There’s nothing wrong with embracing the “Ivy League Look” – when done right, Lilly Pulitzer’s vibrant patterns or a tapered Oxford shirt can look great (“and you’ll be the picture of grace when you are viewed face to face!”).
But if you’re going to go preppy, you might as well add your own flavor to the standard preppy items. That doesn’t mean to abandon your Sperry’s for a pair of Vans, but mix it up a little bit. Incorporate punk and prep, hipster and the Hamptons.
We came up with some possibilities, and had so much fun pushing the limits of preppy! You’re not obliged to shoehorn yourself into the preppy look, or even our suggestions. Be creative and bold with your outfits.
You can be the next Blair Waldorf: redefining what it means to be preppy as we know it.
Try combining the vibrant Lilly Pulitzer prints with equally colorful iridescent accessories. Instead of the typical statement jewelry, go for a dainty pair of FRENDS earbuds.
- Dress: $45, RENTTHERUNWAY.COM
- Sandals: $18, OFFICE.CO.UK / $290, MODAOPERANDI.COM
- Bag: $24, NEWLOOK.COM
- Phone Case: $15, CLAIRES.COM
- Sunglasses: $125, DOLLSKILL.COM
- Earbuds: $50, AHALIFE.COM
Mini skirts with preppy patterns have become staples of the prep-style spring/summer. Here are two different directions you can go with these cute skirts!
- 2nd Hand Lilly Pulitzer Skirt: $53, CURRENTBOUTIQUE.COM
- Sweatshirt: $220, THEOUTNET.COM
- Nike Sneakers: TENNISEXPRESS.COM
- Backpack: $25, TARGET.COM
- 2nd Hand Lilly Pulitzer Skirt: $65, CURRENTBOUTIQUE.COM
- Top: $15, PINKQUEEN.COM
- Kate Spade bag: $159, TRADESY.COM
- Statement Necklace: $17, NORDSTROM.COM
- Converses: $55, ZAPPOS.COM
- Sunglasses: $84, NELLY.COM
Who says rainy days need to be dull and drab? Break up the monotony with an interesting pattern – like the tropical leaves on this A&F skort or an interesting pair of shades. Wellies and/or Bean Boots recommended.
- Blouse: $38, HM.COM
- Skirt: $20, ABERCROMBIE.COM
- Hunter boots: $150, MOOSEJAW.COM
- Watch: $115, THE-DRESSINGROOM.COM
Sperry Top Siders and polo shirts combined with preppy NO NO NOs. Because why not?
- Polo Shirt: $40, LANDSEND.COM
- PANTS: $52, VERYEXCLUSIVE.COM
- JEAN JACKET: $23, CHICNOVA.COM
- SPERRY’S: $70, ZAPPOS.COM
- Polo Shirt: $25, LANDSEND.COM
- Boyfriend Jeans: $35, LOOKBOOKSTORE.COM
- Shoes: $495, MIUMIU.COM
- Pearl bracelet: $735, BLUENILE.COM
Dare to go where no prep has gone before… bare your midriff! IN THE FALL!
When the weather gets too chilly, cover up with a cape, or a duster jacket (a looser take on the blazer that still maintains a put-together, preppy look).
- Top: $40, ZARA.COM
- MAROON CAPE: $1,370, MATCHESFASHION.COM
- YELLOW COAT: $129, ZARA.COM
- BROWN CAPE: $189, ZARA.COM
- SKIRT: $50, ZARA.COM
- BOOTIES: $77, HM.COM
- HAIR PINS: $14, NORDSTROM.COM
Let’s admit it; Bean Boots and vests are not only preppy, but also two of the comfiest things you can put on in the fall/winter. The simple design of these items leaves space for creativity- like these crazy jeans to combine with them!
- Shirt: $230, NET-A-PORTER.COM
- Sweatshirt: $28, BLACKFIVE.COM
- Vest: $165, JCREW.COM
- Jeans: $345, MATCHESFASHION.COM
- Bean Boots: $109, LLBEAN.COM
“Plaid Skirt” is one of the oldest, and therefore, possibly one of the most boring preppy items. Then again, there’s no such thing as a “boring fashion item” when styled right!
- Leather Jacket: $189, ZARA.COM
- Plaid Skirts: $50, USA.TOMMY.COM
- Tights: $11, MAURICES.COM
- Booties: $190, REVOLVECLOTHING.COM
- Bag: $1,521, BLUEFLY.COM