Men's Leather Work Shoes

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67 hand-picked finds across 15 curated searches — most relevant first, cheapest first within each

Styled in 8 outfits ↓
Eastland Men's Lumber Up Fashion Boot
$124.99
Eastland★ 4.3

Eastland Men's Lumber Up Fashion Boot

Styled in 1 outfit
Amazon
Twisted X Men's Chukka Driving Moc Boot
$139.95
Twisted X★ 4.8

Twisted X Men's Chukka Driving Moc Boot

Styled in 1 outfit
Amazon
Wolverine Men's Overpass Composite Toe Waterproof Work Boots
$179.95
Wolverine★ 4.3

Wolverine Men's Overpass Composite Toe Waterproof Work Boots

Styled in 2 outfits
Amazon
Irish Setter Wingshooter 7" Mens Hunting Boot
$199.95
Irish Setter★ 4.6

Irish Setter Wingshooter 7" Mens Hunting Boot

Styled in 2 outfits
Amazon
Danner 6” Bull Run Moc Toe Work Boots for Men - Oiled Full-Grain Leather Upper with Non Slip Wedge Outsole and 3-Density Cushion Footbed, EH Resistant
$239.95
Danner★ 4.3

Danner 6” Bull Run Moc Toe Work Boots for Men - Oiled Full-Grain Leather Upper with Non Slip Wedge Outsole and 3-Density Cushion Footbed, EH Resistant

Styled in 1 outfit
Amazon
Thorogood Men's American Heritage 6" Moc Toe, MAXwear Wedge Non-Safety Toe Work Boots
$264.95
Thorogood★ 4.4

Thorogood Men's American Heritage 6" Moc Toe, MAXwear Wedge Non-Safety Toe Work Boots

Styled in 1 outfit
Amazon
Men's Classic Moc-Toe Ankle Boots, Premium Leather, Lace-up Combat Style, Brown and Tan, Casual Work Wear
Generic

Men's Classic Moc-Toe Ankle Boots, Premium Leather, Lace-up Combat Style, Brown and Tan, Casual Work Wear

Styled in 1 outfit
Amazon
Amazon Essentials Men's Lightweight Chukka Moc Toe Boots
$46.40
Amazon Essentials★ 4.2

Amazon Essentials Men's Lightweight Chukka Moc Toe Boots

Styled in 1 outfit
Amazon

Seen in these outfits

Olive Corduroy Overshirt and Charcoal Chinos Utilitarian Autumn Outfit$134
Olive Overshirt
$27
Cream Shirt
$27
Charcoal Pants
$24
Dark Brown Boots
$38

Olive Corduroy Overshirt and Charcoal Chinos Utilitarian Autumn Outfit

6 pieces · Nov 6, 2026

Forest Green Wool Chore Jacket and Cuffed Raw Indigo Jeans$254
Forest Green Jacket
$44
Cream Shirt
$27
Dark Indigo Jeans
$70
Brown Boots
$65

Forest Green Wool Chore Jacket and Cuffed Raw Indigo Jeans

5 pieces · Nov 6, 2026

Rugged Buffalo Check Flannel Overshirt and Black Jeans Casual Outfit$115
Red Overshirt
$20
Grey T-Shirt
$17
Black Jeans
$26
Dark Brown Boots
$38

Rugged Buffalo Check Flannel Overshirt and Black Jeans Casual Outfit

5 pieces · Nov 6, 2026

Rust Corduroy Sherpa Vest with Grey Waffle Henley and Olive Cargos$112
Rust Vest
$30
Grey Shirt
$24
Olive Pants
$20
Dark Brown Boots
$38

Rust Corduroy Sherpa Vest with Grey Waffle Henley and Olive Cargos

4 pieces · Nov 2, 2026

Tan Suede Trucker Jacket, Black Crewneck & Raw Selvedge Jeans$172
Tan Jacket
$33
Black Sweater
$20
Dark Indigo Jeans
$56
Brown Boots
$63

Tan Suede Trucker Jacket, Black Crewneck & Raw Selvedge Jeans

4 pieces · Oct 31, 2026

Distressed Leather Bomber, Cream Henley & Raw Jeans$202
Brown Bomber Jacket
$59
Cream Shirt
$27
Dark Indigo Jeans
$56
Dark Brown Boots
$60

Distressed Leather Bomber, Cream Henley & Raw Jeans

4 pieces · Oct 30, 2026

Light Wash Trucker Jacket, White Tee & Raw Selvedge Jeans$165
Jacket
$35
White T-Shirt
$13
Dark Indigo Jeans
$56
Dark Brown Boots
$46

Light Wash Trucker Jacket, White Tee & Raw Selvedge Jeans

5 pieces · Oct 30, 2026

Tan Suede Trucker Jacket, White Ribbed Tank, and Grey Jeans$125
Tan Jacket
$33
White Tank Top
$13
Grey Jeans
$22
Dark Brown Boots
$38

Tan Suede Trucker Jacket, White Ribbed Tank, and Grey Jeans

5 pieces · Oct 30, 2026

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Men's ShoesMen's Leather ShoesMen's Work Shoes

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