Men's Classic Shoes

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15 hand-picked finds across 3 curated searches — most relevant first, cheapest first within each

Styled in 4 outfits ↓
Reebok Shadoray Casual Tennis Mens Shoes
$54.95
Reebok★ 4.6

Reebok Shadoray Casual Tennis Mens Shoes

Styled in 1 outfit
Amazon
Reebok Mens Club C 85 Vintage Tennis Sneakers for Men
$65.72
Reebok★ 4.6

Reebok Mens Club C 85 Vintage Tennis Sneakers for Men

Styled in 6 outfits
Amazon
Nunn Bush Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology
$69.95
Nunn Bush★ 4.2

Nunn Bush Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology

Styled in 35 outfits
Amazon
Nunn Bush Men's Lincoln Classic Penny Loafer Slip-On
$69.95
Nunn Bush★ 4.3

Nunn Bush Men's Lincoln Classic Penny Loafer Slip-On

Styled in 5 outfits
Amazon
Cole Haan Men's Pinch Penny Loafer
$117.60
Cole Haan★ 4.2

Cole Haan Men's Pinch Penny Loafer

Styled in 2 outfits
Amazon
Johnston & Murphy Men's Hayes Penny Loafer Dress Casual Shoe
$129.90
Johnston & Murphy★ 4.2

Johnston & Murphy Men's Hayes Penny Loafer Dress Casual Shoe

Styled in 2 outfits
Amazon
Florsheim Berkley Flex Penny Loafer Men's Slip On
$140.00
Florsheim★ 4.2

Florsheim Berkley Flex Penny Loafer Men's Slip On

Styled in 2 outfits
Amazon

Seen in these outfits

Navy and Cream Leather-Sleeve Varsity Jacket With Grey Wool Flannel Pants and Burgundy Loafers$219
Navy Jacket
$47
Grey Sweater
$59

Navy and Cream Leather-Sleeve Varsity Jacket With Grey Wool Flannel Pants and Burgundy Loafers

5 pieces · Oct 17, 2026

Light-Blue Chambray Western Shirt With Charcoal Wool Flannel Pants and Burgundy Loafers$152
Light Blue Shirt
$24
Charcoal Pants
$34

Light-Blue Chambray Western Shirt With Charcoal Wool Flannel Pants and Burgundy Loafers

5 pieces · Oct 16, 2026

Classic Ivy Sartorial Navy Wool Sport Coat Rust Knitted Tie and Grey Flannel Pants Look$157
Navy Sport Coat
$60
White Shirt
$15

Classic Ivy Sartorial Navy Wool Sport Coat Rust Knitted Tie and Grey Flannel Pants Look

6 pieces · Oct 10, 2026

Vintage Tennis Club Cream Cable Cricket Sweater with Navy Chino Shorts and Classic Sneakers$102
Sweater
$26
White Polo Shirt
$15

Vintage Tennis Club Cream Cable Cricket Sweater with Navy Chino Shorts and Classic Sneakers

5 pieces · Oct 9, 2026

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Men's Low-Top ShoesMen's Dress ShoesMen's Chelsea ShoesMen's Oxford ShoesMen's Penny ShoesMen's Woven ShoesMen's Cap-Toe ShoesMen's Slip-On ShoesMen's Hiking ShoesMen's Derby ShoesMen's Lug Sole ShoesMen's Brogue Shoes

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