You were out with some buddies. She was out too. She had that perfect mix of cute and slightly dangerous. You gathered up enough liquid courage to ask her to dance. She agreed and the next few minutes were a blur. You managed to ask her for her number and got it…scribbled on a wet napkin. You saw your best friend fist pump into the air because, well, he is your best friend and she was the hottest girl at the bar. Someone got sick and you were whisked away to a waiting cab but you were fine…you got her number.
You woke up the next morning and searched frantically through your pockets for the napkin when you realized that it was all a dream.
Nobody gets numbers like that anymore.
First dates have changed over the years. In the past you likely had met at least once before the actual “first date” even if parts of that meeting are blurry. Maybe you met through a group of friends once before and are getting set up on the first date. Chances are you have even talked to each other on the phone before the date! Either way you had a real world perspective (albeit sometimes blurry with bad lighting) of your potential date. That perspective was based upon the real “eye test” and not on Facebook stalking or photos that come from a variety of strange, always flattering angles.
Today, you have likely met on line. You fell for a photo. If the photo was good you might have read her profile. In the profile, you found you have some shared interests (who doesn’t love to travel). Your phone told you that you were perfect for each other without even talking. You have messaged each other and set up the impending date. Now comes the big question. How do you decide what to wear on a date with this complete stranger? Assuming that you are an adult, here is my list of what not to wear and what to wear.
What not to wear
- Don’t overdress. Avoid the heavily tailored double breasted blazer unless this first date is a gala. If it is good for you! Go all out. Assuming the first date isn’t a gala, you don’t want to come across as pretentious or no fun. If you are overdressed, you probably look great but you are probably making your date feel uncomfortable.
- Don’t underdress. You want to look like an adult. Don’t wear your favorite t-shirt (read really comfortable, washed 1000 times and almost sheer) and comfy pants. Your date will not be interested in you if you look like a manchild who lives in your parent’s basement. Avoid shirts with slogans unless it’s the words that you live your life by.
- Don’t wear running shoes (unless your first date includes the gym, sports or a hike). Especially don’t wear runners with jeans unless your jeans are super skinny and your runners are stylish and retro.
- Don’t wear your dressiest watch or jewelry. It just looks like you are trying to hard.
- Don’t wear sunglasses if it isn’t sunny or if your date is indoors. Your date will not trust you if she can’t see your eyes some of the time.
- Avoid overly sporty, bright colored sunglasses. The key to this look is to be classic not plastic.
- Don’t overdo the cologne. She shouldn’t smell before she sees you.
To summarize, the goal of the first date is to not look like you are trying too hard yet look like you take care of yourself. Sure, this sounds boring but it is not the time to shock or make a statement. Keep it classic with a touch of personal style in the details. If you do this right, you will have plenty of time to scare or impress her on a later date.
What to wear
- If its appropriate wear a nice pair of slim fitting jeans in a darker color. The key here is the fit. If you wear it in a darker color it will transition from casual to slightly more formal. Every woman likes the look of a guy in a nice fitting pair of jeans.
- Depending on the situation, opt for a well fitted henley, polo or button up oxford. The goal here is to look timeless and put together. These options are all comfortable and if the fit is right, it will create the perfect backdrop for you to woo her with your wit and charm.
- Wear layers. Not only does layering create a well put together look, it is also effective at regulating temperature. When you’re nervous and getting sweaty, you want the option to take off a layer.
- This one is important. Women understand shoes so make sure your shoes are on point. If you have managed to follow the first few points, you have many different options with shoes. You can go with brogue shoes or boots (maybe a stylish Chelsea boot) which will fit nicely with the dark jeans and carry a rugged, masculine look. If comfort is your thing opt for a simple, yet elegant slip on or a classic like a Converse All-Star or Adidas Stan Smith. Make sure they are in good condition and not completely beat up.
- Wear a watch. It makes you look like a grown up. Just don’t show off with your fancy Rolex (it may attract the wrong kind of person)
- Wear classic sunglasses just make sure you take them off inside or when you are in a deep conversation.
- Wear a touch of cologne so that when she gets in tight for a goodbye hug or kiss she is left with the perfect scent.
The purpose of dressing for a first date is to get a second date. You don’t want to overdo it and make it look like you are trying too hard. You want to look masculine and put together. The details in the watch, shoes and sunglasses will convey a confidence and personal style. The rest is up to you.