polo shirt outfit

Prepster Meets Chic: Styling a Polo Shirt

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I have to admit- I’m not a huge fan of polo shirts. Well, at least going into the making of this post I wasn’t. They’re a little old school and remind me of all the preppy people back in school that thought they were way cooler than me haha.

Which hey, wasn’t that hard because I was the first person in my grade to beat the 100 Book Reading Club and they had to create a new list of prizes for me. My teacher actually had to make me go outside for recess because I just wanted to stay inside. So yeah, I guess you could say I probably wasn’t the coolest kid on the block.

But why do a post about styling something you don’t like? Good question. I thought it’d be a fun challenge to take a style I don’t really like and see if I can make it chic!

If you search “polo shirt” you come up with a gazillion ways for how to wear a polo shirt for guys. Polo shirts aren’t usually thought of as a staple in a woman’s wardrobe. When you think of a polo shirt you might think of old school days, prepsters, rich college kids, or what you wear when you are actually going to play polo (at least that’s what my husband thought hehe).

Styling a Polo Shirt

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I chose to pair it with a faux leather skater skirt to add a little bit of edge to an otherwise classic top and a big ol “look at me” necklace because it never hurts an outfit to throw a little bling on it 😉
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These thigh high socks are a nod to the typical prepster look. But I paired block heels with them instead of going with an oxford or riding boot because I wanted this pairing to keep you guessing. Are they boots? Socks? Is it a bird? Is it a plane?

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These socks are actually from the very first collab I ever did and I still break them out each fall season!
polo shirt outfit
polo shirt (similar here) | skirt (Kohls, similar here) | necklace (similar here) | heels (Target, similar here) | socks

The point of this post was to show you a new way you could wear a polo shirt and how you can make it look chic! But by the end of doing this post I gotta say, I converted myself haha! I’m also seeing that chic is only the first step. I think putting together a cute fall preppy look would be fun!

In other news, Thanksgiving is just a day away! Are you going for a look that’s comfortable or preppy chic like in this post? Still in need of ideas? You can check out this post I made last year about Thanksgiving outfit ideas!

Now this is the part where you’re supposed to get all sappy and thankful about everyone and everything 😉 I’ll try to spare you the dramatics, but THANK YOU for coming by, reading, commenting, and all your great feedback. Couldn’t do it without your support. So this year I’m thankful for you.

I hope you have a great day with loved ones tomorrow!

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polo shirt


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making mychicobsession.com a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.