These aren't the penny loafers your dad (and even your grandad) wore back in the day. Today's loafers are leaner and meaner than ever. The silhouette has been slimmed down and designers are modernizing the materials along with stepping up the details by adding such tweaks as crepe rubber soles. The resulting slip-ons are more stylish and more comfortable than ever. Not to mention versatile.

Shown left: $328 by Oak Street Bootmakers