Outfit of the Week: Homegirl

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You can tell by the steel toe of her heels she's tough, despite her tendency toward floaty feminine details, like a billowy lilac shirt dress. Dare to do the same: Wear a similar dress with dark wool, thigh-high stockings paired with a pleated skirt for a twisted prep touch. Top it off by throwing on Brian Lichtenberg's cheeky Homiès beanie and a leather backpack for a relaxed-but-with-it vibe.

Charcoal Homiès Beanie with White Embroidery Made in USA$48 at Brian LichtenbergBasic Short Sleeve Crop Top, $16 at Topshop; Gorjana Alphabet Coin Necklace, $75 at Shopbop; Steven Alan Tristan Skort, $119 at Steven Alan; Jeffrey Campbell Don't Care Platform Shoe, $148 at Nastygal; Mustard Seed Silver Spoon Dress, $58 at Nastygal; Hansel from Basel Wool Rib Thigh High Socks, $32 at La Garconne; Stella McCartney Stella Eau de Parfum Spray, $72 at Sephora; Sunday Riley Effortless Breathable Tinted Primer, $48 at Sephora; Coach Studio Legacy Leather Backpack, $258 at Coach.