They say with age comes wisdom, and hopefully you've accumulated some by now (along with a few questionable outfit choices that we'll need to address).
Your 50s are the perfect time to learn how to choose the right clothes and dress better.
Maybe you're navigating a career transition, attending more weddings than graduation parties, or finally ready to elevate your everyday look.
Either way, we’ll help you retire your "dad uniform" to create something that's both sophisticated and effortlessly wearable.
Let’s start with a hard look at what’s hanging in your closet.
*(Not 50 yet? Go over to “How to Dress in Your 30s” or “How to Dress in Your 40s,” you young whippersnapper.)
Audit your wardrobe
The first step is cleaning out your closet. Your mission is to remove the clothes that no longer suit you and make room for clothes that do. It’s time to send these garments to the thrift shop:
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Clothes that are too big or too small: If that suit makes you look like a kid playing dress up, or that shirt is a sneeze away from an Incredible Hulk moment, they go in the pile.
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Outdated styles or trends: You and I both know your vintage PRO-Keds and concert shirts are still rad, but their time has passed, my friend. Toss ‘em. (Maybe keep the PRO-Keds.)
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Anything worn out: If it's full of holes or so worn you can see through it, turf it. No exceptions.
Once you’ve finished purging your closet, it’s time to rebuild your wardrobe (and self-esteem) with classic, stylish pieces.
The style essentials for every man
It’s time to fill all that empty closet space with fresh, new clothes. One of the best ways to do this is to build a capsule wardrobe of classic pieces that never go out of style.
Here are the basic wardrobe items you need.
Quality T-shirts
The bread-and-butter of any man’s wardrobe. Wear ‘em with jeans and sneakers for a chill weekend morning, or dress them up with a blazer for a night out. Get at least four high-quality fitted T-shirts in solid colors — two white, two black. No logos.
Button-down shirts
Button-downs are the Swiss Army knife of shirts. They make deciding what to wear super easy. Need something dressy for work? Wear a striped blue button-down with a jacket and tie. Just want something casual for hanging out? Throw on a pair of jeans or chinos. Want to look as incredible as George Clooney? Wear a charcoal sports jacket over a button-down and undo the top two buttons.
Grab a couple of shirts — one in solid blue, one with a subtle pattern.
Dark jeans
Know who wears dark blue jeans?
The Fonz.
Get a pair. They go with everything, and they’re forever cool. Just like Fonzie.
When it comes to good jeans, you’ve got a lot of choices. You can go high-end with a pair in selvedge denim. Or, you can grab some classic 501s in dark wash and put the money you save towards a sweet bike.
Wear dark jeans with absolutely anything. Like how John Travolta wore them with a purple blazer and denim shirt in The Poison Rose. Didn’t save the movie, but it was an awesome look. Google it.
Pro tip: Wash dark jeans inside out with minimal detergent so they don’t fade. Or go old school and don’t wash them ever. Whatever works best for you.
Good pants
We may be biased, but we believe that good pants are the foundation upon which your personal style is built. Having a selection of well-fitting trousers expands your options beyond jeans and khaki pants.
Save the khaki chinos for work and experiment with different colors and styles to find what suits you best. Neutral earth tones like olive green and brown pair well with blues and other earth tones. Try matching brown pants with a black t-shirt and tan blazer for a casually dressy look.
Choose slim fit pants for a more streamlined, athletic style. Or go with a standard/straight cut for a classic fit.
Whatever you do, make sure the pants fit well. Made with our exclusive Japanese Rebound™ fabric, Jack Archer Jetsetter Tech pants are never baggy or too tight in the wrong areas.
Polo shirts
Another wardrobe workhorse, polo shirts are ideal for more than just work and golf. Think of them as a dressier big brother to t-shirts. Go for the classic “dad look” by wearing them with chinos or jeans. Or throw on a black polo (like our Space Black polo) under a tan sports jacket and tan pants (like our standard fit Oat Khaki Tech pants).
Suits and blazers
Even if you’ve managed to avoid wearing suits so far, you’re going to be wearing them a lot more in your 50s. You’ll be going to a lot more weddings and formal events, so you’ll need a couple of versatile suits and blazers in your wardrobe.
