5 Must-Have Preppy Shoes for Autumn

With bold varsity colors, rich textures and collegiate details, our AW19 collection is all about preppy shoes with a contemporary spin.

September 3, 2019
in Style

Fall is finally upon us—the pinnacle season of prep style. And we’ve got you covered.

Bold varsity colors, blazers, rugby stripes, rich textures and the collegiate tradition were the inspiration behind our autumn 2019 collection. So just like the leaves, change up your wardrobe with these five classic, yet contemporary preppy shoes made for you.

Must-Have Preppy Shoes for Autumn 2019

Women’s Authentic Original 2-Eye Varsity Boat Shoe
Boldly going back to basics, the varsity take on the Authentic Original brings vibrant colors and striped satin laces to our best-selling style. Featuring 360° lacing and a moccasin construction designed for maximum all-day comfort, these new A/Os are ready for anything. Whether you’re watching crew races by the water or strolling through an open market, this casual-cool style pairs nicely with everything from distressed skinnies and a cable knit sweater to a corduroy mini and a tee.

Women's Authentic Original 2-Eye Varsity Boat Shoe

Men’s Authentic Original Lug 3-Eye Boat Shoe
No matter the weather, the Authentic Original Lug will take your style game to new heights—literally. The Authentic Original Lug is as versatile as it is attractive, not to mention it’s made to withstand rain and even light snow with waterproof leather and wool uppers. That means you can go from a casual stroll on the trails to an evening out with friends without a second thought. Just toss on a puffer vest or neutral-toned bomber when it gets cool.

Men's Authentic Original Lug 3-Eye Boat Shoe

Women’s Crest Vibe Varsity Stripe Satin Sneaker
For those insta-ready autumn activities, the Crest Vibe Varsity Stripe in a new satin material is a picture-perfect and polished choice. We love how this bold and feminine style makes the statement of an icon while giving all the comfort of a sneaker (plus a memory foam footbed). Give these kicks all the attention in dark wash skinnies and an oxford button down or go more is more with a graphic sweater on top of wide-leg pants.

Women's Crest Vibe Varsity Stripe Satin Sneaker

Men’s Striper II Varsity CVO Sneaker
Work? Weekend? Whatever, wherever. The comfortable Striper II Varsity is buttoned-up enough for casual Fridays with chinos and a polo yet relaxed enough for a weekend of adventures with denim and a tee. This slip-resistant sneaker features hidden elastic gore, which means you can slip them on and off easily. Classic and comfortable, these are a closet staple ready for wherever autumn takes you.

Men's Striper II Varsity CVO Sneaker

Women’s Seaport Penny Suede Stud Loafers
Everyone needs a good autumn loafer. The cozy suede in these Seaport Pennies with studs complements layered scarves, wool berets, tartan blazers, houndstooth trousers and so much more. This wardrobe essential is the perfect neutral base for all your favorite autumn pieces. A memory foam insole and moccasin construction means comfort

Women's Seaport Penny Suede Stud Loafers

Looking for more style inspiration? Scroll through our AW19 Lookbook for ideas on how to rock your Sperry boat shoes, sneakers and casual styles this season.

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