Double-breasted suit
Double-breasted wool suit by Brunello Cucinelli, $4,395; striped shirt by Ermenegildo Zegna, $375; silk tie, $215, and shoes, $1,230, both by Louis Vuitton; pocket square by Ralph Lauren Black Label, $125; socks by Allen Edmonds, $19.
Credit: Photograph by Jeff Ridel

The latest iteration of Letterman's go-to suit is slimmer than its predecessor, with high armholes, a shorter jacket – adding to the overall modern look – and an unconstructed shape with very little padding. This Brunello Cucinelli ($4,395) suit is the ultimate workplace luxury: lightweight wool and silk stitched to flatter your body.

Double-breasted wool suit by Brunello Cucinelli, $4,395; striped shirt by Ermenegildo Zegna, $375; silk tie, $215, and shoes, $1,230, both by Louis Vuitton; pocket square by Ralph Lauren Black Label, $125; socks by Allen Edmonds, $19