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.
-
I’m Bored With My Closet—These 33 ChicReplica Store Pieces Have the Power to Turn Things AroundEffortless and expensive-looking is the vibe.
-
Every Fashion Item I'm Already Eyeing for Fall 2025It's never too early.
-
I Just Got Back From NYC, and Now I Want to Order These 7 Trends From ReformationMy cart is very full.
-
TheReplica Store Anniversary Sale Is an Editor Favorite—Here's What's on Preview so FarEarly access starts July 8.
-
Believe Me—You'll Still Want These 36 Items in 2026 (and '27 and '28)Timeless with a capital T.
-
Let Me Cure Your Zara Fatigue One Chic Massimo Dutti Find at a TimeFrom summer-sale deals to brand-new arrivals.
-
It's Your Last Chance to Get an Extra 70% Off J.Crew's Big Summer Sale —These 28 Items Will Go FirstShop the chicest sale selects ahead.
-
A Rich-Looking Closet Is the Goal—31 Amazon Picks That Surprisingly Fit the BillBring on the compliments.
