Arguably the most masculine of sunglasses styles, the “aviator” is synonymous with the birth of the modern air force. Developed in the 1930s, aviator sunglasses or “pilot’s glasses” have become a trend-proof addition to men’s accessories thanks to their association with military greats and fly leading men.

“Like so much in menswear, the origin of the aviator derives, unsurprisingly, from the air force,” says Simon Spiteri, a buyer at Mr Porter. “In 1929, a US Army General challenged optical firm Bausch & Lomb (then owners of Ray-Ban) to create a pair of sunglasses that would protect test pilots from the headache-inducing glare found at altitude; thus the signature teardrop-shaped lenses were born.”

The first pair of aviators arrived in 1937 with green lenses and were marketed as “Ray Ban” and promised “real scientific glare protection”. The name “aviator” wasn’t coined until the Second World War and became a well-known style of sunglasses when General Douglas MacArthur landed on a beach in the Philippines and newspaper pictures of him wearing them became a lasting image of the war.

The aviator was soon worn by sportsmen and fisherman, and quickly became a fashion accessory thanks to the likes of Elvis Presley. Since then, they have never gone out of style. Michael Jackson turned up at the 1984 Grammys in a pair of Ray-Ban aviators. Johnny Depp’s coloured lenses in 1998’s Fear and Loathing in Las Vegas gave them more of a counter-culture vibe. And in between, they were confirmed as a man’s ultimate wingman accessory.

“Their mainstream popularity came as a result of Top Gun,” says Spiteri. “Tom Cruise and Val Kilmer cemented their popularity, and have since been an accessory that every man should have in his possession.”

How To Wear Aviators

If you’re wondering whether aviators suit you, let us paraphrase that very movie: don’t let your sunglasses write cheques that the rest of your look can’t cash. In other words, if you’re going to wear aviators, they have to fit your style and personality.

“Ultimately the challenge is that one has to be effortlessly cool in order to pull off aviators, as opposed to wearing aviators to try to look effortlessly cool,” says David M Watts, editor-in-chief of Wattswhat magazine.

If you look like an extra from Dunkirk then you’ll be fine. Other than that, the teardrop shape works on diamond, heart, oval and square face shapes. If you have a strong jaw, wide cheek bones or generally angular features, you’re cleared to fly. If your face is narrow or your features rounder, sorry – you’re grounded.

Aviators vary in size so it’s important to get the right proportion of frames for your face and also the correct fit.

The bridge should sit comfortably. If it is too short, the bridge will be too high on the face; if it is too wide, it will droop low down your nose. Your eyelashes should not be able to touch the lenses and they should not be too snug on your nose or you’ll have those annoying indents.

Aviators typically cover the eyebrows as they were designed to cover the entire eye socket. If yours don’t at least partially cover your eyebrows they are probably too small.

How To Style Aviators

The current fashion for larger sunglasses suits the aviator style while still staying masculine. The good thing about aviators is that you can choose the right style for you: there are many finishes and materials, from metal to plastic frames and reflective to coloured lenses.

Aviators can be quite a strong look, so you can either keep everything else simple or have fun with it. Minimise any military references, especially if opting for reflective lenses, as it can look a little try-hard. Don’t team them with a flight bomber, but take one thing from Top Gun: the white T-shirt. Add jeans or chinos and you have a timeless 1950s style look.

Dark lenses and/or frames are more subtle and look good with almost anything casual. The large frames add an air of anonymity, especially with black lenses, and ooze a masculine confidence.

Coloured lenses have become popular lately and add an eccentric element. They can look good with Hawaiian shirts or football tops, especially on holiday. These are more fashionable styles and can come in blue, yellow, orange and red lenses and show your personality and confidence while adding a retro and vintage touch.

“Their versatility ensures they look great whether worn in the city or by the pool or beach. You can’t beat a classic pair of Ray-Ban aviators, but my particular favourites this season are from either Gucci, Prada or Tom Ford,” says Spiteri.

The Best Brands For Aviator Sunglasses

Ray-Ban

The original flyboy choice, Ray-Ban, has become an optical mega brand with sales in the billions. While arguably better known for their Wayfarer style, the aviator is where it all began. They offer a customising service where you can choose multiple options including the colour of the frames, details and lenses, even prescription, and add engraving to personalise.

