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| Best Seller  | Men's Geox Walk Pleasure Wingtip Derby - Black - Derbies A wingtip toe and refined broguing add timeless style to this leather derby set on a patented tech sole with thermoregulating properties to keep feet dry. more | FREE shipping go to store |
 | Men's Rodd & Gunn Dargaville Chelsea Boot - Black - Casual boots Walk the line between formal and functional with confidence and ease in this leather Chelsea boot featuring a supple leather upper and a grippy rubber sole. more | FREE shipping go to store |
| Best Seller  | Men's Rodd & Gunn Dargaville Chelsea Boot - Brown - Casual boots Walk the line between formal and functional with confidence and ease in this leather Chelsea boot featuring a supple leather upper and a grippy rubber sole. more | FREE shipping go to store |
 | Madewell Shoes | Madewell Chelsea Boots | Color: Black | Size: 8 Madewell Chelsea Boots. Worn A Handful Of Times And Show Little To No Wear. Chunky Heel And Very Comfortable To Walk In. more | go to store |
 | Madewell Shoes | Final Sale Madewell Regan Chelsea Boots Size 7.5 | Color: Brown/Tan | Size: 7.5 In Good Worn Condition, True To Size! Madewell Boots Are In A Gorgeous Cognac Leather And Have A Great 2.5” Heel That Add Height But Are Comfortable To Walk In And Go With Everything. Feature Some Wear And Slight Discoloration, As Pictured. Originally... more | go to store |
 | Free People Shoes | Free People - James Chelsea Boots | Color: Black/Brown | Size: 41 Gently Worn But Still In Great Condition. Rubber Heel Is So Comfortable To Walk On, So Easy To Wear! I Have In Two Other Colors Also And Have Walked All Over Chicago In Those And My Feet Felt Fine The Whole Day. Color Is Chocolate more | go to store |
 | Thomas and Vine Watson Wide Width Wingtip Chelsea Boot - Black - 13 A handsome Chelsea boot featuring genuine leather uppers, stretch gore at the sides, wingtip details, and brogue accents. more | go to store |
 | Thomas and Vine Thomas & Vine Nash Wingtip Chelsea Boot - Brown - 8.5 A durable design with dapper details, the Nash by Thomas & Vine. This ankle-high boot is crafted with rich genuine leather accented by a wingtip element enhanced with brogue and medallion embellishments. Stretch gore paneling at the shaft provides a... more | go to store |
 | Thomas and Vine Watson Wide Width Wingtip Chelsea Boot - Brown - 12 A handsome Chelsea boot featuring genuine leather uppers, stretch gore at the sides, wingtip details, and brogue accents. more | go to store |
 | Madewell Shoes | Madewell Ivy Chelsea Leather Boots 7 | Color: Black | Size: 7 Madewell Ivy Chelsea Leather Boots New Without Tag Made Of Rich Leather Leather Upper Utilitarian Lug Sole Cloudlift Padding For Long Walk On A...Well You Know 5.5" Shaft 3/4 Heel Size: 7 No Original Box more | go to store |
 | Levi's Shoes | Nw Man's Boots Levi's Shoes Chelsea Logger 2.0 Wax Size 13 | Color: Brown | Size: 13 Walk In Style And Comfort Wearing Levi's Shoes Chelsea Logger 2.0 Wax. Synthetic Upper. Man-Made Lining. Man-Made Removable Insole. Pull-On Style Closure. Raised Platform Round Toe. Ankle Pull Tab. Ankle-Length Shoes. Lug Sole For Comfort. Man-Made... more | go to store |
 | Madewell Shoes | Madewell City Walk Lug Sole Booties | Color: Black | Size: 6.5 Like New, Excellent Condition. Worn 2x. I Usually Wear A 7 But Thought I Might Be Able To Break These In To Fit. Unfortunately They Are Too Small. A Classic Pair Of Chelsea Boots To Wear With All Sorts Of Looks. These Madewell Booties Are Crafted In... more | go to store |
 | Madewell Shoes | Madewell Black Chelsea Heeled Ankle Booties 8.5 | Color: Black | Size: 8.5 Madewell Black Heeled Chelsea Boots In Size 8.5. Used But In Good Condition. Very Comfortable Booties That Are Easy To Walk In With A Chunky Heel. more | go to store |
 | Thomas and Vine Watson Wide Width Wingtip Chelsea Boot - Brown - 11 A handsome Chelsea boot featuring genuine leather uppers, stretch gore at the sides, wingtip details, and brogue accents. more | go to store |
 | Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Brown - 10 Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more | go to store |
 | Thomas and Vine Thomas & Vine Nash Wingtip Chelsea Boot - Brown - 10 A durable design with dapper details, the Nash by Thomas & Vine. This ankle-high boot is crafted with rich genuine leather accented by a wingtip element enhanced with brogue and medallion embellishments. Stretch gore paneling at the shaft provides a... more | go to store |
 | Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 9.5 Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more | go to store |
 | Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Blue - 12 Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more | go to store |
 | Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Brown - 11 Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more | go to store |
 | Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Brown - 10.5 Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more | go to store |
 | Thomas and Vine Watson Wide Width Wingtip Chelsea Boot - Black - 12 A handsome Chelsea boot featuring genuine leather uppers, stretch gore at the sides, wingtip details, and brogue accents. more | go to store |
 | Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Brown - 11.5 Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more | go to store |
 | Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 9.5 Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more | go to store |
 | Thomas and Vine Thomas & Vine Nash Wingtip Chelsea Boot - Black - 9.5 A durable design with dapper details, the Nash by Thomas & Vine. This ankle-high boot is crafted with rich genuine leather accented by a wingtip element enhanced with brogue and medallion embellishments. Stretch gore paneling at the shaft provides a... more | go to store |
 | Thomas and Vine Thomas & Vine Nash Wingtip Chelsea Boot - Black - 10.5 A durable design with dapper details, the Nash by Thomas & Vine. This ankle-high boot is crafted with rich genuine leather accented by a wingtip element enhanced with brogue and medallion embellishments. Stretch gore paneling at the shaft provides a... more | go to store |
 | Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Blue - 8.5 Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more | go to store |
 | Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Brown - 14 Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more | go to store |
 | Thomas and Vine Watson Wide Width Wingtip Chelsea Boot - Brown - 8 A handsome Chelsea boot featuring genuine leather uppers, stretch gore at the sides, wingtip details, and brogue accents. more | go to store |
 | Thomas and Vine Watson Wide Width Wingtip Chelsea Boot - Brown - 8.5 A handsome Chelsea boot featuring genuine leather uppers, stretch gore at the sides, wingtip details, and brogue accents. more | go to store |
 | Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Black - 11.5 Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more | go to store |
 | Thomas and Vine Thomas & Vine Watson Wingtip Chelsea Boot - Black - 8 The Watson, a handsome pull-on Chelsea boot. The designers at Thomas & Vine have tastefully garnished this silhouette with wingtip and brogue details. This smart design is carefully crafted with quality authentic leather uppers, stretch goring, and a... more | go to store |
 | Thomas and Vine Thomas & Vine Watson Wingtip Chelsea Boot - Brown - 9 The Watson, a handsome pull-on Chelsea boot. The designers at Thomas & Vine have tastefully garnished this silhouette with wingtip and brogue details. This smart design is carefully crafted with quality authentic leather uppers, stretch goring, and a... more | go to store |
 | Thomas and Vine Watson Wide Width Wingtip Chelsea Boot - Brown - 9 A handsome Chelsea boot featuring genuine leather uppers, stretch gore at the sides, wingtip details, and brogue accents. more | go to store |
 | Thomas and Vine Watson Wide Width Wingtip Chelsea Boot - Brown - 14 A handsome Chelsea boot featuring genuine leather uppers, stretch gore at the sides, wingtip details, and brogue accents. more | go to store |
 | Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Brown - 12 Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more | go to store |
 | Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Brown - 10 Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more | go to store |
 | Thomas and Vine Thomas & Vine Nash Wingtip Chelsea Boot - Brown - 9 A durable design with dapper details, the Nash by Thomas & Vine. This ankle-high boot is crafted with rich genuine leather accented by a wingtip element enhanced with brogue and medallion embellishments. Stretch gore paneling at the shaft provides a... more | go to store |
 | Thomas and Vine Watson Wide Width Wingtip Chelsea Boot - Brown - 10.5 A handsome Chelsea boot featuring genuine leather uppers, stretch gore at the sides, wingtip details, and brogue accents. more | go to store |
 | Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 14 Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more | go to store |
 | Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 11 Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more | go to store |
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