Skip to content
Free Shipping on all Orders over $98*
Free Shipping on all Orders over $98*
Size Charts Shipping Policy Returns & Exchanges Rewards Contact Us

Men Casual

Filters

$
$
Red Wing Men's Postman Oxford 101 Black Chaparral Leather - 5022593 - Tip Top Shoes of New York
Red Wing Men's Postman Oxford 101 Black Chaparral Leather - 5022593 - Tip Top Shoes of New York

Red Wing Men's Postman Oxford 101 Black Chaparral Leather

Red Wing
$289.95 - $289.95
$289.95
$289.95 - $289.95
$289.95

Classic Heritage Design: Inspired by the original 1950s postal service shoe for timeless style. Premium Materials: Crafted from Red Wing Bl...

View full details
$289.95 - $289.95
$289.95
$289.95 - $289.95
$289.95
Red Wing Men's Beckman 9423 Black Leather - 5022580 - Tip Top Shoes of New York
Red Wing Men's Beckman 9423 Black Leather - 5022580 - Tip Top Shoes of New York

Red Wing Men's Beckman 9423 Black Leather

Red Wing
$399.95 - $399.95
$399.95
$399.95 - $399.95
$399.95

Timeless Design: Classic vintage charm paired with modern sophistication. Premium Quality: Crafted from top-grade full-grain leather for...

View full details
$399.95 - $399.95
$399.95
$399.95 - $399.95
$399.95
Red Wing Men's Shop Moc Oxford 8092 Oro Legacy Leather - 5022567 - Tip Top Shoes of New York
Red Wing Men's Shop Moc Oxford 8092 Oro Legacy Leather - 5022567 - Tip Top Shoes of New York

Red Wing Men's Shop Moc Oxford 8092 Oro Legacy Leather

Red Wing
$289.95 - $289.95
$289.95
$289.95 - $289.95
$289.95

Classic Design: Inspired by the iconic Classic Moc family for a timeless appeal. Low-Profile Style: Tailored for casual, year-round wear...

View full details
$289.95 - $289.95
$289.95
$289.95 - $289.95
$289.95
Red Wing Men's Classic Moc 6" 8881 Olive Mohave Leather - 5022541 - Tip Top Shoes of New York
Red Wing Men's Classic Moc 6" 8881 Olive Mohave Leather - 5022541 - Tip Top Shoes of New York

Red Wing Men's Classic Moc 6" 8881 Olive Mohave Leather

Red Wing
$299.95 - $299.95
$299.95
$299.95 - $299.95
$299.95

Iconic Design: Features a classic moc toe for timeless style. Premium Quality: Made with durable materials synonymous with Red Wing Heri...

View full details
$299.95 - $299.95
$299.95
$299.95 - $299.95
$299.95
Red Wing Men's Blacksmith 3340 Briar Brown - 10036592 - Tip Top Shoes of New York
Red Wing Men's Blacksmith 3340 Briar Brown - 10036592 - Tip Top Shoes of New York

Red Wing Men's Blacksmith 3340 Briar Brown

Red Wing
$0.00 - $0.00
$0.00
$329.95
$329.95 - $329.95
$329.95

Classic Design: Features clean lines and traditional round toe styling for a timeless appeal. Premium Leather: Crafted with Briar Oil Sl...

View full details
$0.00 - $0.00
$0.00
$329.95
$329.95 - $329.95
$329.95
Red Wing Men's Classic Chelsea 3194 Black - 10036304 - Tip Top Shoes of New York
Red Wing Men's Classic Chelsea 3194 Black - 10036304 - Tip Top Shoes of New York

Red Wing Men's Classic Chelsea 3194 Black

Red Wing
$0.00 - $0.00
$0.00
$299.95
$299.95 - $299.95
$299.95

Handcrafted Comfort: Experience a sleek pull-on silhouette designed for immediate out-of-the-box comfort. Durable Footbed: The fully cus...

View full details
$0.00 - $0.00
$0.00
$299.95
$299.95 - $299.95
$299.95
Red Wing Men's Work Chukka 3141 Briar Slick - 10036291 - Tip Top Shoes of New York
Red Wing Men's Work Chukka 3141 Briar Slick - 10036291 - Tip Top Shoes of New York

Red Wing Men's Work Chukka 3141 Briar Slick

Red Wing
$0.00 - $0.00
$0.00
$299.95
$299.95 - $299.95
$299.95

Inspired Design: Combines Red Wing's rugged work boot heritage with a modern chukka silhouette. Premium Materials: Crafted from high-qua...

