15+ Preppy Wardrobe Staples Editors Are Shopping for Fall 2025

“Never underestimate the power and versatility of a blue chore coat. I can wear it with an oxford and tie to the office, or throw it over a t-shirt to run some weekend errands. And it never goes out of style.” —Maxwell Losgar, Senior Entertainment Director

“Boat shoes are back! But chose an unexpected color or text to tone down the uber preppiness, like these olive-colored Alex Mill beauties.” —Dorothy Scarborough, Assistant to the Editor in Chief

“Does it get any more timelessly preppy than a navy double-breasted blazer? This best-selling version from Veronica Beard not only serves as a perfectly polished standalone, it can also be paired with the brand’s interchangeable dickeys for effortless layering.” —Lauren Hubbard, Contributor

“I’ve never been a loafer girl, but Rothy’s shoes are so comfortable I’m a new convert.” —Emily Burack, Senior News Editor

“I’ve noticed an interesting trend at the U.S. Open over the last few years of women showing up more and more in tennis dresses. Personally, I have no hand-eye coordination whatsoever, but I do love the tennis dress look, so I say if you can’t beat ‘em, join ‘em.” —Rachel King, News Writer

“I can’t wait for fall, so I can stock up on these Brooks Brothers french cuff dress shirts, monogram them, and go full prep with Stubbs flats and a cable sweater over the shoulders.” —Leena Kim, Editor

“Nothing gets more preppy than Ralph Lauren, and this blazer is a testament to that. A closet staple and a classic piece you will keep and wear forever.” —Dania Ortiz, Fashion & Accessories Director

“Rugby shirts are all the rage, thanks to Dries Van Noten & Miu Miu. Back to school just got much cooler.” —Hannah Morrolf, Assistant Fashion Editor

“This short-sleeved sweater radiates preppy charm, making it the ideal piece for that sweet spot between late summer and early fall. Back-to-school vibes, anyone?” —Erin Hobday, Executive Managing Editor

“Vest weather is the best weather. I’ll look for appropriate occasions to pair this one with jeans and wellies.” —Danielle Stein Chizzik, Deputy Editor

“The Blucher is a vital piece of footwear for young preps transitioning from sneakers to grownup shoes. Bonus: flat toe area makes them excellent for playing hackysack on the quad.” —Norman Vanamee, Articles Director

“Does it get any preppier than loafers? Flattered’s Bon Bons have been on my wishlist for years—and in this specific color too. Imagine how they’d look with a great pair of rigid straight jeans and a white button down, or a slip skirt and sweater?! This is not a want, it’s a need.” —Sophie Dweck, Shopping Editor

“Sure, gingham is traditionally a summer print, but come fall, I want to be wearing this adorable jacket from Boden’s latest collection. It comes with matching pants, too! I’m obsessed.” —Sophie Dweck, Shopping Editor

“Loafers? Sure. Boat shoes? Sometimes. But an overlooked casual preppy classic? The moccasin. Emme Parson knocks these out of the park, per usual. Everything from the unique, sleek sophistication to the perfect pop of color make these the perfect preppy accent for any of my fall looks. I am obsessed.”—Roxanne Adamiyatt, Digital Lifestyle Director

“Before we hit cashmere sweater season fully, there’s that blissful few weeks where you can wear lightweight knits. Think of this paired with a fun preppy skirt or classic pair of chinos? Very academia chic! And definitely on my list for fall.”—Roxanne Adamiyatt, Digital Lifestyle Director