How should I dress to impress on a date with a pretty sophisticated woman?

I don't want to look like a dork, because I'm not the most well versed when it comes to fashion. I'm thinking maybe a dress shirt or polo with black jeans, or maybe khaki's, dress shirt, and sports coat, for a fancier date. Girls, what do you find attractive (or the opposite)? I could use some help, because one girl I dated thought I was gay because I wore a paisley dress shirt on our first date. She said," Only gay men wear paisley shirts," and she didn't take anything else into consideration making that judgment. For all I know the next shirt I put on could make her think I'm a poltergeist or something. I'm in good shape and supposedly decent looking.

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Most Helpful Guy

  • Dress in something that a. matches the event, and b. feels comfortable.

    by the way. it's not what you wear, but how you wear it.

    if a girl says: only gay men wear paisley shirts

    my response selection pool: and only librarians wear glasses. but you manage to pull emotions off, and I'm liking it. (shows sarcasm to let her know not to stereotype and simultaneously compliments her)

    or: Yeah, I try to dress gay. It's be unfair for other guys if their dates thought I was straight. (either end the joke there and make it clear you were kidding, or if she took the statement as arrogant, add a second joke that then depreciates the arrogance of the statement, such as... "haha. at least, I'd like to tell myself that... you know... pat myself on the back and make me feel better about life."

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    • ugh. autocorrect. that word "emotions" I meant "you manage to pull em off."

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What Girls Said 4

  • I would go for darker colors... dark blue dress shirt, with the dark jean or slacks. It does depend on what you're doing though because sophisticated lady or not, if you're doing something casual, you should tone it down or if it's something like a fancy restaurant, put on a suit coat.

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  • Depending on where you're going jeans or khakis and a button down shirt will take you most anywhere. I am personally turned off by unnecessary jewelry on men , though that's just a personal preference

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  • No jeans. A tucked in button up shirt. If its super fancy you can opt for a fancy suit

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    • Thanks, I'll keep that in mind for the future. This women seemed to have an ego problem unfortunately, and seemed mad that I wasn't intimidated by her career and education. It wasn't like I was being disrespectful, so wonder she has never been married. Sorry for the rant lol, but yeah the date sucked. I wore black khakis and a button down shirt.

  • what does she wear?

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What Guys Said 2

  • Tailor your clothes on the type of activity you are planning. Regardless what you wear make sure they are fitted to your size. nothing worse then baggy clothes

    If you PM me. I can give you some tips (The outfit I have on my profile pic is one such example)

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  • You can wear almost anything with a good pair of shoes, don't wear sneakers (especially "sporty" ones).

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