As a minimum, invest in a charcoal-gray suit and navy blazer. They’ll get you through most formal occasions. Throw in a navy blue or gray pinstripe suit or colored blazer for more options.
You’re older now, so go for more conservative cuts. But that doesn’t mean boring — nothing makes a style statement quite like a perfectly fitted three-button suit. The secret is investing in high-quality fabric and a good tailor. And confidence, of course.
Footwear
More outfit choices means more shoes. Grab dress shoes and loafers, one pair each in black and brown. Add a pair of dressy leather boots and a pair of classic sneakers (Stan Smiths and Chuck Taylors are timeless). Don’t be afraid to mix and match, but always make sure your belt and shoes are the same color.
Hats
First off, hats are awesome. Second, here’s a reality check: You’re over 50, your hair is thinning, and — if you had a mom like mine — you probably didn’t wear a lot of sunscreen as a kid.
In other words, you gotta wear a hat to protect your head from the sun. But that doesn’t mean you can’t look good doing it. Ballcaps are always cool (especially if it’s the Detroit Tigers), but you’re at an age where you can wear almost any hat and look good.
You can channel De Niro and wear an Irish flat cap with a leather jacket or tweed blazer, or rock a classic fedora like Daniel Craig.
Now that we’ve covered the basic wardrobe for your 50s, let’s cover the dos and don’ts.
Style tips for men in their 50s
After years of trial and error (emphasis on error), think of these as the style shortcuts you wish someone had told you decades ago.
Know your body type (and measurements)
Clothes look 100% better on you when they fit well. Know your measurements (and be honest about them), and choose clothes that fit your body type. While you may have been able to get away with ultra-slim shirts in your 20s, odds are they’re not going to be as flattering in your 50s.
Find a good tailor
Even the best-fitting clothes can use some tweaking to fit your body well. A skilled tailor is worth their weight in gold. Ask at local men's wear shops to see who they recommend.
Choose quality over quantity
As the saying goes, “buy cheap, buy twice.” Although it may cost more upfront, good quality clothing looks better and lasts longer. Choose well-crafted clothing made from quality fabrics. If you need a hand, there are plenty of great resources like Esquire’s Handbook of Men’s Style to guide you through.
Conceal the beer gut
It happens to the best of us. Fortunately, men’s clothing has plenty of options to conceal your belly. Dark colors, high-waisted pants, and thick sweaters will make you look slimmer. Layering your clothes and having suits and shirts tailored can also help.
Be subtle
You have nothing to prove. Be subtle and cultivate an understated style that reflects quiet confidence.
Avoid these fashion pitfalls
We've all been there — thinking we look great until we catch a glimpse of ourselves in a mirror or photo. Avoid these pitfalls so you can avoid those cringe-worthy moments.
Wearing clothes that are too young
You know exactly what I mean. Graphic tees, fast fashion, flashy sneakers. Dressing too young is the first slippery step to a combover. Don’t be that guy.
Leaving your shirt untucked
Many men leave their shirts untucked. Don’t do it. It makes you look sloppy. Plus, if you’ve got any gut at all, it will make you look like a tent. Tuck that shirt in. The only exceptions are camp shirts or Hawaiian shirts.
Wearing logos
You’re not a billboard. A discreet logo (think LaCoste alligator) is okay. One that covers your whole chest is not, unless you’re Batman.
Having untrimmed nose hair
Trim your nose hair. I know, it sucks, but you want people checking out your clothes — not your nostril garden. Do your ears too.
Putting comfort over personal style
Ok, you’re saying, “But every other article about dressing over 50 says comfort is king!” That’s true, up to a point. But there is absolutely no reason for you to wear sweatpants or cargo pants in public. Instead, look your best by choosing well-tailored clothes made from quality fabrics that are designed to be both stylish and comfortable.
Now get out there and look sharp!
Consider this your style graduation — you've learned what works, what doesn't, and most importantly, how to dress like the accomplished man you are.
For a great start, head over to the Jack Archer store. We’ll set you up with everything you need to build a stylish wardrobe.
