How to Wear A Flat Cap Without Looking Flat (2024)

Ever doubted that you can pull off a flat cap? We’re here to put your concerns to rest and show that you can’t go wrong with a cap that survived 400 years of trends and is still thriving.

Fashion trends come and go. How many guys do you see walking around in top hats? Trends end because they are just that… trends. The flat cap didn’t begin as one of those, it began as a necessity and grew to become a staple in men’s fashion for centuries.

If the idea of a flat cap conjures up images of ‘Lunch Atop a Skyscraper’ or a grandpa golfer in Miami, you would only be half right. The flat cap’s classic shape and construction are still as popular today as it was back when newsboys were only a street corner away, and grandpa… well, he’ll always do whatever he wants.

Before we dive into defining a flat cap, let’s answer the age-old question – What is the difference between a hat and a cap?

A hat is a head covering with a brim that goes all the way around it. Picture a fedora or a cowboy hat. Or look up Bruno Mars or Indiana Jones.

Caps are different from hats in their design. They have a visor or a bill but aren’t encircled by a brim, and they have a crown (top) that is unshaped (compared to a fedora with its highly structured crown). Some caps, such as baseball caps, snapbacks and strapbacks have added structure to the crown but no brim like the one found on a cowboy hat.

A classic example of a traditional cap is the flat cap. It’s important to note that the words visor and brim are often used interchangeably.

Hats have a circular brim while caps do not.

In its purest form, the body of the flat cap is pulled forward over the visor and sewn or snapped to the top edge of it. Flat caps are recognizable by their triangular profile and are suitable for most face types – from David Beckham to the man who thinks he’s not a ‘hat guy’.

Traditionally constructed from tweed (wool) or cotton, men’s flat caps nowadays come in a variety of materials including vegan leather, linen, cotton, and synthetic blends.

Depending on the material, flat caps will keep your head warm in winter and cool in the summer all while complementing everything from a summer suit to a wool overcoat.

The flat cap goes by many other names as well – Ivy cap, Gatsby, driving cap, sixpence, duckbill, and paddy to name a few. Despite what you call it, the flat cap is easier to pull off than a fedora and looks better with a suit than a snapback.

Explore our entire collection of flat caps for men and see why they’ve been a men’s wardrobe staple for over 400 years.

The flat cap has been around for ages – since the 1570s to be exact. From the 1570s to the 1590s, the British government tried to support the wool industry by demanding that all men had to wear a woolen cap on Sundays. This law didn’t apply to noble Englishmen… guess we would’ve been stuck wearing a cap.

The law didn’t last long, but the flat cap stayed a part of the working man’s uniform.

Scan any photo from the 1910s and 20s and you’ll notice a sea of flat caps. What began as a requirement had officially been adopted as an essential part of life. The cap had another boost in popularity in the 1990s with everyone from rappers to pop stars donning the ivy cap and making it a go-to fashion choice.

Fast forward to today and you’ll see that the flat cap is still as relevant. Maybe it’s that wearing one looks great with casual or dressed-up looks… maybe it’s the face-flattering profile a flat cap provides. Or maybe it’s that good things never go out of style.

We’re the first to admit that calling a newsboy cap a flat cap is no big crime. While the fashion police won’t show up and cart you off to jail, being able to spot the differences between these 2 styles will help determine which is best suited for you… and it’ll make a fun know-it-all moment the next time the topic comes up.

The newsboy cap – also known as a paperboy cap, newsie cap or newsy – was first worn in the late 1800s and early 1900s by newspaper sellers. It’s similar to a flat cap in that both are typically constructed from tweed and have a rounded, low profile and a small visor or brim.

The largest distinction is that newsboy caps are puffier and baggier than a standard flat cap. Newsboy caps are sewn together with 8 panels on top that look like pizza slices and almost always have a button on top where the panels meet.

When in doubt, look for slices of pizza and you’ll know if it’s a paperboy or a flat cap.

1. Wrap a tape measure or a piece of string firmly around your head about 3/16" (0.5 cm) above your ear (middle of the forehead).
2. Record the measurement, order your flat cap and conquer the world.

Because this type of cap works with everyday casual looks and when you want to dress up, wearing and styling one is easier than you think.

