Hamilton II Ven Shoe - Men's...

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

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

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

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

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

Annapolis Desert Chukka Boot - Men's...

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

Annapolis Plain Toe Shoe - Men's...

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

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

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

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

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

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

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

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

Camden Chelsea Nubuck Boot - Men's...

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

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

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

Soletide Harmony Shoe - Men's...

Striper Storm Hiker Boot - Men's...

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

Moc Sider Nylon Shoe - Men's...

Striper II CVO Sneaker - Men's...