A. Clothes that make you look available but not desperate. Your outfit should convey fun, charm, and sex appeal without straying from an age-appropriate comfort zone. Avoid anything that looks too easy to remove, that might be described as ultrashort, sheer, tight, or plunging, or bare. Heavy makeup can be distracting, and killer stilettos and garish colors can scare—you don't want to look like a housewife of Orange County.
No-fail date gear for grown-ups: A casual-chic strategy is dark trouser jeans (Freedom of Choice, $167) and a silk belted top (April, May, $280). Bag, Celine. Shoes, Jimmy Choo.
Or get dressy with a curvy sheath (Chaiken, $374), clutch (Kara Ross), and pumps (Giuseppe Zanotti Design).