Clothes make the man. You've no doubt heard it before. Actually clothes don't make the man – but they do express the man. So who are you? When dealing with people you don't know very well, your wardrobe is the best chance you have to let them know. Especially the opposite sex.

What to wear for a casual date: Something – uh, casual? OK, that much is painfully obvious. But there are no formulas. Who are you going out with? The idea is to find some common ground with your date without sacrificing your own individuality – either ignoring her style or copying it will set a bad precedent for anything to come. There are too many choices to give many specific recommendations. Some specific ground rules do apply, though.

  • Unless it's part of a carefully-crafted "grunge" look, wrinkled clothing is a gigantic no-no. In case of emergency, dampen the offending garment and give it a 20-minute run-through in the dryer.
  • Unless she is a goddess of the fashion industry, you don't have to show up looking like you just got done shaking your little tush on the catwalk. "Oh, that look is so 2008!" is not a comment you're likely to hear – and if you do hear it, you can always plead nostalgia.
  • If you're looking to project a little bit of the "bad boy" look (rarely a bad idea, by the way!), leather and denim go great together. Just avoid the classic "biker jacket" dripping with chains and studs – unless she's got an earring sticking though her nose, in which case anything goes.

What to wear for a for a romantic dinner date: Let's see now…a T-shirt featuring a Smiley Face is definitely out, unless she's got one heck of a good sense of humor.

  • Make sure you tailor your personal dress code to the level of formality of the restaurant you're taking her to. A five-star restaurant will require a five-star outfit, and so on down the line. If you're not sure, scout out the restaurant in advance.
  • No matter how formal the restaurant is, wearing a full suit will reveal you to be an eager-to-please dweeb who has never had a second date in his life. A tuxedo is an even worse choice – if you're caught with one, your only way out will be to tell her you just got back from a wedding. By the way – bring her a bouquet of flowers on the first date and you might as well kiss her good-bye before the date even begins.
  • Dress jeans are a good choice for all but the most formal establishments. A well-fitting sports shirt and a blazer (required in some establishments) could complete a tasteful ensemble. Pay attention to color coordination – you don't want to look like a popsicle.
  • Remember – a gentleman is a gentle man – as long as you can avoid grossing her out with your bad taste, your behavior will make a much stronger impression on her than your clothing. You can even make a bad outfit look good, depending on how you play it off. The man makes the clothes far more than the clothes make the man.