At one point or another, every great man has paused and ruminated on the following questions:
“What are the best kind of sunglasses for my face?”
“Wayfarers or Clubmasters?”
“Can I pull off round frames??”
These are important questions, indeed, and I'll attempt to answer them in this post.
There's a lot of conflicting advice out there about sunglasses and face shapes. I actually created an in depth guide about choosing the right shades:
How to Choose the Best Sunglasses for Your Face 
But it doesn't have to be complicated. There are a few timeless sunglasses styles, and I guarantee one or two of them will look great on you.
Note: Huge thank you to Sunglass Warehouse for making this article possible. Sunglass Warehouse has hundreds of styles of sunglasses for $20 or less (including the ones I'm wearing in the photo above), all with UV400 protection.Just like clothing, sunglasses are subject to trends. You don't want to buy shades that will look ridiculous next year, but there are literally thousands of styles to choose from.
The key is to stick with the classics that have withstood the test of time – and that will never go out of style.
#1: Wayfarers
If there's one frame to rule them all, this is it. Manufactured by Ray-Ban in the mid 1950s, Wayfarers might just be the most popular sunglasses of all time.
In fact, Wayfarers have been so popular for so long that their name has become synonymous with their shape.
These days, many retro-looking, square shaped plastic sunglasses are just called Wayfarers.
So, while the name Wayfarer technically describes Ray-Ban sunglasses, we'll just use it to describe the style (thick plastic frame and square lenses with rounded corners).
Side note: Back in the 90s, Ray-Ban was bought by Luxottica, an Italian company that has a virtual monopoly on the eyewear international eyewear market.
When I'm buying sunglasses, I try to buy from companies that aren't owned by Luxottica, especially since you can find similar styles elsewhere.
Moving on…
What They look Like
Wayfarers have thick plastic frames and tall, rectangle lenses with rounded corners. These glasses are often described as “retro” or square shaped, although the lenses aren't exactly square.
Although the most popular color is black, Wayfarer style sunglasses come in almost any color you can imagine.
Wayfarers definitely have an old school, almost nostalgic look. When you see these glasses, you think of John Belushi cracking a joke Blues Brothers or Tom Cruise sliding across the floor in Risky Business.
In a word, these sunglasses are classic.
Who Should Wear Them
Pretty much everyone looks great in Wayfarers, as long as they're the right width.
Avoid wearing any square frames that are way too big for your face. Try them on first, or make sure you can find the dimensions online.
Most shops, like Sunglass Warehouse, provide detailed measurements of their frames, including overall frame width.
When NOT to Wear Them
You can wear these frames anytime. They even look great with a suit (at an outdoor wedding, for example).
The only time you wouldn't want to wear them is when you're doing something active, like hiking or playing a sport. They'll probably fall off your face!
Buy 'em: affordable / mid-range / pricey
#2: Aviators
If these aren't even more popular than Wayfarers, they're a very close second. They were created in the 1930s by Bausch & Lomb for, you guessed it, pilots who needed to protect their eyes while flying.
The popularity of aviator style sunglasses ebbed and flowed throughout the second half of the 20th century.
People couldn't get enough of the tear drop lenses and metal frames throughout the 60s and 70s.
Aviators went out of vogue in the early 80s, but then Tom Cruise wore them in Top Gun, and they came back with a vengeance – this time to stay.
What They Look Like
There are different types of aviators, but in general, they have a metal frames and oversized “tear drop” shaped lenses (often with a reflective or gradient coating).
You can find aviators with more rectangular lenses, but for the most part, aviators are rounder than Wayfarers.
Who Should Wear Them
Aviator sunglasses aren't quite as forgiving as Wayfarers, but most people can pull them off just fine. Just pay attention to two things:
First, make sure your aviators aren't too wide for your face. Aviators are often oversized, and shades that are too big will produce an unflattering “bug eye” effect.
Second, consider your facial features. Do you have soft, round, curvy lines? Or hard, straight, angular lines?
If you have soft features, choose aviators that have squared off lenses. If you have hard features, you'll look great in classic tear drop aviators.
When NOT to Wear Them
Like retro square frames, aviators are pretty versatile. Whether you're wearing swim trunks at the beach or a three piece suit at an outdoor wedding, aviator sunglasses will look great.
