Skip to content
Free Shipping on Orders of $98 or more*
Free Shipping on Orders of $98 or more*
Size Charts Shipping Policy Returns & Refunds Rewards Contact Us

Sperry

In the Sperry world, there’s no “wrong way” to prep. And everyone is invited. Prep For All.

Filters

$
$
Sperry Men's Striper II SW Navy - 5011705 - Tip Top Shoes of New York
Sperry Men's Striper II SW Navy - 5011705 - Tip Top Shoes of New York Save 50% Save %

Sperry Men's Striper II SW Navy

Sperry
$69.95
$69.95 - $69.95
$69.95
$34.99
$34.99 - $34.99
$34.99

The Sperry® Striper II Slip-On Sneaker offers a streamlined silhouette with incredible interior comfort that will make this your ideal casual, ev...

View full details
$69.95
$69.95 - $69.95
$69.95
$34.99
$34.99 - $34.99
$34.99
Save 50% Save %
Sperry Men's Striper II Black Washed Canvas - 3006019 - Tip Top Shoes of New York
Sperry Men's Striper II Black Washed Canvas - 3006019 - Tip Top Shoes of New York

Sperry Men's Striper II Black Washed Canvas

Sperry
$69.95 - $69.95
$69.95
$69.95 - $69.95
$69.95

The Sperry® Striper II CVO Canvas sneakers have a timeless style, and with their cotton canvas upper, minimalist silhouette, and flexible rubber ...

View full details
$69.95 - $69.95
$69.95
$69.95 - $69.95
$69.95
Sperry Men's Authentic Original Leather Boat Shoe Brown/White - 400247302019 - Tip Top Shoes of New York
Sperry Men's Authentic Original Leather Boat Shoe Brown/White - 400247302019 - Tip Top Shoes of New York

Sperry Men's Authentic Original Leather Boat Shoe Brown/White

Sperry
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95

The one that started it all, the Authentic Original is a tried-and-true icon of prep style. Product features: Full-grain, unlined leather uppers r...

View full details
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95
Sperry Men's Authentic Original Leather Boat Shoe Brown Nubuck - 400115703016 - Tip Top Shoes of New York
Sperry Men's Authentic Original Leather Boat Shoe Brown Nubuck - 400115703016 - Tip Top Shoes of New York

Sperry Men's Authentic Original Leather Boat Shoe Brown Nubuck

Sperry
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95

Since 1935, Authentic Original boat shoes have been a favorite of those who spent time in, on or around the ocean. Each season, new colors and fabr...

View full details
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95
Sperry Boy's Sperry Top-Sider Authentic Original Brown Leather (Sizes 10.5-3) - 406549711023 - Tip Top Shoes of New York
Sperry Boy's Sperry Top-Sider Authentic Original Brown Leather (Sizes 10.5-3) - 406549701017 - Tip Top Shoes of New York

Sperry Boy's Sperry Top-Sider Authentic Original Brown Leather (Sizes 10.5-3)

Sperry
$59.95 - $59.95
$59.95
$59.95 - $59.95
$59.95

By land or by sea, he’ll look handsome in this classic Sperry Top-Sider Authentic Original shoe with handsewn moc styling. Featuring a removable fo...

View full details
$59.95 - $59.95
$59.95
$59.95 - $59.95
$59.95
Sperry Men's Striper II Twin Gore Navy - 849678 - Tip Top Shoes of New York
Sperry Men's Striper II Twin Gore Navy - 849676 - Tip Top Shoes of New York
Save 50% Save %

Sperry Men's Striper II Twin Gore Navy

Sperry
$59.95
$59.95 - $59.95
$59.95
$29.99
$29.99 - $29.99
$29.99

Slip ons and sailing go hand-in-hand. A relaxed sneaker that combines both with an easy on/off fit. Product features: Relaxed, breathable canvas u...

View full details
$59.95
$59.95 - $59.95
$59.95
$29.99
$29.99 - $29.99
$29.99
Save 50% Save %
Sperry Men's Gold Cup Authentic Original Boat Shoe Tan/Gum - 1025388 - Tip Top Shoes of New York
Sperry Men's Gold Cup Authentic Original Boat Shoe Tan/Gum - 1025388 - Tip Top Shoes of New York
Save 50% Save %

Sperry Men's Gold Cup Authentic Original Boat Shoe Tan/Gum

Sperry
$159.95
$159.95 - $159.95
$159.95
$79.99
$79.99 - $79.99
$79.99

Create epic moments in impeccable style, with the premium leathers, elevated craftsmanship, and the understated luxury of Gold Cup A/Os.Product fea...

View full details
$159.95
$159.95 - $159.95
$159.95
$79.99
$79.99 - $79.99
$79.99
Save 50% Save %
Sperry Men's Authentic Original Leather Boat Shoe Sahara Tan - 404233302014 - Tip Top Shoes of New York
Sperry Men's Authentic Original Leather Boat Shoe Sahara Tan - 404233302014 - Tip Top Shoes of New York

Sperry Men's Authentic Original Leather Boat Shoe Sahara Tan

Sperry
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95

Since 1935, Authentic Original boat shoes have been a favorite of those who spent time in, on or around the ocean. Each season, new colors and fabr...

View full details
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95
Sperry Men's Billfish Dark Tan - 406477303017 - Tip Top Shoes of New York

Sperry Men's Billfish Dark Tan

Sperry
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95

Sturdy and rugged boat shoes feature 360° lacing for more stability. Their air mesh and perforated upper panels, along with enhanced shock-absorbin...

View full details
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95
Sperry Women's Saltwater Duck Boot Brown Rubber - 408017601010 - Tip Top Shoes of New York
Sperry Women's Saltwater Duck Boot Brown Rubber - 408017601010 - Tip Top Shoes of New York
Save 50% Save %

Sperry Women's Saltwater Duck Boot Brown Rubber

Sperry
$119.95
$119.95 - $119.95
$119.95
$59.99
$59.99 - $59.99
$59.99

Embrace the elements in duck inspired wet weather boots. With rawhide lacing for a secure fit and Wave-Siping for ultimate wet/dry traction, this v...

View full details
$119.95
$119.95 - $119.95
$119.95
$59.99
$59.99 - $59.99
$59.99
Save 50% Save %