Preppy College Outfits for Class and Library

Olivia T asked sent me a question asking me about preppy outfits.

She asked: “i have a question…

i’m a senior in high school and i’m getting ready to graduate and go to college, anyway…i have a wardrobe full of preppy clothes however i can never seem to put together a preppy outfit. can you give me some outfit ideas so i can be my complete prepster self before i move away to college ? :)”

My number one suggestion is to only wear clothes that you’re completely comfortable. The whole “You have to suffer for beauty” idea does not apply to getting dressed for class or to study in the library. If your jeans are too small, your shoes give you blisters, or your sweater itches, you won’t be able to concentrate on your work. At the same time, this doesn’t imply you should wear sweats and hoodies everyday. Sweats and hoodies have a time and place though (snow days for instance!).

Here are some preppy clothes ideas that I put together on Polyvore.


Spring Weather Class

Spring Weather Library
Fall Weather- Class

Fall Weather Library

Cold Weather Class
Cold Weather- Library
Some College Prepster Preppy Outfit Staples:

Sperry Top Siders
Jack Rogers
Riding boots
Ballet flats
Hunter Wellington

Skinny jeans
Corduroy skirt
Lilly skort
J Crew critter shorts

Lacoste polo
RL Oxford shirt
Target White Tee*** (I have like 5 and wear them all the time!)
J Crew Tank top

Cable knit
Cardigan (monogrammed of course)
J Crew patterned

Burberry quilted
J Crew pea coat
RAIN JACKET (essential!)

When in doubt- any outfit can be instantly be made more preppy by adding pearls! A grey college t-shirt looks pretty and preppy with a headband and some pearls!

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A fashion designer, a fashion consultant…so…in the summer when you are home, start a little business as a personal shopper! I am aware this is not a new idea, but a very lucrative business for someone with shopping know-how. I bet you would have a large clientele for the college bound girls.


Since feeling good in your skin is just as important as what you're wearing…could you do a health/diet post? Just explaining what you eat in a typical day/daily exercise/tips, stuff like that. Thanks!<3


Love these outfits! I too am a huge fan of JACK ROGERS. Did you know they expanded to making more shoes? I bought a pair of their ballet flats on their website and I'm so happy bc I can wear them year round. Check it out:


I love being preppy and I agree headbands make any outfit cute. I also am obsessed with Jack Rogers new website Thanks for letting me know! I just bought a pair of ballet flats and hi wedge navajos. I like the extra height.


I think you took a peek into my wardrobe! I have another fashion question…what do you recommend for going out outfits? I'd love to stay classy while still looking cute enough for parties, but always have trouble picking out outfits at night. Any suggestions?


I love this post! I hope you had a fabulous weekend!
Check out my recent blog post when you get a chance- I tagged you for an award!



I'm really allergic to cotton. Any suggestions? I want to look preppy, but everything is just made out of cotton! Like…helloooo if I'm going to spend $69.50 on a Ralph Lauren button-down I'm pretty sure it should be better made.

Also, my daughter told me she yelled at a girl in her third grade class today who said pink and green were stupid. I mean what a dumbass, right?!?!? Prepsters: 1, Ugly children: 0

Olivia T

This is fantastic, just what I was looking for!! THANK YOU SO MUCH! You're blog is the greatest. Keep up the great work <3


Seriously, I just fell in love. I am sooo getting this outfits! Can you pleaseeeee make more outfits for class? thank you!! You're amazing! 🙂

Brianna Marie

These outfits are so cute! I currently have a semi-preppy style but this school year I'm going all out:) Time to show these New England Public School-ers how to really dress!


Okay so I know that I am totally late but I love love love the outfit selections above. Even a year later I am so excited to mimic the warm weather class option. Thanks!!!!!