Photo: Jonathon Kambouris

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Old School: Never wear shorts to the office.

New Rule: Shorts can succeed in creative workplaces, so long as they provide the same coverage as a pencil skirt. Add a blazer, and avoid beachy fabrics. Pair shorts with stacked heels or wedges—never stilettos.
Blazer, Lauren Ralph Lauren, $275; Bloomingdales.com
Blouse, $69; Talbots.com
Shorts, Risto, $430; NeimanMarcus.com
Bag, $550; ToryBurch.com
Shoes, White House Black Market, $125; WHBM.com