How to Wear a Wide Brim Hat

Co-authored by Rachel Michael

Last Updated: February 24, 2023 References

Wide brim hats used to be a standard piece of attire in the 50's and 60's but are less commonly worn nowadays. Selecting the perfect hat can be a daunting challenge for many people. Choosing a hat that works with your style and your face are important factors when considering this fashion statement. Luckily, if you take your time in selecting the perfect hat, you can achieve a good fit and flattering style and wear a wide-brimmed hat with confidence.^{[1]
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Method 1

Method 1 of 3:

Choosing a Hat Based on Your Face Shape

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Choose a hat with a smaller brim if you have a diamond shaped face. If you have an angular face with wide cheekbones, then you most likely have a diamond shaped face. Wearing a hat with a smaller brim and pinched crown like a fedora or trilby hat may be good options for you.^{[2]
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2
Wear hats with larger brims if you have an oblong face. An oblong face is longer than it is wide. Most people with oval faces also possess a round chin. Wear Fedoras with wider brims or western hats to pull attention off the length of your face. Avoid hats that have narrow brims.

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3
Choose a pointed hat if you have a round face. If your face is as long as it is broad then you have a round face. Try on asymmetrical hats because they create contrast with your symmetrical face. Hats with a high crown and peaked or a slanted brim look best on you. Avoid hats with tall rounded crowns or a rounded brim because it will bring attention to the roundness of your face.
4
Choose a hat that has curves if you have a square face. If you have wide cheekbones and a large jaw, then you probably have a square face. Wear larger floppy hats like the Derby hat, or choose a hat that has rounded curves and edges like a bowler. Wearing a hat with a prominent crown can make your head look longer.
- Fedoras look great on square faces (and round faces too).
- Cowboy hats are suitable for those with square faces.

Method 2

Method 2 of 3:

Selecting a Style

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Look at different styles of hats. There are many different varieties of wide-brimmed hats on the market. Take a look at different brands and styles of wide-brimmed hats and figure out a style that you like. Look online or visit a hat store to get an idea of what styles you like. Think about where you live and how the hat will be received from others around you. For instance, cowboy hats are commonplace in the south and midwest but are far less common in northern states.
- Popular examples of wide-brimmed hats include boater hats, skimmer hats, fedoras, trilbys, gambler hats, derby hats, and cowboy hats.^{[3]
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- Bowler hats have a two-inch brim with a rounded top. This style was popular in 1800’s and early 1900’s.
- Western hats, sometimes known as cowboy hats were worn in the Midwest. These hats have characteristically wide brims.
- Derby hats are usually worn by women and have elaborate bows and are usually worn at derby racing.^{[4]
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2
Choose the material of hat that you want. Wide brimmed hats use a variety of different materials for different kinds of hats. Decide on the type of material you want, based on style and climate. Materials like wool, leather, and fleece are good for the cold weather while materials like straw, bamboo, and linen are best for hotter weather.^{[5]
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- Try on different styles of hats to see what kind of material feels best on your head.
3
Consider your budget. Take a look at budgetary constraints and decide how much you would like to invest in a hat. It's typically advised to purchase a more expensive hat made of a finer material instead of buying a cheaper hat made of synthetic material if you plan on wearing it often.^{[6]
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- Kentucky derby hats can cost anywhere from $135 to thousands of dollars per hat.^{[7]
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- Bucket hats are often constructed of cheaper materials like polyester or cotton.^{[8]
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Choose a color based on your skin tone. Decide what color you want your hat to be and what works well with your skin pigmentation and undertones. Determine if you have a warm, cool, or neutral skin tone. To find your undertones, look at the veins in your wrist under light and determine their color. You have a warm tone if you have dark brown or dark blonde hair and a green or golden undertone. You have a cool tone if you have very dark hair or light blonde hair with a blue undertone. Neutral toned people fall somewhere in the middle and often have hazel eyes with warmer toned hair.
- People with a warm tone look best in blues, greens, golden yellows, and creamy whites.
- People with cool skin tones look best in bright blue, lavender, ruby, gray, and navy.
- People with neutral skin tones look best in light peach, red, yellows, and off-whites.
5
Wear the right clothes with your hat. When you wear a wide-brimmed hat, it's important that you select the right clothing so that it doesn't come off like you are trying too hard. Try to select outfits where the hat accentuates the overall look. Don't try to plan an outfit around your hat. For men, make sure that the rest of your clothes are fitted well and not loose or baggy. For female clothing, this means wearing longer and looser clothing the larger your brim gets.^{[9]
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Research source} And keep in mind that not all outfits will work with a hat.
- A denim jacket, white t-shirt, and slim fitted jeans work well with a fedora or bowler hat.
- A flowing dress, sandals, and sunglasses go great with a derby hat.
- Wearing a baggy sports jacket or suit can make you look childish in a wide-brimmed hat.^{[10]
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- Make sure that your hat color does not clash with the colors that you're wearing on the rest of your body. You don't want the hat detracting from the rest of your outfit.
6
Have the confidence to wear a wide brimmed hat. While wearing a wide-brimmed hat may have been normal in the 40s and 50s, they are much less worn today. If you do decide to wear a wide brimmed hat, make sure that you wear it with confidence. Remain self-confident and own your look instead of fidgeting and touching your hat constantly.^{[11]
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- If you can't feel confident when wearing your wide brimmed hat, consider choosing another option for your hat.

