The trick is not to be so literal—you don’t want to look as if you just walked off the set of Mad Men. Contrast “old” (estate jewelry, a Peter Pan collar shirt, and Mary Janes) with “new” (a glitzy loose dress, a cross-body bag, and a wraparound belt).
To buy (clockwise from top): Adam silk dress with sequins, $358, shopadam.com. Keds at Opening Ceremony silk top with cotton collar, $150, openingceremony.us. Marais USA patent-leather flats, $98, maraisusa.com. C. Wonder bag in calf hair and pebbled leather, $198, cwonder.com for stores. Raoul leather belt, $110, 212-206-8264. Samantha Wills ring of sterling silver and crystal, $220, samanthawills.com. Lulu Frost vintage Deco earrings, $360, 212-965-0075.
1 of 9Jens Mortensen
American Apparel Top
Retro looks and rich color make this faux-silk shirt a standout.