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Todd has teamed up with Sperry on a limited-edition, luxe update of their iconic Authentic Original™ boat shoe featuring premium English suede exteriors, Vibram soles and cork insoles. They are finished with traditional handsewn moccasin-style construction. And, just as boat shoes are having a moment, we asked a trio of tastemakers who are each having their own moment, to take these “Todd-Siders” for a spin around New York’s Lower East Side.

Brynn Wallner

Founder of Dimepiece

How would you describe your style? If Princess Diana dated a skater boy.

What's your favorite thing about Sperry? I love that Sperry has been around for forever...and how different the boat shoes look depending on who wears them…the range! [My] dad used to wear them in the '70 [and] 80s in Southern California — if you've read the latest Bret Easton Ellis novel, The Shards, you know that they were THE shoe to wear amongst the preppy, New Wave-listening, San Fernando Valley set. That my dad and I can be two different people, living in completely different places and times...but wear the same shoes...?? That's very cool to me and speaks to [Sperry’s] timelessness.


Jordan Page

Stylist, DJ + Founder of Colour Plus
& @veryadvanced

How would you describe your style? I would definitely describe it as a mix of urban, prep and Americana influences, with a prioritization on comfort.

Socks or no socks? Always socks. Socks are one of my favorite ways to make an outfit more interesting.

Jake Woolf

Men's Style Writer + Content Creator

How would you describe your style? It's always evolving, but these days, I'm most often aspiring to cultivate something that evokes "off-duty 90s actor." All that really means is I wear a good amount of oversized blazers, slouchy sweaters, and light-wash jeans.

Where are you most excited to wear your Sperrys this summer? Hopefully on a boat, or at least somewhere where there's the possibility of getting on a boat.



After falling overboard in 1934 in the Long Island Sound, Paul Sperry — an avid sailor, inventor and intrepid explorer — created the first non-slip deck shoe, modeling the sole after his cocker spaniel's foot pad. And in World War II, it became the official deck shoe of the US Navy. Since then, it’s been worn by style icons like JFK, Paul Newman, and Mister Rogers. And in the same way that the Stan Smith went from an unassuming white court shoe to a fashion fave circa 2014, it is now the Top-Sider’s time to shine. Todd’s limited-editions bring a modern, luxe spin to the seafaring classic.

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