
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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Belfast Dark Brown Suede Penny Loafer
Sale price$425.00
Belfast Mid Brown Suede Loafer
Sale price$425.00
Ravello Mid Brown Calf Penny Moccasin Slip-On
Sale price$425.00
Belfast Dark Brown Calf Penny Loafer
Sale price$425.00
Ravello Black Penny Moccasin Slip-On
Sale price$425.00
Dylan Mid Brown Suede Penny Loafer
Sale price$425.00
Jagger Dark Brown Calf Penny Loafer
Sale price$450.00
Aldrin Brown Calf Leather Penny Loafer
Sale price$450.00
Belfast Black Suede Penny Loafer
Sale price$425.00
Clapton Burnished Brown Calf Penny Loafer
Sale price$475.00
Ronny Navy Aero Suede Slip-On Penny Loafer
Sale price$224.99
Regular price$450.00
Aldrin Brown Aero Suede Penny Loafer
Sale price$450.00
Dylan Taupe Suede Slip-On Penny Loafer
Sale price$425.00
Aldrin Black Calf Leather Penny Loafer
Sale price$450.00
Jagger Black Calf Penny Loafer
Sale price$450.00
Jagger Medium Tan Calf Penny Loafer
Sale price$450.00
Clapton Medium Tan Calf Penny Loafer
Sale price$475.00
Browne Taupe Suede Penny Slip-On Loafer
Sale price$395.00
Merritt Dark Brown Deerskin Leather Penny Loafer Slip-On
Sale price$450.00
Clapton Black Calf Penny Loafer
Sale price$475.00
Nino Brown Calf Lug Sole Penny Loafer
Sale price$450.00
Balboa Dark Brown Leather Penny Slip-On
Sale price$450.00
Aldrin Mid Brown Suede Penny Loafer
Sale price$450.00
Nino Black Calf Lug Sole Penny Loafer
Sale price$450.00



