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Fashion Challenge: Make Your Sperrys Stylish


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
Jeans, Sperry’s, Cardigan, Cami, Scarf

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
Cargos, Sweater, Tank, Sperry’s, Headband

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!

Posted on on January 20, 2011 / Filed Under: Fashion Tips / Tags: , , , , ,

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40 Responses to “Fashion Challenge: Make Your Sperrys Stylish”

  1. 1
    January 20th, 2011 at 11:36 am

    I LOVE sperrys. A couple years ago, I found a pair of wedged cute sperrys that were navy with ribbon strung around them. They were about 10 dollars, as it was black friday, so it was a great deal, but the store I got them from only sells kids shoes now! Sad day. But I’ve worn them so much that they’re coming apart, so I’m thinking about getting another pair of sperrys, but the more classic version.
    I love reading this blog, even though I’m in high school! So excited for college.

  2. 2
    January 20th, 2011 at 12:14 pm

    I loathe these shoes with a passion.

  3. 3
    January 20th, 2011 at 12:35 pm

    I just got a pair of yellow canvas Steve Madden boat shoes from endless … AMAZING! They fit my feet better than the uber narrow Sperrys I’ve tried on, and I like the canvas material because it feels more casual. I love both outfits you put together, they really show how easy it is to wear boat shoes in the winter!

  4. 4
    January 20th, 2011 at 12:41 pm

    These shoes “Sperrys” are call dub’s or decks in Ireland and are worn wit school uniforms, some people wear them wit tracksuit bottoms or jeans around college!!!also seen as a preppy thing here!!but there r unisex both guys and girls were them, there were 1st only made in mens sizes but after high demand they started to make womens sizes. Mad!!!

  5. 5
    January 20th, 2011 at 12:50 pm

    i bought a pair of these last summer n i love them….i dont really see many here in so cal but they r still one of my favs!!

  6. 6
    January 20th, 2011 at 12:51 pm

    These were literally EVERYWHERE in 2010 in Denmark – both men and women wore them in all the different colors. I am a bit tired of them now, but they did look good on the stylish guys!

  7. 7
    January 20th, 2011 at 12:55 pm

    I love the first outfit!!
    Something I would wear for sure!

  8. 8
    January 20th, 2011 at 1:08 pm

    I’ve always wanted a pair of these but didn’t have the money to in the summer. Considering they’re waterproof, they sound like a great investment to make now during the winter! I’ve had my eye on a floral pair… NEED TO ORDER NOW.

  9. 9
    January 20th, 2011 at 1:22 pm

    I love, love, LOVE my Sperry’s. I’ve had the same pair for over 2 and half a years (the classic tan leather), and they’re still holding up great. They’ve survived a semester abroad, two summers of being worn nearly everyday to work, and numerous wet & rainy days. Initially, I was turned off because they were somewhat expensive, but they have held up so well and are extremely comfortable. They are my favorite causal shoes, and I wear mine at least once a week year round.

  10. 10
    January 20th, 2011 at 1:24 pm

    All about the label, just like the North Face jackets.

  11. 11
    January 20th, 2011 at 1:51 pm

    I have never seen these in the UK apart from on my uncle! I wouldnt have thought of them as stylish things, but i kinda like them here…i might have to get a pair to try!

  12. 12
    January 20th, 2011 at 1:51 pm

    Hello I just wanted to comment on your blog, this is my second time going on your page. & I LOVE IT! <3
    I get so many tips here, I literally went looking page by page reading your blog as if it is a Magazine!! I didnt read the whole thing, but up to 40 is enough!? haha LOVE YOUR BLOG keep up the great work ;)

  13. 13
    January 20th, 2011 at 2:09 pm

    i got a pair of these on for my birthday that are red tie-dyed…i always get people asking if i did them myself (which would have been awesome). i wear them with pretty much anything, but if people are buying the tie-dyed model, they should know they’re not super comfy. i love them anyway, and they would look cute with both outfits. i love the first one especially…those jeans are amazing.

  14. 14
    January 20th, 2011 at 2:17 pm

    The Angelfish style is much more feminine. I have those and they are so adorable!

  15. 15
    January 20th, 2011 at 2:39 pm

    Even though I’ve been hearing about these on the internet forever, I have never actually seen anyone wearing them. Uggs are popular at my college, but most students are wearing sneakers or moccasins.

