Not dressing for the occasion.
So you've picked a classy location because you're a grown up. Good job, your Mom would be proud of you! Now you actually have to match your outfit to the venue. This involves a small level of effort. Effort. Ugh! But listen up—even hipster doofuses put some effort into how they look. You should, too! This doesn't just mean putting some gel into your hair and calling it a day. The girl you're about to see probably perseverated (look it up and use it on your date) over what exactly to wear on your first date. It's ok for you to put some thought into your attire as well. Having a well put-together outfit will communicate to your date that you are mature, thoughtful, interesting (at least before you open your mouth) and that you care about the occasion. I'm not saying you need to suit up. Just show her that you care and you'll make her feel like you are excited to spend time with her.
Wearing Clothes that Don't Fit.
This isn't a hilarious 90s sitcom with puffy shirts. It's 2016. And newsflash, bub: clothes are ALL about fit. You know that one item of clothing you have where you feel like you can conquer the world as soon as you slip it on? It fits great, right? Sure, the pattern or color might be killer. But if it's a great color that doesn't have a flattering fit, forget about it. Have you ever seen James Bond don a shirt that didn't fit perfectly? Of course not. Where do you think he gets his confidence from? Wearing clothes that fit will not only make you feel better, it'll also make you stand out in a sea of baggy and boring. And of all the items in a man's wardrobe, finding a perfect button-down shirt is the toughest – which is exactly why we started Pacific Issue. We were tired of being generically sized up as smalls, mediums, and larges, endlessly searching for shirts that fit in the waist but not in the
Have you ever seen James Bond don a shirt that didn't fit perfectly? Of course not. Where do you think he gets his confidence from? Wearing clothes that fit will not only make you feel better, it'll also make you stand out in a sea of baggy and boring. And of all the items in a man's wardrobe, finding a perfect button-down shirt is the toughest – which is exactly why we started Pacific Issue. We were tired of being generically sized up as smalls, mediums, and larges, endlessly searching for shirts that fit in the waist but not in the neck or vice versa. So we developed an algorithm that spits out the nine precise measurements needed for a perfect-fitting custom shirt, all based off of a few simple questions. Never again will you have to brave cramped dressing rooms trying on shirt-after-shirt that fits like billowing sails.
Not thinking ahead.
Doing something creative, like going for a hike? Awesome! Alternative dates are a great way to break through the awkwardness and get away from the standard resumé-review first date. But, what about after the hike? It's probably worth bringing a change of clothes in case you want to grab a drink or a bite afterward. It's also important to think ahead for the standard bar/restaurant date. A walk is a great way to change venues and relax, all while getting to know each other better. This is your time to shine: maybe that perfect outfit the girl had spent so much time on is great for inside, but not so much outside. Handing over your blazer is one of the classiest things you can do on a date. Chivalry isn't dead: but you have to be prepared on all but the hottest of summer nights just in case the opportunity presents itself. Also: blazers look and feel amazing.
Trying to be someone else.
So you read GQ and went out and bought a bunch of really expensive clothes. Cool. But they somehow feel like they don't actually have anything to do with who you are, or how you see yourself. While a lot of us would like to think we're George Clooney, we're not. Being yourself is key while dating: you don't want the girl to like (or dislike!) you for the wrong reasons. If you wear something that doesn't represent who you are or tries to make you into someone you're not, you'll come across as needy. If the girl you're out with doesn't like you being yourself, better to find that out over one drink instead of several dates, or months, later. Dress like your favorite version of yourself, and you'll be able to relax and not worry about a thing other than getting to know the girl sitting across from you.
Aaron is a co-founder of Pacific Issue, a new take on men's custom shirts. After attending NYU for his undergrad, he was sent to the wild world of software sales, based out of New York and the UK. After discovering custom clothing on a business trip to Asia, his world would never be the same. He returned to the US and earned his MBA at USC, where Pacific Issue was born.