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Wear casual dresses when running errands, visiting with friends, or attending special events

Oversized jerseys from brands like Sean John or Rocawear, paired with Timberland boots or Air Force 1s, became everyday staples in Y2K mens outfits

Rectangle or straight figures can play with ruffles, tiers, or cinched waists to add dimension and create the illusion of curves

A little black dress, strappy leather pumps, minimal diamond jewelry and some oversized shades are all it takes

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Its topped off by the textures in her grey blazer for a look that nails the smart casual dress code brief but could also look sophisticated in certain board rooms