One of the most iconic sunglasses of all time and arguably Ray-Ban’s most famous, the Wayfarer was designed by Raymond Stegeman of Bausch & Lomb (Ray-Ban’s parent company at the time) in 1952, the trapezoidal frame inspired in part by Eames chairs and Cadillac tail fins and were quick to become one of the most popular pair of sunglasses, continuing to endure as a favorite today. It doesn’t get much cooler than this. If you’ve always admired the Wayfarer style but never felt you could quite pull it off because it’s too bold or angular, the New Wayfarer updates the OG silhouette for a subtler take, sizing down the frames slightly and softening the edges. But don’t worry — the New Wayfarers are icons in their own right.Still undeniably cool, the strong vintage aesthetic of the Clubmaster offers a look that veers more rockabilly than the Wayfarers and its iterations. Featuring the “browline” style that gained popularity in the ’50s, the pair is largely recognizable for its wire-rimmed lenses, which lend them a slightly studious appearance. They remain as timeless as the Wayfarers, but they’re definitely more conspicuous. Other Clubmaster styles include: Clubmaster Round, Clubmaster OvalThe quickest way to look cool? Throwing on a pair of aviators. Designed by Bausch & Lomb in 1937 to help protect U.S. aviators while flying, they’ve since come to be a signifier of cool, beloved by movie stars and politicians alike. The style also introduced G-15 lenses, their green color working to provide more clarity, comfort and protection for pilots. Since the release of the original aviator, plenty of iterations have been spawned, but if you want to keep it classic, it’s best to stick to the original. Another pair inspired by the Wayfarer silhouette, the Justin swaps out the usual acetate for a rubber finish that gives the frames a matte look that in turn feels sportier than the style from which it was inspired. With a ’60s inspired silhouette the Meteor sunglasses have an innate vintage feel to them, evident in the sharp corners at the temple that creates an elongated effect, but can range from bold to bolder depending on the frame you choose, whether you opt for classic black or the more unusual Blue Havana. Don’t be swayed from sporting this style just because of it’s name, as it’s actually unisex and pretty damn handsome if we say so ourselves. The oversized round shape will help to bring some softness to those with more angular and square faces, without looking feminine in the least if you’re at all worried.

If you’re a wannabe rockstar, try these strong frames pulled straight from Ray-Ban’s 1970’s archive. Straight on, the Nomad sunglasses offer a relatively simple look, but turn to the side and the extra-thick temples help to elevate them beyond just a plain pair of rectangle sunnies. Working from the Wayfarer silhouette, the State Street offers an exaggerated version of the iconic style with sharp angles that help it to stand out from the rest. If you’re not ready to go full John Lennon, the Frank Legend sunglasses are a good compromise, the squarer (yet still slightly rounded) lenses working better for those with round or oval face shapes.

Transport yourself to a tropical island circa the 1960s with Ray-Ban’s Caribbean sunglasses, a pair that hearkens back to the Golden Age of air travel and true jet-set style and are thus perfect for the current season. You might notice similarities between this pair and the Wayfarers, but where they differ is the slimmer D-shape frames of the Caribbean. (which gives them a more angular look that’s almost like a cat-eye but not quite) and the vertical bar at the temples rather than usual dot.The Iverness takes its name from the Scottish down where it debuted in the 1970s, the influence of the era still evident in its design. The thick frames are reminiscent of the chunkier styles that were prevalent during the decade, just now slightly pared back so as not to appear too costume-y.If the Balorama style looks at all familiar to you, then you might have seen them donned by a stone-faced Christian Bale in the 2019 film Ford v. Ferrari, or before that an equally stoic Clint Eastwood in Dirty Harry. As these leading men would suggest, these sunglasses are perfect for those who want something that’s uncomplicated yet casually elegant.It’s often easy to forget that sunglasses are as much about function as they are style, but the Predator 2 manages to deliver on both with a streamlined, sporty silhouette that’ll work seamlessly for both athletic and casual occasions.Released in 1965, the Ray-Ban Olympian still manages to keep their distinctly vintage feel, which can largely be attributed to the sleek, metal browline that helps to contrast the roundness of the rectangle lenses, making for a pair of sunglasses that feels like what those in the ’60s thought we’d be wearing in the future. They’ve been sported by the likes of Jon Hamm in Mad Men, Ben Affleck in Daredevil and Peter Fonda in Easy Rider.

If you are ready to go full John Lennon, there’s no pair suited to the job than these bad boys, a style donned frequently by revolutionary musicians and icons of counter-culture in the 1960s. And now you. For those partial to the ’70s, the Oval Legend sunglasses perfectly capture the carefree spirit of the era — the perfect statement accessory for adding just a touch of retro vibe to an outfit without going full-fledged hippy. The Fleck sunglasses take the typical round style and makes them a little more interesting and contemporary with detailing like the optically textured premium acetate rims and matte finishes on the metal temples. The mixture of metal and acetate is perfect for those who have trouble choosing between a wire-rimmed or tortoiseshell pair.A true round silhouette can be a tad intimidating, so for those hoping to ease themselves into the style, start with this pair of the RB4258s, whose lenses are still round-ish, just not so circle-like. An understated pair of sunglasses, the RB4258s allow one to fly under the radar without sacrificing style or comfort.

Round frames unfortunately don’t work for everyone, so for those who desire the look of the aviator but with a stronger shape to add some definition to their face, the hexagonal lenses of the Marshall sunglasses will help to offset any roundness while still offering the iconic silhouette of the aviator. Accents like a brow bar and cable temples that hook behind the ears help to give the Outdoorsman a vintage edge that’s just as suitable for the outdoors as they are for strictly stylistic purposes, or both — because why should you sacrifice style even while you’re in nature?Aviators can easily overwhelm the face, especially those that are more on the petite side, so if you like the look but feel like a child trying on their dad’s sunglasses when wearing regular sized frames, consider the Cockpit style, which keeps the classic aviator silhouette yet updates it to feature smaller, more universally flattering lenses. The black frames contrasted against the gold metal accents help to further emphasize an already bold silhouette for a look that’s part pilot, part rockstar. For those unfamiliar with the Blaze Collection, what sets them apart from the rest of the brand’s sunglasses is the over-frame lenses, which essentially means that instead of being embedded in the frame, the lenses lay on top.This pair might not look much different from the standard aviator styles, but it actually references the first pair of aviators designed by the brand in 1937, featuring original design cues and mother-of-pearl accents. A limited-edition pair that you can only shop online, it’s as close to the real thing as you’ll get. If the traditional aviator silhouette feels a bit overdone for your taste, opt for a contemporary take on the style via the brand’s Round Double Bridge sunglasses.Throw it back to the ’80s with this bold pair of aviators. The oversized frames will help give you an air of mystery as they obscure a good fraction of your face, simultaneously keeping out the wind.

If you can’t decide between a completely round or square frame, the Hexagonal offers the best of both worlds, mixing a circular top with an angular bottom. It makes for a nice look that’s subtly interesting.Like the previous pair, the Jack style blends two silhouettes, the Round and Hexagonal frame, offering the reverse of the Hexagonal Flat Lenses — strong lines at the top and soft curves at the bottom. Another pair from the Blaze Collection, the Blaze Hexagonal takes one of the brand’s most recognizable shapes and updates them with mirrored, Onesie shield lenses while the metal profile lends them a sleek look. We've put in the work researching, reviewing and rounding up all the shirts, jackets, shoes and accessories you'll need this season, whether it's for yourself or for gifting purposes. Sign up here for weekly style inspo direct to your inbox.