How to Wear Your Hair With a Hat

Hats are such a fun way to add versatility to your wardrobe and they come in so many shapes and styles. But if you have long or medium-length hair, it might be hard to know how to wear your hair with a hat. Be aware that wearing your hat could give you dreaded “hat hair” once you take it off, so plan to wear your hat to places where you can keep it on. Changing up your hairstyle can add even more looks to your hat wardrobe. Here are some ideas for how to wear your hair with a hat.

Hot Tip for Styling: Put your hat on before you style your hair, that way, you can see how the hair falls to pull it into the style.

Hat with a low ponytail

You can’t really do a high ponytail with a hat. Put your hat on, gather your hair into a ponytail, pull an elastic around it, then tighten to how high or low you want it to sit under the hat. I like to wear a side ponytail so you can see my hair. Another spin on this is to do a pom-pom pony. Put elastics about two inches apart down your ponytail. As you put each one in, pull the hair in the middle, from front and black, then side to side, so it creates a round pom-pom shape. Work your way down the length of your ponytail until you reach the end.

Hat with a low bun

Nothing is easier than pulling hair into a bun, especially on bad or dirty hair days. Put your hat on and gather your hair into a low ponytail and tie with an elastic. You might want to pull it tight against your head for this look. Either wrap the pony into a tight bun and pin it with bobby pins or just pull it back through the elastic to create a messy loose, loop bun. Again, I like to style mine to the side so you can see my hair, but you can also do this in the back for a sleeker look.

Hat with pigtails

Pigtails are a classic casual look with a hat, especially with a cowboy hat for a bit of western flair. Put your hat on and gather the sides of your hair together. For a neater look, part your hair down the middle from front to back before putting your hat on. 

Then tie the elastic around the pigtails on each side, check to make sure they are an even length on both sides. For a variation, braid your little piggies and put elastics at the end.

Hat with loose hair

Of course, the easiest way to wear your hair is just to let it hang loose. You can let it hang so it frames your face or push it behind your ears. Keep in mind this may not be the coolest way to wear in the hot summer months because your hair cans start to feel like a big blanket on your head after a while. But it is the easiest!

So now that you have some ideas for how to wear your hair with a hat, what style will you try?

See more of my looks in the Stiletto City blog and my Instagram page.

How to reshape a straw hat

Do you have a straw hat that needs reshaping? Check out this tutorial on How to Reshape a Straw Hat in a Few Simple Steps

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Join the conversation
  • Grandmasue10 Grandmasue10 on Aug 22, 2021

    I like all the looks except the one used in the headline. I always think of Princess Dianna when I think hats. She wore the correctly; low on the forehead. I don't think bangs should show. To me that's like a cute little girl look.

    • Kastle Waserman Kastle Waserman on Aug 22, 2021

      Hi Grandmasue10, thanks for your comment! For a sun hat, I think it can be worn either way. Obviously, you'll want to pull it low on the forehead to shield your face from the sun. I like to wear it tilted back when I'm wearing it more as an accessory. These looks are mainly to show the hairstyle options. As for Diana, Princess of Wales, she was a style icon with everything she wore!