Sunglasses are kind of like the Kardashians of the menswear world:
It sometimes feels like there are millions of them out there, but at bottom they’re all kind of the same.
Likewise, when it comes to men’s sunglasses there are thousands of different frames on the market from a wide-range of sunglass brands.
[image: Creative Lab / Shutterstock]
But when you look closely, you’ll start to notice that the vast majority of designs are variations of just a few basic archetypes.
And there’s a (rather obvious) reason why designers rarely stray far from these classic shapes.
Because they make men look cool.
Sure, they also happen to block harmful UV rays and make it easier to see on bright days, but let’s be honest:
Lens quality and UV protection aren’t the real reasons why we like to wear shades.
The Most Classic Sunglass Styles of All Time…
The best sunglasses can instantly elevate your look by adding a stylish touch of mystery to the equation, especially when you opt for the sort of classic design that makes any man look cool and confident.
To that end, below you’ll find seven of the most classic sunglass styles ever designed.
Of course, even the most classic sunglasses style can sometimes use a little refreshing, which explains the huge growth of direct-to-consumer eyewear retailers.
Brands like Warby Parker, LookOptic and Diff Eyewear have made a huge impact on the sunglass world by offering unique styles at a fair price point.
But here’s the secret that they don’t often advertise:
For the most part, their “modern” styles are really just updated versions of the classic styles listed below.
…and a Few Modern Updates
So, to give you multiple ways to find a good pair of sunglasses, below I’ve linked to both the original, classic style and a couple updated takes from some more modern brands.
Whether you’re the kind of person who wants the vintage OGs or their more modern updates, the cool sunglasses listed below will let you shield your eyes in classic style.
(And by “classic” I mean “handsome as hell.”)
The 7 Most Stylish and Classic Sunglasses for Men
Breaking Down the Most Timeless, Unimpeachable and All-Around Best Men’s Sunglasses Styles ↓
Wayfarers
Why They’re Classic:
First designed in 1952 by American optical designer Raymond Stegeman, the original Ray-Ban Wayfarers are damn near the perfect pair of shades.
These vintage sunglasses are also one of the most versatile sunglass styles of the past century, and have helped make Ray-Ban a truly iconic eyewear brand.
Wayfarers were designed in the same mid-century modern era that gave birth to classic furniture trends like the Eames Chair and the Womb Chair, and presented the eyewear world with equally timeless options.
As the design critic Stephen Bayley has noted, the key to their success lies in the iconic design of the acetate frame shape:
“[The] distinctive trapezoidal frame spoke a non-verbal language that hinted at unstable dangerousness, but one nicely tempered by the sturdy arms which, according to the advertising, gave the frames a ‘masculine look.”
The result is arguably the most versatile, classic and handsome style of sunglasses ever designed, and one that looks good on any face shape.
They’ve been sported by everyone from Muhammad Ali, John F. Kennedy and the Resevoir Dogs to Justin Timberlake and Matthew McConaughey.
So you could say they’re Alright, alright, alright…
Of course, that’s a terrible joke, so you probably shouldn’t.
The Classic Option:
The Modern Update:
Ray Ban New Wayfarers
Why They’re Classic:
It’s hard to improve upon a legend, but Ray-Ban somehow managed to pull it off.
Fifty years after Stegeman designed the original Wayfarers, Ray-Ban created a new pair that slightly tweaked the timeless style of the original.
These more modern Wayfarer styles featured slightly smaller lenses that maintain much of the original’s shape, but are a bit more rounded at the temples.
In addition, the new Wayfarer features less lens tilt, meaning that the lenses hue more closely to your face while wearing them.
The result is quite possibly the 21st century’s most stylish pair of shades, and (not surprisingly) one of the popular men’s styles on the market today.
The Classic Option:
The Modern Update:
Aviators
Why They’re Classic:
When it comes to wire frames (as opposed to the Wayfarer’s plastic), it simply doesn’t get more classic than a pair of aviators.
