Penny loafers are sleek, elegant, and incredibly versatile—they can be dressed up or down, making them a worthwhile investment. That’s why I wanted to round up some of my favorite penny ...

Basically, the more unexpected way you can think of wearing a loafer, the better. So, now that it’s May, give your sneakers and house slippers a break and bust out a pair of these.

Consider the penny loafer: It’s an iconic style with deep roots in men’s fashion. It was first worn on school campuses, and it has long been top choice for stylish men the world over.

From cowboy boots to designer loafers, these are the shoes successful men swear by By Amanda Krause Feb 28, 2025, 2:25 AM PT ...