How to Wear Flat Caps

Co-authored by Melissa Young

Last Updated: December 17, 2024 References

Flat caps are a type of hat known by their elongated structure and triangular side profile. The body of this cap is pulled over the brim to create its iconic shape. Flat caps look great styled casually and formally, and they provide a lovely British charm to your outfit. Choose a flat cap that fits comfortably in a tweed or wool material, and add it to your fall and winter outfits for a charming addition.

Part 1

Part 1 of 3:

Picking Your Flat Cap

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1
Measure your head around your forehead to determine your hat size. To figure out what size you need, use a tape measure. Place the tape measure at your forehead, and bring it around your head until you reach the same spot. This measurement is the size of your head in inches or centimeters. Then, search online for a hat sizing converter based on your location.^{[1]
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- Some locations such as the United States has particular hat sizes. Other countries use the measurement to the nearest inch or centimeter for sizing.
2
Get a flat cap that sits comfortably on your head. When you choose a hat, try it on to check the size if you can. This is the most accurate way to tell if a hat fits you. When you put it on, check to see if it fits snug or if there is extra space around the sides.^{[2]
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- If the hat is too tight, you may get a headache.
- If the hat is too loose, it may blow away in the wind.
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3
Choose a hat in a tweed or wool fabric to keep you warm and stylish. Proper flat caps are made out of thick, warm tweed or wool. These fabrics are designed to retain heat, making them great for the fall or winter. In addition, they come in many neutral colors, so you’ll look like a proper gentleman in many different outfits.^{[3]
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- For example, you can go with a solid grey tweed flat cap.
4
Pick a neutral, solid-colored flat cap if you want a day-to-day hat. It is most common to see solid-colored flat caps, as they look handsome and neat. These look great with both casual and dressier outfits, so you can wear this hat throughout the season no matter what the occasion may be.^{[4]
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- Many tweed hats have other colors stitched into the fabric. These colors are very subtle, but they make it easy to pair with many different outfits.
- Common colors include black, grey, tan, brown, and navy.
5
Go with a brightly-colored or quilted hat if you want to stand out. While these hats aren’t as common, you can find flat caps in bright, plaid patterns or loud shades of blue, red, or green, for instance. If you are confident in colors, consider choosing this option.^{[5]
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- This looks great on the golf course, for instance.

Part 2

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Pairing Your Hat with Outfits

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1
Pair your hat with an outfit in contrasting colors for a daily look. If you want to wear your flat cap all the time, it is best to choose outfits in colors that are not super similar to the color of your hat. This way, you look stylish in either casual or dressy outfits. If you wear an outfit that is similar to the color of your hat, your outfit may seem “matchy” and look off.^{[6]
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- For example, a navy flat cap looks great with grey and khaki clothing. You can wear grey tailored pants or khaki trousers and a neutral shirt.
- If you are wearing a bright blue or red cap, go with grey or tan clothing to balance your bold hat.
2
Choose a suit that matches the color of your hat for a dapper style. If you want to look like a true trendy gentleman, choose trousers, a button-down, and a blazer that is the same color as your hat. Wear this look to formal events such as meetings and parties.^{[7]
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- This is not recommended for every-day wear, as the monochromatic outfit can get monotonous.
- For example, go with a solid black or army green outfit.
3
Create a casual outfit with a T-shirt, jeans, and blazer. If you want to wear your flat cap while running errands or out to lunch, combine it with a pair of jeans and a plain or graphic T-shirt. For a polished touch, put on a blazer in a neutral color.^{[8]
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- Go with dark-washed denim for a flattering pair you can wear with many outfits.
4
Pair your hat with a fitted shirt and slacks for a professional look. If you want to wear your hat on your way to and from the office, wear a button-down shirt tucked into a pair of fitted trousers. Then, take off your hat before you get to the office, as they are not appropriate for most offices.^{[9]
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- This way, your head can stay warm as you commute.
5
Add a nice tie and pocket square to your blazer for formal events. If you want to look dashing and refined, pick a colorful silk or satin pocket square and scarf. Pick matching colors and patterns for a uniform look. Then, place the tie around your neck and tuck the pocket square into 1 of your breast pockets.^{[10]
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- This accent makes for a stylish, formal occasion. Wear this to the theater or concert hall, for instance.
6
Wear a tweed or wool jacket to keep warm in the winter. To finish off your cold-weather ensemble, pick a tweed or wool jacket in a contrasting, neutral color as your hat. The jacket should fit you well in the shoulders and wrists.^{[11]
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- The length of your jacket depends on personal preference. You can get a waist-length or trench coat style jacket, for instance.
- For example, if you have a dark brown hat, choose a tan or navy coat.
7
Put on a pair of Oxfords or Brogues for a fancy footwear option. While you can wear nearly any shoe with a flat cap, these options are particularly attractive with a flat cap. Choose shoes in a similar hue as your shoes, such as brown, navy, or black. Then, wear these with your elegant ensemble.^{[12]
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- Additionally, you can wear boots with your outfits for a stylish, seasonal choice.
8
Avoid wearing your flat cap with old-fashioned items like suspenders. If you wear your cap with old-time, traditional looking accessories like monocles, walking sticks, or suspenders, your outfit may appear too much like a costume.
- Instead, wear your hat with modern, classic pieces for a timeless style.