Ray-Ban Gold Tone Aviators, available at Mr Porter, priced £120.

RAY-BAN Aviator Gold-Tone Sunglasses

Gucci

Not for wallflowers, though they do have some more conservative styles, Gucci’s renaissance is a maximalist take on fashion. More is more on the details with the new direction at Gucci while still conforming to the timeless look of the aviator.

Gucci Acetate Mirrored Aviators, available at Mr Porter, priced £275.

GUCCI Aviator-Style Acetate Mirrored Sunglasses

Cazal

Go bold or go home in anything from Cazal. This 80s German eyewear brand, created by Austrian designer Cari Zalloni, is big, brash and in demand. Thick frames in large, over sized geometric shapes make a memorable style statement. Think Robert De Niro in Casino.

Cazal Vintage 163, available at Cazal, priced 345 Euros.

Cazal Vintage 163

Tom Ford

The king of refined cool, this is a man who loves sunglasses. Tom Ford knows exactly how to update something classic to make it relevant and contemporary. Look for his water buffalo horn frames with rose gold hardware if your pockets are deep enough.

Tom Ford Terry Sunglasses, available at Mr Porter, priced £175.

TOM FORD Terry Aviator-Style Acetate Sunglasses

Ted Baker

Ted Baker offers two contrasting options with their aviator styles. You can find fully metallic versions with tortoiseshell arms, but we’re drawn to the more contemporary Nover style, which comes in a choice of navy or steely black with the signature horizontal bar and matching coloured tips.

Ted Baker Nover Sunglasses, available at Ted Baker, priced £75.

NOVER Metallic pilot sunglasses

ASOS

Affordable sunglasses allow you to play around with styles that you wouldn’t necessarily invest in. ASOS sunglasses are ideal for festivals or parties or for when you don’t want to be too precious about your eyewear. Go for gold frames and faded lenses and all for under £15.

ASOS Aviator Sunglasses In Matte Gold, available at Asos, priced £14.

ASOS Aviator Sunglasses In Matte Gold And Side Cap Detail

Persol

Derived from the Italian phrase “per il sole”, translated as “for the sun”, Persol was founded in 1917 in Turin. Producing eyewear for military pilots and racing drivers, they are known for their keyhole bridge, tortoiseshell finishes and signature fittings. This is La Dolce Vita, Italian Riviera eyewear.

Persol PO 9649S 9649, available at Amazon, priced £91.10.

Persol Men's PO 9649S 9649 Aviator Sunglasses

Cutler & Gross

For more than 40 years Mr Graham Cutler and Mr Tony Gross have been producing sunglasses with no logos, letting the bold designs and quality speak for themselves. Look for the brand’s “Precious Metals” line. Handcrafted in Italy from palladium-plated metal, their aviator-style is fitted with blue lenses that, despite being light in colour, provide complete protection against harmful UV rays.

Cutler & Gross 1266 Palladium, available at Cutler & Gross, priced £405.

1266 PALLADIUM PLATED WITH PALE BLUE LENS

Selected Homme

The Scandi brand’s growing rep for well-priced essentials extends to its eyewear. Its aviator styles lean toward the 70s with thicker frames and dark tinted lenses. Perfect for anyone who refuses to stop wearing black, even at the height of summer.

Selected Homme Aviator Sunglasses, available at Asos, priced £18.

Selected Homme Aviator Sunglasses

Hook LDN

Inspired by and designed in London, Hook LDN is a new British eyewear brand that specialises in creating high quality, style led designs that are influenced by music and fashion. Hook LDN showcases “intelligent” construction and refined aesthetics all for around the £100 mark.

Hook LDN Juke Sunglasses, available at Hook LDN, priced £95.

JUKE SUNGLASSES

Police

Inspired by America, in particular New York, this Italian brand brings to mind the reflective lenses of the motorcycle cop. Hence the name, Police. Established in 1983, their current styles follow the fashion for flat lenses: updating the aviator to look fresh and futuristic.

Police Rival 2, available at Police.

RIVAL 2

Topman

Topman’s low prices and trend-led approach make them a fine choice for a seasonal back-up pair sunglasses that you won’t necessarily keep forever. That gives you room to experiment, so try the Cali-inspired pinkish hue on these mirrored shades.

Topman Silver Mirrored Aviators, available at Topman, priced £12.

Silver Mirrored Aviator Sunglasses