
Penny Loafers
Discover the Penny Loafers collection from To Boot New York, where timeless style meets exceptional Italian craftsmanship. Expertly handcrafted in Italy, each pair features supple leather or suede uppers with meticulous hand-stitching across the vamp and classic penny strap for a refined, heritage look. Built with Blake-stitched leather soles for flexibility and durability, these slip-on loafers offer a comfortable fit that molds to your foot and becomes easier to wear with every step. Lightweight, breathable, and effortlessly versatile, they transition seamlessly from tailored looks to relaxed ensembles—delivering the perfect balance of sophistication, comfort, and everyday ease.
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Atlantis Two-Tone Black & White Box Calf Leather Penny Loafer
Sale price$349.99
Regular price$495.00
Bennett Burnished Tan Brown Baby Calf Leather Penny Loafer
Sale price$279.99
Regular price$398.00
Le Grand Taupe Suede Penny Loafer with Aerograph Detail
Sale price$199.99
Regular price$398.00
Evans Black Calf Penny Loafer Slip-on
Sale price$450.00
Spalding Dark Brown Suede Penny Loafer
Sale price$495.00
Smythe Dark Brown Suede Penny Loafer
Sale price$450.00
Spalding Dark Brown Calf Leather Penny Loafer
Sale price$495.00



