Fall Essential: Sperry Top-Siders

Devon Hay
Fall Essential: Sperry Top-Siders
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The slow slide from summer to fall can be a sad affair: The days are getting shorter, Summer Fridays are a distant memory, and for some, it’s back to the classroom. But fear not fashionable friends! The arrival of fall brings its own tradition: new fall wardrobe essentials!

High on our list for fall are shoes, of course, and one of our faves is the ever-so-versatile Sperry Top-Sider boat shoe. No longer just for providing grip on a slick boat deck or for Ivy League fraternity folk, these kicks are perfect for transitioning into cooler temperatures. To further convince you that you don’t need to know your port from your starboard to wear them, designers are now offering up all kinds of street-friendly options in dozens of styles and varieties to suit your mood — from zippy neon brights and racy animal print accents to sophisticated wedge soles. We can’t wait to try classic tan loafer styles with a pop of colored jeans and a slick, tailored trench, or to use our tough glitter versions to add a little punk rock private school vibe to knee-length skirts.

Here, we’ve rounded up a whole bunch of chic options for you to check out — all in the interests of helping get you more excited about fall. These comfy classics will help put a spring in your fall step, even if you’re still dreaming of lazing away summer days spent on a yacht.

For more information on our relationship with Sperry: cmp.ly/3

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Click through the slideshow to see our favorite Sperry Top-Sider options!

Channel a little Ali McGraw with this classic penny loafer style
in tan leather. Hayden Loafer, $85.00.

These glitter numbers are slick enough for Janelle Monáe, paired with sleek cropped black trousers. Authentic Original 2-Eye Boat Shoe, $95.00.

Add a little glitz with these triple-tone metallic beauties. Cloud Logo Authentic Original 2-Eye Boat Shoe, $90.00.

Needing an upgrade for your ballet flats? Trade them in for these chic patent leather loafers. Audrey Hepburn would approve. Hayden Loafer, $85.00.

Feeling a little more boho? These ikat printed lace ups fit the bill with shredded jeans and lots of gold jewelry. Cloud Logo Authentic Original 2-Eye Boat Shoe, $80.00.

Perfect for tooling around on weekends, these cheery red patents add a little pop to your errand-running. Authentic Original 2-Eye Boat Shoe, $90.00.

Mix in a little of the animal print trend on your toes with these adorable pony hair slip-ons. Hayden Loafer, $95.00.

Designed in collaboration with Jeffrey New York, this cobalt suede pair puts a seriously chic twist on a classic shape. Authentic Original Barrel Lace Boat Shoe, $125.00.

These glitzy silver versions will fit the high fashion bill – and won’t hurt your wallet. Authentic Original 2-Eye Boat Shoe, $95.00.

This plaid-accented suede option is a cute take on the ballet flat and lends an Anglo vibe to your look. Angelfish Slip-On Boat Shoe, $80.00.

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