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filed in Fashion Forward, Sex and Dating

What to Wear When You’re Flirting

“I see fashion as a way to play with your personality, to flirt with a part of yourself. It’s like when you go on a date with someone. You’re excited, you dress up, and you look phenomenal. When you get dressed, you should always be dating someone — even if it’s just yourself.” – Anna Dello Russo, fashion director at large for Vogue

Tucked away in the back of my closet is an expensive pair of low-rise, skinny jeans, which I usually drag out, along with wobbly high-heeled boots, if I have a date. More perfect when flirting with MYSELF, however, are the far roomier (and ironically titled), BOYFRIEND jeans. I made the mistake of wearing these baggy jeans once, while flirting with an actual man, who said right to my face: “I hate those. I can’t see your butt.” (Needless to say, that relationship never got to first base)

Illustration by Ana Albero

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