When American conglomerate Bausch & Lomb introduced the Wayfarer in 1952, they had no clue how monumental it would become. Designed by Raymond Stegeman, the glasses were designed as an alternative to the prevailing (and expensive) metal frames that many competitors produced. Made from a highly pliable acetate, the sturdy and affordable material gave the new lenses both utilitarian and mass appeal. As opposed to the modern shape we know today, the original Wayfarer was a squared-off cay-eye lens, rather than the more rounded shape Ray-Ban still produces. The combination of affordable and experimental attracted numerous clients including, most famously, Bob Dylan. For years, Dylan was never spotted without his signature Wayfarers, even while performing or conducting interviews. The massive celebrity cosign elevated the shades to cult status, the de-facto uniform of the counter-culture. Within a decade, the Wayfarer was simply part of pop-culture at large and with fans ranging from The Blues Brothers to President John F. Kennedy, the glasses became an integral part of American fashion history. While production ceased in the early-’70s for a number of years, today the frame is more popular than ever, in large part due to its deep history and universal appeal.

That said, the original Ray-Ban Wayfarer is a far cry from the shades that moves by the tens of thousands today. Originally cat-eye (pointed outward at the top corners of the rim), today’s Ray-Ban Wayfarer lacks the square rims of the original. Instead, the bottoms are rounded, the lenses more circular and the edges softer, a more universal (and palatable) look. Still, if you are looking for something more akin to the original, not only Ray-Ban (see its “original” wayfarer) but countless other brands make sunglasses inspired by the ‘52 originals. As for as the actual lenses themselves, since Ray-Ban was acquired by the behemoth Luxottica Group in 1999, the Italian glass is on par with the industry standard. Note, if you’re searching for a polarized pair, a “P” will proceed the iconic Ray-Ban logo on the right lens.

One of the oldest eyeglass companies in the world, Italian-based Persol—well, nearly every label on this list is technically Italian based due to Luxottica group’s near monopoly on the category, but no matter—has crafted luxury eye and sunglasses for over a century. Founded by Guiseppe Ratti in 1917 in Turin, Italy, the label began when Ratti—who owned his own glasses store—began producing flexible frames for athletes and tram drivers in his native city. The label slowly expanded through Italy, then Europe and, by 1962, landed statestide. While the label has numerous iconic models ranging from the 714SM (as in Steve McQueen, who wore them in Bullitt) to the Calligrapher, they pale in comparison to the 649.

Introduced in 1957 and designed for tram drivers in Turin, the lens originally intended for conductors exploded internationally all thanks to an appearance in one film: Divorce, Italian Style. Released in 1961, the film was a critical darling, winning the award for Best Comedy at Cannes and the Oscar for Best Original Screenplay. Not only one of the most notable films of the ‘60s, the movie gave birth to one of cinema’s most stylish characters, Ferdinandu Cifalú. Played by beloved Italian actor Marcello Mastrianni, the character wore Persol 649s throughout the film and helped put the small Italian company on the map. Granted, that was nearly 60 years ago. Today, the glasses–well, one specific iteration, the P06649S—are more famous for another notable figure: the late Anthony Bourdain. A noted Persol fan, Bourdain rotated through a number of vintage frames including the 714 and the 971 series, however the 649 was by far his favorite. Notable for its “keyhole” shape under the bridge and wide frame with chunky temples, the 964 is the Italian equivalent of an aviator–however infinitely more classy. With so much history behind these frames, they are a guaranteed talking point. Plus, these frames look good on literally everybody. Persol has made them for 60-plus years for a reason.

When Oliver Peoples opened the doors to its West Hollywood boutique in 1987, it never could have expected the barrage of press, celebrities and costume designers that would run through its doors. With near instant international recognition, the brand saw countless styles go viral before quickly fading in popularity, however a notable few have remained since the brand’s inception. The MP-2 is one such style.

The small circular lenses—referred to as “teashades”—feature a combination acetate and metal frame, with filigree eyewire, bridge and temple alongside matching lens tips and rim. While they may not boast the sort of historical significance others on the list command, the style has another quality worth mentioning: it has not gone out of style. In a timeless yet still fashion forward shape, the round lenses are a hard sell for many, however if you already have another staple pair of sunglasses, going round is the next logical conclusion. With contrasting eyewire and acetate, the way light hits the lens is magnificent, appearing entirely different depending on angle and lighting. If you are looking for a new signature or simply want to make a statement, the MP-2 is a wise choice.

Often, sunglasses fashion collaborations miss the mark. Either they are too wildly directional or simply an existing silhouette in a slightly different colorway with an added “exclusivity” tax, considering the cost of forming new molds and creating a truly unique silhouette, most fashion collabs in the glasses world are duds. Maison Margiela x Mykita is the exception. The ongoing collaboration between the French fashion house and the German eyewear maker is consistently one of the most interesting in fashion. While each season introduces new and increasingly inventive designs, the reliable core collection injects just enough Margiela-ness to create shapes that while conceptually intriguing are still grounded in function and wearability.

