mine is Daniel Craig). He looks badass in black, and the costume designers know it, therefore he wears darks a lot in the film.

He’s supposed to appear secretive and rich, which a light tan suit or a loud pattern shirt would not do.

Now, I’m not saying you should always wear black, but try experimenting with dark blues, dark browns, dark burgundy, and black.

If you enjoy patterns, try with delicate, small designs or patterns with similar colors. A dark navy shirt with slightly lighter navy patterns, for example, vs a dark navy shirt with a lot of white stripes.

If you want to go shopping, I recommend Nordstrom and Banana Republic for age-appropriate apparel.

HOW TO LOOK YOUNGER (AS A MAN)

There are some small things you can do to look younger without being too obvious about it.

#1: WEAR BLUE

To begin, instead of charcoal or grey, you can wear navy or blue. This is especially true with suits.

Blue is suitable for any age, but it is a more younger color than grey (see Ralph Lauren above).

#2: POPS OF COLOR

You can incorporate little “pops” of color into your clothing. They can be subtle or statement-making (as in Nick Wooster’s bright sneakers).

In any case, you’re demonstrating to others that you’re not just a dull old man.

#3: ACCESSORIZE

Feel free to get crazy with the accessories. Warby Parker has a fashionable new pair of glasses. Add some unique ties and bright socks to your wardrobe (but avoid “novelty” socks).

This is one area where you can make unconventional decisions.

#4: GROOM BETTER (OR DIFFERENT)

Have you been shaving for a while? Attempt the scruffy look. Have you had a beard for a few years? Shave everything off!

Grow it out if your hair is still healthy. Get a clean, modern haircut if you haven’t had one in a long time.

Also, remember to take care of your face. Use SPF moisturizer and anti-aging cream. Trim your brows, nose, and ears.

#5: TRIM THE FAT

While clothing fit is incredibly trend-driven, smaller silhouettes have been popular for years and are unlikely to fade anytime soon.

This is fantastic since it looks amazing on most people, including those over 40 and over 50.

So get your things tailored: shirts taken in, slacks hemmed, and sleeves reduced. Trim the fat from your clothes for a younger, slimmer appearance.

CLOTHING BRANDS FOR 40 YEAR OLD MEN (AND OLDER)

There are numerous clothing labels for guys over the age of 40, 50, and beyond.

In fact, because older men have more money, most popular menswear manufacturers cater to this market.

You should avoid fast fashion brands like H&M, Zara, and Pacsun that are shamelessly marketed at younger boys.

Instead, stick to men’s apparel labels that promote a more classic aesthetic and a mid-range fit.

QUESTIONS ABOUT HOW TO DRESS IN YOUR 40S

Here are some of the most often asked questions regarding dressing appropriately as an older man:

SHOULD MEN OVER 40 WEAR JEANS?

Yes, guys over the age of 40 may and should wear jeans. Just make sure they’re slim-straight and tapered (rather than slender or relaxed) and free of rips and obvious damage.

SHOULD A 40 YEAR OLD MAN WEAR SKINNY JEANS?

Men over 40 should avoid wearing narrow jeans unless they have really thin legs. Instead, opt for skin-tight slim tapered jeans.

WHAT SHOULD A 40 YEAR OLD MAN WEAR TO A NIGHTCLUB?

Check the dress code of the club you’re going to. Slim dark wash jeans or slim chinos with a casual button down shirt are appropriate for a nightclub. Wear simple leather sneakers or Chelsea boots, and accessorize with a good watch, necklace, and/or bracelet.

CAN A 50 YEAR OLD MAN WEAR A HOODIE?

A 50-year-old man can wear a hoodie, but I wouldn’t encourage it outside of the gym or yard work. Wear a plain sweatshirt, wool sweater, cardigan, or overshirt instead of a hoodie.

HOW SHOULD A 50 YEAR OLD MAN DRESS CASUALLY?

A man over the age of 50 should dress casually in slim-straight jeans or chinos, solid-color tees, polos or untucked button-up shirts, and appropriate outerwear (like a Harrington jacket, leather jacket or bomber). Shoes should be kept simple, such as leather boots, casual loafers, or plain leather or suede sneakers.

SHOULD OLDER GUYS WEAR LEATHER JACKETS?

Yes, older men look fantastic in leather jackets! Just make sure they’re the appropriate size. Leather jackets should be well-fitting. Nothing shouts “grandpa style” like a leather jacket that’s a size or two too big.