Madonna/Y-3: We know she’s Madonna, so why go undercover? This Y-3 look is the perfect chic yet sporty alternative. (She can add her own sunglasses if need be.)
Gina Gershon/Dries van Noten: Gina Gershon’s maxiskirt and T-shirt ensemble is dated. A calf-length skirt and sweater — as in this Dries van Noten — would be the current thing to do.
Rachel Dratch/Cacharel: We don’t think Dratch was trying to be funny when she wore this frumpy house dress out. How gorgeous would she look in this discreet print on a belted Cacharel dress?