This comparison obviously reflects two extreme cases, but believe or not, many guys will still over exaggerate their attire for a first date. The chances are, on your first date you will be dining at an above average restaurant. As a result, wear a nice pair of classy pants, a matching shirt and elegant shoes, to be on the safe side. A simple combination of clothing such as those mentioned above will be suitable for any occasion. Another very popular place people bring their dates to is the movie theater.
Some people make big efforts to dress up simply to go catch a movie.
If it is a habit for you to dress sharply, then suit up nicely even when going to the movies. The reasons for this are simple. First, you might not feel comfortable wearing more formal clothing, and second, if you start seeing your date on a more regular basis, she will have higher expectations and will expect you to dress up for every occasion. A more unconventional thing to do during a first date is to go clubbing. When attending one of downtown's trendiest nightclubs, it's the right occasion for you to dress up semi-casually with a blend of funkiness.