Fourteen-year-old Best Supporting Actress Oscar nominee Hailee Steinfeld killed it in a glam, yet age-appropriate Prabal Gurung gown at the Golden Globes. That meant today's reference point—Great Expectations' tragically faded Miss Havisham—was an unexpected and potentially risky choice for red-carpet favorite Gurung, whose latest offering was noteworthy for its midi-lengths and ultra-rigorous fits. But this ambitious designer is nothing if not up for a challenge; the question he asked himself: "Can I do undone?" The answer: why, yes. There was a seductive, déshabillé quality to the washed red faille full-skirted party dress that was slipping off Karlie Kloss' shoulders as she swanned her way down the runway. And you likewise saw a lot of languor in the to-the-floor bias-cut chiffon gowns, especially a lovely pink one that was topped by a long-in-front, short-in-back cashmere vest cinched with a leather sash. If the zipper embellishments on a cocktail number, to name one example, erred on the gimmicky side, Gurung captured the disintegration that was central to Miss Havisham's character in a more believable way with dégradé furs that were echoed by the colored streaks the models wore in their mussed-up hair.

While showing that he's not afraid to stretch himself, this young designer also sent out the sort of things he already does well: a red sheath dress with an exacting off-the-shoulder fit, another in white with a graphic, oversize black lace placement print (talk about a challenge, getting all those curlicues to match up along the seams). And he deserves points for flaring trousers with an ultra-flattering fit. The question the crowd asked as they left: Which one of the gowns—the strapless tulle smothered in iridescent feathers, maybe, or perhaps the hand-painted ombré number—will wind up on the Oscar red carpet later this month?