Our Seaport Penny keeps it ultra-classic with a traditional penny-keeper silhouette, a true moccasin construction and an upper made from soft pull up leather.

By adding a 2.5-inch block heel to a classic penny-keeper silhouette made from smooth leather, we've raised the preppy classic to new stylistic heights.

Classic penny loafer silhouette with subtle heel. Premium leather upper with caning-embossed details. Memory foam footbed. Flexible, non-marking rubber outsole ...

The Seaport Penny is our seafaring take on the classic penny loafer. This shoe pulls in the moccasin construction with a traditional penny loafer feel.

Good quality and great look! Easy to clean. They do run a bit snug. Some leather stretching but patent leather feels like not in my opinion. Soft footbed. All ...

Pair it to denim and a blazer for an easy going-out look. Premium leather upper with 2.5-inch block heel. Leather memory foam cushioned insole. Flexible non- ...

The Seaport Penny is our seafaring take on the classic penny loafer. This shoe pulls in the moccasin construction with a traditional penny loafer feel.

These shoes are so cute and comfortable and really well made. They have a decent heel but do not feel uncomfortable on the ball of the foot whatsoever. If you ...

Free shipping BOTH ways on sperry seaport penny loafer from our vast selection of styles. Fast delivery, and 24/7/365 real-person service with a ...