15 Wayfarer Sunglasses That'll Always Be Cool and Classic

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Since the early 1950s, there's been one style of sunglasses that signifies you're a certified Cool Guy: the Wayfarer. The original Wayfarer, created in 1952 by Raymond Stegman of Ray-Ban, sought to do something simple yet revolutionary—create a sleek, masculine frame that would become a staple in wardrobes worldwide.

The Wayfarer has since become one of the most popular, recognizable styles of sunglasses. You've seen 'em on every celebrity from Bob Dylan to Kanye West, in movies from The Wolf of Wall Street to The Breakfast Club. The silhouette is undeniably iconic, and so damn wearable that it pervades decades, genres, and aesthetics.

While Ray-Ban pioneered the OG Wayfarers, other sunglasses brands have since caught on and created their own iterations. Timothée Chalamet, for instance, is rarely seen without a Wayfarer-esque pair of shades on, usually by Celine Homme. Brands like Fossil and Oakley have trusty pairs for under 100 bucks. And even Ray-Ban has expanded upon the originals, with a handful of varieties within the Wayfarer family.

Really, if you don't have a pair of Wayfarer sunnies, you're missing out on an easy, effortlessly style staple. These are the sunglasses that grant instant rockstar vibes and timeless fashion appeal. True to the name "Wayfarer," start your journey here, with the 15 best styles on the market.

Original Wayfarer Sunglasses

The myth, the legend, the classic Wayfarers by Ray-Ban. This is the style that started it all, with its distinctive rectangular silhouette, acetate frames, and simple, sleek look. Why mess with what works? These are tried and true, with 100% UV protection, different lens and frames colors to choose from, and 50mm or 54mm options.

Frogskin Sunglasses

We'd be remiss not to mention Frogskins, the oversized, Terminator-esque style that brings a definitive '80s look into the modern age. Oakley's lightweight, timeless style is customizable, so whether you have a prescription or you just want to rock some dope sunnies, these are an easy, effortless pick.

New Wayfarer Sunglasses

These are Ray-Ban's modernized, updated version of the shades above, and the ones you probably see most people wearing today. With thinner frames and a slightly more squared shape, these are a straighter, sleeker version of the originals, complete with durable, lightweight acetate frames and iconic green glass lenses.

Wayfarer Folding Classic Sunglasses

If you're the kind of guy who likes to stick his sunglasses in his pocket—or maybe the kind of guy who's been victim to a pair of pocketed sunglasses snapping in half once or twice—these foldable Wayfarers are you. With all the cool, classic style, these kick things up a notch by folding at the nose, so when they're not on your face, they can fit in the palm of your hand.

Wayfarer II Classic Sunglasses

While the OG Wayfarers are distinctively squared, the Wayfarer II is characterized by rounded frames, skinny arms, and a high bridge fit. Whether you go for gradient or solid lenses, you're going to reach for these again and again—even when it isn't even that sunny outside.

New Wayfarer Washed Lenses

Wayfarers may have been invented in the '50s, but Ray-Ban would be a fool to overlook the colored lenses craze that's stuck around since the '70s. In five colors, these squared, low bridge frames take the timeless look of the Wayfarers and add a groovy, fun flair.

PO3269S Sunglasses

Combining the retro and the modern, these chunky, thick-framed sunglasses are at once sophisticated and casual. You can wear 'em anytime, anywhere—and this shape is universally flattering, too.

D-Frame Recycled-Acetate Sunglasses

With an elegant, sleek look, these squared frames by Saint Laurent have all the timeless style of Wayfarers, with some extra elevated vibes. The silver arms and straight, flat bridge add instant Cool Guy appeal.

Square-Frame Acetate Sunglasses

Channel your inner Chalamet with Celine Homme's Wayfarer-style sunnies. The silver hardware brings a certain rock 'n' roll aesthetic to these understated, elegant glasses, finished with Celine's signature two-dot logo.

Myles Sunglasses

With 50mm lenses, these Wayfarer-style sunnies have a smaller fit, but still keep that iconic rectangular silhouette. For narrower faces, this iconic look is a great option.

04 Black Sunglasses

If you're balling on a budget, you can't go wrong with Chimi's sunglasses. The brand is known for its cool, trendy accessories, and this style has all the classic appeal of Wayfarers with extra-thick, modern frames.

Blaze Wayfarer Sunglasses

You know those guys who you see wearing tinted sunglasses indoors, and you can't even be mad because they look cool as hell? Yeah, these are the sunglasses that give you that effect. With large, squared, gradient frames, these add a dose of sophistication to the iconic style.

Steadfast Polarized D-Frame Sunglasses

At 75 bucks, Le Specs' Wayfarer-style sunnies have all the parts of the originals, from a squared frame to a unisex, casual look. Being lightweight, these are super comfortable, so don't forget to bring 'em with on the next sunny day (whenever that is).

Hayden Rectangular Sunglasses

With squared frames, blocky arms, and an all-black look, Burberry's Hayden sunglasses combine the elegance of the British label with the everlasting coolness of this sunglasses silhouette.

Wells Rectangle Sunglasses

If you like the tortoiseshell look—and it is, to be fair, a very old-money, elevated vibe—then these are the sunglasses for you. The timeless shape and green lenses lend easy style to your look, with virtually no effort required on your part.

Why You Can Trust Esquire

We’re not about writing how great things are if they aren’t actually great. Every product in Esquire’s round-ups are carefully curated by our fashion and e-commerce teams.

When it comes to sunglasses, you can rest assured that we’re hand-selecting picks from brands that we’ve personally tested, tried, and loved, along with styles that the rest of our stylish colleagues here at Esquire endorse, whether they're emulating Jordan Belfort or Bob Dylan. We’ve had to go through a lot of trial and error, and these picks are the ones that are simply the best.

Every style on this list (and our other lists!) comes from years of wearing different things, seeing what we love and what we don’t, and going from there. No two tastes are the same, and no two men are the same. Your proverbial mileage may vary. But if you’re looking for the right place to start, with advice from folks who and care (possibly too much!) about this sort of stuff, this is the place to be.

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