Skip to content Skipto navigation

    To Boot New York

    Calfskin Penny Loafers

    $349.99  ($495.00)   Save 29%

    A timeless style from To Boot New York, these Italian-made loafers feature a vamp strap and apron toe. Fashioned from smooth, supple cocoa brown calfskin, its styling options are endless. They're set atop a sleek leather sole for a streamlined silhouette.

    Harry Rosen Exclusive


  • Apron toe
  • Strap with cutout across vamp
  • Made in Italy
  • Style & Measurements

  • Select your North American size
  • Fits true-to-size
  • Fabric & Materials

  • Calfskin upper
  • Leather lining
  • Leather sole
  • Cocoa brown
  • Style #20030588


    • FREE Expedited for orders over $100, otherwise $8. Ships to most locations in 2-4 business days

    • FREE In-Store Pickup. Ready in 0-5 business days

    • $20 ExpressPost. Ships to most locations in 1-2 business days


    Sartoria Recognition Program tier members Silver and above receive free shipping.



    If your purchase doesn’t live up to reasonable expectations, we invite you to return it. Whether we need to replace it or refund your money, we will do whatever is required for your utmost satisfaction.

    All clients receive Complimentary Returns on orders over $100 before tax. Sartoria Recognition Program tier members Gold and above receive free returns on all orders.


    Click here for our full shipping and return policies.