For as long as there has been a sun in the sky, there has been a need for sunglasses. However, like most other menswear staples born out of necessity, there is much more to these frames than meets the eye. Pun intended.

Legend has it that the OG specs were invented by Roman emperor Nero who, aside from an unsightly neckbeard, was known for fending off the midday glare with polished emeralds held in front of his eyes. Later, during the 12th century, judges in China would wear pieces of smoky quartz to conceal their faces while questioning witnesses. Talk about shady.

With precious gems in short supply (and no plans to join the Bar anytime soon), here are six classic sunglasses styles, each with their own equally impressive backstory, to consider instead.


It wasn’t until the 1930s that sunglasses started filtering into the mass market, but their use today isn’t worlds away from that of Nero or the Chinese judges; with just as many men using tinted lenses to avoid forcibly squinting at the sun as to disguise the tell-tale signs of a hangover.

Despite being a product of science rather than fashion – designed to protect WWII pilots’ eyes while flying at high altitude – it didn’t take long for the achingly stylish aviator to cross over from cockpit to catwalk.

(Related: Menswear Pieces That Started In The Military)

Tom Cruise in Top Gun (1986) is often the go-to reference for this style. But plenty of shady people wore the classic tear drop shape before Maverick, including Robert De Niro in Taxi Driver (1976) and Michael Jackson at the 1984 Grammys.

This frame suits those with square faces best, but because of its pop culture associations,’s senior menswear editor Rob Nowil advises against wearing them with anything that could appear “costumey” – that’s boiler suits out the window, then.

“The trick is to swerve anything that screams 1970s, instead save them for smarter occasions. A minimal navy suit worn with a white T-shirt and tinted aviators is a solid uniform for smart-casual summer weddings,” says Nowil.

JEEPERS PEEPERS Black Aviator Sunglasses - Click to buy Reclaimed Vintage Aviator Sunglasses - Click to buy RAY BAN AVIATOR FOLDING SUNGLASSES - Click to buy garrett leight INNES SUN sunglasses - Click to buy TOM FORD Cliff Aviator-Style Metal Polarised Sunglasses - Click to buy Linda Farrow Linda Farrow 398 C6 - Click to buy

Round Frames

For every stylish co-sign that round glasses have received over the years (Samuel L Jackson, Steve Jobs, Stanley Tucci), there are also less desirable ones (Ozzy Osborne, Harry Potter, Where’s Wally). Yet none wore the statement specs in a more iconic way than the legendary John Lennon.

Despite being initially dismissive of donning frames (he thought they weren’t ‘cool enough’ for a rock star), the Beatle propelled the vintage look first worn by monks while reading manuscripts onto the main stage during the 1970s after years of them being in the shade of new designs such as the wayfarer.

Louise Lasson, creative director of H&M’s new Scandinavian-inspired fascia Weekday, which recently launched its first eyewear range, says the shape is making another comeback. “Round glasses are great because they are so flexible in regard to style,” she says. “They are classic yet always modern, and they are playful yet can also look serious.”

As well as ensuring they’re worn by the right face shape (square or oval, with angular features), David Lochhead, co-founder of British eyewear brand Finlay & Co, believes they should also match an individual’s style.

(Related: How To Determine Your Face Shape In 5 Easy Steps)

“If your wardrobe is made up of neutral tones and your look is pared back and minimalist, consider going for clear or black frames with dark lenses,” he says. “To make more of a statement, try a light tortoiseshell frame or gradient coloured lens.”

weekday Explore Rounded Sunglasses - Click to buy JEEPERS PEEPERS Black Metal Brow Bar Sunglasses - Click to buy finlay & co ONSLOW EBONY sunglasses - Click to buy RAY BAN CLASSIC ROUND FOLDING SUNGLASSES - Click to buy PERSOL Round-Frame Tortoiseshell Acetate Mirrored Sunglasses - Click to buy OUR LEGACY Bold Round-Frame Acetate Sunglasses - Click to buy

Square Frames

One man who knows all too well what sunglasses can do for a face (or indeed, a career) is Elton John. The British singer is thought to have the largest personal collection in the world, with around 20,000 whacky pairs.

(Related: 22 Interesting Facts About Menswear You Probably Didn’t Know)

While we could never endorse owning that many – or novelty styles at all – on dress-down days, the Rocket Man does well to use square-shaped frames to balance out his round features. A similar trick used by Michael Caine and Jack Nicholson in the 1950s and 1960s.

Because of this heritage appeal, luxury brands like Saint Laurent and Tom Ford have produced more square styles in recent years, but there are plenty of affordable options on the high street, too.

To keep the old-school appeal alive, Tom Courcey, deputy editor at online menswear retailer The Idle Man, advises opting for a look that channels the French Riviera. “A pair in tortoiseshell teamed with a crisp white polo shirt and beige chinos, topped off with a pair of summer loafers, is the perfect smart summer look.”