• Consider the Classics – Remember that natural materials offer better insulation and breathability. Stick to the originals – tweed (wool), cotton or linen.
• Make It Your Own – Round the brim to frame your face by applying gentle pressure and shaping it to a slight curve.
• Wear It Correctly – No matter what super-fly throwback song is playing in the background, keep your flat cap on the correct way and not in backwards 1990s style. It may seem contradictory to say ‘make it your own’ and then demand that you wear it correctly... but think of it as a friendly recommendation.
• Know the Season – Breathable linen and lightweight cotton are perfect for spring and summer, while wool tweed and heavier cotton are great for winter.
• Keep it Simple – Like with a
  bow tie, avoid pairing too many old-fashioned accessories in one look. Men’s flat caps do wear well with bow ties, braces and vests… but too many may go a bit steampunk costume party.
• Choosing a Pattern – If you’ve chosen a patterned flat cap, make sure that other patterns you wear with it complement each other. Think of your cap as an accessory and not as an afterthought. Think of it as something that you consciously choose to wear instead of something you grab on the way out the door.
• Keep an Eye on the Lining – Just as important as the outside, the inner sweatband (the fabric band attached inside the cap that sits directly next to your skin) is equally worth your focus. All of our Fawler flat caps are handmade in Italy and include a soft, itch-free sweatband. This not only helps with the breathability factor but also keeps you comfortable all year round.

Flat caps and newsboy caps can work from everything to jeans and t-shirt to a summer suit. If you start with a neutral-colored cap (one in black, brown, grey or beige), you’ll have more options when it comes to styling and deciding what to wear with it.

We’ve put together 3 complete looks below. Notice the overall neutral color tones and casual vibe.

Read more about how to match accessories, colors, and patterns in our 7 Essential Rules for Matching Men’s Accessories.

Layers are must-have for the cold winter months. When layering, think of the flat cap as a stylistic part of the outfit instead of something purely functional.

In this look, we’ve combined a thick wool scarf in black with a textured brown flat cap. The brown isn’t an exact match to the coat (you don’t want an exact match) and works with the leather shoes and brown leather bag.

The result is a look that is both put-together and yet relaxed enough to be comfortable.

Showcase that you know a thing or two about dress-up style in a light-gray suit with navy details. And top it off with a houndstooth newsboy cap.

Be sure that the cap you choose isn’t an exact match to the suit. Here, the houndstooth pattern complements the solid-color of the suit while the subtle colors in the cap pick up the navy details in the tie and pocket square.

If you’re a jeans and tee kind of guy, this elevated version of casual may be right up your alley.

This dark-gray flat cap matches perfectly with a light-colored blazer, white t-shirt, and grey slacks. Staying in the same neutral color palette keeps this outfit fresh. Finish it off with black-and-white accents and a pair of leather loafers or white sneakers.

Still prefer your jeans? Keep the blazer and switch the trousers for your favorite denim pair.

Wool, linen, and cotton flat caps and newsboy caps can be cleaned by hand. It’s very important to not get the brim wet and to go about the process with care – it’s not a job that can be rushed.

1. Fill a bowl with warm water. Do not use hot water as it may ruin the cap.
   Add a small amount (about a teaspoon) of a mild, bleach-free laundry detergent.
2. Soak a small part of the hat (preferably somewhere unnoticeable) to see if the color will bleed. If not, continue. If yes, stop.
3. Place the back of the cap in the water – keep the brim out of the water. Gently wash from the back of the cap to the front. Avoid washing the brim unless it’s exceptionally dirty.
4. Focus on the inner sweatband and give it an extra scrub to remove built-up oil and sweat.
5. Once you’ve given it a light wash, remove it from the water and rinse with cold water to remove any detergent. Gently press between a towel to remove excess water. Do not ring or twist the cap.
6. Air dry the cap away from direct sunlight and heat. When you lay it down, shape the cap as best as possible as it will dry in the shape you leave it in.

In most cases, you’ll only need to wash the inner sweatband… unless you’ve been attacked by a flock of pigeons.

Avoid getting the brim or visor wet because many are constructed with cardboard and will crack and lose their shape when wet. If you must clean the brim, do so with a small amount of water and a clean towel.

The ‘best’ depends on you and your story.

If you like a fuller, baggier feel, choose a newsboy cap like this lightweight cotton classic by Fawler. Or if you want to try something a bit more modern, go for this weathered vegan leather flat cap in gray.

You can wear a flat cap in the summer if it’s made from breathable linen or lightweight cotton. The last thing you want is a sweaty forehead.

Make sure that the lining is equally as moisture-wicking as the shell. Try this 100% linen flat cap on for size.

Flat caps are quite popular in casual circ*mstances but can be dressed up for more formal affairs. Remember to take yours off when you’re inside the church.

For more on dressing for a wedding, explore our guide on wedding guest attire for men.

Craftsmanship and construction are the most important things to remember when buying a flat cap or a paperboy cap. Each of our flat caps from Fawler is handmade in Italy using traditional methods and classic materials.

Shop our latest collection of Italian-made hats and caps and winter-ready favorites that are exclusive to Trendhim.