Would You Wear This On Your Next Night Out?

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If there's one thing we take personally, it's style. And, part of that means defying definition — refusing to limit our options to the canon of womenswear. Yet, we know crossing the aisle into the men's department can be a big step, and finding the yin and yang of your style requires experimentation. With that in mind, we called in two of our favorite experts in gender-bending style: Hannah Hart, the hilarious host of My Drunk Kitchen on YouTube, and Deryck Todd, a fashion designer and the nightlife icon behind BowieBall. See how the two get ready for a night out in the video above, and get inspired to take some risks of your own.

Deryck, before: His own caftan and hat, ASOS shoes, Karen Walker sunglasses. Deryck, after: ASOS shoes, shirt, and jacket; The Kooples shorts; Deryck Todd hat; Melissa + Campana bag (his own); his own jewelry.

Hannah, before: Zara top, ASOS collar clips, Alternative Apparel pullover, H&M pants, Oscar de la Renta shoes. Hannah, after: 2nd Day jacket, Zara top, ASOS collar clips, H&M pants, Oscar de la Renta shoes.