30 Best Tips For Dressing Well in Your 50s

At 50, your style game is important now more than ever.

30 Best Tips For Dressing Well in Your 50s

Hitting the milestone of a middle-age marker is no reason to let style fall to the wayside. In fact, it’s more of a reason to step up your game and dress sleeker than ever. While you may feel like your body isn’t exactly working with you like it used to, there are so many tricks out there you can use to make dressing well in your sixth decade of life easier said than done.

Confidence levels spike with age, and now that you’re well-seasoned, let your wardrobe reflect that self-esteem! And for more awesome style advice, read on for 50 Ways to Look Red Carpet Ready.

dressing well 50s

Choose small prints that work in your favor

Ladies, a large, bold pattern can unfortunately be your downfall. A smaller print, however, that’s not worn head-to-toe can do wonders for slimming the body and serving as a bold conversation piece. For more on what prints to avoid, check out the Ugliest Dresses of 2017.

dressing well 50s

Go for the chicness of a pocket square

Men, you’ve been waiting your whole life to be mature enough to pull of a pocket square. Now that you’re in your 50s, you’ve aged like fine wine and there’s no better time. For more advice on looking great in a suit, take a look at the 7 Must-Have Vintage-Inspired Watches.

dressing well in your 50s

Leggings are for the gym

Fine, you can wear them around your house, too, but that’s it. Leggings are officially no longer appropriate to wear in public once you hit 30.

dressing well 50s

Choose subtle branding

Now that you’re in your 50s, you can likely afford better quality stuff. But just because you’re indulging in more well-known, expensive brands, doesn’t mean that you should be flaunting it across your chest. Choose pieces with subtle branding only–as in the form of a small logo rather than a large print word. For more on shopping smart, consider the 30 Best Ways to Save Money on Clothes.

dressing well 50s

Keep heels to a minimum

Too-high heels sometimes encourage bad posture behavior. And worse: They can create the illusion of saggy boobs, which let’s face it—no woman in her 50s wants! Instead, keep heels age-appropriate and on the lower side.

dressing well 50s

Embrace your glasses

All four of your eyes may have gotten you made fun of in middle school but now, they’re officially your best, most wise-looking accessory.

dressing well 50s

Say no to ankle boots

Booties are for teenagers (especially when paired with skirts or dresses). Say no to ankle boots unless it’s with a well-tailored trouser that tapers off at the ankle.

dressing well in your 50s

Build your tie repertoire

You should have ditched the novelty tie a long time ago but if you’re still only working with a handful of ties, it’s time to step it up. Wool ties, knitted ties, silk ties–all should be staples in your tie collection. Throw a bow tie in there for good measure, too. For more on what makes a suit look good on anyone, here are 20 Secrets Your Tailor Won’t Tell You.

dress well 50s

Balance patterns out with color

We’ve already established that large, bold prints can feel tawdry. So in addition to keeping patterns small, contrast them with a solid color, too, in order to slim the body down, keep things feeling classic, and not too overwhelming. And while you’re at it, definitely steer clear of the 50 Things No Woman Over 40 Should Own. 

ripped jeans are not appropriate for your 50s

Say no to ripped or “distressed” anything

No. Just no.

dressing well in your 50s, Things You Should Always Do at a Fancy Restaurant

Opt for flattering, tailored coats

Guys: Outerwear should be flattering, well tailored to your body, and sleek. Any coats or jackets that are bulky, overly furry, or frumpy should be donated immediately.

dressing well in your 50s

Actually shine your shoes

Doesn’t matter if you do it yourself or pay someone to shine those loafers. You shouldn’t be sporting dull shoes in your 50s. You just shouldn’t.

dressing well in your 50s

Be wary of cheap denim

Inexpensive and inherently poorly-made denim is easy to get away with when you’re young and your body tight and firm. But in your 50s, it’s a dead giveaway. Opt for a bootleg jean, which will lengthen your legs and flatter your tummy in the best way possible. dressing well 50s

Don’t be scared of scarves

Maybe when you were a younger lad, you shied away from scarves for fear of looking too put-together or metrosexual. But that’s such a thing of the past. Not only will a scarf keep you warm but it can also do wonders for tying your outerwear together.

