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Learn How to Wear a Hat and Have It Sized Properly

As the sun slowly but surely creeps back into our lives after a long winter, you might well be in possession of a stylish new hat — and you might be wondering how to wear a hat the right way as a result of that investment. It's a pressing question on the minds of stylish guys everywhere, especially as so many of us re-enter the world and start dressing again in ways that allow you to rock a hat (so, beyond just cozy sweatpants and a T-shirt).

When we talk hats, we're not quite talking about a baseball cap (although there are tons of hat styles for men that work in plenty of situations). We're thinking of more commonly found, slightly dressier hats, like the boater, the derby, or the Panama hat — the wool flat cap is an excellent choice for colder months, too. Adjust your hat game to the season at hand, we say.




15 minutes

What You Need

  • Measuring tape

Wearing a hat is a terrific way for a guy to express himself, especially in the warmer confines of spring and summer. Vibrant and more subdued colors find their way into shirting, pants, and suiting — be it a breezy polo and chinos or a timeless seersucker suit for the Kentucky Derby, the proper hat can add a little flair to an already well-tailored look. The same goes for soft, brushed, and rugged fabrics like wool or tweed, best worn as temperatures get cooler.

Before you can step out in style though, you've got to know what you're doing. That's where we come in.

How to Find the Right Hat
Image used with permission by copyright holder

How to Find the Right Hat for You

Before you can break out your new hat — whether it's a classic fedora or a warm weather-friendly straw boater — you need to know your head size. That same hat size can help you fit your head to a variety of hats. The brim should be neither too snug nor too loose. Too snug: It leaves a nasty mark on your forehead. Too loose: It won't stay on your head.

Step 1: Determine the size of the circumference of your head using a soft, thin measuring tape — not the same measuring tape you use in the garage.

You can do this with a friend or by yourself. If you have serious doubts, visit a hat shop.

Goorin Brothers straw hat
Image used with permission by copyright holder

Step 2: Once you've determined the circumference of your head, use a size guide to fit the hat to your head properly. Specialty hatmakers even make it easy to do this online. This measurement gives you a baseline for sizing across the board.

Step 3: To figure out how to wear a hat, it's best to start out choosing the hat that works for you and your lifestyle. In warmer months, a straw hat offers versatility with a linen shirt and trousers. In cold weather, a wool fedora offers protection from the snow and wind in an old-school way. Retailers provide lots of options at fair prices for quality hats.

Best hats for men
Goorin Bros.

Step 4: Pair your hat accordingly with the proper accessories. When wearing a lightweight, warm-weather hat, make sure your outfit pairs up nicely with lightweight, breezy fabrics. Keep lightweight hats to the warmer months, and choose hats with sturdier fabrics, like wool, for the colder months. This ensures your clothes match (it'd look out of place to wear a straw hat with a heavy wool overcoat, for instance) and gives your look an air of seasonal style.

Learning how to wear a hat actually starts with the basics, like knowing your proper head size and measuring your noggin accordingly. Once you've accomplished that task, you can use that knowledge as a baseline to figure out the hat or hats you'd like in your life. Visiting a local hat store can help streamline the process, but modern brands make it easy to find your perfect fit online.

As you discover the hats that work with your wardrobe, you'll discover hats you enjoy wearing with certain outfits, too. Keep seasonal style top of mind, and you'll always be able to know how to wear a hat with plenty of different ensembles.

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Beau Hayhoe
Beau Hayhoe is a freelance men's style writer, consultant and PR pro based in Brooklyn. Beau's menswear and gear writing has…
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