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4 Outfits Inspired by Preppy Schoolwear


Preppy tie
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I’m sure we can all agree that there’s nowhere quite like a college campus during the fall. With the changing leaves, old buildings, and academic ambiance, I can’t help but feel like I’m at Hogwarts or on the set of Dead Poets Society. Football games and chilly weather especially make me want to bundle up in a peacoat, sip hot cocoa, and figure out how lacrosse works. (In my dear ol’ Oklahoma, sports like field hockey, lacrosse, and rowing are almost impossible to come by.)

These reasons, among others, probably explain why I’m so intrigued by the look and feel of the prep schools I’ve come to know through TV shows, movies, and books. Something about preppy, athletic, and tailored styles leaves me feeling so inspired in the fall!

Below, I’ve put together four prep school-inspired looks for you to rock on your college campus. Enjoy, girls!

A Few Tips on Getting the Right Look

  • Keep it simple. Preppy, “varsity” type looks are characterized by clean lines, tailored cuts, and solid colors. Avoid anything too baggy or tight.
  • Utilize patterns. Horizontal stripes are a staple of this look — think sailor shirts and striped scarves. Plaids and tiny polka dots are good, too, for that preppy, academic look.
  • Play with color. During the spring and summer, preppy style is all about pastels and seersucker material. In the fall and winter, deeper shades like maroon, navy, army green, and charcoal take over.
  • Cuff your pants. An easy way to get some prep school charm is by rolling up your jeans or khaki pants. Rolled up pants look awesome with a boat shoes, Converse, or penny loafers.
  • Rock a varsity jacket. Some girls think letterman jackets feel more “Midwestern” than “East Coast Prep,” but I think that they give off the same classic, throwback, “All-American” vibe that penny loafers and seersucker shorts do. Plus, they look both classic and trendy at the same time. A varsity jacket or letterman cardigan will look great with jeans and ballet flats.
  • Don’t go overboard. A cardigan, plaid skirt, knee socks, loafers, and pigtails worn all together will look more Britney Spears circa 1998 than chic. Make the look your own by adding a piece of edgy jewelry, a biker jacket, or an eye-catching pair of shoes.

Outfit Inspiration

Preppy schoolwear outfit 1
Jeans, Jacket, Sweater, Bag, Shoes, Belt

Nothing screams “prep” quite like a cable-knit sweater and a D-ring ribbon belt. Round out the look with a pair of skinny cuffed jeans (boyfriend jeans would look just as chic if that’s more your thing), a pair of loafers, and a messenger bag. To keep yourself warm, throw on a varsity jacket like this one or grab your favorite trusty peacoat.

Preppy schoolwear outfit 2
Top, Skirt, Boots, Coat, Bag, Necklace, Socks

Although this look is reminiscent of a Catholic school girl uniform, you can put a trendy spin on the classic style by wearing riding boots with your knee-high socks. This shirt is awesome, too, because the Peter Pan collar is already attached! Finish the look with a warm coat, a necklace, and a fun book bag. (Hi, uncle Karl!)

Preppy schoolwear outfit 3
Sweater, Khakis, Tank, Shoes, Earrings, Scarf

Here at CF, we’re crazy about cardigans, and how awesome are all of the popular letterman styles we’ve been seeing lately? Wear a cardigan like this with a striped tank and khaki pants. Finish the look with boat shoes, an infinity scarf, and pearl studs.

Preppy schoolwear outfit 4
Pants, Sweater, Scarf, Shoes, Socks, Headband

Confession: I love turtlenecks! Call me crazy if you want, but I think they look so elegant, wintery, and perfectly preppy. Pair one with tailored trousers and a belt for a classic vibe. Prep the look up by adding a striped scarf, loafers, argyle socks, and a headband. (Lacoste headbands like the one pictured above are crazy hot on my college campus!)

What Do You Think?

Is your style preppy? Do you like adding a prep school vibe to your fall looks? Did you go to private school or a prep school? How did kids at your school dress? What other fall styles are you interested in? Leave a comment and tell us what you think!

Posted on on November 1, 2012 / Filed Under: Inspiration / Tags: , , , , , ,

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17 Responses to “4 Outfits Inspired by Preppy Schoolwear”

  1. 1
    November 1st, 2012 at 1:16 pm

    I’m all over heels in pleated skirts, cardigans, striped t-shirts, blue and white shirts and loafers right now! You are talking like you are in my head! :)
    Look stealed from chic school girl is it for me this fall and I think there si so many ways how to easily rock it!

  2. 2
    November 1st, 2012 at 1:36 pm

    I am the farthest thing from preppy you can get but i would take that 2nd outfit love it, would just add some doc martens instead :-)

  3. 3
    November 1st, 2012 at 1:56 pm


  4. 4
    November 1st, 2012 at 2:02 pm

    I love plaid skirts!
    Glad to see a few on this list. :)

  5. 5
    November 1st, 2012 at 2:25 pm

    I love the 2nd outfit <3

  6. 6
    November 1st, 2012 at 4:07 pm

    I adore the 2nd and 3rd outfits. They kinda remind me of GossiP Girls first few seasons and old Jennys style!

  7. 7
    November 1st, 2012 at 4:43 pm

    Love these outfits! There are actually two prep school fashion tumblrs that I love browsing just to kill time! They feature the typical New England prep school *preppiness* with some funky elements mixed in sometimes.

  8. 8
    November 1st, 2012 at 5:37 pm

    I”m loving the idea with the plaid mini skirt but I despise turtlenecks sweaters. It always leaves me too hot and uncomfortable :(

  9. 9
    November 1st, 2012 at 7:04 pm

    Oh woow!! Best post ever, thanks soo much!
    But i kinda miss the navy/checked blazer! ;)

  10. 10
    November 1st, 2012 at 8:09 pm

    Awesome post! I went to school where there was a uniform, so the whole schoolgirl look is totally familiar to me. I actually just covered a post on preppy/academic/schoolgirl dressing myself. Please go to and look for a post called “Get Your Geek On!” (This blog is generally geared towards girls who dress modestly for religious/personal reasons.

  11. 11
    November 1st, 2012 at 8:39 pm

    I hate the term “preppy” even though that technically describes that certain style of clothing. Maybe because i associate that word with snobs and their lifestyle. But I use a lot of classic and casual pieces of clothing that constitutes the “preppy” style.

  12. 12
    November 1st, 2012 at 11:00 pm

    Great looks! The second one reminds me of Gwen Stacey’s look in The Amazing Spider Man ;)

  13. 13
    November 2nd, 2012 at 9:33 am

    love this :)
    especially the two first outfits , and i have the sàme jàcket from the first outfit ànd the same h&m over the knee socks from the second :D they are so warm and comfy :D it s Nice to see how to wore them best :)

  14. 14
    November 2nd, 2012 at 10:05 am

    Reminds me of my Catholic school days! Aha.

  15. 15
    November 4th, 2012 at 9:24 am

    You had me at Dead Poets Society! *swoon* My favorite movie, really makes me think about my favorite season, changing leaves, back-to-school everything, pumpkin everything… These outfits are amazing and totally capture the feeling of autumn. I love that top with the Peter Pan collar, SO adorable!

  16. 16
    January 20th, 2015 at 5:35 am

    Really it is an awesome post. Also, so useful for all fashionable schoolwears. Products are looking fabulous. Thanks for sharing a wonderful blog with us.

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