Of the many great options, our personal favorite is the MMCRAFT006. Mykita is best known for its stainless steel frames and patented hingeless, screwless design, and Maison Margiela builds on this beloved lightweight frame, adding oversize square lenses and a top bar, all in a rose gold as opposed to the classic Mykita silver finish. Unlike its Luxottica group competitors, Mykita—still a private, self-sufficient business—assembles every pair of its sunglasses entirely by hand, meaning that while the cost is high, you are getting what you pay for. If you are one of those who always complains about sunglasses weight or how they feel sitting on your nose, Mykita lenses are literally so light you will forget they are even there. That alone is worth the extra $200.

For those with more experimental taste, Kuboraum is the only name in the game. A favorite of Rick Owens and wife Michèle Lamy, as well as Acronym's Errolson Hugh, the German sunglass label sits at the intersection of goth and tech, beloved by both style tribes for its primarily dark and dystopic aesthetic.

Somewhere between Bauhaus and Berghain, Kuboraum juxtaposes elements of minimalist design with goth, rave and steampunk reference to create frames that are hard to effectively categorize. Sold in the world’s most respected boutiques, the handmade sunglasses vary greatly from model to model, with one boasting Louboutin-esque spikes while another resembles what Helmut Lang would have worn in the early 2000s.

For those already experimenting with avant-garde fashion, we recommend the K2 BM. With an acetate square frame and fairly standard temples the glasses are relatively straightforward. However, a sculptural form reminiscent of a Donald Judd sculpture encapsulates the outside of the frame, adding additional levels of dimension and complexity. Unlike its metal adorned siblings, it's this type of subtle ingenuity that makes the K2 BM—and Kuboraum for that matter—great.

When Virgil Abloh was appointed artistic director of Louis Vuitton Men’s in 2019, he took it upon himself to not only design collections, but offer a fresh take on the entirety of the men’s business. With a specific focus on accessories—fitting, considering it’s by far the fashion house’s most popular (and lucrative) category—the designer presented a new permanent collection of bags, wallets, jewelry and, of course, sunglasses. So far, one frame in particular has stood out.

Debuted during his inaugural Spring/Summer 2019 fashion show, the “1.1 Millionaires” features an oversized square acetate frame with metallic hardware encasing the hinges and upper frame. While technically a new design, the frame is in fact a callback to the original “Millionaires,” a product of the Marc Jacobs era. An attempt to broaden the label's audience, Jacobs tapped NIGO and Pharrell—then still working together on Billionaire Boys Club](https://www.grailed.com/designers/billionaire-boys-club)—in order to design a pair of sunglasses with pop-culture appeal. The originals—available in the same varsity red as Abloh’s runway debut—was an instant hit amongst celebrities, particularly favored by one Kanye West.

Now, more than 15 years later, Abloh has recontextualized the iconic frame for a new generation. Considering he is a direct descendant of that creative lineage, it’s only right that he continues to carry the torch. As for the frames, they are a blockbuster success and most colorways sell out immediately. Thankfully, there’s always a few pairs floating around on Grailed.

Unfortunately, former Celine designer Phoebe Philo did not introduce menswear during her stint at the French fashion house. While women fawned over her cult-favorite bags and lush knits, guys were left out in the cold. Thankfully, a few items—while not designed as such—were very much unisex, including oversized sweaters, sneakers—(Air Force 1 Mid homage, anyone?)—and, our personal favorite, sunglasses. A favorite of leading Instagram fashion bloggers and rappers alike, the Celine square sunglasses quickly grew into a cult classic, unavoidable in major metropolitan areas due to how incredibly well they frame your face.

Made from acetate, the shape is reminiscent of the original cat-eye wayfarer, with a flat top with a slight hitch on either end and squared off bottoms. Apart from the shape, the only other defining characteristic are three small studs where the temple meets the hinge—today not only a Celine signature, but a subtle mark that signifies you’re in the know. Philo may be gone, but even with Slimane restructuring the entire business, LVMH is smart enough not to do away with these classics.

We're torn on the Ray-Ban Aviator—but this list would not be complete without it. It’s not that we dislike the shape. In fact, we adore it. Rather, the frame is so ubiquitous and so specific that in most cases the sunglasses just do not suit the wearer. Originally designed for U.S. aviators in 1937, over the past century the iconic shape has remained relatively untouched. With large oval lenses, a thin wire frame and a small top bar, today the simple silhouette is easily the most famous sunglass design in the world. No self-respecting glasses brand doesn’t attempt to design its own, and the overwhelming popularity leads many to gravitate towards them—even if they don’t do you any favors.

The way we see it, if you have a large head or wide set eyes, aviators will work well. Unfortunately for pretty much everyone else, they are so gargantuan they detract from your facial structure. That said, from Top Gun to Jaws and The Big Lebowski, you simply cannot deny the Ray-Ban Aviator’s cultural standing and, as we mentioned from the outset, when it comes to sunglasses, all that matters is confidence. If you think you will look just like Goose then, by all means, go for it.

