Before you even begin to think 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 (and we’re about to simplify it even further); well-informed sartorial selection is key. The latter notion, on the other hand, involves—quite literally—doing nothing: Dress well, then don’t think about your clothes until she takes them off.
Everyone’s heard the old cliché “don’t try too hard”. Well, we disagree. First of all, your appearance, at least to her, is an indicator of your level of respect for both her and the date. Second, no matter how hard you try, when you show up to meet her, you’re just you; she doesn’t know how you normally dress (although hopefully your look isn’t too dramatic a departure from your usual style). So relax. She’s not going to think you’re a stuttering virgin because you’re wearing a suit.
But you probably shouldn’t wear a suit. Opt for a dark pair of slim-fitting 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 her. 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, you’re 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 or a gray placket (pictured).
Last, and anything but least, come the shoes. Women are obsessed with shoes: your shoes, their shoes—literally, everyone’s shoes. Assuming that she appreciates those retro 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. Even if you remember full well where you bought them, if she asks, you can’t quite recall. “Oh, no, wait—these are Dockers.” See what we did there? Do that.
And not that you wouldn’t anyway, but pick up the check when you’re done.