How to wear hats without hats wearing you

March 6, 2020 12:00am

Trying out a new look can be very nerve wracking, but the key to rocking any look is confidence. Hats in particular are a tricky accessory and one that people tend to be hesitant to try out. But fear not! Listed are some popular styles of hats and tips on how to rock them. In the end, wear whatever makes you feel good and happy. 

Baseball caps

Baseball caps tend to get the side-eye when it comes to women and fashion, since they can seem like a tomboy look, but they can be made super chic and cute as well. 

Baseball caps can be worn with different hair types, as they're very versatile when it comes to how to wear them with your hairstyle and type. 

A cute and more chic look for a baseball cap would be pairing leggings or jeans with a cute, more dramatic top, wearing heels or sandals, and finishing the look with some neutral makeup and a nice wavy hairstyle. This takes the tomboy look from Saturday ball game to Friday night out with the girls. 

Baseball caps work on everyone if you know how to style them. Playing with hairstyle, determining how much hair is visible and picking accessories surrounding the head, such as earrings and a necklace, can make the simple look more fashionable. If you like the simple tomboy look then that isn't problem: All you have to do is figure out how to style your hair to shape your face to make the look of wearing a hat more flattering.

Floppy hat 

The floppy hat is a summer staple and a personal favorite of mine. It's such an underrated look but it is so chic and classy. Floppy hats are large and round and therefore may not flatter round faces. Face shapes that work great with this style are diamond shaped faces, long faces and square faces. 

The floppy hat works well with both long and short hair, curly or straight, but I recommend wearing your hair down: It's much more flattering and classy that way. The floppy hat can be paired with many looks: sundresses, a bathing suit at the beach, or jeans and a silky spaghetti strap blouse. My go-to look for the floppy hat is a nice, beachy wave with a neutral eye and a bright lip paired with a long sundress. 

This look can be taken from casual to classy so easily. It is a versatile, yet pretty look no matter how it is worn. I highly recommend this hat, because it will boost any summer look and keep the sun away. 


The beret is a classic and timeless Parisian staple. Long thin faces and diamond shaped faces look best in this style hat. The beret is typically wool or a heavier material, and therefore, it is more of a winter or fall hat. The looks that work best with a classic Parisian beret are most obviously looks with French and Parisian influence, but once again it is a versatile hat that works with any hair length. But is best worn with hair down to optimize the look.

The beret can work with jeans, trousers, a flowy skirt or a dress. It really works with any look. A few typical Parisian-inspired beret looks include anything with black and white polka dots or navy and white stripes, tight ankle-length pants or a calf-length flowy skirt.

Kitten heels or flats work best with this hat. Flowy silky blouses paired with heavy double breasted coats are classic Parisian-inspired looks. Pairing this look and the beret with a smoky eye and a bright red lip is an iconic staple that will never go out of style. 

Bucket hat

The bucket hat is a newer trend that has grown in popularity in the last year or so. This look has caught the internet by storm and made its way onto everyone's heads. This type of hat works on just about every face shape and looks best with hair worn down. It is a summer style and definitely gives off beach vibes. 

The best look to help rock the bucket hat would be a summer beach look with either a distressed denim short and an oversized T-shirt. This kind of hat also looks really nice with a more thrifted and vintage style, paired with a more tomboy attitude. 

Long baggy pants or jeans, patterned button downs or large graphic T-shirts and sneakers work perfectly with any pattern or color of bucket hat. This hat is very portable and great for the beach or just going out for lunch and looks good dressed up or down.


Finally, we have the beanie. 

This is a classic and a reminder of the skater pop-punk emo child in all of us. This hat and its look is synonymous with skater vibes. The hat looks good on all face shapes.

It can be paired, and often is paired with distressed denim or black denim and graphic T-shirts, along with large puffer jackets and sneakers. But this hat can also be worn easily with leggings, a college sweatshirt and some sneakers as well. It is a very laid back casual look that is great when you're in  a rush or you're having a bad hair day, and it keeps you warm when it's cold out. This kind of hat almost always works with any casual look and is a timeless style.