10 Styles That Instantly Date You and What to Wear Instead, According to Professional Stylists

Fashion experts and celebrity stylists share what not to wear and how to modernize your look with these easy wardrobe swaps

Keeping up with fashion trends can be challenging. But you don’t have to be trendy to be stylish. In fact, jumping on every micro trend can be a big fashion mistake and untrue to your personal style. And if you ask us, that’s good news for fashion over 40. But what are some ways to update your look without chasing the latest trends?

We talked to professionals about the styles that can date you—and what you can wear instead. And while the occasional wardrobe update is a must, you don’t need to revamp your closet every season. Here are their style tips, easy fashion ideas and what not to wear.

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Update your wardrobe, thoughtfully

Before you start purchasing new clothes, get a good handle on your own personal style—what looks and feels good on you, whether it’s the silhouette of your favorite dress or the rise of your denim. “This fall, wear something that makes you feel free,” says Louis Mairone, a stylist and host for ShopShops, a livestream shopping app. Consider which colors you reach for most and where you look for fashion inspiration. Developing your own go-to style will allow you to act deliberately when putting together an outfit and leaving certain style choices behind. Here’s what to keep—and what to swap.

Swap micro purses for a roomier bag

Have a mini bag, wristlet or baguette that looks great but doesn’t hold all your essentials? According to Mairone, mini bags look great, but they just aren’t functional. Luckily, big bags are making their way back into the wardrobes of many. “Don’t leave your mini behind,” he says, “but don’t be scared to lean into something more roomy.” Consider a medium-size satchel, a shoulder bag, a bucket bag or a structured tote made from high-quality leather. Most of these have spacious interiors to hold everything from your keys to your tablet.

Swap your stretchy jeans for relaxed denim

The war on jeans has been real (thanks, Gen Z), but don’t let them talk you out of your skinny jeans. Whether you prefer high-waisted, low-waisted, slim-fit or a bit of flare, the best jeans are the ones that best suit your body, assures Emma Trask, celebrity stylist and founder of The Chrysalis Lab. And while figure-hugging jeans have given way to more relaxed, straight-leg options, well-fitting skinny denim can still work if the denim is high quality and the outfit is styled right.

That being said, Trask views denim as the ideal canvas, especially for some personality, such as distressing. Mairone agrees. “Perfection is tired,” he says. “Holes, rips and tears tend to convey a story and depth.” So go ahead and pull out the classic Levi’s Premium 501 jeans or the thick, distressed denim and loose-tapered legs of years gone by. Classic straight-leg jeans are the perfect canvas if you’re into distressing jeans yourself. If you’re opting for a pair of deconstructed jeans that are ready to wear, pair with a crisp top or a more elevated sweater.

Swap round-toe boots for Chelsea boots

person wearing grey Blundstone Chelsea Boots outside on a sidewalk near a turquoise coloredwallNicola Ferrari/getty images

“Sandals and shoes with a rounded traditional toe shape are dated and dates the wearer,” cautions Victoria Staten, owner of shoe brand Famolare. Instead, opt for shoes that tend to be “forever styles,” according to Staten. That includes ballet flats, loafers, heeled ankle boots or Chelsea boots. She suggests pairing Chelsea boots with slim, boot-cut or flare pants or a maxi skirt or dress for a style update.

Swap color blocking for a monochromatic look

Both Trask and Mairone agree that monochrome looks are in. According to Trask, matching just looks good. “Monochromatic dressing is a surefire way to look put together, and it’s also quite flattering on a wide range of body types,” says Mairone. Not comfortable wearing one color from head to toe? That’s OK. Choose different hues or tones in the same color family or complementary shades. And don’t forget the accessories—outerwear, sneakers and bags can get in on the fun too.

