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What To Wear on a Blind Date?

boyfriend-jeanTo clarify. An acquaintance (okay, an old fling) is certain he knows the perfect man for me, and to that end, he has arranged an upcoming evening for the three of us to meet and greet. Art gallery opening, followed by dinner and drinks. But what to wear? Pencil skirt with high black boots? Boyfriend jeans with a fitted t-shirt? I consulted my best girlfriend, who also happens to be a world-class clothing designer. Her response: “Don’t over think it.” Spoken like a married woman who hasn’t been on a date for years.

I’m taking suggestions.

Discussion

4 comments for “What To Wear on a Blind Date?”

  1. Sophie says:

    Simple: whatever makes you feel most like you. If that’s the boots and skirt, go for it. If it’s jeans and a tee, likewise. I do advise against pajamas, though. . .

  2. Laura says:

    I vote for skirt. If the boots don’t feel right, perhaps kitten heels?

    I’d lean towards a more formal outfit for an art opening and dinner, but I’m in NYC; I think boyfriend jeans are too casual. If you feel best in jeans, perhaps a more fitted pair would work?

  3. As a guy I can’t give you specific fashion advice but I’d repeat what others said. Where something that you like and feels comfortable. I’ve gone on lots of blind dates and I can say the ones that have gone well it wasn’t because of my clothes (or her clothes).
    I hope that helps,
    ~Bryan

  4. AKM says:

    Ooh, I like what Bryan said! Very true.

    I have an upcoming date myself and I was wondering about this as well. I’m thinking jeans and a cute top, because that’s the outfit in which I feel most attractive AND comfortable, and in turn I can then be my most honest, fabulous self if I’m feeling attractive and comfortable.

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