But few, if any, have been more enduring than the penny loafer, which became inextricably linked to American style after young people started stuffing pennies in the notched strap atop it.

Handmade penny loafers are crafted with care and expertise, starting with the careful selection of premium leather. A shoemaker with decades of experience uses specialized tools to cut, stitch, and ...

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 ...

You might like classic black penny loafers with bright white calf socks, or velvet slip-ons that look like they belong in a cigar lounge — either way, you're dressed to impress. The best loafers ...