How to Wear a Hat With Glasses?

How to Wear a Hat With Glasses?
6 Min Read | 25 Aug 2025
Aanchal Sethi
Aanchal Sethi

Head Marketing and Communications

Hats and glasses are two accessories that many people find tricky to wear together. Since both sit on the face and head, pairing them can feel like a styling challenge. If done right, it can make you look good; if not, it can throw your outfit off balance. People wear hats for so many reasons, from protection against harsh weather conditions to fashion. When wearing them with glasses, you need to ensure comfort, fit and confidence. In this blog, let’s understand how to wear different hats with glasses in the right way.

Different Hats With Different Glasses

The winter season is a few months away, and wearing a hat in this season is all about keeping yourself warm and cosy. But what if the glasses and sunglasses you wear with them make you uncomfortable? Here are some top hats and glasses styles to pair with them.

Beanie hat with oversized glasses and sunglasses

The image has a young woman with open hair wearing a yellow shirt. She is wearing a yellow beanie hat with oversized orange sunglasses.

A beanie hat and sunglasses are one of the most iconic looks. In winter, many people are spotted carrying this look across the streets. Initially, these hats were popular among Hip-hop stars and skateboarders. Now, they are a part of the winter wardrobe and offer a subtle hippy vibe. These are made from stretchy fabrics like wool and cotton. As they are made from comfortable fabric, they do not put pressure on your ears when you wear glasses and sunglasses with them.

The glasses and sunglasses made from versatile acetate and metal materials look effortlessly great with these. The transparent and light-coloured frames in acetate beautifully enhance the overall look. If we talk about style, then oversized glasses will be great to style with.

Aviator hat with glasses

A man is standing in front of an open aircraft wearing a beige jacket. He is wearing pilot glasses and an aviator hat. He has a frowning expression on his face.

An aviator hat, also known as a trapper, is your best friend if you don’t like too much cold getting to your head. It comes with flaps that surround the ears to ensure you stay warm and cosy. These hats are made from leather or wool and come with an inner faux lining to ensure maximum comfort. Some of these hats are also waterproof and work great in snowy and extremely cold weather conditions.

To create a classic retro look, you should pair pilot glasses with a metal material. These glasses blend beautifully with the style and design of a trapper hat. However, if your hat covers a large part of your forehead, you must go for understated eyewear pieces like rectangular glasses.

Fedora or trilby hat with glasses

In the image a man is standing wearing a black blazer and white shirt. He has a smile on his face and he is wearing fedora hat with round black metal glasses.

A timeless and well-executed design is what you can expect in these fedora or trilby hats. They get all the numbers when it comes to style, but one drawback is that they will not protect your ears in extreme winter conditions. But you can always add a scarf or coat to protect from the cold and look stylish at the same time.

With this, you must opt for minimal frames of glasses and sunglasses. Doing this will ensure that all the attention is on your hat. Go for sleek, round or rectangular glasses to keep up with a minimal look. Also, you can add a little touch of drama with tortoiseshell glasses.

Baker boy or flat cap with glasses

A bearded man is wearing rectangular black eyeglasses with baker boy cap in grey colour with black checkered style. He is also wearing a plaid shirt and he has side facing pose.

Do you remember these from Peaky Blinders? Yes, these are those iconic hats and trust me when I say this- these are the most trendy ones among all. Made from cotton, tweed or wool, they are sewn to perfection and feature a visor at the front.

To complement this hat style, you should go for browline glasses, as they balance out the curves of the hat. You can also go for round acetate or oval metal glasses; they also look great with a baker boy hat.

Beret hat with glasses

The image has a smiling girl wearing green colour turtleneck ribbed top. Her hand is placed over her shoulder and she is wearing black round glasses and brown beret hat.

Do you remember how Lilly Collins in Emily in Paris was adored wearing a classic French Beret? Well, I definitely did, because it's chic and adds the right amount of style to your look. Be it keeping it tilted on the corner or placing it in the centre, a beret hat can instantly elevate your look. However, adding glasses with a beret hat can be a tricky thing.

If you are someone who wants to wear glasses with a hat, then go for geometric metal frames, chunky black acetate square glasses or cat-eye glasses. These will beautifully complement the style of the beret hat.

Baseball cap with sunglasses

Young woman wearing oversized white rectangular sunglasses and a white cap, with long brown hair, standing outdoors in sunlight against a green leafy background.

One of the most worn and loved combinations is a baseball cap with sunglasses. Stylish, modern and easy to style- this one is definitely my go-to combination. These are mostly made from cotton and feature a visor at the front to protect your face from harsh sunlight. You can find them in so many styles and get something that suits your style and needs.

When it comes to sunglasses, you can choose from sporty, round, and square styles because they are versatile and suit most face shapes.

Hats As Per Face Shape

Just like not all frames suit all face shapes, hats work similarly. It is important to find the right hat according to your face shape. Here are different face shapes and hats that will complement them.

  • Round Face: Go for a fedora hat, a woolly hat with a bobble, or a baker boy flat hat.

  • Square Face: For a square face shape, you can choose between baker boy, baseball cap or aviator hat.

  • Triangular Face: You are blessed, as almost all hats will complement your face shape, but the ones with a round style will work best.

  • Heart-shaped Face: To complement your broad forehead and pointed chin, you should go for a beret, beanie or trilby hat.

  • Oval Face: Just like a triangular face shape, you can also go for a lot of hats, as all of them will suit you. Berets, baker boy hats and flat caps will look the best.

  • Diamond Face: This face shape is known for its wide cheekbones, narrow forehead and chin. The best caps for this face shape are a flat cap or a baker boy cap.

Want to know what your face shape is and find glasses that will suit you? Check our face shape guide.

Concluding Thought

Hats and glasses are all-weather essentials, and doing them right is extremely important. Now, through this guide, you know how to balance your styling with accessories. You can choose hats that suit your face shape and find glasses that complement them. You can explore our range of 1000+ fashion-forward frames and get ready to take your fashion game to the next level.

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