THE IDLE MAN Square Frame Sunglasses Black - Click to buy MONOKEL ROBOTNIK SUNGLASSES - Click to buy OLIVER SPENCER Spencer Square-Frame Tortoiseshell Acetate Sunglasses - Click to buy SAINT LAURENT Square-Frame Tortoiseshell Acetate Sunglasses - Click to buy cubitts judd sunglasses - Click to buy Ralph Lauren RL8155 Square Sunglasses - Click to buy


Malcolm X, Lyndon Johnson and Colonel Sanders. All changed the world (OK, maybe not that last one) and all favoured the thick upper frame and curved metal-rim of the now iconic clubmaster sunglasses.

Ray-Ban already dominated the eyewear market with the wayfarer and aviator by the time the iconic ‘Browline’ shape was invented by South Carolina firm Shuron in the 1940s. This may explain why the brand with which it’s most commonly associated today took several decades to put its name on the style with the clubmaster.

(Related: The Best Sunglasses Brands For Your Money)

The design became the most common of all throughout the 1950s and early 1960s, likely owing to the fact they suit a range of men – including those with oval, heart, round and square face shapes – and are still one of the most popular.

“The clubmaster has been a key part of our eyewear buy for years,” says Selfridges buying manager Richard Jones. “[It’s] a sophisticated twist on the more casual wayfarer. Pair with a great suit, or a shirt and short combo and you’re guaranteed to look sharp.”

For a next-level styling move, Jones also suggests matching the metals on pieces like a watch or tie bar with the colour of the metal accents on the glasses.

JEEPERS PEEPERS Clear Grey Half Frame Sunglasses - Click to buy SUPER BY RETROSUPERFUTURE TERRAZZO SUNGLASSES - Click to buy RAY-BAN RB2176 folding Clubmaster sunglasses - Click to buy oliver peoples Masek sunglasses - Click to buy GUCCI D-Frame Acetate And Gold-Tone Sunglasses - Click to buy MOSCOT Yukel Square-Frame Acetate And Silver-Tone Sunglasses - Click to buy


The wayfarer is considered to be to sunglasses what the 501 is to denim, the ultimate badge of cool and a modern icon that transcends trends and eras. However, the popular frames – recognisable by their clean lines and subtle curves – have spent more than their fair share in fashion no man’s land.

In the 1970s, just 20 years after first being introduced, wayfarers had all but disappeared, and the style verged on discontinuation. Luckily, a decade later Ray-Ban signed a deal to have them show up in numerous films such as The Breakfast Club (1985), re-establishing their popularity and making them a regular fixture on noses (particularly those with oval, long or round faces) ever since.

“You only have to look at the diversity of people the wayfarer has appeared on, from Bob Dylan to Jude Law via Andy Warhol and Robert Pattinson, to understand their versatility,” says MatchesFashion men’s style director Simon Chilvers.

(Related: The Fail-Safe Guide To Finding The Perfect Sunglasses)

“The simplicity but distinctiveness of the frames, coupled with their lack of anything particularly tricky in terms of finish are part of what has given them style longevity.” And the fact they pretty much go with anything is, naturally, a bonus.

THE IDLE MAN Tortoise Shell Wayfarer - Click to buy RAY-BAN Wayfarer Sunglasses Classic RB2140 902 Brown sunglasses - Click to buy cubitts CALTHORPE sunglasses - Click to buy SAINT LAURENT D-frame acetate sunglasses - Click to buy OLIVER SPENCER Spencer D-Frame Acetate Sunglasses - Click to buy RAY-BAN Original Wayfarer Acetate Sunglasses - Click to buy

Keyhole Nose

In 1968, a little-known actor and occasionally referenced style icon called Steve McQueen wore a custom pair of Persol 714s in the film The Thomas Crown Affair. And, just like that, the retro keyhole nose was turned into an overnight superstar.

Sure, it helped that McQueen was really, really good-looking; but to its credit, the unique bridge detail has endured and remained used on some of the most iconic designs ever since.

(Related: 10 Men’s Accessories That Will Never Go Out Of Style)

Because the detail is not strictly a style of sunglasses and can be applied to any shape, the creative team at Marcolin, which turns out specs for the likes of Ermenegildo Zegna, Diesel and Moncler, says it suits a range of faces.

“It’s a detail that most people can carry and the keyhole adds a touch of individuality without being overstated or showy. [It’s] for the man who wants to be noticed while still having a casual and elegant approach.”

Jaeger’s head of menswear, James Jee, suggests choosing frames that nod to the style’s heritage. “Rich tortoiseshell frames with dark green lenses create an original vintage feel. This style is a classic and is easy to dress up with a suit or dress down with a T-shirt and chinos.”

oliver peoples Gregory Peck 47 Sunglasses - Click to buy jaeger Jimi Sunglasses - Click to buy PERSOL 649 AVIATOR SUNGLASSES - Click to buy GARRETT LEIGHT BROOKS SUNGLASSES - Click to buy ILLESTEVA Capri Round-Frame Acetate Sunglasses - Click to buy TOM FORD Frank D-Frame Acetate Sunglasses - Click to buy