Summarize the following:
People tend to react more positively toward people they can relate to, including people who dress more like them. The more you know about him, the easier it will be to appeal to what he likes. Think of a few questions you can ask to learn more about his personality and style. Ask where he grew up. Certain regions have different styles. Someone from Brooklyn may be more on the cutting edge of style than someone who grew up in the country in Montana. Ask what his hobbies are. If he spends time in coffee shops and record stores, he is probably more of a hipster. Someone interested in sports is probably more of a t-shirt and shorts type of guy. There are already enough unknowns in a first meet. You want to appear confident. Now is not the time to try to put together a new outfit. Choose clothes you already really like, that make you feel good. Think about what outfits you have gotten compliments on in the past. Choose comfortable clothing which fits well. You don't want to have to worry about adjusting yourself all night. Avoid wearing something that you think is too much of anything. This could mean it is too short, too tight, too flashy, or too boring. If you are already questioning it, don't wear it. Save the daring choices for a later date when you want to spice things up. It's sad but true that people react more positively to girls who are wearing makeup than bare-faced girls. It's a double-edged sword, because that respect can also be negated if you are wearing too much makeup. Stick to just some powder, blush, mascara and lip color. Avoid excessive eye makeup or bold lip color for the first meeting. He may not be the type of person who puts a lot of thought, effort or money into his own clothing. If this is the case, he is less likely to pick up on clothing cues or really care too much about what you are wearing. If he does spend a lot of money or time on his outfit, then he is probably just as worried about how he looks as you are.
Learn as much as you can about him before you meet. Be confident in what you are wearing. Stay near the middle of the road. Wear some makeup, but not too much. Don't sweat it too much.