Photo by Devon Jarvis/Studio D.

Silk Bomber
A 1950s staple is of-the-moment thanks to a little embroidery.
Aqua, $98; Bloomingdales.com

Photo by Devon Jarvis/Studio D.

Coatigan
Half cardigan, half coat; totally chic worn indoors or out.
Sweater, $168; NYDJ.com
Belt, $20; Express.com

Photo by Devon Jarvis/Studio D.

Leather Pencil Skirt
Sleek and sexy in the darkest blue. Navy is the new black!
Skirt, $249; Talbots.com

Photo by Devon Jarvis/Studio D.

Rockin' Handbag
Trade your purse strap for one of these, which look like they were just plucked from a guitar and work on any bag with a removable strap.
Bag, $295, and Straps, $95 each; RebeccaMinkoff.com

Photo by Devon Jarvis/Studio D.

The Cold Shoulder
Show off your shoulders with strategic cutouts.
Sweater, $50; Express.com

Photo by Devon Jarvis/Studio D.

Classic Kicks
Old-school Tretorns now have a modern twist—a touch of gold. Just the thing for your next #TBT moment.
Tretorn, $85; Bloomingdales.com
From the September 2016 issue of O, The Oprah Magazine