How to Stretch Your Summer Wardrobe

Working in a clothing store doesn't leave retail manager Fran Cha, 37, in much of a shopping mood. "During the week, I wear structured clothes, so in my personal life, I dress for comfort," says Cha, who loves pairing a tunic with jeans. In cooler weather, the breezy top demands more substance—a scarf instantly says "summer's over."

Tunic, Dana Buchman, $52; Kohls.com. Jeans, Hudson, $178, Bloomingdale's; 877-612-7257. Scarf, Love Quotes, $95; ShopTheTrendBoutique.com. Belt, Leatherock, $100; 800-466-6667. Shoes, Joan & David, $260; ShoeWoo.com

"I rarely consider wearing white jeans," says Karen Sperling, a 43-year-old radiologist. But these pants are really a seasonless essential. This time of year, match them with fall-winter pieces like a leather jacket, paisley scarf, and thin sweater. This outfit opened her eyes to lots of new possibilities, says Sperling.

Sweater, Hilton Hollis, $285, Neiman Marcus; 800-365-7989. Jacket, Adam, $495, Pamela Robbins, Scarsdale, New York; 914-472-9033. Jeans, $158; JBrandJeans.com. Scarf, Tilo, $525; ShopBop.com. Shoes, Stuart Weitzman, $525; 702-369-9222

For Ann-Marie Joseph, a 39-year-old flight attendant, wardrobe versatility is a must: "I can go from mild weather to 90 degrees. My clothing needs to be flexible." A chiffon caftan is exactly that when worn under a cowlneck sweater in a similar shade. "There's an excitement when summer lingers. I can take that feeling all the way to November," says Joseph.

Sweater, Autumn Cashmere, $300, Lester's, Brooklyn; 718-375-7337. Caftan, Diane von Furstenberg, $325; IntermixOnline.com for stores. Belt, $80; KarenWalker.com. Shoes, $450; ToryBurch.com

More O style:

• 4 new ways to wear a basic black suit
• 14 must-have items for fall
• The perfect penny loafers