You should pull yourself together always and everywhere, but there are exactly six times a week when the way you dress really, really matters. Five of those are from about nine to about five during the workweek, and they can be pretty tough. But the sixth is date night, and it is not to be underestimated. Especially when this particular sixth day happens to be first-date night. Because an impression, like a good outfit, is difficult to make, but when your etiquette is in concert with your wardrobe, well, good things happen. The first thing you need to realize is that your presentation of yourself shows your level of respect for her, and… See? We’re already dropping tips before the list actually starts.
Women are obsessed with shoes. Not just their own shoes or shoes on other women— your shoes. So wear nice ones, because her judging you on them is unavoidable. Pick an appropriate pair — lace-ups or loafers for the evening; driving shoes, moccasins, or simple sneakers for the afternoon; flip-flops for nothing, ever — and you’ve scored points before the handshake.
Going out with her, especially for the first time, is an occasion. Dress for it. Don’t sweat the tie, but a jacket would be an excellent idea.
Unless your destination requires a tie. Then wear one. But check first — you don’t want to feel too dressy.
Also, don’t wear a suit. This might seem counterintuitive, but hear us out: If you are going to the opera, fine. The theater, maybe. Otherwise, you’ll seem uptight. Sure, the nicest things you own are probably those suits of yours, but those suits are for work — leave them in the dry-cleaning bag ’til Monday. Your goal on date night is to be at leisure, or at least maintain the illusion of it. And separates, or a nice sweater, will convey just that.
Wear clothes that fit you. This always applies, but now more than ever. The ultimate goal of this exercise is to see each other naked. Might as well give her a reasonable approximation of your dimensions underneath.
Grooming: clip your fingernails, wash your hair. Women check the details. They look at a man’s hands more often than a man looks at his own. Make sure yours are presentable. They’ll see those little flakes on your shoulder, too, so don’t be too shy to break out the dandruff shampoo. If this is a problem for you, avoid wearing a dark shirt.
Take it easy on the cologne. They like it when you smell nice, but there’s no need to bludgeon the poor woman.
Don’t wear anything to which the words “zany” or “interesting” might apply. T-shirts with sayings on them, your “Mr. Burns for Mayor” pin, dad’s old hunting cap — they’re not going to show her how clever you are. Your words and actions will. New jokes help, too.
Put your phone on silent.
Check your fly.
Originally Published with Photo: http://www.esquire.com/style/mens-fashion/a8122/what-to-wear-on-a-first-date/