Paul Sperry designed the Authentic Original boat shoe in 1935 in an effort to provide traction for sailors on wet boat decks. Over 80 years later, the A/O or “Top-Sider” has become a core staple of nautical style and a symbolic part of New England’s rich heritage and seafaring history.
As one of our most versatile styles, the A/O boat shoe can be worn with a number of different looks from the boat deck to the beach, or from the boardwalk to the board room. Looking for ideas on how to wear boat shoes, we set out to ask the Instagram community for tips and gathered photos from influencers, bloggers, and stylish fans. Scroll below to see our showcase on how men and women from around the globe are styling our Authentic Original boat shoe.
No watch, no problem. A shirt picked up when the boat docks finds comfort with simple khaki shorts a classic Sperry boat shoe. By anchoring this look with go-to, heritage pieces, John Philip Thompson III keeps the Guayabera shirt from looking costumey, and the rolled sleeve and tortoise glasses amp up the cool factor. Try this look for a party outside on a hot Saturday night, or use it as an excuse to host a Mezcal tasting.
Here’s how to wear boat shoes so that they’re the perfect complement to Mali Karakurt’s clean, tailored essentials. Nautical nods like the striped shirt, woven belt, and of course the Sperry A/O boat shoes make this a look that’s both quintessentially American and yet, still at home anywhere in the world, like in Mali’s home country of Germany. Try this look to get the local treatment while sightseeing. (And here’s hoping the sunglasses keep the papazzi off your trail.)
We admit, we’re partial to all things New England. (We can’t help it; it’s our heritage.) And we’ve fallen hard for Robin’s pairing of revolutionary reds, whites and blues with our tried and true boat shoe. Denim shorts and bangles make this look trend-forward and boardwalk ready, while adding a neutral A/O to the mix keeps the flag-waving from going overboard. Also, that smile. Hey, we’d be grinning too if we pulled off casual cool like this.
This just in: a completely unexpected way to bring back a little of class and gentlemanly style in the day-to-day, brought to you by Trevor Green. For his downtown reading break, Trevor pairs a tapered leg khaki with a crisp white shawl-collared sweater and (you heard it here first) a bow tie. Pulling all these pieces together is the a pair of Sperry boat shoes, which can easily be dressed up or down.
Navy and white are perennially nautical and newsworthy. A lean striped cardigan and a pair of denim short shorts are the proportional mix we all wish we could master. The navy tank and crisp boat shoes keep Ashley Schaffert Laderer’s look from feeling too precious. This look has windy summer day vibes. Bonfire later, anyone?
Looking for how to wear boat shoes like Willie Sparks? His look features nods to heritage and Ivy League style. By buttoning the top button and choosing khakis with a lean line, Willie makes a modern statement. Classic elements like the traditional color pairing, the round face watch, and his choice of our Authentic Original boat shoes in Amaretto keep his look grounded. We’d rock this look anywhere from a round of post-golf beers to a second date. Third date guaranteed.
We love a look that says “I’m not trying at all,” even when (shhhh) we totally are. When in doubt, go for tried and true basics—just make everything about them perfect. It’s this attention to detail that makes Siren’s look work, from the breezy cut of her tank to the folded frayed denim to the choice of a crisp, navy Sperry A/O. These are pieces we’d toss in a straw bag to look cute in the ice cream line at the beach; they’d also work for a sailing date. Hint, hint.
We wouldn’t have thought to top off our fave linen shirt with a shawl-collared cardigan, but now that we’ve seen it, we can’t stop thinking about it. Cream and white is a crowd-pleasing combo we can’t live without in warmer weather, and the thoroughly modern pop of blue linen keeps the sweater from skewing too old school. Finished with spot-on accessories and a pristine Sperry A/O boat shoe, Blake Scott’s look is a clear win.
Clean in Cutoffs
Cutoff jean shorts and a white top have always been the core of women’s summer style. Alitzah Stinson rocks this look in boat shoes beachside.
You don’t need much more than a sharp swimsuit and your A/Os. (6-pack optional.) When going for it with a serious punch of color, follow Willie Sparks’s lead and pick a neutral boat shoe that complements your bright trunks.
Veronica Lopreato pairs our Authentic Original with a bright yellow top and cuffed jeans (rolled up to combat the rolling tide) for this simple, stand-out look.
Menswear blogger Charlie Irons suits up in a gray blazer and flat-front chinos to bring our boat shoes to the next level. Dressed up with class and style, Charlie’s look is accented perfectly with a soft lavender shirt and purple tie.
Wondering how you can be featured in our next blog post? Post a photo with #SperryMyWay on Instagram or Twitter, and you could soon find your image in our fan gallery, or even featured here on our blog. We’re always looking for your take on how to wear boat shoes. Share your style!
To learn more about the invention of the boat shoe and Sperry’s history on land and at sea, visit the Our Story page.
There’s only one Authentic Original boat shoe, but there are lots of ways to tie it. Browse through our Lacing Guide to learn how to lace your boat shoes with a few of our favorite knots.