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Men's Boots

Sturdy and stylish men's boots from local Vermont shops and brands. Curated styles for any weather, with fast local delivery across Vermont.

213 products

Red Wing Men's Iron Ranger 6 Inch Boots - Amber Harness by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Red Wing Men's Iron Ranger 6 Inch Boots - Amber Harness

$349.99
$349.99 $349.99
Red Wing Men's Classic Chelsea 6 Inch Boots - Amber Harness by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Red Wing Men's Classic Chelsea 6 Inch Boots - Amber Harness

$299.99
$299.99 $299.99
Justin Men's 11 Inch Drywall Wyoming Waterproof Soft Toe Work Boots - Brown by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Justin Men's 11 Inch Drywall Wyoming Waterproof Soft Toe Work Boots - Brown

$209.95
$209.95 $209.95
Thorogood Men's American Heritage 6 Inch Moc Steel Toe Work Boot - Crazy Horse by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Thorogood Men's American Heritage 6 Inch Moc Steel Toe Work Boot - Crazy Horse

$275.00
$275.00 $275.00
Lacrosse Men's Alphaburly Pro 1000G 18 Inch Winter Boots - Mossy Oak Country DNA by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Lacrosse Men's Alphaburly Pro 1000G 18 Inch Winter Boots - Mossy Oak Country DNA

$210.00
$210.00 $230.00
Red Wing Men's Iron Ranger 6 Inch Boots - Copper Rough by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Red Wing Men's Iron Ranger 6 Inch Boots - Copper Rough

$349.99
$349.99 $349.99
Lacrosse Men's Alpha Agility 17 Inch 1200G Boots - Realtree Edge by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Lacrosse Men's Alpha Agility 17 Inch 1200G Boots - Realtree Edge

$210.00
$210.00 $210.00
Lacrosse Men's Burly Boots - Green by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Lacrosse Men's Burly Boots - Green

$120.00
$120.00 $120.00
Thorogood Men's 8 Inch Side Zip Waterproof Composite Toe Work Boot - Black by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Thorogood Men's 8 Inch Side Zip Waterproof Composite Toe Work Boot - Black

$171.00
$171.00 $171.00
Danner Men's Caliper 8 Inch Aluminum Toe Work Boot - Brown Leather by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Danner Men's Caliper 8 Inch Aluminum Toe Work Boot - Brown Leather

$220.00
$220.00 $220.00
Carolina Men's Pipeline Waterproof 10 Inch Composite Toe Wellington Work Boots - Brown by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Carolina Men's Pipeline Waterproof 10 Inch Composite Toe Wellington Work Boots - Brown

$214.99
$214.99 $214.99
Hoffman Men's 14 Inch Mountaineer Double Insulated Plain Toe Pac Boots - Black/Brown by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Hoffman Men's 14 Inch Mountaineer Double Insulated Plain Toe Pac Boots - Black/Brown

$290.00
$290.00 $290.00
Wolverine Men's I-90 EPX Waterproof Soft Toe Work Boots - Sudan Brown by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Wolverine Men's I-90 EPX Waterproof Soft Toe Work Boots - Sudan Brown

$180.00
$180.00 $180.00
Danner Men's Vital Trail 5 Inch Hiking Boot - Brown/Olive
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Lenny's Shoe & Apparel

Danner Men's Vital Trail 5 Inch Hiking Boot - Brown/Olive

$190.00
$190.00 $190.00
Rocky Men's Worksmart 8 Inch Composite Toe Work Boots - Crazy Horse by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Rocky Men's Worksmart 8 Inch Composite Toe Work Boots - Crazy Horse

$160.00
$160.00 $160.00
Danner Men's Vicious 8 Inch Composite Toe Work Boots - Brown Leather by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Danner Men's Vicious 8 Inch Composite Toe Work Boots - Brown Leather

$270.00
$270.00 $270.00
Thorogood Men's American Heritage 8 Inch Moc Steel Toe Work Boot - Crazy Horse by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Thorogood Men's American Heritage 8 Inch Moc Steel Toe Work Boot - Crazy Horse

$285.00
$285.00 $285.00
Timberland Pro Men's Boondock HD Logger Waterproof Composite Toe Work Boots - Turkish Coffee Brown by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Timberland Pro Men's Boondock HD Logger Waterproof Composite Toe Work Boots - Turkish Coffee Brown

