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Style Guys' Style Guides

Men’s Wardrobe Essentials for Your 50s

Roll into your next decade in style
the actor Key Huy Quan wearing a red sweater and dark suit

by Megan Collins Updated: March 11, 2025

Products are curated by Style Girlfriend editors. Purchases through our links may earn us an affiliate commission.

Look your best at every age. In this guide, find men’s wardrobe essentials for your 50s. And check out the wardrobe must-haves for your 20s, 30s, and 40s.


Paul Rudd. Daniel Craig. Ke Huy Quan. All in their 50. All still so, so cool.

If you think the quest for that “look good, feel good” connection ends when you get older, think again! At this age, you may be transitioning into a more relaxed wardrobe in your off-duty hours. Or maybe you’ve managed to retire early and need an all-new casual wardrobe.

Shop seasonal style picks for your fifties and beyond →

The bottom line? You still want to look and feel your best, and a wardrobe that suits you right now can help.

In this guide, check out 4 men’s wardrobe essentials for your 50s (and beyond!):

1. A “Look At Me” Suit

man wearing a navy corduroy suit with an off-white dress shirt and dark brown tassel loafers
Italian corduroy Sutton suit: Todd Snyder, $896

In your 20’s and 30’s, a man’s suits are extremely functional. Suits are for job interviews. They’re for for weddings. For showing how serious and grown up you are.

In your fifties, however, it’s pretty clear you’re a grown up. And you’ve probably amassed a closet full of work and wedding-appropriate suits.

Now is the time to have a little more fashion-y fun with your suiting. Why not treat yourself to a suit in a bold pattern or color? Or a cut you haven’t worn before?

Who’s going to say anything about it? You’ve earned the right to push your style boundaries!

With these bolder suits, don’t be afraid to have a bit of fun with your shirt as well. The key is not doing too much.

If you are going for a brightly colored suit, go for a more subdued colored shirt with a very subtle pattern. If your suit has a strong pattern, opt for a plain shirt in a fun, coordinating color.

All things in moderation, right?

Sport the shirt sans suit jacket? The same rules apply.

There’s nothing objectively wrong with a paisley printed shirt, but a bold print in a bold color can be, well, overwhelming. A good rule of thumb is bolder the print, the more subtle the color and vice versa.

2. A perfectly-fitting piqué polo

black lacoste polo shirt
piqué polo shirt: Lacoste, $110

The polo shirt is the grown man’s t-shirt. And we all know there’s nothing better than a guy in a well fitting t-shirt.

As you reach your fifties and begin thinking about your golden years wardrobe, a solid arsenal of polo shirts is a must.

Polo shirts come in a range of styles and fabrics, of course, but nothing beats a classic cotton piqué polo shirt.

“Piqué” is essentially a mesh weave that offers durability and breathability. A well fitting polo will fit close to the body, with the sleeves ending mid-bicep and the hem of the shirt falling about an inch below the belt line.

The black Lacoste short-sleeve polo above is a men’s style classic, and you should definitely own one (or, ahem, a few). That’s just a must.

Once you’ve got this wardrobe must-have checked off your shopping list, you can start to expand your repertoire. Think: cotton polos in colors that flatter you, and polos in a more sophisticated knit, too.

You’ll find yourself reaching for this staple again and again, from date nights to family gatherings.

3. A favorite pen

ballpoint pen in a floral pattern
Estie ballpoint pen: Esterbrook, $125

A benefit of getting older is you’ve had more time to learn what you like. There’s something attractive about a man with personal favorites.

A beloved vintage of wine. The cashmere sweater you buy over and over again. The shoes whose price tag made you throw up a little in your mouth when you bought them, but you’ve now had them for longer than your oldest kid, resoled them once, and fit like a favorite pair of socks.

And a good — no, a great — pen.

A favorite pen, like an heirloom watch, is an incredibly personal item that becomes a symbol of you for those around you.

Having a favorite pen on you at all times shows how well you know yourself. The wisdom that comes with age.

As what what brand? Which style? It’s less about price and more about consistency.

Once you know what you like, buy a couple and put them in your blazer pockets. Nothing like a man who knows what he likes and is always prepared.

4. Sunglasses you’d hate yourself for breaking

american optical flynn sunglasses
polarized sunglasses: American Optical, $260

No more dollar store sunglasses. No more sport sunglasses you wear fly fishing and grab on your way out the door because they’re there.

In your fifties, it’s time to invest in a nice, stylish pair of sunglasses. The kind that you’d throw up a little in your mouth for losing.

A bold pair of sunglasses is an easy way to inject style into your wardrobe.

And no, bad eyesight doesn’t relegate you to ugly frames you pick up at the optometrist.

Lens technology has opened up options for frames, and newer companies offer fashionable styles at affordable prices.

A bold frame can become a statement as well as a great way to stay as active make sure you look just as good as you did in your earlier decades.

5. 5-pocket twill pants

man from the waist down wearing a cream-colored knit polo with navy 365 pants from flint and tinder with suede loafers
365 Pant in athletic fit: Flint and Tinder, $98

Jeans, you’re good on, we’ll bet. Same with dress pants, and even chinos (khakis).

But what about those off-duty days where you want to look more put together than wearing denim, but not so formal that you feel like you’re at the office on a Saturday?

That’s where 5-pocket twill pants come in.

The fit and feel of denim, but in colors that suggest you put in *just* a bit more effort. Wear them the same way you would your favorite pair of jeans. Dress them up with a sportcoat, and down with a crewneck sweater or sweatshirt.

RELATED: Everything you need to know about twill pants

You could start with a neutral color—think: browns, tans, blacks, even various shades of blue. Or, you could jump right into the deep end with a hue that’s currently absent from your everyday wardrobe. Sea green, a deep merlot, even a light lavender!

So long as the fit is on point (not too tight at the waist, not too long at the ankles), you’ll be surprised at how useful you find this style of pants.


More Men’s Style + Grooming Resources for your 50s and Beyond:

What Are You Waiting For? Go Get Botox

How to Dress Over Sixty

What to Expect From a Telehealth Hair Loss Visit

Megan Collins

I started Style Girlfriend to help guys look, feel, and act their best.

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