O, Yes You Can!
Old-Fashioned at 29
As sales director for the NYC-based vintage store What Goes Around Comes Around, Jennifer McClain doesn't just wear the clothes, she lives the lifestyle: "My apartment is furnished with antiques, and I organize my closet by decade," she says. "I love playing dress-up every day." When looking to capture a specific era or style, the key is in the details, from the print on McClain's dress to her carefully coordinated jewelry, hat, belt, gloves, and shoes (What Goes Around Comes Around). "The '40s were a time when women could be comfortable but also look put-together," McClain says. "The dresses especially are kind to curves."
To go retro:
Start with small doses. You can pair vintage costume jewelry with jeans and a tee. Gradually work up to more pieces, like a scarf, hat, or skirt.
Pay attention to fabrics. Clothes from the '20s were often made of thin silk and tend not to preserve well. Later decades incorporated synthetics like rayon, which drape nicely. (Ignore sizing—a 14 then might be a 6 now.)
Cuff, The Family Jewels.