View full details
$0.00 - $0.00
$0.00
$299.95
$299.95 - $299.95
$299.95
Red Wing Men's 6-Inch Classic Moc 8828 Alpine Portage - 10036237 - Tip Top Shoes of New York
Red Wing Men's 6-Inch Classic Moc 8828 Alpine Portage - 10036237 - Tip Top Shoes of New York

Red Wing Men's 6-Inch Classic Moc 8828 Alpine Portage

Red Wing
$0.00 - $0.00
$0.00
$319.95
$319.95 - $319.95
$319.95

Iconic Design: Modeled after Red Wing’s original work boot style for classic aesthetics. Premium Material: Crafted from durable Copper Rough &am...

View full details
$0.00 - $0.00
$0.00
$319.95
$319.95 - $319.95
$319.95
Red Wing Men's 6-Inch Classic Moc 8833 Hawthorne - 10036212 - Tip Top Shoes of New York

Red Wing Men's 6-Inch Classic Moc 8833 Hawthorne

Red Wing
$0.00 - $0.00
$0.00
$299.95
$299.95 - $299.95
$299.95

Iconic Design: Modeled after Red Wing’s original work boot style for classic aesthetics. Premium Material: Crafted from durable Copper Rough &am...

View full details
$0.00 - $0.00
$0.00
$299.95
$299.95 - $299.95
$299.95
Red Wing Men's Blacksmith 3345 Black Prairie - 10035630 - Tip Top Shoes of New York
Red Wing Men's Blacksmith 3345 Black Prairie - 10035630 - Tip Top Shoes of New York

Red Wing Men's Blacksmith 3345 Black Prairie

Red Wing
$0.00 - $0.00
$0.00
$329.95
$329.95 - $329.95
$329.95

Classic Design: Features clean lines and traditional round toe styling for a timeless appeal. Premium Leather: Crafted with Briar Oil Sl...

View full details
$0.00 - $0.00
$0.00
$329.95
$329.95 - $329.95
$329.95
Red Wing Men's Iron Ranger 8111 Amber - 10012565 - Tip Top Shoes of New York
Red Wing Men's Iron Ranger 8111 Amber - 10012565 - Tip Top Shoes of New York

Red Wing Men's Iron Ranger 8111 Amber

Red Wing
$0.00 - $0.00
$0.00
$349.95
$349.95 - $349.95
$349.95

Iconic Style: The Iron Ranger boasts a timeless design that is a hallmark of American craftsmanship. Durable Construction: Built to last...

View full details
$0.00 - $0.00
$0.00
$349.95
$349.95 - $349.95
$349.95
Red Wing Men's Weekender Chelsea 3311 Copper Rough and Tough - 10012550 - Tip Top Shoes of New York
Red Wing Men's Weekender Chelsea 3311 Copper Rough and Tough - 10012550 - Tip Top Shoes of New York

Red Wing Men's Weekender Chelsea 3311 Copper Rough and Tough

Red Wing
$0.00 - $0.00
$0.00
$259.95
$259.95 - $259.95
$259.95

Ultimate Comfort: Enjoy sleek, off-the-clock comfort right out of the box with stitchdown construction that requires no break-in. Timele...

View full details
$0.00 - $0.00
$0.00
$259.95
$259.95 - $259.95
$259.95
Red Wing Men's Roughneck 8146 Classic Moc Briar Brown Leather - 406182704017 - Tip Top Shoes of New York
Red Wing Men's Roughneck 8146 Classic Moc Briar Brown Leather - 406182704017 - Tip Top Shoes of New York

Red Wing Men's Roughneck 8146 Classic Moc Briar Brown Leather

Red Wing
$319.95 - $319.95
$319.95
$319.95 - $319.95
$319.95

Iconic Design: Modeled after Red Wing’s original 1950s work boot style. Premium Materials: Crafted from Briar Oil Slick leather for dura...

View full details
$319.95 - $319.95
$319.95
$319.95 - $319.95
$319.95
Red Wing Men's 6-Inch Classic Moc 8864 Russet Taos Gore-Tex Waterproof - 7725030 - Tip Top Shoes of New York
Red Wing Men's 6-Inch Classic Moc 8864 Russet Taos Gore-Tex Waterproof - 7725030 - Tip Top Shoes of New York

Red Wing Men's 6-Inch Classic Moc 8864 Russet Taos Gore-Tex Waterproof

Red Wing
$0.00 - $0.00
$0.00
$369.95
$369.95 - $369.95
$369.95

Fully Waterproof Construction: Equipped with a GORE-TEX membrane for ultimate moisture protection. Durable Russet Taos Leather: Features...

