Accessorize: Baseball Hats


I love baseball, and I love baseball hats. While a fedora or an oversized floppy hat can feel glamorous, a baseball hat stays where it’s supposed to be, keeps the sun off your face and is as cute as it is sporty. Years ago, when I worked at a boutique in Philadelphia, we had a client named Judy. She came in every few days wearing her Tommy Bahama baseball hat with “Relax” embroidered across the top. I thought it was the cutest thing ever. I bought my own and wore it for years. They are perfect for long beach days, painfully long days at amusement parks, or rigorous hikes.

My husband and I are headed to Napa and Sonoma in a few weeks. We have a day set aside to bike ride around Sonoma, stopping at wineries along the way. (We may be strapping our bikes to the back of an Uber car to get home!) I was going to bring one of my favorite fedoras but had a vision of it flying off my head mid ride. That’s when I thought of a baseball hat. You can pull your hair into a pony tail, keep it off your face and be low maintenance all day long.

Baseball hats have been popping up on the trend radar for quite a while. You can find them in every form, from overpriced designer to leather, to beachy and casual. Below, a few of our favorites:

We pulled a few that can fit any style, budget or personality.

Madewell quilted cotton baseball hatMadewell Quilted Cotton Baseball Hat, $16

This is my choice.  It’s simple, it’s casual and it goes with everything.  It’s also under $20.  Done.

 Gucci original gg baseball hat with web detailGucci Original GG Baseball Hat with Web Detail, $285

This is what my best friend would wear.  She’s a designer girl.  If she was a race car driver, Gucci would be her sponsor.  This is the same best friend that came to Disney with us and wore a Gucci back pack.

Lucky Brand ZIG ZAG STRAW BASEBALLLucky Brand ‘Zig Zag’ Straw Baseball Cap, $9.99

Neutral with a twist.  I love the pattern. Also available in black.

MLB Baseball HatMLB Baseball Hat, $39

It pains me to list any team other than the Phillies, but it’s hard to argue how perfect a lived in baseball hat can be.  Bonus points for supporting your team.

Apt. 9 Metallic Straw Baseball HatApt. 9® Metallic Straw Baseball Hat, $12

A little metallic with a little texture and still a neutral.

J. Jill lightweight baseball hatJ.Jill Lightweight Baseball Hat, $20

This is a lovely option that looks like one of the more expensive options out there.

Faux Leather Baseball HatFaux Leather Baseball Hat, $16

Don’t spend your money on a leather baseball hat.  If you want to try out the look, go for the $16 version.

Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

  1. I love that you like baseball caps! I’m consistently disagreeing with my step-mom who thinks they are gauche. Maybe its a Southern thing with her but I where I grew up (not the South) they were the epitome of casual, sporty practicality. Then maybe, it is just her own prejudice. Either way, I love them and have many, in a variety of “fanciness”. Thanks for the enabling…

    1. My pleasure! I think they will always be on the far end of the casual spectrum, but you can still look chic even when you’re being sporty.

  2. I super love this post and yes… I would absolutely wear the Gucci one! I love the options for everyone – such a great blog and so many great choices~ your blog is one I LOVE to read daily and share with anyone who wants to look more stylish and feel more fabulous.

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  • Actual footage of me going to my workout this morning. #workout #fitmom #fitpregnancy #mondaymotivation (lol) #idontwanttodosplitsquats

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