Dressing nice doesn't mean you have to sacrifice comfort, especially with the Sperry Top-Sider Gold Crepe...

Whether you're working on a piece of poetry at the local coffee shop or venturing out to catch the perfect...

The Sperry Top-Sider Mako 2-Eye Shoe takes the boat shoes you love, and adds a nice dollop of comfort to...

A boat shoe with the ease and lightweight feel of a sneaker, the Sperry Top-Sider Men's Caspian Leather...

We like Sperry's Striper II CVO Seacycled Shoe for its smooth looks and mostly recycled design. They...

A tried and true icon of classy, casual style, the Sperry Top-Sider A/O 2-Eye Pullup Shoe travels right...

Annapolis Plain Toe Shoe - Men's...

Hamilton II Ven Shoe - Men's...

Leeward 2-Eye Boat Shoe -Men's...

Moc Sider Nylon Shoe - Men's...

Soletide Harmony Shoe - Men's...

Striper II CVO Washed Shoe - Men's...

As classic as they come, the Sperry Top-Siders Men's Captains CVO Shoe delivers modern comfort with a...

Captain's CVO Bionic Sailcloth Shoe - Men's...

Striper II CVO Baja Shoe - Men's...

Striper II Storm CVO Waterproof Leather Shoe - Men's...

Striper II CVO Corduroy Shoe - Men's...

A long day at sea calls for the comfortable construction and classic good looks of the Perry Top-Sider...

Often imitated, never duplicated could be the tagline for the A/O 2-Eye Loafers from Sperry Top-Sider....

Keep the Cold Bay Chukka ready for adventure after unexpected winter storms cover the city streets with...

Who says you need to sacrifice refined styling for a waterproof rain boot' With the Watertown Chukka, you...

You finally decided to start dressing like a grown-up, but now you're fretting even more because you can't...

Some days you're less than thrilled to head out to sea. The roiling waters are nearly black, and the spray...

You'll almost be looking forward to cold, rainy days when you have the Sperry Men's Avenue Duck Boot...

Annapolis Desert Chukka Boot - Men's...

From shoveling the walk to commuting to the office, the Sperry Top-Sider Avenue Duck Wool Boot will keep...

Avenue Duck Cordura Boot - Men's...

Blend style and function by lacing up the Sperry Top-Sider Seamount Duck Boot. This weather resistant boot...

Camden Chelsea Nubuck Boot - Men's...

The Sperry Gold Crepe Chukka Boot is trying to prove that relaxed looks can still be classy. The key to...

Striper II Storm Waterproof Chukka Boot - Men's...

Striper Storm Hiker Boot - Men's...

Striper II CVO Sneaker - Men's...

Ice Bay Boot - Men's...

The 7 Seas 3-Eye Sneaker is great for days paddling or boating around lakes. Its breathable upper is highly...

Duck Float SeaCycled Zip Up Boot - Men's...

Duck Float Lace Up Boot - Men's...