Lisa's New Look
O's creative director, Adam Glassman, helps Lisa Lucchese find a chic new style to call her own.
Lisa Lucchese makeover - before image
Before: "I Dressed Not to Be Naked"
To gear up for O's tenth anniversary in May, we're kicking off a series of reader makeovers. First up: Lisa Lucchese, a 44-year-old woman who lost 140 pounds, eight dress sizes, and any excuse to avoid shopping. O's creative director, Adam Glassman, helps her find a chic new style to call her own. 

See Lisa's transformation!
Lisa Lucchese O Magazine Makeover
Today: "I Want to Look as Good as I Feel!"
Lisa's mother had undergone gastric bypass surgery in 1998 and lost 180 pounds, and her sister had the procedure in 2006 and took off 160 pounds. In the fall of 2007, Lisa had surgery, too. Eleven months later, she reached her goal weight of 145 pounds, and with the help of two support groups, she's kept it off. Now she wants clothes to match her personality. "I want to look as good as I feel," she says. "I don't want to dress blah."
Lisa Lucchese makeover - weekend outfit
For Weekends
During a week with O's makeover "dream team," Lisa has her hair cut and colored, her teeth whitened, her makeup done, and her bra fitted. Adam begins his makeover with pieces from her closet that have potential, along with several new outfits. He wants to create distinct looks for work, for weekend, and for evening.

He starts with white jeans (Lauren Jeans Co. by Ralph Lauren, $70) and adds a purple wool blazer (Lauren by Ralph Lauren, $270) over a crewneck (Lord & Taylor, $70) and white button-down (Express, $40). "The coat (Lands' End, $130) is a cross between an anorak and a trench," says Adam. "This makes it a perfect three-season piece that goes with everything." 

Hoops, Slane & Slane. Shoes, Kate Spade New York.
Lisa Lucchese makeover - evening outfit
For Evening
"Given Lisa's lifestyle, which doesn't require a fancy evening dress, I like separates," says Adam. He chose a red silk ruffle top (Ellavie, $69) and hot pink brocade skirt (Lafayette 148 New York, $348). "You can take this outfit apart: The blouse looks good with jeans; the skirt would work with a crisp white shirt." He finishes the look with a croc-embossed leather clutch (Kaia Peterka) and metallic shoes (Naturalizer). 

Earrings, David Yurman.
Lisa Lucchese makeover - work outfit
For Work
Lisa needs to be comfortable in her job, but too often comfortable equals sloppy. "These flannel pants (Lands' End, $50) work because they stretch, while also giving Lisa some shape," says Adam, who finishes the look with a dressed-up T-shirt (Banana Republic, $34) and a cashmere waffle henley sweater (L.L. Bean, $119). 

Earrings, Jenny Bird. Scarf, Bindya New York. Watch, Michael Kors. Bag, CC Skye. Shoes, Gap.
Lisa Lucchese makeover - floral dress
A Dress for All Seasons
"Lisa's weekend look, unlike most people's, is dressier than her work look," Adam says. He had this summer dress of Lisa's tailored to fit her better and showed her how to make it transition to fall by layering on pieces like a yellow cashmere cardigan (Lord & Taylor Cashmere, $110), light brown leather belt (Banana Republic), and a signature piece of jewelry like this statement necklace (Lindsay Colbus). 

Boots, J.Crew.
Lisa Lucchese makeover - striped turtleneck
Changing Your Stripes
Lisa says she's had this turtleneck "forever." Adam pairs it with mustard yellow corduroys (Lands' End, $40) and purple suede loafers (Jessica Simpson). Women of a certain age shouldn't be afraid of skinny-leg pants, he says. "As long as you're not pear-shaped, they'll look great with boots, heels, or ballet flats. Just don't tuck in your shirt."
Lisa Lucchese makeover - little black dress
Lisa has owned this dress and its matching jacket for nearly 20 years. She always wanted to be able to fit back into it, and now she can. "It's difficult to tailor a jacket, so get rid of those that are out-of-date," Adam says. A more contemporary covering is a chiffon bolero (Rickie Freeman Teri Jon, $145, or a shawl over the shoulders. Adam also modernized the dress by having it lengthened and pegged (that is, tapered inward as it comes down the leg). Bag, Kaia Peterka, $345; Satin heels, Nina, $70;
Lisa Lucchese makeover - pink striped shirt
Punk Rock Revival
After her surgery, Lisa picked up this look-at-me top at Marshall's. To keep it from feeling too "juniors department," Adam grounded the bright pink with all black: a knee-length skirt (Shape fx, $39;, and chic suede ankle boots (Via Spiga, $225, select Nordstrom stores; 800-695-8000). "The Lycra in the skirt provides built-in shaping, and the belt (Hobo International, $58; enhances an hourglass figure," he says. The solid color from waist to toe also helps to elongate Lisa's legs.