A Man's Guide To Pairing Hats With Glasses

Posted on March 10 2021

According to some fashion designers, there is a match made in heaven of which you may not be aware. It is that of hats and glasses. But it can be a look that not everyone knows how to pull off! It could be a bit of overkill, wearing a funky pair of frames with a hat. It can look confused and dizzy. Then again, you can be the coolest looking dude in the room with the right glasses/hat combo.

 A Man's Guide To Pairing Hats With Glasses

Pairing hats with glasses may be somewhat of an art, so we're going to give you as many tips as we can as to how to pull this look off convincingly, like a pro. Remember… it should look effortless.

Hat Styles

Before we look at combining hats and glasses, we have to explore hat styles. Think about your personality. What suits you best? Here are a few choices:

  • Baseball caps
  • Breton hats
  • Small fedoras
  • Berets
  • Boaters
  • Beanies… and more

Possibly best are structured wide-brimmed hats for guys who love all things vintage. Additionally, fur pillboxes, fascinators, and cloches make an impact.

Let's explore winter hats first.

Deer Stalkers

You don't have to hunt deer to wear one of these. If, through style, you wish to make the scene as an ultimate hipster, this casual, cool hat is for you.

Pairing it with glasses: To add a dash of style, opt for sunglasses. Think color popping rims or mirrored aviators.

Felt Trilby

Show off your cool, carefree style and your individuality with a felt trilby paired with an open dinner jacket, casual tee, and jeans. Yes, urban chic is for men, too. Either a touch of jazz or a touch of nerd can be supplied by your glasses.

Pairing It with glasses: Vintage inspired, oversized dark rimmed glasses or (for lack of a better term) geek eyeglasses.

Flat Cap

For Bluebloods and British upper class, this is a style icon. For the alternative Hollywood crowd, the flat cap is also quickly becoming popular. Think Ethan Hawke, David Beckman, etc. Your gentlemanly manner will only be increased by the combo of flat cap and glasses.

Pairing it with glasses: Consider an urban, retro vibe for your frames. Think wood-like, thick rimmed rectangular glasses to combine a countryside hunter look with a bit of urban cool.


Depending on your region, there are lots of different names for the beanie. Some of these include burglar cap, bob cap, tuque, and stocking cap (knit cap). As winter fashion accessories go, this is a must-have.

Pairing it with glasses: With a pair of thick rimmed, hipster inspired frames, you can geek up your beanie.

Now, let’s move on to summer hats…

Baseball Caps

Worn by both women and men, the baseball cap is a common piece of headwear. It transcends all styles and is one of the few accessories to do so. This is incredibly easy to combine with glasses.

Pairing it with glasses: Choose from classic aviators or rectangular geek eyeglasses – or just about any style at all!

Pork Pie

This year, a huge revival has been experienced by this classic hat. With a bit of a hipster edge, this is for the guy who likes to dress up. A pair of classic boat shoes, skinny chinos, and favorite blazer work perfectly with this hat.

Pairing it with glasses: Semi rimless, brow line frames and wide rectangular sunglasses will perfectly complement your pork pie hat.

The Beloved Panama Hat

Hailing from Ecuador, this traditional straw hat is sometimes referred to as the "tequila straw hat". If you're a guy with loads of charisma, and a bit of boyish charm, this is a must-have for your wardrobe.

Pairing it with glasses: Patterned frames and dark lenses pair best with this hat. Decorated lens arms, if you're not ready for an all over pattern, will suffice. Huge, right now, are animal prints – yes, even among guys.

Hat Heaven has the new baseball cap that you need to go with your classic aviators or rectangular geek eyeglasses – or anything else. You have but to pick out your favorite pair of glasses to go along with it. Shop Hat Heaven today.


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