Then: Weekend staples, wall-to-wall khakis
Now: Dressy, fastidiously engineered jeans and separates
"When Gap started 40 years ago, jeans were really casual," says executive vice president of design Patrick Robinson. "Now they're a $300-and-up status item." Robinson's solution: the just-launched 1969 premium-denim collection, which boasts high-end Japanese fabrics and meticulous fit for $70 or less. "I was afraid I'd be wearing 'Mom' jeans, but these are cute and sexy," says fashion stylist Ann Caruso (far right), 42, of her skinny dark-wash pair ($70). Ann also likes the slim-fitting shirt ($50), leather vest ($228), and shearling-lined boots, the latter a collaboration between Gap and French footwear designer Pierre Hardy. Hardy also made the denim wrap boots worn here by jewelry designer Zani Gugelmann (near right), 32, whose no-frills style shows in the silky shirt ($60), puffer vest ($70), and lean jeans ($60). Her bullet-shaped, jewel-encrusted pendants (Santo by Zani) unscrew to reveal a tiny scroll on which you can write your own message. Socks, Falke.