Dear Mr. Manners,
I have been out of the dating game for a few years, and now I am trying to once again find love. I recently mustered up the courage to ask a guy on a date, but it has been so long since I have gone on a date that I don’t even know what to wear! What is the best way to make a good first impression?
—Business and Pleasure
Before you begin thinking about the date, consider the subtle yet critical difference between “dressing” and “wearing.” This distinction is the single most important factor in looking great, no matter what your day’s plans are —date or not. The first one is simple; well-informed selection is key. The latter notion involves — quite literally — doing nothing: Dress well, and then don’t think about your clothes until he takes them off.
Everyone has heard the old cliché, “don’t try too hard.” I disagree. First of all your appearance, at least to him is an indicator of respect for both him and the date. Second, no matter how hard you try, when you show up to meet him, you’re just you. He doesn’t know how you normally dress (although hopefully your look isn’t too dramatic a departure from your usual style.) So relax. He’s not going to think you’re a virgin because you’re wearing a suit.
You probably shouldn’t wear a suit.
Opt for a dark pair of well-fitted pants with a slightly shortened hem —something that implies you’re taking a break from an important job and busy schedule to make time for him. So throw on a dress shirt — nothing too busy, top button undone — and a slightly loosened tie on the narrow side.
If this sounds too dressy, your right: you want to show that you’re an adult but also that you’re capable of having fun. Nothing takes the edge off in style quite like a cardigan with a nice texture — keep it dark, and extra points for subtle details like cool buttons.
Last, and anything but least, come the shoes. Assuming that he appreciates the Jordan 3s as much as you do is a gamble you can’t afford right now, so opt for a pair of well-polished dress shoes instead. And not that you wouldn’t anyway, but pick up the check when you’re done.