Preppy fashion, derived from the style found at preparatory schools, has kind of a bad rep. Or rather, it has strayed from what it originally looked like and toward obnoxious whale embroidery and an overabundance of gingham. But that's not really what preppy fashion is, and J.Crew—specifically under the helm of its head of womenswear design, Olympia Gayot—has been among the handful of brands to remind people of its origins and fashion codes. Think oxford button-down shirts, classic penny loafers, corduroy, and cable-knit sweaters. It's far more classic than many think.
If you, like me, are far more inclined to dress preppy in this more timeless version of the aesthetic, then today's your lucky day. Right now, J.Crew is hosting a sitewide Black Friday sale that's stocked with everything one could ever need to achieve the preppy look in 2023. From Breton tees to Mary Jane flats, cashmere knits to trench coats, the 31 sale finds below will help you to rediscover true preppy fashion.
This entire look is giving "Ralph Lauren in Bedford, New York."
There are almost too many styling possibilities with this cardigan.
Clean, cool, and ready to be paired with fun socks and a miniskirt.
Oh, this trench is good. It's very good.
For all the inevitable bad hair days in our cumulative futures.
I'm obsessed and buying a pair for everyone I love this season.
Extra fuzzy.
Everyone needs one of these, whether it's for a weekend in the Hamptons, an overnight in the country, or just a day at the beach.
This look will always remind me of Ivy League English professors.
An old money staple.
Dress socks are a staple of the preppy look.
Another must.
I grab for my classic trench far more than any other jacket in my closet.
Barn jackets are having a serious moment right now.
Stripes, stripes, and more stripes.
The perfect everyday jeans—found.
The holidays are here, and that means lots of velvet.
No one does knit jackets quite as well as J.Crew.
This whole look is begging to be copied.
At most prep schools, these are a core part of every student's uniform.
Always say yes to red.
Love is an understatement.
Blazers were meant to be paired with miniskirts. It's just a fact.
Every outfit could benefit from a fun pair of tights during the holidays.
This mini can easily be dressed up and down depending on the occasion on your calendar.
Prepare yourself now for everybody you come into contact with thinking this is a designer bag.
I buy these in bulk every time they go on sale.
A Breton tee with vintage Levi's and a peacoat in the winter—what could be better?
Well, swapping in this coat maybe.
I'm telling everyone I know about these marked-down mesh slingbacks.
Your fellow holiday-party guests won't know what hit them when you walk in wearing this dress.
-
10 Winter 2026 Wardrobe Staples to Gift to Yourself This DecemberYou deserve it.
-
J.Crew Just Released Its Holiday Campaign—Shop Curated Gift Guides for Everyone You're Shopping ForStarring Delaney Rowe, Aki and Koichi Kim, Kareem Rahma, Abby and Baskin Champion, and Terrence O'Connor.
-
I Got My Love for Cozy Sweaters From My 63-Year-Old Mom—Here Are 24 We're Both Eyeing RNSpecifically from J.Crew, Reformation, and Banana Republic.
-
Surprise! J.Crew Extended Cyber Monday Deals—Score 50% Off Best-Selling Last-Chance DealsSo many amazing items left to grab.
-
5 Sweater Styles Every 2025 Winter Wardrobe NeedsOur must-have knitwear list.
-
Hold On,Replica Store Sneakily Extended Its Cyber Monday Sale—These Are the Chic Last-Chance Finds You Won't RegretUp to 60% off fashion finds!
-
Girls That "Get It" in London and Palm Springs Are Wearing This Anti-Denim Pant Trend With Loafers and MulesPlus, they're currently on sale for $60 or less for Cyber Monday.
-
Celebs Love This Specific Denim Style, and It's 40% Off RN—Here Are the Pairs to Buy Before They Sell OutThe most versatile jeans you'll ever own.
