February Fashion Faux Pas Last February, I made a fatal fashion mistake. The man I was dating — and crazy about — asked me to "dress sexy" for our Valentine’s Day lunch. "What fun," I thought. I pulled out my shortest skirt — which I should have relegated to one of my daughters’ closets years ago — and paired it with a form-fitting Chinese-inspired blouse, thigh-high fishnets, and what I like to call my tango shoes. My overcoat was a silky black designer trench that was also way too short. The moment I left the privacy of my home, I realized I’d gone off the deep end. My outfit was more like a parody of sexiness than the real thing. At the elegant and stuffy hotel restaurant where we dined, I could feel people scrutinizing me as if I were a cash pickup. Forget about a romantic aftermath. My outfit quashed any notion of that. I’d felt playful getting dressed, but when I went public, my whole being screamed, "Imposter!" My date thought I looked great, but I couldn’t go through with the fantasy. My friend Karen, a forty-something newlywed, faced a different version of the same dilemma when her husband asked her to wear something sexy to a business dinner. She felt confused: What did he mean by sexy? "I’ve never thought about buying ‘sexy’ clothes," she told me. "I just wear what I like." Karen is a confident woman, but this small fashion problem left her absolutely flummoxed. My very attractive friend Maggy, meanwhile, feels guilty about never wearing the lacy lingerie her husband continues to buy for her. "I should try," she tells me, "but the lace itches." Not to mention that she’s going through menopause and not exactly bursting with desire: Wearing anything overtly sexy, she feels, would send the wrong signal. My "Sexy" ResolutionSo what are we supposed to do — dress to please the guy or to please ourselves? The latter, obviously. But on a romantic occasion, especially one as loaded with expectations as Valentine’s Day, it can be easy to try a little too hard and maybe fall back into ways of dressing that no longer suit us. The clothes I wore to my lunch date fiasco last year were relics of a past life. But they were right there in my closet, ready to grab. This is why regular wardrobe purges are so important. They save us from dressing like the women we used to be. The things that make me feel sexy now speak to me in a private fashion language I’ve learned over the decades: fabrics that feel luxurious against my skin; bold, artistic jewelry; toe cleavage. Once we’ve reached a certain age, we know what we like. The trick is knowing how to kick it up a notch. This Valentine’s Day, Karen may wear a version of the outfit she finally decided on for that business dinner: a black off-the-shoulder top with fitted jeans, dangly earrings, and killer shoes. Her husband likes it, and that makes her feel sexy. Maggy may put on her very favorite black dress and consider, perhaps, wearing that lacy lingerie as a gift of love to her husband. And me? I don’t know where Cupid will find me this year, but I’ll know enough to wear clothes that make me feel comfortable in my own skin — just as I do every other day of the year. When you want to look slim and feminine, yet tailored…Black flat-fronts in a stretchy wool hide weight fluctuations and flatter thighs and rear. Add heels, a curve-controlling wrap sweater, and a wide, sexy belt at the hip. Brooks Brothers merino sweater, $98. Theory stretch-wool boot-cuts, $250. Lauren by Ralph Lauren faux crocodile belt, $58. Payless faux-lizard pumps, $20. Neckisses silver necklace, $300.When you want to look more sensual than sexy…Go for body-skimming skirts and sweaters in supple fabrics (think cashmere and suede). A slightly off-the-shoulder neckline or wide boatneck can be as eye-catching as a deep V. Ralph Lauren Black Label cashmere-blend sweater, $598. Newport News suede skirt, $99. Calvin Klein kidskin pumps, $110. Fossil silver concha belt, $48. Julie Sandlau silver hoops, $175. When you want to look ageless and just trendy enough…A richly cabled sweater dress adds sporty, confident style to knee-high boots and opaque tights. Try this (or a slightly shorter sweater dress) over slim jeans as a tunic. The hip belt defines curves. Zambesi sweater dress, $449. Eddie Bauer boots, $178. Suzi Roher belt, $225.When you want to feel pretty but a little naughty…A ruffled silk blouse is sensual but subtle. Pair it with a slightly flirtatious tailored skirt (think flippy pleats or a trumpet hemline), gold necklaces and bangles, and pointy black patent Mary Janes. Lauren by Ralph Lauren silk blouse, $109. Philippe Adec wool skirt, $265. Isaac patent leather Mary Janes, $240. Cousin Claudine necklace, $150. Gold bangles by Ben Amun, two for $45, and Alex Woo, $88 each. Originally published in MORE magazine, February 2006.