Before Acne Studios ever produced the Mustang, the shape was already iconic. If Acne’s now-signature sunglasses look familiar, it’s because you’ve likely seen them in recent years—or you’re familiar with those Kurt Cobain glasses, off which the Mustang are undoubtedly inspired. Clout goggles are forever linked with Cobain and his pair of Christian Roth Archive 1993/Series 6558 glasses. They’ve inspired dozens—if not hundreds—of imitations and replicas, ranging in price from a few dollars to hundreds. But Acne Studios’ Mustangs have enjoyed outsized success in a crowded market.

The Mustang rose to prominence in the late-2010s, thanks to the resurgence of clout goggles, as an extension of normcore. Playboi Carti was among the shades’ biggest endorsers. Also integral to the Mustang’s popularity is Acne’s reputation as one of the foremost quirky, affordable and plugged-in luxury brands. Sure, there are similar sunglasses available on the low, but are they clout goggles if they’re likely to break after one or two wears, or if they’re not name-brand? No. Acne’s Mustang, on the other hand, are handmade from high-quality acetate, with premium lenses, offering the perfect balance between quality and price—which means that second-hand pairs offer great value for what you’re getting. Plus, they’re from a recognizable luxury brand—which is kind of the whole point of clout, right?

With their oval, almost bug-like shape, these might not be your everyday glasses for the next decade, but for a pair of statement glasses, you’d be hard-pressed to do better.

You might not know it, but Jacques Marie Mage is your favorite buyer/editor/writer/influencer/store/sunglasses brand’s favorite sunglasses brand. You’ve probably seen a pair of Jacque Marie Mage glasses in the wild, and thought, “Wow, those are nice,” without realizing what brand they were.

The Los Angeles-based brand has carved out a niche for itself with “micro-produced, artisanal” eyewear. Others describe Jacques Marie Mage’s frames as “rare and collectible,” which is also true. In short, designer Jacques Mage treats eyewear like an art, with hours going into the research, sourcing and production of every single pair of glasses, creating styles that are unique but still recognizable.

The Zephirin perhaps best encapsulates what sets Jacques Marie Mage apart. It’s inspired by pre-WWII frames and is a touch more angular than your typical rectangular frames. They’re handmade using polished acetate, sterling silver and precious metal hardware. The finished product is classic enough to be an everyday pair of glasses, well-made enough to last years, and just different enough to bring a touch of swagger.

The glasses are beautiful, but so, too, is the packaging: handcrafted natural leather cases, pressed certificates of authenticity with serial numbers and signatures, and a cleaning cloth that doubles as a pocket square. These are glasses made to collect—but also to change hands down the line.

Once upon a time, around a decade ago, Retrosuperfuture was the hottest eyewear brand around. Daniel Beckerman’s upstart Italian company was only launched in 2007, but quickly rose to prominence. Part of that owed to high-profile clients like Kanye West and Kid Cudi, who embraced a number of Retrosuperfuture’s early silhouettes, but much owed to the brand’s unique combination of simple, sleek lines, colorful acetates and commitment to quality. Without that, it’s unlikely that Kanye or Kid Cudi would go on to be de facto ambassadors for the brand.
Cudi was particularly fond of the Flat Top, sporting it regularly in the late-2000s and early-2010s, and among Retrosuperfuture’s early shades, the Flat Top is probably one of the most important. It’s gone on to become one of Retrosuperfuture’s evergreen models.

The Flat Top is, as the name implies, defined by its straight line across the brow, rather than a curving silhouette that drops down to the bridge of the nose. It typified Retrosuperfuture’s clean lines and ability to infuse classic styles with a certain chicness. Cut from acetate, the Flat Top uses Zeiss lenses—considered to be among the very best in the world.

The Flat Top is Retrosuperfuture distilled into a single pair: clean lines, celebrity cosign, quality materials and a palatable pricepoint.

Sunglasses are deeply associated with California, whether because of their ties to Hollywood or to sunny beaches. And, overwhelmingly, when we think of sunglasses, we think of classic styles (as seen on this very list) like Aviators or Wayfarers. There’s not much in the way of truly avant-garde eyewear—barring a few pairs. It’s fitting, then, that one of the most recognizable and popular pairs of avant-garde eyewear to emerge in recent years has been from dark fashion’s preeminent Californian: Rick Owens.

The Shield uses a surgical stainless steel frame with curved lenses and hardware that’s as aesthetic in nature as it is utilitarian. The lenses have been available in various colors and smoked hues, but it’s the mirrored versions that have become the most popular since being introduced for Spring/Summer 2019.

While these are definitely statement shades, they do offer protection from UV rays, proving that good fashion—even avant-garde—usually has utilitarianism at its roots. If you’re in the market for your first pair of sunglasses, these might not be the pair for you, but if you’re a diehard Rick fan, or just looking for something a little different, these are sure to do the trick.