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Tomboy fashion and styling surfaced throughout the post-war era with famous Hollywood celebrities like Katharine Hepburn popularizing the tailored suits and wide-leg pants for women

Matteau The Tiered Sundress, $520, shop online at Matteau

Ill usually pair them with a tucked-in shirt or a simple blouse to keep the outfit feeling a little more put together

Angelina Jolie at the Salt Premiere Angelina Jolie came to wow when she arrived in this sparkling Emporio Armani mini-dress at the Los Angeles premiere of Salt in 2010

Best Ballet Flat: LifeStride Womens Ballet Flat A comfortable pair of ballet flats are worth their weight in gold