Satiate the hard-to-shake craving of new duds for a new school year by keeping your eyes on your own paper this season and ignoring copycat trends; focus instead on building out core school uniform–inspired staples. These solid pieces will serve as the ABCs of a year-round wardrobe, intended to be paired with other essentials or items with a little more flair. And what better way to drill down on the basics than with a “required wardrobing” shopping list?
To prepare this, we hit the literal books, tapping the satirical and now-iconic The Official Preppy Handbook, which was originally published in 1980 to poke fun at elite Ivy League style. Somehow, the joke landed differently and had the reverse effect—The Official Preppy Handbook actually became a serious reference for adopters of this lifestyle and way of dress. And thus, preppy staples were written into stone.
Over the past 70-or-so years, school uniform silhouettes have served children and adults alike well, with slow tweaks of reinvention here and there. Elitist no more, these go-tos have touched every style and taste high to low—many more of a nod to preppy than a full-on ode to its snobbish and exclusive past. As with all mainstay trends, it’s important to acknowledge the origins but propel them forward with edgy and unexpected details. On this list you’ll see touches of animal print, oversized proportions, workwear details, and unique textures woven into the classics. Many of the pieces featured also are made up of regenerative wool, organic cotton, and viscose–long-lasting pieces that hold up well, as they will be sure to rotate heavily in any closet.
However they intend to be worn, know that this roundup of stylish straight-A options is definitely as smart as it looks.
The Blazer
Boden
Boden Marylebone Ponte Blazer
The foundation of most uniforms, the fitted blazer is a key wardrobing piece for preppy dressing. This classic navy number from Boden boasts a sustainable viscose ponte that’s both sturdy and stretchy for maximum comfort.
The Pleated Skirt
Reformation
Reformation Mina Regenerative Merino Pleated Skirt
You can’t spell preppy without “knife-pleat skirt” (just ask any English major), and Reformation’s Mina in a lightweight regenerative merino is equal parts classic and earth-friendly. Pair with any of the tops mentioned in this roundup for an instantly timeless combo.
The Rugby Shirt
Rowing Blazers
Rowing Blazers Men’s Cotton Rugby Shirt in Starboard Stripe
A heavyweight rugby shirt is the ideal layer for September weather, with chilly mornings and sunny afternoons. Rowing Blazers does them perfectly, in bold and playful color combos that read a little more fashion than sport. Style tip: Going oversized looks effortlessly cool and is supremely comfortable.
The Argyle Sweater
& Daughter
&Daughter Ava Argyle Crewneck
Buzzy brand &Daughter has gained a cult following for their vintage-inspired (but extremely luxurious) knitwear. And their take on the argyle sweater is super covetable. This graphic preppy classic will be on serious rotation in my closet all fall long.
The Penny Loafer
Boden
Boden Nya Penny Loafers
Boden’s classic loafer shape gets a quirky makeover with colorblocked red and leopard accents. Leopard is indeed a neutral in our book and gives any overtly preppy look a bit more of a rebellious edge.
The Striped Button-Up
Gap
Gap Organic Cotton Poplin Big Shirt
Gap’s organic cotton oversized shirting feels both crisp and cooling—just what’s needed from a button-up. Stripes are more versatile than you’d imagine, especially when layered under a solid sweater or over a turtleneck.
The Polished Backpack
Lindquist
Lindquist Cyl in Leather Brown
Rhode Island–based line Lindquist designs with longevity in mind. Made in small batches by a nimble team in Providence, the Cyl backpack is the timeless hands-free option I wish I had back in high school.
The Khakis
Ralph Lauren
Ralph Lauren The Ricky Pant
How could I not include the Kingpin of preppy style, Ralph Lauren, in this list? His hybrid of classic khaki and study workwear pants in the iconic Ricky shape (aptly named after his wife and muse) feels like a fresh take on this staple that is so right for right now.
The Knee Socks
Baserange
Baserange Overknee Socks
It might feel a little on the nose, but a chic cotton knee sock is a fun accessory to experiment with. Try pairing these playful yellow ones with a mini skirt, but add an extra-oversized sweater or shirt to balance out the proportions.
The Tote
Bottega Veneta
Bottega Veneta Andiamo Tote
Bottega Veneta’s grown-up take on the boat tote is a tongue-in-cheek version of the classic style with a signature intrecciato leather strap that offers various ways to wear it. Monogramming is also available and feels almost mandatory.
The Pearls
J. Crew
J. Crew Freshwater pearl necklace
The rugged shape of these freshwater pearls rough up the idea of your mother’s strands. The organic, hippy feel reads less fuddy-duddy and more effortlessly classic.
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