$260.00
$260.00 $260.00
KEEN Utility Men's Louisville 6 Inch Steel Toe Work Boot - Black by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

KEEN Utility Men's Louisville 6 Inch Steel Toe Work Boot - Black

From $185.00
From $185.00 $195.00
Thorogood Men's American Legacy 6 Inch 400G Insulated Waterproof Work Boot - Crazy Horse by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Thorogood Men's American Legacy 6 Inch 400G Insulated Waterproof Work Boot - Crazy Horse

$305.00
$305.00 $305.00
Danner Men's Caliper 6 Inch Work Boot - Brown Leather by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Danner Men's Caliper 6 Inch Work Boot - Brown Leather

$190.00
$190.00 $190.00
Lacrosse Men's Atlas 8 Inch Waterproof 1200G Insulated Hunting Boots - Mossy Oak Break-Up Country by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Lacrosse Men's Atlas 8 Inch Waterproof 1200G Insulated Hunting Boots - Mossy Oak Break-Up Country

$240.00
$240.00 $240.00
NEXGRIP Men's Ice Victor - Black Olive by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

NEXGRIP Men's Ice Victor - Black Olive

$195.00
$195.00 $195.00
Crispi Men's Nevada Legend Non Insulated GTX Boots - Brown by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Crispi Men's Nevada Legend Non Insulated GTX Boots - Brown

$450.00
$450.00 $450.00
Oboz Men's Bridger Ridge Mid GTX Waterproof Hiking Boot - Classic Brown by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Oboz Men's Bridger Ridge Mid GTX Waterproof Hiking Boot - Classic Brown

$240.00
$240.00 $240.00
Thorogood Men's Logger 9 Inch 400g Insulated Waterproof Steel Toe Work Boot - Brown Trail Crazy Horse by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Thorogood Men's Logger 9 Inch 400g Insulated Waterproof Steel Toe Work Boot - Brown Trail Crazy Horse

$399.95
$399.95 $399.95
Asolo Men's Fugitive GTX Hiking Boot - Wool/Black/Red by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Asolo Men's Fugitive GTX Hiking Boot - Wool/Black/Red

$335.00
$335.00 $335.00
Danner Men's Super Rain Forest 8 Inch Composite Toe Work Boot - Black by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Danner Men's Super Rain Forest 8 Inch Composite Toe Work Boot - Black

$530.00
$530.00 $530.00
Lacrosse Men's Uplander II 10 Inch Boots - Brown by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Lacrosse Men's Uplander II 10 Inch Boots - Brown

$159.95
$159.95 $159.95
Carolina Men's 6 Inch Amp Steel Toe Moc Toe Wedge Work Boot - Brown by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Carolina Men's 6 Inch Amp Steel Toe Moc Toe Wedge Work Boot - Brown

$259.99
$259.99 $259.99
Crispi Men's Wild Rock GTX Boots - Brown by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Crispi Men's Wild Rock GTX Boots - Brown

$520.00
$520.00 $520.00
Thorogood Men's American Heritage 6 Inch Moc Steel Toe Work Boot - Tobacco by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Thorogood Men's American Heritage 6 Inch Moc Steel Toe Work Boot - Tobacco

$275.00
$275.00 $275.00
Grundens Men's Tough Seas Ankle Boots - Black by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Grundens Men's Tough Seas Ankle Boots - Black

$145.00
$145.00 $145.00
Bogs Men's Sauvie II Slip On Waterproof Boots - Black by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Bogs Men's Sauvie II Slip On Waterproof Boots - Black

$105.00
$105.00 $105.00
KEEN Utility Men's Liberty 6 Inch Soft Toe Work Boots - Leather Brown/Birch by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

KEEN Utility Men's Liberty 6 Inch Soft Toe Work Boots - Leather Brown/Birch

$285.00
$285.00 $285.00
Justin Men's 11 Inch Drywall Wyoming Waterproof Steel Toe Work Boots - Brown by Lenny's Shoe & Apparel
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Lenny's Shoe & Apparel

Justin Men's 11 Inch Drywall Wyoming Waterproof Steel Toe Work Boots - Brown

$219.95
$219.95 $219.95