If you want to make a killing, it helps if you dress the part. With Wall Street on the rise again and the national nightmare of casual Fridays far behind us, men are ditching their workweek khakis and sneakers for that alpha-male wardrobe staple: the power suit. But whereas nineties deal makers – think Leonardo DiCaprio in Scorsese's upcoming 'The Wolf of Wall Street' – favored linebacker-size shoulder pads and oversize cuts, the modern business suit is more minimal. "A suit's shoulder gives away its decade," says Nick Wooster, former Neiman Marcus fashion director. "Today's power suit is narrow and more tailored – a man doesn't want to wear a costume." Or a clownish color: Go with gray and no matter what, you'll look like a boss.
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
Credit: Photograph by Jeff Ridel