Dress Shoes

Dress Shoes

Discover the Men’s Dress Shoes collection from To Boot New York, where timeless design and meticulous Italian craftsmanship converge. Featuring expertly crafted oxfords, brogues, derbys, monk straps, and formal styles, each pair is made by skilled artisans using premium materials and meticulous techniques. Luxurious Italian calf leather meets hand-stitched uppers, refined leather soles, and stacked leather heels to create a foundation of quality and durability, while crisp, elegant silhouettes deliver a commanding presence whether you're in the boardroom, office, or out on the town. Designed for moments that matter, these dress shoes offer a sophisticated finish that earns respect and admiration with every step.

72 products

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Atlantis Dark Brown Box Calf Leather Penny Loafer by To Boot New York

Atlantis Dark Brown Full-Grain Calf Leather Penny Loafer

$495.00
Gallagher Black Suede Belgian Loafer by To Boot New York

Gallagher Black Suede Belgian Loafer

$425.00
Merritt Black Deerskin Leather Penny Loafer Slip-On by To Boot New York

Merritt Black Deerskin Leather Penny Loafer Slip-On

$450.00
Keats Cognac Calf Leather Slip-on Men's Penny Loafer by To Boot New York

Keats Cognac Calf Slip-on Penny Loafer

$398.00
Keats Black Calf Leather Slip-on Men’s Penny Loafer by To Boot New York

Keats Black Calf Slip-on Penny Loafer

$398.00
Stevie Brown Deerskin Lace-Up Derby by To Boot New York

Stevie Brown Deerskin Lace-Up Derby

$450.00
Joey Water-Repellent Dark Brown Suede Penny Loafer by To Boot New York

Joey Water-Repellent Dark Brown Suede Penny Loafer

$425.00
Keats Dark Brown Calf Leather Slip-on Men’s Penny Loafer by To Boot New York

Keats Dark Brown Calf Slip-on Penny Loafer

$398.00
Williamsburg Dark Brown Deerskin Oxford Lace-Up by To Boot New York

Williamsburg Dark Brown Deerskin Oxford Lace-Up

$450.00
Wheeler Vernice Patent Oxford Formal Dress Shoe by To Boot New York

Wheeler Vernice Patent Oxford Formal Dress Shoe

$450.00
Brunswick Black Deerskin Leather Slip-On Loafer by To Boot New York

Brunswick Black Deerskin Leather Slip-On Loafer

$450.00
Joey Water-Repellent Mid Brown Suede Penny Loafer by To Boot New York

Joey Water-Repellent Mid Brown Suede Penny Loafer

$425.00
Bennett Burnished Tan Brown Baby Calf Leather Penny Loafer by To Boot New York

Bennett Burnished Tan Brown Baby Calf Leather Penny Loafer

$398.00
Stevie Black Deerskin Lace-Up Derby by To Boot New York

Stevie Black Deerskin Lace-Up Derby

$450.00
Dustin Brown Leather Plain Toe Lace-Up Oxford by To Boot New York

Dustin Brown Leather Plain Toe Lace-Up Oxford

$450.00
Curtis Black Calf Leather Apron Toe Derby Oxford by To Boot New York

Curtis Black Calf Leather Apron Toe Derby Oxford

$450.00
Shayne Black Suede Bow Pump Belgian Loafer by To Boot New York

Shayne Black Suede Bow Pump Belgian Loafer

$398.00
Simon Burnished Tan Calf Leather Penny Loafer by To Boot New York

Simon Burnished Tan Calf Leather Penny Loafer

$425.00
Bernard Dark Brown Calf Leather Penny Loafer by To Boot New York

Bernard Dark Brown Calf Leather Penny Loafer

$450.00
Bernard Black Calf Leather Penny Loafer by To Boot New York

Bernard Black Calf Leather Penny Loafer

$450.00
Roman Dark Brown Suede Longwing Brogue by To Boot New York

Roman Dark Brown Suede Longwing Brogue

$425.00
Sonoma Black Calf Leather Slip-On by To Boot New York

Sonoma Black Calf Leather Slip-On

$425.00
Dustin Burnished Brown Leather Plain Toe Oxford by To Boot New York

Dustin Burnished Brown Leather Plain Toe Oxford

$450.00
Dom Ebano by To Boot New York

Dom Brown Suede Monkstrap

$450.00
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