View full details
$0.00 - $0.00
$0.00
$369.95
$369.95 - $369.95
$369.95
Red Wing Men's 6-Inch Classic Moc 8849 Black Prairie Leather - 7723606 - Tip Top Shoes of New York
Red Wing Men's 6-Inch Classic Moc 8849 Black Prairie Leather - 7723606 - Tip Top Shoes of New York

Red Wing Men's 6-Inch Classic Moc 8849 Black Prairie Leather

Red Wing
$0.00 - $0.00
$0.00
$299.95
$299.95 - $299.95
$299.95

Iconic Design: Modeled after Red Wing’s original work boot style for classic aesthetics. Premium Material: Crafted from durable Copper Rough &am...

View full details
$0.00 - $0.00
$0.00
$299.95
$299.95 - $299.95
$299.95
Red Wing Men's 6-Inch Classic Moc 875 Oro Legacy - 7723580 - Tip Top Shoes of New York
Red Wing Men's 6-Inch Classic Moc 875 Oro Legacy - 7723580 - Tip Top Shoes of New York

Red Wing Men's 6-Inch Classic Moc 875 Oro Legacy

Red Wing
$0.00 - $0.00
$0.00
$309.95
$309.95 - $309.95
$309.95

Iconic Design: Modeled after Red Wing’s original work boot style for classic aesthetics. Premium Material: Crafted from durable Copper Rough &am...

View full details
$0.00 - $0.00
$0.00
$309.95
$309.95 - $309.95
$309.95
Red Wing Men's Iron Ranger 8084 Black - 929462 - Tip Top Shoes of New York
Red Wing Men's Iron Ranger 8084 Black - 929462 - Tip Top Shoes of New York

Red Wing Men's Iron Ranger 8084 Black

Red Wing
$0.00 - $0.00
$0.00
$349.95
$349.95 - $349.95
$349.95

Iconic Style: The Iron Ranger boasts a timeless design that is a hallmark of American craftsmanship. Durable Construction: Built to last...

View full details
$0.00 - $0.00
$0.00
$349.95
$349.95 - $349.95
$349.95
Red Wing Men's Blacksmith 3343 Copper Leather - 479067 - Tip Top Shoes of New York
Red Wing Men's Blacksmith 3343 Copper Leather - 479066 - Tip Top Shoes of New York

Red Wing Men's Blacksmith 3343 Copper Leather

Red Wing
$0.00 - $0.00
$0.00
$329.95
$329.95 - $329.95
$329.95

Classic Design: Features clean lines and traditional round toe styling for a timeless appeal. Premium Leather: Crafted with Briar Oil Sl...

View full details
$0.00 - $0.00
$0.00
$329.95
$329.95 - $329.95
$329.95
Red Wing Men's Iron Ranger 8085 Copper - 461974 - Tip Top Shoes of New York

Red Wing Men's Iron Ranger 8085 Copper Rough & Tough

Red Wing
$0.00 - $0.00
$0.00
$349.95
$349.95 - $349.95
$349.95

Iconic Style: The Iron Ranger boasts a timeless design that is a hallmark of American craftsmanship. Durable Construction: Built to last...

View full details
$0.00 - $0.00
$0.00
$349.95
$349.95 - $349.95
$349.95
Red Wing Men's Weekender Chukka 3322 Tan - 461954 - Tip Top Shoes of New York
Red Wing Men's Weekender Chukka 3322 Tan - 461954 - Tip Top Shoes of New York

Red Wing Men's Weekender Chukka 3322 Tan

Red Wing
$0.00 - $0.00
$0.00
$249.95
$249.95 - $249.95
$249.95

Premium Material: Crafted from durable Copper Rough & Tough leather for long-lasting wear. Sturdy Outsole: Features a reliable Hill ...

View full details
$0.00 - $0.00
$0.00
$249.95
$249.95 - $249.95
$249.95
Red Wing Men's 6-Inch Classic Moc 1907 Copper Rough & Tough - 404579404014 - Tip Top Shoes of New York
Red Wing Men's 6-Inch Classic Moc 1907 Copper Rough & Tough - 404579404014 - Tip Top Shoes of New York

Red Wing Men's 6-Inch Classic Moc 1907 Copper Rough & Tough

Red Wing
$0.00 - $0.00
$0.00
$329.95
$329.95 - $329.95
$329.95

Iconic Design: Modeled after Red Wing’s original work boot style for classic aesthetics. Premium Material: Crafted from durable Copper Rough &am...

View full details
$0.00 - $0.00
$0.00
$329.95
$329.95 - $329.95
$329.95