dressing well 50s

Wear red

While red is a timeless color, it’s particularly sultry and bold in the winter time. “In winter, I always buy something red because it makes me feel festive, but now the red is more of a bluey crimson than an orangey pillar box, which I can no longer get away with,” former Vogue UK editor Alexandra Shulman explains.

dressing well 50s

Rethink your best suit

In your 50s, a drainpipe suit with a slim lapel can be pretty difficult to pull off. Phase any of these that might be left in your wardrobe out and instead commit to a double-button jacket with wider lapels GQ suggests. Additionally, trousers should be flat-fronted and (obviously!) tailored to your body.

dressing well 50s

Use ruching to your advantage

Can’t deny the fact that a little bit of texture is essential to hiding any lumps and bumps ‘round the middle!

dressing well 50s

Invest in a well-made leather jacket

We’ll give you a hint: You’re not going to find it at H&M. A quality leather jacket, a la David Beckham, isn’t going to be cheap, so invest in a quality one – like a Belstaff – and take solace in the fact that you’ll have it for the rest of your life.

dressing well 50s

Pick fabrics with some stretch

We don’t mean a full Spandex bodysuit circa 1980s exercise tapes. We just mean a little bit of stretch can go a long way, especially when your metabolism betrays you with a little (or a lot of) bloat.

dressing well 50s

Buy a variety of blazers

In a variety of materials. “Look out for understated windowpane checks and houndstooth or materials like linen and textured or quilted wools,” GQ recommends. “Just make sure to take each to your tailor to ensure they fit right.”

dressing well 50s

Choose short, fitted tops

It may not be your blouse of choice but during times when it may seem your waist is getting wider and wider, a short, fitted top really adds the illusion of a smaller, more cinched-in middle.

dressing well 50s

Only buy clothes that fit

The time for buying something just because you like it, even if they don’t have it in your size, has past. If something doesn’t fit perfectly but is easily salvageable, take it to your tailor.

dressing well 50s

Never match your bag with your shoes

Being too matchy-matchy is an overt fashion faux pas that can instantly age you. Don’t succumb.

dressing well 50s

Color block your ensembles

Lines are cleaner, sleeker, and overall, more classic-looking when you color block. “Avoid anything in bright acid colors or pastels,” GQ explains, “and instead opt for classics like camel, light grey, navy blue, forest green, and dark red.”

dressing well 50s

Embrace the boat-neck neckline

It’s the perfect neckline to accentuate your best features. “Stylists often get round-necked pieces altered to boat necks for their older clients since the shoulders, along with the wrists, are parts of the body that weather well and are worth showing off,” Vogue‘s Alexandra Shulman says.

dress well 50s

Less t-shirts, more knit sweaters

While a shirt and tie is always a classic go-to look, having an arsenal of knitwear at your disposal is a fashionable way to change things up and also, keep warm during the fall and winter. According to GQ, “Make sure you have representation for both thick, shawl collared cardigans and chunky fisherman’s jumpers, as well as thinner cashmere crew necks and long-sleeved merino Wool polo shirts.”

dressing well 50s

Be cautious of glitter

You shouldn’t be afraid to sparkle or shine but do it subtly, like with a fabric that has a light sheen or a slightly metallic accessory. But please, don’t dress like a disco ball.

dressing well 50s

Opt for a shorter ‘do

As you age, it might seem intuitive to keep your hair longer to create the appearance of more locks but it’s actually the opposite. A shorter hair-cut makes the hair look fuller if you’re experiencing hair loss or a receding hairline.

dressing well in your 50s

Invest in trousers, not jeans

Sure, you can still have your jeans but when it comes to pants, drop more cash on durable, comfortable, and effortlessly chic trousers. It goes without saying but make sure they’re well-tailored and flattering, too.

dressing well 50s

And while you’re at it, use a thickening shampoo

Whether you’re a man or woman, thickening shampoo in your 50s is key, no matter how lucky your genes.

To discover more amazing secrets about living your best life, click here to sign up for our FREE daily newsletter!

Filed Under
Best Life
Live smarter, look better,​ and live your life to the absolute fullest.
Get Our Newsletter Every Day!
Enter your email address to get the best tips and advice.
close modal
close modal