How to wear a flat cap

Man who knows how to wear a flat cap to suit his style

A flat cap is a versatile accessory that effortlessly blends timeless charm with contemporary style. Whether you're aiming for a casual, smart-casual, or formal look, here’s how to wear a flat cap to match your fit.

Key considerations when choosing how to wear a flat cap

The beauty of a flat cap is that you can truly make it your own. The versatile style fits with outfits ranging from casual to formal. It’s easy to dress up or down depending on the occasion. 

Some tips to keep in mind:

    • Fit: Make sure the cap fits your head snugly but not too tight. Take a look at our guide for choosing the right size hat before you buy. 
    • Fabric: Natural materials are more breathable but still have great insulation. Tweed, wool, cotton, or linen are your best bets.
    • Season: From these options, choose the best fabric for the season — wool or tweed for colder months, and cotton or linen for warmer weather. 
    • Color: Neutral colors like gray, brown, navy, or black are versatile and can be paired with various outfits. However, experiment with patterns like herringbone or plaid for a more distinctive look.
    • Positioning: Wear the flat cap slightly forward on your head, just above your eyebrows, for a sharp and neat appearance.
    • Brim: The brim should be flat and not curved. Ensure it stays in good shape by storing the cap properly without crushing it
    • Styling: Though flat caps are a timeless style that have been around for over a hundred years, avoid pairing your cap with other ‘vintage’ accessories like a bow tie, suspenders, or a vest – it may end up looking a little like a costume. 

How to wear a flat cap 3 ways

No matter the dress code, there are ways to seamlessly incorporate a flat cap into your outfit. 

Casual

When we’re talking casual, we mean jeans or chinos, well-fitting t-shirts, and jackets – no sweatpants here! Slim, straight jeans are a wardrobe staple for any casual occasion, as are chinos. 


T-shirts and polos are fine, so long as they’re well-fitting and clean. Casual doesn’t mean sloppy! Likewise, nothing ruins an outfit faster than dirty or muddy shoes. 

Smart-casual

While it’s easy to get confused by this dress code, smart-casual is a lot easier to nail than you might think, especially when you add a flat cap — the perfect centerpiece of any smart casual outfit.


Again, straight-leg jeans are a great go-to, or opt for chinos in a neutral beige, navy, gray, or black. On top, you’ll want a button-up shirt, preferably long-sleeved unless it's the height of summer. A checked shirt is a nice way to add a pattern to your outfit while staying classy. 


Sleek boots or loafers will tie the outfit together, along with a jacket that compliments or matches your flat cap. If in doubt, you can’t go wrong with a tweed blazer for a smart-casual look. 

Formal

Don’t be intimidated by a formal dress code. It’s all about having the right basics.

To pull together a foolproof formal outfit, you’ll need three things in your closet: a well-fitting tailored suit, a crisp white shirt, and a smart wool flat cap. Whether you’re attending a country wedding or a workplace fundraiser, you’ll be one of the most well-dressed men in the room.

Flat cap styling ideas and inspiration

Still not sure how to wear a flat cap? Here are eight looks to help inspire you.

Look 1: Timeless elegance 

Black and white photo of a man wearing a flat cap with a pinstripe suit

Pinstripes and a flat cap are the perfect combo for evoking a sense of old-world sophistication. Ideal for formal events, a black pinstriped suit will look best with a dark gray cap. Look for a tie in a similar color and material to tie the outfit together. 


As always, your suit needs to be tailored and well-fitting – if it’s too baggy you could end up looking like a ‘70s gangster. 

Look 2: Contemporary sophistication

Man reading the newspaper wearing a black flat cap and tweed jacket

Pair a cotton or knit turtleneck with a tweed jacket for a failsafe winter outfit that keeps you warm while looking professional. These pieces pair perfectly together, especially when topped off with a dark flat cap, preferably in the same material as your jacket. 

Look 3: Urban romance

 

Man wears a grey-brown flat tap with a bright, patterned shirt

A flat cap can be a great piece to prevent an outfit from looking too casual. The best way to style a bright, patterned shirt is to let it be the focal point of your outfit. Pair it with black or white jeans, then elevate the look with a neutral flat cap.

Look 4: Effortlessly cool

 

Man wearing a black flat cap with jeans and a white T-shirt

Jeans and a well-fitting white tee is a classic outfit that will never go out of style. However, it can sometimes make you blend into the background. Bring your outfit up a level with a simple black flat cap, which shows you’ve put thought into your look. 

Look 5: Enduring elegance

 

Alt text: Man wearing a classic tweed suit with a tweed cap

For a stylish classic, you can’t go past a three-piece tweed suit. Though, we think that term should be upgraded to ‘four-piece’, as a tweed cap is a perfect accompaniment. Look for a cap in the same material and a complementary color, so the final look is cohesive and slick. 

Look 6: Classic meets trend

 

Man wearing a flat cap with a leather jacket

Layers are a must in winter, but that doesn’t always have to mean tweed jackets or overcoats.  A worn leather jacket is stylish and easygoing, without looking sloppy. Keep the rest of your outfit similarly sharp — think dark slacks instead of jeans and avoid bright colors or patterns. 

Look 7: Casually refined

 

Man wearing flat cap with a cardigan

If you’re more of a casual guy, this is the perfect way to elevate your daily look. A light grey cap pairs well with tailored pants in a similar shade, while a cozy cardigan and dark turtleneck bring the outfit together. Sneakers are a no-no here – opt for brown or black loafers to keep the style cohesive. 

Look 8: Elevated ease

 

Man wearing flat cap with dark blue trench coat

This look is a stellar example of how a hat and coat can take an outfit from casual and boring to smart and slick. Combine a well-fitting trench coat with a flat cap in a similar shade to bring a simple tee-and-pants outfit to the next level. It’s put together, yet relaxed enough to be comfortable. 


Ready to build the perfect outfit for any occasion? Order the perfect flat cap of your choice from Tweedtopper today.

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