10 Best Penny Loafers of December 2025

• Featured in navy leather
• Hand sewn constuction
• Lightweight rubber outsole
• Imported

Eastland

• Used Book in Good Condition

Wisconsin Historical Society Press

• A classic yet modern penny-keeper silhouette that can beeffortlessly dressed up or down
• Premium leather uppers in a moccasin construction
• Leather memory foam insole provides all-day comfort, with a flexible non-marking rubber outsole

Sperry

• CLASSIC STYLE: Made with premium leather uppers with classic moccasin toe detailing give the Noah a polished look that looks great either dressed up with suits and dress pants, or dressed down with jeans and chinos.
• COMFORT: Fully padded sock lining with Comfort Gel provides outstanding comfort right of the box. Can also be worn sockless.
• PERFECT FIT: Available in medium width and wide width for the perfect fit.
• OUTSOLE: Non-leather, long wearing man-made outsole
• VALUE: Nunn Bush is highly regarded as a premier footwear brand by providing the best value and style in fine men's footwear since 1912.

Nunn Bush

• Moccasin-toe penny loafer with stacked heel
• Perforated footbed
• sturdy heel

Cole Haan

• Polished man-made uppers
• Easy slip on and off the foot loafer construction
• Signature penny strap
• Cushioned latex footbed for exceptional comfort
• Durable rubber outsole

Dockers

• Adiprene provides shock absorbing heel cushioning with resilient forefoot cushioning
• Ethyl vinyl acetate footbed conforms to the shape of the foot for cushioning and a personalized fit
• Leather upper material is easy to clean and maintain to extend product life
• polyurethane outsole provides durable shock absorption to help reduce foot fatigue

Rockport

• Penny loafer in vintage-finish leather featuring moccasin stitching and split pod sole with driving heel
• Perforated arch support
• Fit Tip: Sizing runs small. We recommend ordering a half size up. ; Calfskin upper ; Contrast stitch and signature hardware detail at the heel.

Cole Haan