How to Wear Your Hair with a Hat

Wearing Your Hair under a Baseball Cap

Go curly. No matter the length, curly hair looks cute and playfully feminine when it is paired with a baseball cap. Add some styling mousse to bounce up your curls, or sleep with twisted buns the night before. When you wake up, let the curls fly and throw on a cute baseball cap. This is a great option for the day before you need to wash your hair.

Pull it into a loose side braid. Pull your hair to the side and separate it into three equal chunks. Braid each strand, one over the other, without pulling too tight. Tie it off at the bottom. This will create a cute loose braid that you can add a baseball cap to for a classically casual look. You can try a loose braid down the back for a variation of this look. For another option, you could try a fishtail braid. This will not work for short hair. It will look best on hair that is at least armpit length.

Let the curls hang out for men. If you’ve got curly hair and you still want to wear a hat, have no fear! Curly hair looks cute peeking out from under a baseball cap. Use a moisturizing agent (like a gel product) to avoid flyaways. Try not to let the curly hair stick out of the hole on the back of the baseball cap – especially if you’re wearing the ball cap backwards. This might look a little sloppy.

Make a man bun or ponytail. For guys with longer locks, you can still find many ways to wear your hair under a baseball cap. You can pull it back into a low man bun that fits out the hole in the back of the baseball cap. Or you can pull it into a low ponytail that sticks out the bottom of the hat. You can even combine the ponytail and man bun styles into one by pulling your hair into a low ponytail at the nape of your neck, and off to one side. Then loop the hair through the hair tie one last time, but only pull it halfway through. This will create a casual loose bun that is very stylish at the moment.

Creating Casual Looks

Wear a woven hat. Woven hats – like Panama hats – are great for a summertime look. You can style your hair into beachy waves, pull it into a side braid, or straighten it out for a more casual sleek look. Try pairing the woven hat with some worn-in jeans or with a cute sundress.

Let your ponytail hang out of a fedora hat. For a cute casual look, you can make a messy ponytail that hides under a cute fedora. Pull your hair into a loose, low ponytail and top it off with a fedora, or another wide-brimmed hat. You can even let a few strands escape the ponytail and fall around your face.

Wear loose, beachy waves with an oversized sun hat. Create beachy waves by applying mousse to your hair, or by letting it air dry if you’ve got naturally curly hair. Top it off with an oversized sun hat and you’re ready for a fun summer day. You can add some frizz-easing product to manage the flyaways if you’re worried about that. If you have naturally straight hair, you can create waves by braiding your hair while it's wet and letting the braids dry before unraveling them. Alternatively, you could use a waving iron.

Cut it short. For men’s hairstyles, the easiest way to get away with hat hair whenever you want is to opt for a shorter buzz cut. This look works with basically any kind of hat, and you don’t have to worry about the embarrassing hat hair creases once you take the cap off. If you decide to sport this look, make sure you use conditioner or moisturizing shampoo that protects against dandruff. You don’t want to get flakey dandruff all inside your hat. This style can work for girls with short hair too. Just throw on a nice hat and you’ve got a cute, active style.

Opting for More Formal Looks

Straighten your hair completely. Straight hair is classic and classy. Add some anti-frizz serum to your post-washing routine, and then blow dry your hair using a round brush. Run a straightener through your hair, one section at a time, until it become straight and frizz-free. Add a cute fedora hat or a floppy hat with flowers. Try to use the blow dryer and the hair straightener on low heat. This may take longer to complete the job, but it will protect your hair in the long run. For protection against heat damage, apply a heat protectant product to the hair prior to applying any form of heat.

Try a cute up-do. Twirl your hair up into a bun, or twist it into a cute semi-ponytail. Focus on the details so that they’ll still be visible once the hat is on. Place the hat carefully on top of your up-do and head out for an elegant night. Try this cute rolled up-do. Start with a loose ponytail and twist the length, bringing it back across the back of your head and tucking in the ends.

Pull your hair into a sleek, low ponytail. Use a brush to comb your hair back into a sleek ponytail. Try doing the bottom half first, then brushing back the top half and combining it with the existing ponytail. Make sure the level of your ponytail works with the position of your hat.

Slick it back for men. Whether your hair is long or short, straight or curly, a slicked back look works well with most hat styles. Apply some hair gel to your hair right after washing it, and smooth it back across the top of your head and down in the back. Let your hair dry a bit and then add the hat. If you don't have any gel, pomade or mousse may also work. You can comb it back with a brush or comb for an extra sleek look. This look works well with fedora hats.