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Rocking Hats with A Short Haircut!

Happy Fall Everyone!

The Fall is my favorite season from a fashion standpoint because we add layering pieces such as jackets, boots, and accessories, including hats. As a woman who rocks a short haircut, finding hats that warm my head, especially ones that don’t look too masculine and fit correctly.

My hair has been cut in a short fade since 2006, and developing my hat collection has been a roller coaster over the years. Depending on your head size and shape, determine the type of hats that work best for you. Additionally, hat fabrics are also important.

Caps/ Trucker Hats

Hats are great for cold weather days, but also when I am in-between haircuts. I used to shy away from wearing caps because I did not want to look like a guy. Over the summer, I found a cool hat at Pack Light, a consignment shop in Washington, DC. The cap showed the word Black and a picture of a sheep. As the 3rd child of 4 siblings, I would technically be the middle child; however, I am the only girl! Standing out using my fashion style could also make me a black sheep, which doesn’t bother me. The hat is from Goorin Brothers, which has a collection of hats with catchy illustrations. I also purchased another hat that reads Queen Bee that I rocked during my last shopping trip with my best girlfriends.


Beanies are also a great hat to wear during the Fall and Winter months. However, as a woman, wearing the beanie straight down on your forehead is not the most flattering. I have learned to style my beanies by pushing the hat further back from my forehead to make to be more slouchy. I also make sure that I wear statement earrings to complete my look. I have purchased beanies from Goodwill and even have a custom with my initials or crocheted from small black businesses.


Last year, my girl Fia of Fia’s Fabolous Finds in Petworth, DC, sold Kate Spade unique earmuffs. I never thought that I could wear earmuffs, but the cool design includes pearls and bows. My ears were very toasty even on a wintry day. Rocking earmuffs can also help if you are concerned with ruining up a hairstyle!

It’s time to build up your hat collection as the temperatures cool down. Please share your new finds!

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