TRACY DWYER, 51Real estate consultantAnn Taylor denim boxpleat skirt ($68) / Elie Tahari silk tank ($198) / Cynthia Steffe crochet shrug ($240) / Peach by Constança Basto sandals ($249) / Kooba leather bag ($595) / Mary Louise at Fragments necklace ($240)"The vertical lines of pleats are always slimming, but this cut is especially flattering. My knees are my least-favorite feature, and this skirt covers them without making me look dowdy. It’s comfortable enough for driving, yet it’s also dressy enough for clients. The other plus is that it will roll up nicely in a suitcase. I spend eight weeks a year in Paris, and I can wear this skirt from café to museum with ease."LISA SIMKIN, 46Lampshade designerMavi denim skirt ($78) / Roberta Freymann polyester/cotton blouse ($65) / Payless wedges ($20) / Forth & Towne straw hobo bag ($148) / Kenneth Jay Lane necklace ($325) and earrings ($75)"The older I get, the lower my jeans get, so it’s appropriate that this A-line skirt sits right on my hips. I’m relatively short and prefer above-the-knee hemlines, so I’d probably shorten it. I like to play up denim by wearing it with offbeat colors and accessories. I’d wear this exactly this way—with a vivid print blouse and trendy gold jewelry. Denim skirts have been in my wardrobe forever, so I’m glad they’re back and better than ever."BONNIE TORRES, 42At-home momCynthia Steffe denim skirt ($175) / Petit Bateau cotton tank ($37) / Walter beaded cashmere-and-silk blend cardigan ($210) / Constança Basto sandals ($269) / Forth & Towne woven leather hobo bag ($168) / Pono bangles ($140 each)"Normally I don’t wear skirts because of my muscular legs, but I feel so sexy in this number! The high waistband seems to flatten my stomach, and the fitted cut accents curves I usually hide. It’s nice to feel feminine in ruffles again, even when I’m chasing my three-year-old. I like the funky attitude of Lisa’s skirt, but Tracy’s is too tailored for me. I try not to dress my age—and in this case, I don’t know any 18-year-olds who can fill this skirt the way I do!"Originally published in More magazine, April 2006.