They are the emblem of all things preppy – but were they always? Take a peek into the history of this iconic American brand.

1930s: Paul Sperry invented the first boat shoe after using a knife to cut treads into the outsole of a sneaker. He was inspired by his dog Prince’s ability to effortlessly trek over ice.

1940s: The U.S. Navy began manufacturing the Top-Sider for its sailors. Due to the rationing of leather shoes during WWII, the design increased in popularity nationwide.

1980s: Top-Sider was mentioned in the tongue-in-cheek style guide, The Official Preppy Handbook (yep, it was a thing), and subsequently featured in many a John Hughes film.

2000s: After a decade out of the limelight (preppy just wasn’t cool in the 90s), Top-Siders appeared on Fashion Week runways, spurring a new generation of Sperry lovers.

Today: The nautical brand is a made-for-everyday staple. They launched their first stand-alone store in 2012 on Manhattan’s 5^th Avenue.

Our Sperry Top-Sider Women and Sperry Top-Sider Men Boutiques open Wednesday, March 27, at 11AM ET.

By Julia Ivins, Staff Writer

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The best part of having a photo studio in your company’s building? You can rely on an expert team of stylists to give you on-trend tips. For this season’s staples, I sat down with stylist Alexandra to get the scoop on what every wardrobe needs for fall.

Cozy Knits
“You can wear a cozy knit with everything,” says Alexandra. Dress it up with a cashmere cardigan or down with an oversized sweater. (I love the oversized look with a pair of dark skinnies.)

Silk Blouses
A feminine fall staple, a silk blouse not only feels indulgent, but is also the perfect transitional piece. Easy to layer, it works with skinny jeans on the weekend or with a pencil skirt at work. “I’m all about blouses with tiny prints,” Alexandra says.

Leather
We’ve been obsessing over leather all season, but Alexandra assures us it’s the right attitude to have. “It’s my number one must-have. You need to invest in a good leather jacket,” she says. “You can wear it over jeans, with flats, or over a dress.” Versatile, indeed.

Loafers
“Penny loafers are back!” says Alexandra. “And I especially love them in a metallic.” The menswear-inspired styles are both comfy and casual, making them a perfect shoe for morning commutes and fall foliage excursions.

Our Stylists’ Picks: Head-to-Toe Fall Looks Boutique opens Tuesday, October 16, at 11AM ET.

By Melissa Mann, Staff Writer

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