"I've always wanted to wear a minidress!" Ireland says. Now that she has the body for it, Glassman has some advice. "If you're showing off your legs—and Brenna's are great—you don't want to show off everything else, too," he says. "This piece works because it has sleeves and a sane neckline." But the real key to pulling off the look is what lies beneath: "With a mini, whether you're size 6 or 16," Glassman says, "shapewear is your best friend."
Worked for Me!
"The whole time I was losing weight, I made sure to have a five-pound bag of potatoes in the house. And every time I lost another five pounds, I'd haul out that bag and take a good look. It was my way of visualizing how much weight I'd just gotten rid of—and it's what I needed to keep going."
Minidress, Aidan Mattox, $300; Neiman Marcus, 800-365-7989. Earrings, R.J. Graziano; 212-685-1248. Shoes, Casadei; similar styles available from neimanmarcus.com.
From the September 2011 issue of O, The Oprah Magazine.