Fashion trends come and go, but a few fashion staples stand the test of time – like a good hat. However, not everyone knows how to wear a hat or is convinced they can pull it off.

How to Wear a Hat: A Girl’s Guide to Styling Your Favorite Hats

If you’ve been wanting to expand your wardrobe but aren’t sure how to wear a hat, keep reading to learn about the different kinds of hats and how to style them in a way that’s catwalk-worthy!

Different Kinds of Hats

Many women think they don’t look good in hats because they aren’t aware of the full range of options available! Just like swimwear and jeans, there are hats suited to just about every occasion and body type.

Baseball Hats

These are your typical cap, the ones that sport your favorite brand or sports team. Most women utilize the baseball cap to hide that they haven’t washed their hair in a few days.

But a traditional baseball cap can be worn to outdoor events, while exercising, and even as an accessory to a lowkey outfit to relaxed social events. Baseball caps look best when styled with a low-slung ponytail or messy bun poking out the hole in the back.

Cowboy Hats

Cowboy hats have been a staple in some regions of the country for decades. They come in all shapes, sizes, and materials – straw and felted being the most popular.

A cowboy hat is probably the hardest hat to wear, entirely dependent upon the region you live in. While you could walk down the street in Montana wearing a cowboy hat with no sideways looks, you’ll garner attention trying to pull one off strutting through Times Square.

A simple braid, loose flowing hair, a bun at the nape of your neck – there are quite a few ways to style a cowboy hair if you’re brave enough to wear one!

Close-brimmed Hats

Cloches, fascinators, and fedoras, among others, fall into this category. These are hats with a bell shape and brim that sit somewhat close to the head.

These hats are trendy, stylish, and nearly always in season. They’re made from various materials, come in banded and un-banded varieties, and there’s one for just about any outfit.

A fedora is a lowkey accessory, especially while traveling and during summer days. A cloche is a sleeker and more sophisticated look. A fascinator is a tiny piece of material pinned on top of the hair.

When styled correctly and sitting happily at the perfect angle, these can accentuate a laid-back look or dress up a casual outfit.


A winter staple, the beanie is a simple tube hat. Styles include those that fit perfectly to your head and those that offer a slouchy profile.

A beanie looks good on nearly everyone and can be worn with loose hair, a side braid, or pigtails. Some beanies now feature a hole in the top to style a messy bun, creating a slightly more sophisticated look.

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how to wear a hat

Wide-brimmed hats

Wide-brimmed hats, like cowboy hats, take the right occasion and styling to come off well. These hats have wide, sometimes floppier brims.

They’re perfect for keeping the sun out of your face at an outdoor picnic. They’re also great for adding flair to an outfit worn while vacationing at the beach. A wide-brimmed hat can add the perfect finishing touch to a romper and oversized purse.

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Choosing the Right Hat for Your Figure and Face Shape

When you’re selecting jeans, shirts, dresses, and swimwear, you decide what looks good on your figure. Hats shouldn’t be an exception. These are the following tips are only a suggestion by some, not a rule. If you love how a hat looks on, you, wear it no matter what! It’s all about being confident!

  • Petite: If you have a smaller frame, choose a smaller hat. Larger brimmed hats can overpower a little frame or face, so choose hats that have a short brim. A cloche or fedora is a perfect choice.
  • Full-figured: If you’re heavier on the bottom, choose a hat that adds some depth to the top to balance your figure out. A wider brimmed will balance your shape.
  • Tall: Make sure you choose a hat that doesn’t add more height. Pick one that clings tightly to your head instead, with a slightly more full brim.
  • Angular face: If you have a face shape that features prominent cheekbones or a strong jawline, a cloche style hat that has extra material and folds can add curves that will soften and accentuate your natural lines.

how to wear a hat

Choosing the Right Hat for the Season

A hat shouldn’t just depend on your outfit – it should match the season!

  • Spring: Spring is the perfect time to wear those light, happy-looking hats. Straw hats of all styles are perfect for spring days, especially a jaunty straw fedora set at a slight angle with a low messy bun and flowy spring dress. White hats are best worn in spring.
  • Summer: The wide-brimmed hats are king in summer, perfect for keeping the glare of the sun out of your eyes and setting off sleek summer dresses while on vacation.
  • Fall: Hats made of felt and tweed make an appearance in fall, just in time to be paired with scarves for the perfect fall outfit. A felted fedora is the perfect fall accessory.
  • Winter: Winter calls for a beanie, which isn’t just stylish but functional. A beanie with a hole in the top allows you to style your hair and create a look that says you put effort into it, but a slouchy style with side braids works is a comfortable and trendy option as well.

How to Wear a Hat – Demystified!

If you’ve been wondering how to wear a hat or if you can pull one-off, now you know how it’s done! There’s a hat for every season, occasion, and face shape, so now that you know how to style a hat, find the perfect one to add to your wardrobe.

Are you looking for more helpful fashion advice and tips? Check out this guide to choosing the perfect sunglasses!

Alicia Trautwein is an Autism advocate, writer, motivational speaker, and dedicated mom of four. Alicia’s desire to advocate for Autism comes from her own autism diagnosis and that of her three children, niece, and brother. Her life’s mission is to educate on autism acceptance and change the world for future generations of autistic individuals.

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