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A good pair of sunglasses is arguably more defining than an entire wardrobe. Think Tom Cruise in Risky Business—nothing against his yuppie attire, but it was his shades (and that Porsche 928) that imprinted the nonchalant cockiness and charismatic appeal that shot the relatively unknown 21-year-old actor to stardom. In case the ’80s classic is a blind spot, Cruise wore Ray-Ban Wayfarers.
There’s something about these particular specs—the timelessness, the sense of effortless cool, the hint of rebellion—that has given them a longevity few eyewear options can rival. (Realistically, only the aviator can compete.) From JFK, lounging in khakis and an Oxford on Martha’s Vineyard, to John Belushi in The Blues Brothers, Quentin Tarantino’s entire crew in Reservoir Dogs, Andy Warhol and Bob Dylan in their prime, to the ultimate—Muhammad Ali—these rectangular shades aren’t just classics. They’ve reached icon status.
Ray-Ban first introduced the style in 1956, and the draw was near immediate. Since then, the Wayfarer silhouette has become a key style across brands. Why do they hold such lasting appeal? Perhaps it’s their democratic structure—the rectangle frame fits all face shapes, though Wayfarers look particularly good on round and oval faces. If you have a low bridge (the bridge of your nose sits level with or below the pupils), these will suit you even more. But, they’re arguably more about attitude. A well-designed wayfarer combines traditional masculine polish with a confident energy that’s hard to miss. The trick to picking the ideal pair? We’ve done the leg work for you with our definitive guide to Wayfarers, below.
Ray-Ban Collection Edition Wayfarer
Ray-Ban, the originator of the style, gives the classic Wayfarer a subtle twist, with gray gradient lenses and an @Collection engraving that adds just a bit of color. It’ll look just as good with a plain tee and standard blazer, or a more playful, fashion-forward option (say, a just-shy-of-ironic bowling shirt). You can’t go wrong with these.
Mr. Leight Getty S Tortoiseshell Sunglasses
Designed by a father and son team in California and handcrafted in Japan, Mr. Leight’s eyewear takes a highly artisanal approach. Its square-shaped Getty S is distinguished by the details: the acetates are custom-made with titanium detailing, the lenses are scratch-resistant (let’s be honest—a major bonus) and anti-reflective, and the tortoiseshell frame is exquisitely subtle.
Tom Ford Dax 50MM Square Sunglasses
Tom Ford knows a thing or two about understated (and, at times, overt) sex appeal. These tortoiseshell glasses are simple enough—the shape is classic as can be—with brown-tinted lenses that give them a warm, devil-may-care vibe.
Gentle Monster W Back Sunglasses
Seoul-based eyewear line Gentle Monster is known for its conceptual approach. Think goggle-shaped glasses referencing old-school rave accessories and aviators inspired by a subconscious imagining of life on Mars. Indeed, the W Back brings a hint of the avant-garde to the everyday. The clean, square silhouette is flattering and works across styles and settings. It’s a refined take on a Wayfarer in a sophisticated, burnt orange shade that is at once retro and near-futuristic.
Cutler and Gross ‘1393’ Rectangle-Frame Acetate Sunglasses
Handcrafted in Italy, Culter and Gross’s rectangle-frame glasses are inspired by styles found in Laurence Corner Army Surplus Store in ’70s London. They are traditional in design and spirit—with a quiet, elegant air.
Saint Laurent Classic SL 28 Sunglasses
These Saint Laurent specs are cool, but not too cool. In black with a grooved bridge, they have a slight retro edge and strike that perfect balance; they’re not trying to be anything more than what they are, but they’re not at risk of being boring. Ultimately, these are classics; you can wear them from season to season, decade to decade.
Celine Square-Frame Tortoiseshell Acetate Sunglasses
Hedi Slimane is known for his vintage rocker edge—in his ads, his ready-to-wear (all the way back to his impeccably-cut, ultra-slender Dior Homme suiting) and, in this case, his sunglasses. These Celine specs embody Slimane’s aesthetic at its best, adapting the Wayfarer mold just enough with a slim, rectangular frame. It’s perfect for adding a hint of disaffected posh to downtown get-ups.
Persol PO3059S Sunglasses
Persol was originally developed for pilots and race drivers. Today, we associate the Italian eyewear master with the definitive cool of Steve McQueen and many more (Daniel Craig, George Clooney and Ryan Gosling, to name just a few). This sleek riff on the folding glasses made famous by McQueen combines the brand’s road-tested functionality with classic, masculine style.
Oliver Peoples x Frère NY 52MM Wayfarer Sunglasses
Oliver Peoples, a brand that evokes days chilling in the bright California sun, and Frère, the Los Angeles-based label celebrated for its colorful suits, joined forces on a collection that perfectly reflects what they do best. The assortment of styles, particularly the Wayfarer, is as laidback as it is refined—great for driving down Big Sur in a convertible with the top down.
Maui Jim Mixed Plate Sunglasses
Maui Jim’s glasses are beachside staples, beloved by some of the most rakish men on the planet: Jude Law, Brad Pitt and Barack Obama, to name a few. The brand’s polarized lenses are super light and incredibly effective under the blazing summer sun. But the frames are so stylish that you’d want to wear them all year round.
Krewe Matthew Sunglasses
In New Orleanian culture, a krewe is a band that comes together to parade during Mardi Gras. This celebratory vibe is exactly what eyewear brand Krewe represents with its vintage-inspired frames, which take after landmarks and the lively atmosphere of the Big Easy.
Warby Parker Harris Sunglasses
In a little over a decade, Warby Parker has become a juggernaut in the eyewear industry, amassing a loyal fan base by offering top-notch shades at prices that are pretty tough to beat. Its selection of sunglasses, especially the celebrated Harris style, has become a perennial in stylish cliques.
Retrosuperfuture Giusto Sunglasses
Retrosuperfuture was founded in the early aughts, offering eye-catching acetate sunglasses in the full spectrum of colors. The brand, as its name suggests, offers styles that meander between vintage and futuristic. The Giusto is a great example.
Alhem Champ de Mars Sunglasses
Rich, glossy tortoiseshell acetate in a particularly sculptural 8mm thickness gives these shades an assertive, cosmopolitan attitude. They’re crafted by a Paris-born, LA-based designer, so the worldliness makes sense. Sport them with a sharply-tailored suit or a button-down and those just-right white jeans or your most comfortable work-from-home basics—they’ll elevate your look regardless.
The Reference Library Eddie Square-Frame Sunglasses
Newly minted British eyewear line The Reference Library looks to industrial design and mid-century film when conceptualizing each of its handcrafted frames. The Eddie is its take on the Wayfarer—based on 1950s eyewear shapes and NHS glasses, with slightly rounded angles on the lenses and Italian acetate frames for a strong, put-together look.