If you buy something via one of our links, we may earn a commission. Cole Haan 4.Zerogrand Penny Loafers are available for $100, 56% less than the normal $225 sticker. A more-than-half-off ...

A few styles are fairly specific to men’s shoes, like the Belgian or the monk-strap loafer, so for this guide, I focused on those geared more toward women — including penny, tassel ...

Unlike the previous slip-on model, both brands have leaned further into the penny loafer silhouette. The original Jack Purcell’s are a comfortable departure from the classic All-Star Converse.