Sperry Top-Sider

For a classic, sockless summer shoe with genuine pedigree, they're hard to beat, though opinions on value vary by model. The premium Gold Cup line draws particular praise for its leather and construction, while some buyers of entry models report inconsistency between batches. The Authentic Original is the one to start with: it's the shoe that began the category, and many owners report theirs lasting years and only looking better as the leather wears in.

Traditionally they're worn sockless, which is the look the Authentic Original was designed for, and going barefoot is the move on an actual boat. If you'd rather not, no-show socks are the popular compromise. One practical tip: socks add a layer that can stretch the leather, so if you break a pair in wearing socks they may feel loose when you later go without.

It comes down to the sole. Inventor and sailor Paul A. Sperry slipped off his boat's deck, and the experience drove him to create a non-slip shoe; he was inspired by his cocker spaniel's grip on ice and mimicked the traction grooves in its paws by cutting a pattern into a rubber sole, a process called siping. The 1935 Top-Sider paired that herringbone-siped sole with a white outsole that won't leave dark scuff marks on a deck.

Sperry Top-Sider was designed in 1935 by Paul A. Sperry, and Sperrys were the first boat shoes ever introduced to the boating and footwear markets. The original featured a canvas upper, herringbone siping and that signature non-marking white sole.

The brand is currently owned by Authentic Brands Group, which bought it from Wolverine World Wide in January 2024 for around $130 million and licenses the North American operations to the Aldo Group. Sperry has changed hands many times over its history, passing through US Rubber, Stride Rite, Payless and Wolverine before its latest owner.

Both names refer to the same brand. In early 2015 Sperry dropped the defining 'Top-Sider' tag as part of a new brand campaign, so newer marketing simply says 'Sperry,' even though the heritage product is still the Top-Sider boat shoe. You'll see the two used interchangeably.

It runs deep, which is fitting for a shoe born on the water. Sperry is the official footwear sponsor of the US Sailing Team, the US Junior Olympic Sailing Team and the US Paralympics Sailing Team. It has a long America's Cup history too: Sperry served as the event's official sponsor as far back as 1987, when champion sailor Dennis Conner raced in the shoes, and returned as official footwear partner of the 35th America's Cup in 2015.

The turning point was the military. Sperry's shoes stayed a niche product for boaters until 1939, when the US Navy negotiated the right to manufacture them for sailors at the United States Naval Academy. That surge in production reshaped the brand, and Sperry was sold to US Rubber Co. in 1940 on the back of it.

Yes. In 2009 Footwear News named Sperry Top-Sider its Brand of the Year, a nod to the lasting cultural pull of the original boat shoe well into the modern era.

The genuine leather on a Top-Sider is meant to age into the shoe, so the goal is to help it wear in gracefully rather than fight it. Many long-time owners get years out of a pair, while reports of early stitching failures tend to cluster around specific models, so buy the line you trust and keep the leather conditioned. Worn well and looked after, a good pair only improves with age.