Melanie Young

Photo: Sergio Kurhajec

The Shirtdress
"My schedule makes it hard to maintain an ideal weight. Between going to school and spending time with my husband and five children, I'm busier than ever," says Melanie Young, 40, a law student. While she's dropped 17 pounds this year, Young can still swing from a size 10 to a size 14.

A shirtdress looks good at any size, says O creative director Adam Glassman. "It creates one continuous line. And with the belt, it will fit her even if she keeps losing weight."

Says Young, "I've been avoiding vibrant colors because of my size. Not anymore."

Shirtdress, Thomas Pink. Earrings, House of Lavande. Belt, Suzi Roher. Bracelets, M.C.L. by Matthew Campbell Laurenza. Cuff, Accessories & Beyond. Pumps, Chelsea Paris.
Suzanne van der Wilden

Photo: Sergio Kurhajec

The Jacket
"As I've gotten older, my weight has varied a lot," says Suzanne van der Wilden, 49, a real estate agent who, in addition to contending with the effects of age, has an autoimmune disorder that can sap her energy. As a result, she can flip-flop between a size 12 and a size 8.

This blue blazer is a dependable year-round classic, ideal for defining the waist without clinging to it.

Glassman pairs it with a slightly billowy shell and dark-wash jeans that contain extra stretch to accommodate weight changes. He suggests leaving the shell untucked when you're up a few pounds, and tucking it in when you're down.

Blazer, Theory. Shirt, Rachel Rachel Roy. Jeans, NYDJ. Earrings, Kanupriya. Necklace, Janis Provisor Jewelry. Shoes, Brian Atwood.
Krista Njapa

Photo: Sergio Kurhajec

The Leggings
Racing after two children hasn't helped event planner Krista Njapa, 31, lose the 25 pounds she gained following back-to-back pregnancies. Because she doesn't have time to shop, she tends to "squeeze into my too-small clothes or wade around in too-big clothes. I don't look as put-together as I should." Leggings with a wrap blouse and belt, are great for work.

"Leggings aren't just for weekends, and they always fit,"says Glassman. "Go for thicker stretch fabric with seaming so they look polished, not like pajamas."

The A-line shirt is all about flexibility—worn loose, it's modern and angular; cinched, it shows off Njapa's figure.

Leggings, Adrienne Vittadini Collection. Wrap Blouse, Lafayette 148 New York. Belt, Meredith Wendell. Necklace, Sethi Couture. Bangles, Cole Haan. Shoes, Via Spiga.
Ivory Kalber

Photo: Sergio Kurhajec

The Jersey Dress
"Ever since I was a teenager, my weight has fluctuated," says Ivory Kalber, 32, who sought treatment for binge eating in her early 20s and now counsels others who struggle with eating disorders. "But I feel much better about my body since I got help. I'm happy living my life at a size 12 or 14."

This sunny dress in supple jersey works like magic to downplay extra pounds.

Glassman says. "It creates a beautiful waistline, and the off-the-shoulder style emphasizes Ivory's upper half while draping minimizes the lower body."

Says Kalber, "I thought this dress would accentuate my hips, but it doesn't. I can just throw it on and go."

Dress, Rachel Roy. Earrings, Melinda Maria. Bracelets, Melinda Maria and By/Natalie Frigo. Shoes, L.K.Bennett.
Danielle Hodge

Photo: Sergio Kurhajec

The Pencil Skirt
"I can be the same weight for six months, then suddenly gain five pounds. And I always carry it in my hips and thighs," says 26-year-old brand manager Danielle Hodge, who routinely veers from size 8 to 10 and back.

When Hodge's weight is in flux, Glassman recommends a monochromatic outfit, like this silver sequined tank and slimming gray pencil skirt.

"Trying to camouflage extra pounds under a full skirt would only exaggerate the problem," he says. "If you're bottom heavy, an outfit like this lengthens the look of your torso, providing balance."

Hodge can wear the skirt higher on the waist when she's up a few pounds; lower on the hips when she's down.

Sequined Tank, Michael Michael Kors. Pencil Skirt, Jones New York Collection. Earrings, Coralia Leets. Ring, Melinda Maria. Shoes, Miu Miu.

Next: How to Find Clothes When Your Weight Is Fluctuating