The men's burgundy penny loafer is the perfect fall transitional ... to the handmade Edward Green loafers you see above, which will run you a blistering (but kinda worth it) $1,220.

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 ...

I’m convinced that if you put a handful of people all wearing black penny loafers into a lineup and asked a stranger to point out the pair that looked the best, they’d point to the Weejuns ...