The priorities of an early date (even the attempt to pick up the date) is first to avoid screwing up, and only second to impress them. People lie - particularly when dating - so attempts to impress get discounted but screw ups get counted double. It takes about three impressive acts to counter one mistake. Worse, certain screw-ups are unrecoverable. It is better to leave a bad phone message than to call back repeatedly to try and fix it. Don't be that guy.
So, when it comes to clothing, don't try to be cool.and wear something funky. Go more conservative than you usually are - dress up. Treat it like a casual interview. You can always loosen up and show off on later dates.
Men need to wear good shoes. Women like shoes. I don't know why, but they do. Not just on them, but on you as well. So no sneakers, unless the date involves athletic activity. You can get away with jeans, if they are in good shape, but not a t shirt. A sports jacket works wonders with jeans, particularly if you have a business shirt on underneath. Or you can go for nice pants and a polo shirt. You don't have to copy Barney Stinson and wear a suit to bed, but a full suit does work, particularly if you are dating a professional woman.
Women - straight men don't care about your shoes. Oh, a few men may admire what high heels do for the rear view, but frankly, we don't look at your feet at all. Our eyes tend to focus on things significantly higher. I can't really give specific advice about women's clothing, it's a lot more variable. But basically look at what I told the guys, and dress to fit in with them. I told the men to dress for a casual interview, but I advise you to dress for an interview but a little sexier, less professional. No man ever complained that his date was too sexy, but keep in mind your plans for how the night will end. You don't want to give an impression you don't intend to live up to.
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