Made famous by – you guessed it – pilots, aviator sunglasses have a badass backstory that dates back to before WWII and continues to add attitude to any look.
Today they’re worn by some of the most stylish men in Hollywood, including Leonardo DiCaprio, Daniel Craig (both in real lief and as James Bond), and a certain ahem Maverick traveler on the highway to the Danger Zone.
The Classic Option:
The Modern Update:
Square Aviators
Why They’re Classic:
When our brave and handsome-ass grandfathers came back from WWII, they brought their aviators with them, sparking a menswear trend that designers quickly jumped on.
Variations of the aviator emerged, including a version with a more squared off lens.
Sported by fictional icons like Don Draper and Hollywood’s many spies, the square aviator also has the distinct advantage of helping real-world men elevate their personal style.
The Classic Option:
The Modern Update:
The Clubmaster
Why They’re Classic:
With its timeless silhouette and undeniable cool factor, Clubmaster style sunglasses have secured their place in the pantheon of iconic accessories.
The distinctive browline and round lenses offer a vintage vibe that exudes sophistication and confidence, making them a perfect choice for any discerning gentleman.
In addition to sophistication, Clubmasters also offer versatility.
They work just as well on rounder faces as they do on square face shapes, and can be paired with everything from a sharp suit to a casual pair of shorts and t-shirt.
The Classic Option:
The Modern Update:
The Steve McQueen Persol 714
Why They’re Classic:
Made famous by one of the most prominent style icons and Hollywood bad boys of the past century, the foldable Persol 714 was an absolute favorite of McQueen.
He famosly wore these classic Persol sunglasses both offscreen and on, most notably in The Thomas Crown Affair.
Today the model is available in a variety of lens colors, but McQueen’s choice of tortoiseshell frame with blue lenses remains one of my all-time-favorite pairs of shades.
It’s the perfect way to add a pop of color to your wardrobe, and an excellent contrast to the (classic, but staid) black frames sported by most guys.
The Classic Option:
The Modern Update:
Carrera Champions
(aka The Paul Newman Sunglasses)
Why They’re Classic:
Kind of a cross between a Wayfarer and an Aviator, Carrera’s Champion model was made famous by yet another style icon – Cool Hand Luke himself, Mr. Paul Newman.
Singlehandedly demonstrating their versatility, Newman wore Champions everywhere from the racetrack to the beach to the red carpet.
The larger size of the lenses make a serious style statement, especially when you opt for a brown tint on the lenses, which again helps you stand out from the standard black, gray and green tints found on most frames.
The Classic Option:
The Modern Update:
FAQ
More Optical Advice from Irreverent Gent:
- The 6 Best Sunglass Brands for Men
- The Best Warby Parker Sunglasses for Men
- The 29 Best Warby Parker Alternatives
- How to Dress Better for Guys
- The Best Affordable Sunglasses Brands
- The 19 Best Pairs of Men’s Wood Sunglasses
- The (Absolute) Best Leather Bags for Men
- The Best Ridge Wallet Alternatives
- The Most Stylish Types of Glasses Frames for Every Face Shape
I’m looking for a new pair of stylish glasses. Real glasses, not sun. any suggestions?
I’m a big fan of Warby Parker’s frames. They’ve got plenty to choose from (and obviously it depends on your personal tastes), but personally I love the Burke frames. They look like something James Dean would wear if he were alive today, which for my money is always a good metric for choosing a piece of menswear!
Clubmasters! I’ve been looking for a pair like them but I never knew what they were called. Was searching for “glasses with plastic on top but not bottom” lol. This was what I needed. Thanks!!
Glad I could be of service, Jonny! And good choice in going for the “glasses with plastic on top but not bottom.” A rose (or pair of shades) by any other name…
Not really loving any of the options here. Any picks (maybe from Warby Parker) that feel a little more modern?
Hey Evan,
Have you seen Warby’s “Downing” model? I wrote about it in my round up of the 11 top Warby Parker styles. I like them because they’re sleek and modern, but they have a timeless feel that will keep them from feeling dated.