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;
Blouse, $69;
Shorts, Risto, $430;
Bag, $550;
Shoes, White House Black Market, $125;