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10 Crosby Derek Lam Shirt Dress With Pleated Skirt

Nothing is more feminine than wearing a menswear-style shirt as a dress. I know that can go in so many awkward directions, but if you stick with strict tailoring and crisp cotton like this 10 Crosby Derek Lam version ($395), you'll avoid all the "where are your pants?" questions. Unless, of course, you like that kind of thing.

— MC

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