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30 Best Tips For Dressing Well in Your 50s

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

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 for how to dress over 50 and enjoy your sixth decade in style. 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.

Choose small prints that work in your favor

woman looking at a rack of clothes outside - how to dress over 50

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.

Go for the chicness of a pocket square

man in a suit reading a book - how to dress over 50

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.

Leggings are for the gym

woman in leggings leaning over a cube - how to dress over 50

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.

Choose subtle branding

colorful sweaters on a rack - how to dress over 50

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.

Keep heels to a minimum

woman in red shoes leaning against a lamppost - how to dress over 50

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.

Embrace your glasses

older woman looking at her phone - how to dress over 50

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. Because if there's one thing we should embrace with fashion for women over 50, it's embracing our natural features, and that includes glasses.

Say no to ankle boots

tailored pants, booties, and bag - how to dress over 50

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.

Build your tie repertoire

a bunch of ties in a tie organizer - how to dress over 50

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.

Balance patterns out with color

woman wearing a floral dress and blazer - how to dress over 50

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. 

Say no to ripped or "distressed" anything

ripped jeans - how to dress over 50

If you're wondering how to dress over 50, the first step is going to be eliminating any juvenile fashions from your wardrobe. That includes ripped and distressed jeans (or anything else!). Just say no.

Opt for flattering, tailored coats

tweed jacket on a man - how to dress over 50

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.

Actually shine your shoes

brown shoes and pants, mens - how to dress over 50

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.

Be wary of cheap denim

stack of blue denim jeans - how to dress over 50

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. 

Don't be scared of scarves

pink and purple scarves hanging on a rack - how to dress over 50

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.

Wear red

woman wearing a white sweater and red blazer - how to dress over 50

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.

Rethink your best suit

tailor measuring a blazer with tape measure - how to dress over 50

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.

Use ruching to your advantage

big pink bow on dress - how to dress over 50

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

Invest in a well-made leather jacket

man wearing a leather jacket - how to dress over 50

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.

Pick fabrics with some stretch

man tugging at a sweatshirt - how to dress over 50

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.

Buy a variety of blazers

man holding his tie and a suit - how to dress over 50

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."

Choose short, fitted tops

woman wearing a black shirt - how to dress over 50

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.

Only buy clothes that fit

colorful skirts hanging on clothes rack - how to dress over 50

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.

Never match your bag with your shoes

structured purse bag sitting on ground - how to dress over 50

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

Color block your ensembles

woman sitting in a window holding a coffee - how to dress over 50

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."

Embrace the boat-neck neckline

woman wearing a blue sweater - how to dress over 50

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.

Less t-shirts, more knit sweaters

man and woman riding bikes on beach - how to dress over 50

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."

Be cautious of glitter

glittery gold dress and gold shoes - how to dress over 50

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.

Opt for a shorter 'do

woman's short haircut - how to dress over 50

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.

Invest in trousers, not jeans

man on a ledge reading a book in a suit - how to dress over 50

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.

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

woman looking at shampoo bottles generic - how to dress over 50

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

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Tehrene Firman
Tehrene Firman is a freelance health and wellness writer. Read more
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