Part 3

Part 3 of 3:

Positioning Your Hat

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1
Wear your flat cap during the fall and winter to keep it in good condition. These hats are designed for cold weather and are commonly made from thick, warm material. If you wear a flat cap in the summer, you will sweat through it.^{[13]
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- There is no need to wear your flat cap in the summer or spring.
2
Ensure your hat is snapped properly when you put it on. Some flat caps have a small metal snap located on the top of the brim. While not all hats have this feature, snap it shut if yours does. You can attach the 2 snaps easily with your hands.^{[14]
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- This way, the brim of your hat stays in place.
3
Shape the brim of your hat based on your personal taste. You can adjust your flat cap to make the hat more comfortable or stylish. For instance, hold the brim of the hat in between both of your hands, and bend it slightly for a curved look. This is a great way to add your own personal flair to your look.^{[15]
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- You can also tilt the brim of your hat to the side for a swanky style.
- In addition, tilt the brim slightly upwards for a modern twist.
4
Avoid wearing your flat cap backward. While the flat cap can be worn casually, this modern hat trend is not appropriate for flat caps. It makes your outfit look awkward, as flat caps are designed to face forward.^{[16]
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- Think of flat caps as the stylish older brother compared to baseball caps.

Expert Q&A

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Question

How to wear or style flat caps for women?

Melissa Young
Freelance Fashion Stylist
Melissa Young is a Freelance Fashion Stylist based in Atlanta, Georgia. With over 10 years of professional experience, Melissa's objective is to elevate people's confidence and comfort through the power of fashion. Her professional background is in commercial styling and she has extensive experience in styling for editorial, television, and film. She has styled for brands including Diageo Crown Royal, Hilton Hotels, IHG Hotels, and Getty Images, and has been featured in several publications, including PUMP Magazine, Moevir Magazine, and Upscale Magazine. She received her Bachelor of Arts in Interdisciplinary Studies from the University of South Carolina.

Melissa Young

Freelance Fashion Stylist

Expert Answer

I suggest opting for a gentle, low bun at the back when wearing a flat cap. The hat's intricate details speak volumes, allowing you to keep your hairstyle minimal. With a hat on, you can effortlessly pull all your hair back and complement it with subtle makeup to accentuate your features. Whether you prefer a makeup-free look or have specific preferences regarding hairstyles, the versatility of flat caps allows for various choices. I lean towards recommending a pulled-back style, like a cute bun, ensuring that there's no hair framing the face. Even if you choose to secure it in a ponytail, consider styling it into an adorable bun due to the hat's distinctive shape. For those not keen on buns, a sleek, straight hairstyle, free of curls or waves, works perfectly. Keeping it simple and chic is key, allowing the hat to take center stage.

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I'm a girl; what outfit can I wear this with?

Community Answer

Plain white and black can always be helpful; a simple white long-sleeve shirt, Ramones jacket and skinny jeans can work with that hat.

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Can I wear tennis shoes with a flat cap? If so, what kind?

MichelleF2

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Of course, flat caps can be versatile to go with many outfits. That being said, it is a more vintage style, and wearing very large and flashy sneakers may be too much contrast. Try to go more for sleek shapes and neutral colors.

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Tips

Typically, flat caps are seen as more casual than hats like Fedoras.

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Flat caps are also known as “newsboy cap,” “cabbie,” “Gatsby,” “Ivy,” and “Jeff.”

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Can't find a cap you like? Considering making your own and adding that special touch to it.

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Warnings

For very formal occasions, flat caps may not be appropriate. If you are going to a black-tie event, consider wearing a top hat instead.

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