Fashion Challenge: Make Your Sperry’s Stylish (Tips and Tricks)

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Sperry Top Siders

Since you’re reading CF, there’s a good chance that you’re not one to blend in with the crowd. That said, there are a handful of products that have struck a chord among the college crowd and formed somewhat of a cult following with people our age. A few weeks ago, I covered North Face jackets, and this week I decided to take on something you probably have sitting in your closet as well — Sperry’s boat shoes.

Boat shoes, also called topsiders or deck shoes, have rubber soles that are cut in such a way to prevent slippage on a boat. They’re often made using water-resistant leather or canvas, and originally became popular in the preppy northeast. Now, these shoes are really popular across the country, notably in southern states.

These shoes feel natural when paired with shorts, so they’re a summertime staple. But here at OU, they’ve developed a bit of a bad rep for being associated with the “uniform” as I like to call it — you know, black leggings, Nike shorts, a v-neck t-shirt and a fleece jacket. Many of us would agree that they’re a better choice than popular Uggs, but still probably wouldn’t call them uber-stylish. That said, these preppy, ubiquitous shoes can easily be incorporated into stylish outfits, and this week’s challenge will help you do so! Wanna learn more? Read on!

Tips and Tricks for Putting Style into Boat Shoes

  • If you’re buying a new pair of boat shoes, look for unusual colors. Sperry’s come in plaid, navy, olive green, and canvas material, so don’t feel like you have to buy the cookie-cutter tan pair that everyone seems to have.
  • There’s a good reason why these shoes are so popular — they’re both comfortable and durable! On Spring Break a few years ago, let’s just say I decided that running into the ocean fully clothed was a BRILLIANT idea. My delicate tank top was ruined from the sand and salt water, but my Sperry’s still look great. So don’t worry too much about wearing them in less-than-stellar weather. They’ll hold up just fine.
  • These shoes are great to walk to class in and look exponentially more stylish than going to class in running shoes or Shape Ups. They provide more coverage than most pairs of flats, so they’re perfect for chilly winter months. They’ll look just fine with any casual outfit.
  • Another awesome thing about these shoes is that they work with any type of jeans, from skinny to boyfriend to flared! (For suggestions on how to wear them without jeans, check out this post!)
  • Don’t get down on yourself for giving your feet a rest every now and then. I prefer heels, but no one’s feet are shaped like Barbie’s! These are a good option for walking across campus or running errands.

Outfit Inspiration

How to wear sperrys


At first glace, this might come off as a preppy yet plain outfit with a simple pair of jeans and cardigan — but you can add interest to it by mixing prints and pairing a floral camisole with a plaid scarf. This look would be perfect for a laid back day at the library.

How to wear sperry topsiders outfit idea


This outfit is trendy but still comfortable and laid back. If you don’t already own a pair of skinny cargo pants, I highly recommend them — they’re an easy way to break up blue jean boredom and add style to basic pieces. Find a comfy fitted tank top, and layer a distressed sweater on top. Finish with your boat shoes and a cute headband.

Rocked the Challenge? Send Us Your Photos!

Did you take an ordinary pair of boat shoes and incorporate them into a faboosh outfit? Before you change clothes, whip out your camera and take a few photos! Send them to fashionchallenge AT along with your name, school, a description of what you’re wearing, and the URL of your blog if you have one. We’ll post pictures here to inspire other CF readers (see examples here and here).

I can’t wait to see what you girls do with the challenge!


Are boat shoes popular at your school? Do you own a pair, or do you prefer another kind of casual shoe? What other items are really popular at your college? What future fashion challenges would you like to see? Leave us a comment and tell us what you think!

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5 thoughts on “Fashion Challenge: Make Your Sperry’s Stylish (Tips and Tricks)”

  1. Sperry’s are very popular at my school. Boys and girls love them. I absolutely love them! they are so stylish and comfy! They are kind of pricey but totally worth it!!

  2. I’ve noticed that there are “more open” sperrys. Like the Angelfish. I got the navy Angelfish ones and I LOVE them! I usually wear them with those thin see through socks with skinny jeans and my northface tight at the bottom. Definitely recommend!

  3. Sperry is now made by a different company and even tho they cost the same the new ones fall apart and look cheep… so fyi take care of the pair you have 🙂


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