Cutest Hat-Friendly Hairstyles for Women

  • , by Alex Torres
  • 2 min reading time
Cutest Hat-Friendly Hairstyles for Women

Hats and hair have historically had a complicated relationship. After all, the term “hat hair” literally refers to hair that has become rumpled and unruly because someone was wearing a hat.

But wearing a hat doesn’t have to be synonymous with a bad hair day. With some planning and the right coiffure, you can create a look that’s stunning and stylish. Here are some of the cutest hat-friendly hairstyles for women to get you started.

Straight and Sleek

As far as simple hairstyles go, it doesn’t get easier than letting your hair hang loose. And, sometimes, simple is the definition of stylishness. Wearing your hair down is a style that works with a wide variety of hats, especially baseball caps, berets, newsboy hats, and bucket hats.

If you’re worried about getting that annoying hat-hair dent around your head, there are plenty of ways to avoid it. First, don’t put on your hat while your hair is still wet. Also, you should ensure you aren’t wearing a hat that is too small for your head. If you can fit your index finger between your head and the brim, you should be okay.

Buns and Ponytails

The bun or ponytail is great for a quick hat hairstyle, especially when you have full, high-volume hair. But just because a hairstyle is easy, that doesn’t mean it has to look lazy. Try one of these looks if you want to dress up your bun or ponytail:

  • Run your ponytail or bun through the hole in the back of your hat when you wear a baseball cap.
  • Use several ponytail holders to create a “bubble” ponytail.
  • Add an accent braid to your ponytail.
  • Make two buns instead of one.
  • Add a ribbon to your ponytail.

Pro-Tip for Curls

If you have tight curls or natural hair, another option is to try to create a bun tucked inside your hat, leaving only your bangs visible from under that hat. This fun look is perfect for keeping your hair from touching your neck in the summertime.


There are myriad ways to wear braids and almost as many ways to wear braids with hats, regardless of your hair texture. If you’re looking for some cute, braid-centric, hat-friendly hairstyles for the ladies, consider one of these:

  • Braided side ponytail
  • Low braided pigtails
  • Box braids
  • Cornrows
  • Accent braids
  • Wrap-around Dutch braid

The trick to wearing braids and a hat is making sure your braids fit under your headwear. You may need to switch to different hat types for different hairstyles in some cases. For example, you may need to wear a hat that sits further back on your head for a wrap-around Dutch braid.

Are you looking to reconcile your hat and your hair? Check out our collection of ladies’ fashion hats to find a hat that fits your hairstyle today.

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