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Home»Life & Style»Life Questions: What’s The Coolest Style Of Sunglasses?
Life & Style

Life Questions: What’s The Coolest Style Of Sunglasses?

Oli LynchBy Oli Lynch7th July 2017Updated:23rd March 2023No Comments5 Mins Read
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Looking good no matter what the weather - pic: Pexels

Table of Contents

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    • Sun’s out, shades out… But whats the coolest style of sunglasses for the discerning playboy?
  • Match Your Style
  • Sunglasses Styles
  • Face Shape Sunglasses Choices
  • Get Your Perfect Cool Sunglasses

Sun’s out, shades out… But whats the coolest style of sunglasses for the discerning playboy?

It’s a summer dilemma for many of us, choosing the coolest style of sunglasses. Of course, we’re all different and there are loads of factors that influence which shades you rock.

No matter if you’re on your international travels or you’re hanging out in the sun down your local, make sure you look your best. Read on for the global playboy style guide to the coolest sunglasses.

Match Your Style

First up, how you look is gonna affect your sunglasses choice. Based on your general style these are usually the best combos for sunglasses.

  • Smart Casual: If you’re normally wearing a shirt (polo or buttoned) then clubmasters or wayfarers are always a safe bet. Aviators too will usually go well with a shirt and a pair of stylish rimless glasses always look dapper.
  • Sporty: Normally running, cycling, climbing or skiing? Wrap around shades will offer the best protection and stay in place amongst all the action.
  • Rock n Roll Star: Usually wearing ripped jeans and a leather jacket? Aviators are the obvious choice but wayfarers will work equally well. Clubmaster will give you that edgier stylish look.
  • Hipster: Rockin’ the tache? Got a straw hat? Wearing your dad’s shirt? Round frames are an obvious choice but in fact the joy of hipsterdom is that you can throw on any pair of shades and look the bomb. Wear some girls ones and see how that pans out (probably look awesome right?).
  • Out There: Set your own trends? Well, you probably don’t need us to tell you what sunglasses to wear… However, wayfarers are always good fun and match pretty much any style.

Sunglasses Styles

Sunglasses for men tend to come under the following categories (with some variations).

  • Wayfarers: The simple and classic square framed glasses. Quintessentially cool and normally referred to as ‘Ray Bans’ (who make the definitive wayfarer style sunglasses); these go with everything, suit men and women and are pretty much indestructible.
Wayfarers, always cool… pic: MassimoDotti
  • ClubMasters: With a kind of retro feel, ClubMasters are the gentleman’s choice. Half framed and horn rimmed, they are the sunglasses of choice for Jazz musicians and globe trotting playboys.
ClubMasters for the sophisticated look – pic: Free-Photos
  • Aviators: Think Top Gun, think airline pilot – you’ll be thinking of aviators. Normally oversized, metal rimmed and mirrored (although tinted looks cool too). The downside for aviators is normally the nose pieces get bent out of shape, or if you sit on them it’s game over.
Aviators look cool even if you’re not flying – pic: Annel69
  • Wrap Around: These sporty shades tend to hug the head a bit tighter and offer more protection from light leakage. Brands such as Oakley are the definitive brand for the wraparound style sunglasses. These are best mirrored and usually polarized to avoid glare from the sun or water reflections.
On the move? Keep your shades on – pic: R17Frances
  • Rimless: Like you grandad’s reading glasses, rimless have very little frame to speak of. However, the modern rimless sunglasses glasses can look pretty cool.  They look a bit more refined so would be ideal for the more smarter dresser.
Rock your grandad’s style with the rimless shades – pic: Andreas160578
  • Round: Normally conjuring up images of long haired hippys or rockers, round frame sunglasses can look pretty dope on the right face. It helps to have a distinctive style, so if you’re kinda out there, try a pair of round sunglasses on for size.
Rockin’ the round sunglasses – pic: AaAndrea
  • Bug Eye: As the name suggests, these tend to be bigger frame glasses which have that ‘bug eye’ look. Not everyone will look good in bug eye sunglasses. But if you follow your own fashion and you’re more on the hipster side with the style, why not?
If you’re rocking bug eye shades you’re probably super cool anyway – pic: Free-Photos
  • Rectangular: Longer and thinner in the frame, rectangular frames don’t suit everyone. You’ll need a relatively thin face (oval faces in particular suit rectangular frames) to pull these off. On the right person they look refined and stylish. On the wrong person they’ll look like they don’t fit properly.
Rectangular shades for the oval heads – pic: 5191107

Face Shape Sunglasses Choices

The shape of your face does make a big difference to how you look in a given pair of sunglasses.

Generally, if you have a round or oval head shape you would suit the thinner wider frames. Rectangular, wrap arounds and rimless would all suit great.

For longer/thinner or squared head shape, you would be better with the bigger rounder style of frames such as aviators, wayfarers and clubman.

Get Your Perfect Cool Sunglasses

No matter if you’re being the international jet set or hanging at your local park, you’ve always gotta look your best.

Check out our guides to dressing cool nerd style, or the traits that define coolness.


If you have any comments of suggestions about finding the perfect sunglasses for the global playboy, feel free to leave a comment below. 

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Oli Lynch
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Freelance content manager and CEO of Sentient Creative. Oli is a keen blogger, regular traveller and sports fanatic.

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