6 Classic Clothing Items That Never Go Out of Style, Fashion Experts Say

Consider these pieces the bones of your wardrobe.

On social media, we're shown so many trends—oversized denim, metallic shoes, winter coats with fur around the sleeves—that it's hard to keep up. The moment you cash on in one trend, it's over, and you're left scrambling to chase the next one. That's why many stylists suggest maintaining a trend-proof closet. To do that, you invest in clothes that make you look and feel your best, no matter what the fashion magazines and influencers say. You might also want to focus on clothes that experts deem timeless. From jackets to dresses to skirts, these are the pieces that will never go out of style.

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Wrap dress

Stylish woman wearing printed or patterned blue wrap dress
MS_Studio / Shutterstock

If you fill your closet with wrap dresses, you'll always have something to wear.

"It is flattering on almost every body type and can be worn on its own or over a long-sleeved top," says Michelle Barrett, stylist and founder of Capsule Closet Stylist.

The wrap dress also comes in many silhouettes so that you can find the best one for you. There are short sleeves, long sleeves, A-line skirts, pencil skirts, and so much more. For summer, try one in a lightweight fabric and fluttery sleeves; in winter, opt for a knit one and pair it with tights and boots.

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White shirt

Attractive senior woman wearing white button-down shirt and jeans
Golubovy / Shutterstock

A crisp white shirt is both timeless and versatile.

"It can be worn as a base layer tucked into suiting, untucked over leggings, layered under sweaters, or worn over tanks—it can even be a beach cover-up in a pinch," says Elizabeth Kosich, certified image stylist and founder of Elizabeth Kosich Styling. "Make sure it's nicely pressed with each wearing, or stock up on wrinkle-free styles that work well for travel."

Accessorize with a statement choker necklace if you keep it buttoned or with a pendant if you leave the neckline unbuttoned.

Straight-leg jeans

A happy middle-aged blonde woman wearing a denim jacket and jeans against a pink background.
ViDI Studio / Shutterstock

Right now, there's a lot of chatter about which jeans are best: skinny, baggy, low-rise, high-rise. But if there's one classic staple, it's straight-leg jeans.

"The original style of Levi's straight-leg jeans is always in and never dates," says Barrett. "It is almost like the basis for all jeans—anything else is an adaptation of that original style."

Wear them on errands with sneakers or sandals, to the office with mules, or on date night with kitten heels. You'll keep this pair of denim for decades.

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A-line skirt

woman in leather midi skirt

The A-line skirt is another classic bottom, although, in some years, it'll become more popular in longer and shorter hemlines.

"The most common throughout has been an A-line skirt that sits on the knee," says Barrett. "It is also the most flattering for most body types."

Buy it in a quality material and neutral color, and you'll have it around forever.

Trench coat

Asian woman posing outdoor in the park on a beautiful Autumn day.

There's no other word to describe the trench coat than iconic.

"It's seasonless, trend-proof, and ageless, proving it's one of the best investments you will ever make," says Kosich. "Consider classic khaki or one of your most serviceable light or dark neutrals like olive green, puddy, stone, black, or winter white."

You can throw it on over casual outfits as well as party dresses and office attire.

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Pea coat

older woman wearing pea coat
Anna Zhuk / Shutterstock

Winter coats are expensive, so if you're going to invest, you want to make sure you get your money's worth over the years. For that, Kosich suggests the pea coat.

"Its iconic midnight navy color is a much-needed break from black, not to mention a less harsh dark neutral for aging faces," she says. "Try a high-low look and pair a classic pea coat with frilly party dresses or flowy boho maxi dresses or with classic suiting to relax the stiff, stuffy edge."

To get the best fit, Kosich advises finding a jacket hem that stops either above or below the widest point below the waist.

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Juliana LaBianca
Juliana is an experienced features editor and writer. Read more
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