What To Wear On Your First Date

We’ve all found someone awesome online, or seemingly awesome, and then couldn’t decide what to wear when it was date time. First things first, congratulations on your date! And if you’re worried about what to wear then it’s a sign you must really like him. I know what you’re thinking: should I try to match his style? Should I dress up? Can I wear my favorite shirt even if it’s getting old? Well I’ve got the answers for you and they might just surprise you. 

1. Be Yourself

I have gone through many phases when it comes to fashion but there’s a few things that almost never change. Up until recently I was adamant on keeping skinny jeans alive and I had a pair for just about every occasion. Than I had a date with a much older man, a man who might not understand skinnies, so should I have changed? No. Dates are a chance to show your best self but still be yourself, because that’s who you will revert back to after the honeymoon phase anyways. If you’re soon-to-be bae dresses the opposite he might still find your approach to style refreshing!


2.  Wear Something Natural Yet Memorable

When you picture your favorite chick flicks, the leading lady is always wearing something signature when she meets the man of her dreams. When you wear something you love that’s new and makes you feel confident, you’ll be your best self. Now this doesn’t mean you have to go to the store, just find an icebreaker statement piece in your wardrobe and make it work. My favorite of these are my bright red Converse high tops. They show some fun and personality without making any future dates too scared to take the seat next to me.


3. Consider Your Location

There’s nothing more embarrassing than feeling out of place on a date that’s planned just for you. If where you’re going requires a dress shirt then find one that will blend with the standard of your meeting spot. Also never forget to consider the temperature. You don’t want to be caught sweating in a warm crowded jazz bar or going to a picnic wearing black jeans! Take a second to google where you’re headed and get a sense for what might be expected. I once went on a date at a little indie coffee shop where hipsters and business professionals tend to hang out. It was summertime but the crowd was still dressed quite formally, because most of them were letting off steam or meeting their own dates after a day at the office. My date strolls in wearing a neon yellow tank top (that was super sexy) and he looked like a muscled version of Big Bird in a sea of suits. He made the mistake of considering the season and not considering the location.


4. “Target Marketing”

Coming from a marketing background I really want to take credit for this concept when it comes to clothes, but alas it was wisdom from a fellow gay man. If you’ve been chatting with this guy for some time you probably know what he’s into, and now’s your chance to give him exactly what he’s after. Is he a top that can’t say no to a great booty like yours? Wear your tightest jeans and serve him up some cake! Is he a fellow bear who can’t get enough of your body hair? Wear a button up and undo the top buttons.


5. Dress For Comfort

Everyone dresses up for an interview and then finds themselves fiddling with their sleeves and trying to keep their jacket from wrinkling. That’s really the last thing you want on a date even if you look absolutely amazing. The only reason you should be in a suit is if you’re NPH or the location has a dress code. Otherwise, I hate to break it to you but you are not going to look very comfortable sitting next to your date. Also did I mention it’s a lot of fabric? You are going to be feeling hot before you even get to dessert!


6. Groom and/or Re-Groom

Whether you’re coming from work, coming from home, or coming from another date, it’s time for a refresh. When you first put on a fresh shirt, style your hair, and shave your face you looked like something out of a magazine. That’s also probably the last time you looked in the mirror. So if there’s more than a few hours in between you may not notice that your final look has begun to fall apart. I work really far from where I live, but I date near wear I work, so that means I can’t always show up fresh from home if I’m meeting someone new. However, that doesn’t mean that you can’t quickly give yourself a refresh in the staff bathroom. You could bring a change of clothes or even just a little product to finish off your falling fringe. Regardless of whether or not you put the time in to look your best, your date will assume this is your best, so make it awesome!


7. Dress As He Remembers You

If you’ve sent him a picture, added him on instagram, or found him on an app, then you can bet he’s probably thinking of you just as you are in that photo. Now if you’re smart, that photo is already super-accurate and current, otherwise what you’re wearing won’t really matter. But you should also take note of what you wore in the pics he’s seen and try to mimic that. However, you absolutely don’t want to wear the exact same shirt, otherwise he might think it’s the only one you own!