style guide

The Best Clothing and Shoes That Never Go Out of Style

Trends come and go, but these 11 timeless pieces have stuck around

By Oscar Hartzog

Oscar Hartzog

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April 11, 2024

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Best timeless clothing shoes

Gucci

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Fashion moves fast, but some things do actually stay the same. Over the years, certain pieces of clothing and pairs of shoes have transcended the rest to earn the badge of “timeless.” We’re talking about things like Levi’s 501s, Dr. Martens 1460s, and the Burberry trench coat: Wardrobe staples that work with just about every personal style, and never seem to feel passé. These kinds of timeless pieces are ideal for putting together great outfits without much thought or creating a foundation to pull off some style swerves.

Below, we’ve rounded up some of the best timeless clothing and shoes worth buying in 2024. We’ve only included pieces that can be found online and in stock, as of writing, with at least a 3.7/5-star average customer rating.

All of our picks are also gender-neutral (or we’ve included men’s and women’s options)

The Best Timeless Shoes for Your Wardrobe

Dr. Martens 1460

the boots

Dr. Martens

$170

Buy 1460 boots at DR. MARTENS

Shoe-wise, we’re in a weird place right now. In most everyday settings, dress shoes can often feel a little, well, dressy, while most sneakers can feel a little too casual. One answer? A great, classic pair of boots like the Dr. Martens 1460s. Famously durable and edgy yet easy to pair with most outfits, the boots have been around for decades for good reason. Pick up a black pair for maximum versatility, or try one of the more adventurous color options that Dr. Martens also offers.

Converse Chuck Taylor All Star

the sneakers

Converse

$65

Buy chuck taylor at converse

Buy chuck taylor at Amazon

Converse’s Chuck Taylor has a case for the most iconic sneaker ever. The low-profile silhouette, toe cap, and badge make the shoe instantly recognizable, but they’re surprisingly easy to pair with a wide range of outfits. Wear them casually with jeans and cargo pants, or team them with slacks or chinos for a fun dressy look.

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Vans Slip-On

the skate shoes

Vans

Buy classic vans slip-on at Amazon

$60

BUY CLASSIC SLIP-ONS AT VANS

Another one of the most famous sneakers of all time, Vans’ Classic Slip-Ons have never really gone out of style. Color is important here: The checkered slip-ons are the most skater-y, while darker colors will pair better with more pulled-together looks. All-white is also a great pick for casual, summery outfits.

G.H. Bass Larson Weejun

the loafers

$175

Buy larson weejun at g.h. bass

$175

Buy larson weejun at macy’s

Loafers have had a resurgence over the last few years, offering a dressy option that’s not as formal as, say, pumps or lace-ups. The original penny loafer is G.H. Bass’ Larson Weejun, which haven’t changed much since they first came out in 1936 (really). Over all those decades, the loafer has remained a wardrobe staple for both men and women.

Gucci Horsebit Loafers

the (fancy) loafers

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Gucci

$990

Buy women’s horsebit loafer at gucci

$990

BUY MEN’S HORSEBIT LOAFER AT GUCCI

Think of the Gucci Horsebit loafer as Larson Weejun’s wealthier younger brother. They were released in 1953, and changed the game with their signature horsebit hardware on the tongue. Today, the distinctive, timeless loafer is one of the best shoes for date nights, dinners, and any other slightly dressier occasions.

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The Best Timeless Clothing Pieces for Your Wardrobe

Levi’s 501 Jeans

the jeans

Levi’s

$79.50

Buy men’s 501 at levi’s

$98

BUY woMEN’S 501 AT LEVI’S

It’s crazy that Levi’s invented jeans as we know them, and the brand is still the go-to for jeans. The 501 is the most classic Levi’s shape, showcasing a mid-rise and a straight leg, and it can be found in almost every stylish person’s closet. Sure, you can try to hunt down that perfect vintage pair, but we think it’s also fine to buy them new, wear the hell out of them, and enjoy a wonderfully worn-in pair soon enough.

Sunspel Classic T-Shirt

the t-shirt

Sunspel

$95

Buy classic t-shirt at sunspel

$90

Buy classic t-shirt at nordstrom

There’s not much to say here: Everyone needs a stock of white T-shirts. If yours is dwindling, or the shirts are stained or tattered, re-up with this one from Sunspel. The brand has been doing T-shirts for more than 100 years, and it shows.

A Black Suit

the suit

J. Crew

$625

Buy men’s crosby suit at j. crew

$324

buy women’s greta suit at j. crew

A few years ago, we thought suits were potentially on their deathbed. We were wrong. Led by stylish Gen Zers, suits have made a comeback in the form of “businesscore” and other trends. If you don’t already have a high-quality black suit, get this men’s Crosby or women’s Greta suit from J. Crew and wear it together for big events, or as individual pieces with different outfits.

A Leather Jacket

the jacket

Coach

$359.20

Buy women’s leather jacket at coach

$358

Buy men’s leather jacket at theory

Leather jackets, in some form, never seem to go out of style. Right now, the leather jacket to get is one with a spread collar and a cropped, boxy fit. We like this one from Coach for women, or this one from Theory for men. Team it with a T-shirt and jeans on the weekend, or wear it with the white dress shirt above and slacks for an office outfit with some edge.

Burberry Kensington

the coat

Burberry

$2,590

Buy women’s kensington trench at nordstrom

$2,590

Buy men’s kensington trench at saks

Designed in the early 1900s, Burberry’s trench coat is a legendary piece of sartorial history that can still be seen on the chic people worldwide. The brand’s founder, Thomas Burberry, was actually the one who created gabardine fabric (the durable twill-woven cloth you find on all trench coats today). But he also gave the trench coat a dramatic look that quickly made its way to Hollywood and, soon after, the shoulders of so many wealthy stylish folks for years to come. (For a more affordable option, check out this one from Ralph Lauren).

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