Method 3

Method 3 of 3:

Getting a Hat that Fits

1
Measure your head with a measuring tape. Take a measuring tape and wrap it around your head to determine its circumference. Place the measuring tape 1/8 inches (3.17 millimeters) above your ear and across your forehead. Make sure to pull the tape firmly to your head but not too tight.
- If you don't have a tape measure, you can download and print a tape measure online.
- You can also ask a professional hat maker or seller to measure your hat size for you.
2
Determine the size of your hat based on your measurements. Take a look at a hat size chart and correspond the measurement of the circumference of your head with the chart. While many hat brands will be similar sizes, they may differ fractions of an inch which can make it harder to find a hat that fits. Many hats are also broken down to their metric measurement, typically ranging from 54 to 65.^{[12]
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- For instance, a 22 1/4 inch head circumference is a 7 1/8 sized hat in the US and a size 57 if you use metric measurements.^{[13]
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- For Stetson hats, a size 7 1/8 is a medium.
3
Check if the hat fits. When you finally decide on a hat, make sure that you try it on to ensure that it fits. The sweatband inside of the hat should fit comfortably around your head. The top crown of the hat should not touch the top of your head.^{[14]
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- If the hat is too big and you can't find a suitable size in the style you want, you can apply felt pads to the inside of your hat.

Expert Q&A

Question

What else can you wear with a wide-brim hat?

Rachel Michael
Personal Stylist
Rachel Michael is a Personal Stylist based in Minneapolis, Minnesota and the Owner of Rachel Michael Styling. With more than six years of experience, she specializes in helping others understand and develop their unique style through wardrobe editing, personal shopping, and styling. Rachel holds a BA from Arizona State University and an Image Consultant Certification from Statement Makers. She has also worked with brands like Stitch Fix to help hundreds of women have a style they love.

Rachel Michael

Personal Stylist

Expert Answer

I think a really fun way to style a wide-brim hat is to wear it with some sort of kimono or duster jacket. Then add a cami, a pair of distressed jeans and some chunky boots. You can just wear that to run everyday errands and not save it for a special occasion.
Question

How do I stretch a linen hat?

Community Answer

Heat up the tea kettle or pot of water until the water begins to boil. Hold the hat's brim to get a good grip and place it over the steam. Remove the hat from the heat after 30 seconds and use the hairdryer on its highest setting to dry. Once it's only mildly damp, wear the hat and let it air dry to stretch into the right size for your head.