Men's Chelsea Boots

Slip-on Chelsea boots built for comfort, weather, and timeless everyday wear.

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31 products

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31 products

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#color_Black#color_Black
Flora Smooth Chelsea Boots Sale price$147.99 Regular price$184.99
2 colors available
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Weatherproof
#color_Black#color_Black
1 color available
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#color_Black#color_Black
Vegan 2976 Felix Chelsea Boots Sale price$161.24 Regular price$214.99
1 color available
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Weatherproof LIMITED EDITION
#color_Teck#color_Teck
1 color available
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Weatherproof LIMITED EDITION
#color_Sienne#color_Sienne
1 color available
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Weatherproof
#color_Black#color_Black
4 colors available
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#color_Dark Brown + Grizzly#color_Dark Brown + Grizzly
2976 Chelsea Grizzly Boots Sale price$179.99 Regular price$224.99
2 colors available
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Weatherproof
#color_Stout Brown#color_Stout Brown
4 colors available
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Weatherproof
#color_Rustic Brown#color_Rustic Brown
Classics Sale price$239.95
4 colors available
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#color_Black#color_Black
Vegan 2976 Felix Platform Chelsea Boots Sale price$199.99 Regular price$269.99
1 color available
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#color_Black#color_Black
2976 Ambassador Leather Chelsea Boots Sale price$171.99 Regular price$214.99
2 colors available
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Weatherproof
#color_Stout Brown#color_Stout Brown
The Original Sale priceFrom $219.95
3 colors available
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#color_Black#color_Black
2976 Leather Casual Chelsea Boots Sale price$135.99 Regular price$169.99
2 colors available
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#color_Black#color_Black
Graeme Analine Leather Chelsea Boots Sale price$164.99 Regular price$214.99
1 color available
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#color_Black#color_Black
1 color available
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MADE IN CANADA
#color_Crazy Horse#color_Crazy Horse
Men’s 14332 Romeos Chelsea Boots Sale price$187.49 Regular price$249.99
1 color available
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#color_Black#color_Black
2976 Harness Analine Leather Chelsea Boots Sale price$179.99 Regular price$224.99
1 color available
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#color_Gunmetal Saddleback#color_Gunmetal Saddleback
Embury Chelsea Wyoming Boots Sale price$135.99 Regular price$169.99
1 color available
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#color_Black#color_Black
1 color available
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#color_Black#color_Black
1 color available
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MADE IN CANADA
#color_Dark Farmer Crazy Horse#color_Dark Farmer Crazy Horse
Men’s 14351 Romeos Chelsea Boots Sale price$191.24 Regular price$254.99
1 color available
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Weatherproof
#color_Black#color_Black
Embury WL Chelsea Boots Sale priceFrom $147.99 Regular price$184.99
1 color available
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#color_Amber#color_Amber
2 colors available
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#color_Black#color_Black
1 color available
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Weatherproof
#color_Black / Pit Quarter#color_Black / Pit Quarter
Hardie II Leather Chelsea Work Boots Sale price$127.99 Regular price$159.99
1 color available
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Weatherproof
#color_Rustic Black#color_Rustic Black
2 colors available
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Weatherproof
#color_Dark Khaki#color_Dark Khaki
2976 Yellow Stitch Artimus Chelsea Boots Sale price$161.24 Regular price$214.99
1 color available
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#color_Hawthorne#color_Hawthorne
1 color available
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#color_Dark Brown#color_Dark Brown
1 color available
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#color_Black#color_Black
Audrick Leather Platform Chelsea Boots Sale price$209.99 Regular price$279.99
1 color available
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Weatherproof
#color_Asphalt Black On Black#color_Asphalt Black On Black
Men's Weekend Chelsea Sale price$131.24 Regular price$174.99
1 color available
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Clean, rugged, and endlessly versatile—NEON’s men’s Chelsea boots collection delivers pull-on ease with built-in attitude. Whether you're after polished leather finishes, workwear roots, or weather-ready performance, our Chelsea lineup blends timeless design with modern durability.

Blundstone leads the charge with its signature elastic-sided boots, including the 500, 558, and Thermal Series—crafted in premium leather with water-resistant finishes and shock-absorbing soles. Dr. Martens adds an edge with the 2976 Chelsea, fusing punk heritage with tough-as-nails construction and signature yellow welt stitching.

Red Wing’s Classic Chelsea boots offer premium USA-made leather and heritage workwear roots, while Palladium brings tactical styling and lightweight function with sleek silhouettes built for everyday movement.

From office fits to outdoor errands, these slip-on boots go wherever you do—delivering instant comfort, durable build, and low-maintenance style.