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Favorite Hats + Hat Hairstyles Round Up

September 16, 2021

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I love wearing hats—especially because I typically only wash my hair once a week, and a hat does a great job of extending the life of a hairstyle without having to start fresh. So today I want to share some of my favorite hats with you!

1. Under Armour Hat

This is my very favorite athletic hat. Whether I’m playing pickle ball with friends, headed to a soccer game, or working out, it’s the perfect hat for the occasion. It’s made from a sporty, moisture-wicking material that’s great for when you’re working up a sweat. It’s neutral and the logo isn’t too in-your-face, so you can easily dress it up or down.

2. Casual Outfit Hats

These Madewell hats go well with casual, everyday outfits. They’re a little more dressy than the athletic hats, but definitely not too fancy. I like the fun detail of the adjustable leather strap on the back. They don’t have any logos and come in several neutral colors, from khaki and cream to black.

3. Corduroy Hat

This brown corduroy hat is my favorite for fall and winter. I found it at a Gap outlet awhile ago, and though it’s no longer sold there, I did find a lookalike from J.Crew Factory! I think it’s a great, unique accessory for the colder months.

4. Denim Hat

I used to own a denim hat from J.Crew that I loved, so I was excited to find this similar style on Amazon recently. It’s a comfortable, distressed denim that looks worn-in from the beginning. It comes in tons of colors and fits really well. I will probably be ordering more colors soon because I love it so much!

Hairstyles for Hats

Now that I’ve shared my favorite hats, I figured it would be a good time to talk about hat hairstyles! I’ve discovered a few looks beyond the basic ponytail that work well with all of my hats. So here they are!

1. Wavy Hair Down

loose wavy hair down

Sometimes I have a bit of greasy hair on top, but still have fresh-looking curls on the bottom. In this case I like to wear my hair down with a hat. It’s amazing how much it hides! Pro tip: Make sure you pull some hair in front to cover your ears before putting on the hat—otherwise it will look a little weird.

2. Loose Side Ponytail

loose side ponytail

If my curls aren’t looking as fresh but I want to still show some of my hair in front, I pull my hair to one side into a loose ponytail. I pull the elastic tight so it hits up to the back of the hat and also pull out a little bit on the other side. This way I still have some hair showing in the front, but I can mask hair more and still look pulled together. These gimme elastics are my favorite for a strong, comfortable hold that doesn’t crease your hair.

3. Side Braid

favorite hats + side braid

When my curls are really just done, I like to braid my hair off to the side. I like to put the hat on first so I know exactly how to position the braid. Then I pull my hair to the side, divide my hair into three sections, and braid with the hair facing forward. I secure the bottom with an elastic and then pull the sections apart a little bit to make the hair look thicker.

4. Classic Ponytail

favorite hats + classic ponytail

Another go-to way to wear my hair with a hat is in a classic ponytail in the back. I usually put the hat on to figure out where the ponytail should go, then take the hat off and secure the hair so it can pull through the back of the hat. Sometimes I pull out a few pieces of hair in the front to soften the look.

5. Elastic-Free Ponytail Hack

elastic-free ponytail hack

There have been many times when I’ve worn my hair down with a hat, started getting hot, and realized I didn’t have an elastic to pull it up. So I was excited to learn this tip from my friend Abby: simply pull your hair back behind you, twist it around, and then tuck it all into the back strap of the hat. You can also pull it all the way through to keep it more secure. It’s genius!

Try These Hat Styles at Home!

So that’s my complete roundup of favorite hats and hairstyles. I hope you found something you liked and can more easily enjoy a life of washing your hair once a week like I do!


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I like to hang out on Instagram and share more in-depth tutorials on everything I make, create, and organize.  Come be a part of our Home & Kind Instagram community.

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