  16. 16
    January 20th, 2011 at 3:09 pm

    Love, love, love that first outfit!

  17. 17
    January 20th, 2011 at 4:19 pm

    I have some vintage Sperry’s that I found at a flea market, never been worn, SIX DOLLARS! They are an awesome camel color and I love them. I just ordered some dark brown rugged looking ones that have studs all over the top from Zappos and I can’t wait until they get here.

    The key I think to Sperry’s is not wearing them with predictable outfits. I often mix mine with military style outfits and they look great.

    Great post, CF!

  18. 18
    January 20th, 2011 at 6:15 pm

    These are so, so cute. I especially love the tan ones in the very first pic.

  19. 19
    January 20th, 2011 at 8:56 pm

    I love my sperrys. They are so comfortable. I have the ubiquitous tan pair, but I see sperrys as a basic shoe, not a statement shoe so who cares if other people have the same pair as me? Other people have white button down blouses or black pants or other basics! Its all about what you wear with the shoes. I don’t think their price tag is too high since they last a long time and are comfortable.

  20. 20
    January 20th, 2011 at 11:09 pm

    I love sperrys! i have black glitter ones and i cant wait to wear knee highs and mini skirt! i would love an outfit suggestion tha involves black sperrys and a mini skirt

  21. 21
    January 21st, 2011 at 12:27 pm

    Thanks Chelsea!
    I have been waiting on this post!!! I absolutely love the top outfit and was pleased to realize I have a very similar outfit out of some clothes I already have! I agree, even us girls who love our dressy heels and outfits sometimes wake up needing a break. It is nice there are some things we can turn to besides an oversize hoodie and sneakers! (not saying sneakers are bad! lol) I really love College Fashion and visit the site often! I love it when you take items that a lot of people already own and find ways to re-vamp them and come up with cute new ways to wear them! Thank you!

    Whether people like to admit it our not…most people own Sperry-like shoes, A North Face or similar brand jacket, and Ugg boots…yes, girls…we know they are lurking in your closets…but at least we can take the challenge of making them more fashionable and wearing them in your own unique way…instead of just blending-in on those “lazy days.”

  22. 22
    January 21st, 2011 at 6:46 pm

    sperrys arent suppose to be “stylish” there suppose to be classic.

  23. 23
    January 22nd, 2011 at 12:02 am

    I go to an all-girls private, Catholic high school in the south and sperry’s are part of our “dress uniform” for mass.

  24. 24
    January 23rd, 2011 at 4:48 pm

    I still haven’t figured out whether or not I like these shoes yet. They may be too preppy for me. I’ll have to try on a pair to see whether or not they work for me.

  25. 25
    April 8th, 2011 at 3:47 pm

    I love sperrys! In Annapolis they are a staple to everyones wardrobe.

  26. 26
    August 13th, 2011 at 2:26 am

    Interesting read!!! Your website is fantastic with informative content which i like to add to my favourites.

  27. 27
    November 3rd, 2011 at 1:01 am

    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 :)

  28. 28
    January 19th, 2012 at 5:14 pm

    TOMS are also another great shoe that can be worn with basically everything. I love my TOMS and my Sperrys. (:

  29. 29
    May 21st, 2012 at 11:53 am

    I love my sperrys. i have a beige pair but i just don’t know what to wear em with. im wearing a pair of denim shorts and a croped top racer back tank with black and stripes on it with a beige racer tank underneath. does that look good together. i need help styling!

  30. 30
    January 8th, 2013 at 7:48 pm

    I love Sperry’s, and I love these cute ideas! So perfectly cute and creative! Thank you, College Fashion!

  31. 31
    January 13th, 2013 at 1:42 pm

    I was reviewing and saw the blog on sperrys or boat shoes. Love the outfit with the jeans, carnigan,cami,and scarf. Where can i find this outfit?it would look great with my silver sparkle sperrys!!!xan you tell me what store orbrand these are from?

  32. 32
    March 16th, 2013 at 6:23 pm

    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!

  33. 33
    April 3rd, 2013 at 11:40 am

    I’m not sure what to wear with my silvery sparkle sparrys though

  34. 34
    September 14th, 2013 at 12:40 pm

    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!!

  35. 35
    May 7th, 2014 at 7:46 am

    i am in need of these tips and tricks as thinking of what to wear and what the shoe style i choose

  36. 36
    August 2nd, 2014 at 12:50 pm

    God loves you

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