10 Best Mens Penny Loafers of December 2025

• 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

• Beautifully antiqued-by-hand leathers and soft, supple suedes.
• Cushioned leather footbed for ultimate comfort.
• Lightweight leather/rubber outsole with heel veneering, combining a classic look with modern, innovative flexibility.

Cole Haan

• All eyes will be on you in the boardroom with the Sebago® Classic Dan loafer.
• Genuine leather upper.
• Slip-on loafer construction.
• Penny keeper strap detail
• Rounded moc toe. Leather linings. Leather-lined stationary insole. Leather outsole. Imported. Measurements: Weight: 1 lb 1 oz Product measurements were taken using size 12, width W. Please note that measurements may vary by size. Weight of footwear is based on a single item, not a pair.

Sebago

• polyester
• rubber sole
• nubuck leather uppers are soft and supple
• foam footbed for all day comfort
• rubber outsole is longwearing and durable

Hush Puppies

• Readyflex technology
• easy on easy off slip on construction
• flexible rubber sole
• spot clean
• man-made upper

Kenneth Cole REACTION

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

Cole Haan

• 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

• 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

• Eva footbed with memory foam provides immediate cushioning that conforms to the shape of the foot for a personalized fit
• Full grain leather is easy to clean and maintain to extend product life
• Eva outsole and midsole provides lightweight shock absorption to help reduce foot and leg fatigue, allows easy mobility and walkability

Rockport