Fashions considered conceptual or intellectual are not always easy to wear. Just ask curator Valerie Steele, who says she can’t walk five feet down Sixth Avenue in her Martin Margiela skirt designed so that part of the hem is permanently hiked and attached to the waistband. “Someone always runs up to me, ‘Miss, miss! Your skirt!’” relates Steele, director of the museum at Fashion Institute of Technology in New York.

Any fellow buying Prada this season might soon have similar travails to relate, given Miuccia Prada’s subversive propositions for her spring men’s wear, including trousers without flies, bralike waistcoats, peekaboo jockstraps and a tutu or two. (Figuring male designers have subjected women to difficult fashions for eons, Prada decided to turn the tables.)

Clothes and runway shows that challenge and confound—or at least get people thinking beyond skirt lengths and the colors of the season—have carved out a place in contemporary fashion history, from Rei Kawakubo’s infamous “humps” collection to Hussein Chalayan’s morphing clothes that are sometimes as compelling and collectible as contemporary art.

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