THE LIMITED-EDITION TOP-SIDER

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 (@dimepiece.co)

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
(@jakewoolf)

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.

Meet Your Maker

Paul Sperry — an avid sailor, inventor and intrepid explorer — invented his signature shoe after slipping off the deck of his boat and into the Long Island Sound in 1934. Since then, Sperry’s Topsiders have been worn by JFK, Mister Rogers, and lately, the classic silhouette has become a fave of the fashion crowd.