Swap poor-quality fabric for cashmere

Choosing investment pieces can help you build a capsule wardrobe, and cashmere sweaters get better with age, says Trask. Because it’s a natural fiber, cashmere is not only lightweight, it’s incredibly long-lasting. It’s also transitional from season to season and adaptable from casual to more formal outfits. Trask suggests a matching set to elevate your loungewear. Pair a cashmere sweater with a matching pair of cashmere joggers, she says. “Matching looks good, and a lot of designers are making it their thing,” she says. And if you think cashmere isn’t in your budget, think again. There are plenty of high-quality cashmere sweater options that allow you to feel cozy without breaking the bank, like this editor-favorite $50 cashmere sweater that sells out every year.

Swap large logos for quiet luxury

Say goodbye to clothing and accessories with loud designer logos—that’s one of the best fashion upgrades you can make to look expensive. “Quiet luxury and apparel that whisper fashion have been under a microscope the past several seasons,” says Mairone. You’re looking for the better, more forward version of your favorite trousers, tees and topcoats, he adds. To build your quiet-luxury wardrobe, start with a satin or silk midi dress, a classic white T-shirt, a cashmere cardigan and a timeless blazer.

Swap a denim jacket for an all-denim look

woman wearing an all denim outfit sitting on steps outsideWestend61/Getty Images

If you rock a jean jacket as an accessory to the rest of your outfit, consider going full Canadian tuxedo. It’s not only OK to wear a denim jacket or a denim shirt with jeans, it’s on trend, as long as the denim washes work well together, says Trask. This ’90s trend has come back around over the past decade, which means you can break out your favorite denim shirt or oversized jacket whenever you want. “This kind of look is so easy, so the evolution is about making it individualistic,” says Mairone. He suggests pairing a denim jacket with exaggerated jeans for a cool, runway-ready look. Or consider an oversized denim shirt or classic jean jacket with a relaxed pair of jeans.

Swap shapeless sweaters for refined knitwear

With the old-money aesthetic on the rise, it’s time to pack away those boxy, shapeless sweaters for something more refined. According to Trask, knitwear has had a big resurgence. There are plenty of beautiful sweaters that will allow you to feel cozy while still looking put together. Trask suggests a 100%-cotton knitted turtleneck sweater for a classic, quiet-luxury look that can be reworked later on.

Swap a zip-up hoodie for a “shacket”

Don’t get us wrong: When the temperatures drop, you’re going to need a proper winter coat. But during those cozy autumn days, trade in your zip-up hoodie for a shirt jacket (or shacket). These shackets tend to have a thicker fabric (flannel or sherpa, for instance) than an overshirt and are meant to be oversized and worn over a T-shirt, hoodie, turtleneck or sweater. Shackets are also the ideal way to upcycle, says Trask. You can find secondhand flannel jackets or thick menswear overshirts that pair well with almost anything in your closet.

Swap costume jewelry for meaningful pieces

A great necklace, cocktail ring or pair of earrings can really elevate your look. But rather than stocking up on cheap jewelry that will tarnish quickly, consider spending money on fewer, higher-quality pieces or making your own. Trask advises wearing jewelry that tells a story. Picking up a piece of jewelry from your travels or using found objects is intriguing. To update your fashion accessories to make them modern and meaningful, try adding birthstones and significant charms to the end of a gold chain pendant necklace.

About the experts

  • Emma Trask is the founder of The Chrysalis Lab. She is a costume designer and celebrity stylist who has worked with some of the biggest names in entertainment for fashion editorials, advertising campaigns, music videos, television and stage shows.
  • Louis Mairone is a stylist and host for ShopShops, a livestream shopping app for fashion, beauty and lifestyle products.
  • Victoria Staten is the owner of shoe company Famolare.

Marisa Hillman
Marisa Hillman is a freelance writer and product expert covering product reviews, gift guides and sales for RD.com. She is a former educator turned professional shopper dedicated to finding the best sales and products on the market. When she's not on deadline, she can be found exploring the East Coast or curled up at home with her nose in a book. She lives in New England with her husband, three children and two dogs.