17 results for "Timberland Penny Loafer" between $50.00 and $150.00

Updated for the new season: Men's Classic Boat Penny Loafer. We've blended the superior traction of a classic boat shoe with the casual appeal of a penny loafer to create our Men's Classic Boat Penny Loafer.

The Timberland ® story began in 1952, when Nathan Swartz bought part of the Abington Shoe Company. He learned how to make shoes and began to work on ways to make them better. In 1965, the Swartz family made history by introducing injection molding to the footwear industry; creating the first, truly waterproof Timberland leather shoe.

Ethylene vinyl acetate sole for light weight cushioning

Smartwool lined for comfort Anti-Fatigue footbed for comfort Green Rubber 42 percent recycled rubber outsole EVA footbed for shock dispersion

Men's slip-on shoe. Back pull on tab for easy on and off. Rubber outsole. Anti-Fatigue insole. Textile lining. Leather upper.

Rich details and buttery leather give these Onuma Driver loafers from Timberland a handcrafted quality. Slip-on these loafers for comfortable all-day wear, courtesy of the flexible sole and cushy padded footbed.Square toeSlip-on styleLogo detail at side heelRemovable padded insole

Rich, smooth suede uppers and Vibram outsole show the true craftsmanship of Timberland, whle the subtle, clean colorway shows the sophisticated style of Stüssy Deluxe.

Your feet can always use a new best friend, and this ultra-comfy, go-everywhere lace-up design from Timberland promises not to disappoint. Crafted with smooth, rich leather, the Pinkham Notch Oxford features a lightweight, low-profile upper, accented with subtle stitching detail and contrast rubber overlays at the toe. The shoe's chic, simple design gives it endless versatility and makes it a fashionable match for everything from a sleek pair of chinos to your favorite jeans.