Then: 20-something and trendy, not for grown-ups
Now: Sophisticated and polished
This strapless black-and-white bouclé dress ($90) combines a simple, feminine cut with menswear-inspired fabric; wear it with a cardigan or its matching jacket (not shown, $168) for an effortless work-to-evening transition. "I've never bought anything at Express except tank tops," says Ann. "But I love the shape of this dress. Who knew Express had clothes like this?" A bold, textured gold-tone necklace (Alexis Kirk) sets off bare shoulders; the above-the-knee hem is youthful but not too skimpy. Rings, Kenneth Jay Lane for QVC and Kara Ross.