Buy 'em: affordable / mid-range / pricey
#3: Browline
These iconic frames feature a thick upper portion that looks like an extra set of eyebrows, hence the name.
Unlike aviators or Wayfarers, brownline shades are unique because they're constructed from plastic and metal.
This style was first manufactured in the late 1940s and was extremely common throughout the 50s and 60s. Like all things retro and mid-century, browline sunglasses made a strong comeback in the 2010s.
Much like square-ish sunglasses are often called Wayfarers, browline shades are often called Clubmasters – which is Ray-Ban's version of the brownline style.
The browline style made its first comeback in the 1980s, and the Ray-Ban Clubmasters became the most popular brownline sunglasses available.
These days, the terms brownline and Clubmasters are used interchangeably.
What They Look Like
The defining feature is, well, the browline – a thick upper portion of the frame that accents your eye brows.
Monolines, which are less popular, feature an unbroken line across the top of the sunglasses.
Clubmasters are decidedly retro. For most people, brownline shades conjure up images of Mad Men or mid-century icons like Malcolm X and Vince Lombardi
They look and feel heavy (not light or minimal), and they make more of a statement than the lower key Wayfarers and aviators.
Who Should Wear Them
Browline sunglasses aren't quite as easy-to-wear as Wayfarers or aviators, but that doesn't mean you can't pull them off.
In fact, if you feel like Wayfarers are too thick and chunky for your face, or that aviators are always too big and wide, you might love the lighter, thinner brownline shape.
Clubmasters are definitely more sophisticated than other sunglasses styles, which makes them perfect for dressier outfits.
So if you dress up a lot (like if you wear a suit to work everyday), then Clubmasters are a great choice for you.
When NOT to Wear Them
Just keep in mind that most browline shades have round features, so they're not the best choice for guys with very round faces (think Cee Lo Green or Danny Devito).
They're also not as casual as other sunglasses (like Wayfarers), so if browline shades are your go-to frames for daily wear, it might be good to have a more casual option as a backup (for beach days and pool parties).
Buy 'em: affordable / mid-range / pricey
#4: Round
Round or circular sunglasses (often called “teashades”) were a popular choice for pop icons in the 1960s and 70s.
John Lennon, Elton John, Jerry Garcia, Ozzy Osbourne and many other musicians rocked circular frames as part of their signature look.
Available in different sizes, modern teashades are usually small and narrow. They can be made from metal or plastic, and most sunglasses brands have at least a few round styles in their catelogue.
What They Look Like
Unlike squared off Wayfarers, tear drop aviators and hybrid browlines, teashades are decidedly round.
This circular shape produces a very distinct look that can be very cool if used appropriately.
Who Should Wear Them
Wearing this style will call attention to your face, so you have to be comfortable with that. If you don't want the extra attention, stick with something more mainstream like Wayfarers.
If you like being in the spotlight, round frames might be for you, especially if you have angular features like a square jawline (think Harry Potter).
When NOT to Wear Them
If you have overtly round features, you should avoid round sunglasses. Instead, choose sunglasses that have sharp angles to balance out your soft features.
Buy 'em: affordable / mid-range / pricey
I hope this post helps you figure out which classic sunglasses style is the best choice for you. If you can't decide, it's always a safe bet to buy 2-3 different pairs.
Which is your favorite style? Leave a comment below!
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Rocking that facial hair, Brock!
Trying it out for a little while!
Thanks for the article! My only pair of glasses is a cheap pair of aviators I bought for $10 at a gas station 10 years ago.
I think it’s time to upgrade!
Question – why won’t you buy from companies that are owned by Luxxotica?
I’ve worn aviators since my days in the USAF. They have been my choice for 50 years. BTW, true aviator sunglasses have straight temples, to allow them to be put on and taken off when wearing a flight helmet.
It might not be that important if style is your concern, but you might want to mention lens tint as well. I am giving up on Warby for sunglasses because they won’t customize the lens tint. I would rather die than look at life through green-grey lenses. Brown or bronze makes everything so much happier. Plus I am color blind and it adds to contrast, which I have trouble seeing well.
I suppose different colors work best for different activities.