Personal Style

Dating Attire 101

Impress your next date, and score a second.

Dressing for success in Modern Dating

Whether you are a fan of it or not, online dating has changed the way we date. We aren’t going out to get to know people; we are going out to confirm if their profile matches their real-life vibe. Nowadays, before choosing to meet someone IRL we go through and analyze their entire social footprint. Even though much of the dating process has been revolutionized by apps like Tinder, Hinge, and even Grindr, one question still remains that same; what should you wear on the first date?

Dressing with the goal of impressing someone is something that we do every day, but when it comes to dating everyone throws up their hands and gets into a tizzy. Why is dating so different? Simply put, we’ve invested time into potentially having a relationship with this person. Let’s be honest, if you get to the first date without getting ghosted, you’ve made it further than 99% of people and you want to protect that time investment. From the moment you ask for or accept a date, you have a predetermined notion as to how the date is going to go.

Before we delve into the subtle differences between your date with Mr./Miss Right or Mr./Miss Right, we gotta talk about two VERY important overarching rules. First, less is more! Yes, of course, you should still be wearing a third piece, duh, however, when it comes to the first date don’t go overboard with a bold and flashy “look at me pattern” and a ton of extra accessories. Doing this makes you look like you’ve tried too hard and have something to hide. Most importantly, you just don’t know how your date is going to react to a bold print. Our second overarching rule is to keep in mind the fit of your clothes. Maybe you just got out of a relationship and the only clothes you have are from 6 years ago… unless your the same size you are 6 years ago (Let’s be honest we all gain weight in a relationship) please get clothes that fit you correctly. Nothing kills a date faster than a button popping your date in the eye.

So, what do you wear on a first date? Like Olivia Pope asks her clients, what is your end goal? First, consider where the date is happening and at what time. Do you see this ending with a kiss at the door or a 2am Uber? Is the check getting split or is something else? I think you get the point.  Where you and your date spend your time together usually tells you about the end objective of your date. If they suggested coffee, they most likely are looking to get to know you. If you are grabbing drinks on a Friday night, your clothes just might end up on the floor. Whatever situation comes your way you will need to be ready for it, so let’s demystify this conundrum.

Afternoon Coffee with the “One”

Here’s the situation, you’ve been talking to this super cool person and you think they are amazing. You’ve told yourself that they are the reason you’ve been single for so long, you were waiting for them; you’re into it, it’s a thing. These situations require a preppy or minimalist outfit choice; keeping casual is the way to score a second date. An outfit in this style range provides an overall cohesive and dressy look without looking like you’re trying too hard. Finding an outfit that can appeal to everyone is crucial. You’re already a bundle of nerves about them liking you, so when you add the factor of them liking your outfit to the mix, it may just cause your brain to explode.

Keep it simple, everything should be a solid color with the exception of one item with a print. Don’t go too bold with the print, a nice gingham or houndstooth will do fine. The patterned piece should appear in the top half of your outfit; that means no plaid pants! Instead, go for a softer, less constructed third piece like a cardigan or pullover sweater. These pieces are less intimidating than their structured counterpart, the blazer. Pants should be jeans or khakis. Remember, this is not the time to be widely adventurous with leather pants or printed joggers.

Shoes are an area where you can have a ton of fun, just don’t wear dress shoes. Nothing screams “my mom dressed me” more than dress shoes with jeans and a button down. Go with a cool and casual shoe, maybe your favorite pair of Sperrys, those perfect fall boots you just bought, or the hip minimalist sneaker. This is where you can really show your personality, so do it! One last tip, ladies please don’t wear heels, that is doing too much.        

Dinner and a Movie with a cool connection

You swiped right, they swiped right. *insert cheesy pick-up line here*. As you started chatting you found out that you have so much in common with them! You both love sneaking bottles of wine in the movie theater and eating at independent local restaurants. It’s a match made in heaven! Later you both decided to go see A Star is Born and check out the new Kurdish restaurant around the corner from the theater. This date has a few possible alternative endings, maybe you consulted with an old-fashioned or two. Either way, you want something with some allure to it.

This is the time to wear those sexier dark clothes that are tucked neatly in your closet. You know what I’m talking about… we all have that pair of come f@$k me jeans. The tight shirt that shows off your body, the heels that make you arch your back perfectly, you know what I’m saying? You can take a few more risks here. It’s finally the right time to try a bolder pattern. Remember to follow the rules, keep it above the waist and no animal print! A cool geometric micro-print top is just right. Lastly, your third piece should have a little more of your personality, think about donning a bomber or leather jacket.

A  super important thing to remember is that your dress, pants, skirt, dress etc should MAKE YOUR BUTT LOOK AMAZING. Seriously, this is not the time for diaper butt. The color/texture of the fabric is super important here. Keep the colors dark like a pair of slim-fit hunter green chinos. The pants should be slim cut and hug you in all the right places. Please don’t wear those baggy jeans that overflow the top of your boots. Think of it this way, if you could want someone to be in your pants, they have to want to picture themselves inside them.

Drinks and “Dessert” with the Hottie

It’s Friday night, you’re at a bar with your co-workers, and while they are busy brown-nosing the boss you are sitting on Tinder trying to add some excitement and fun to your life. You swipe right at 5:30 pm you have plans to grab a drink at 10:00pm. Though they may not have the corner office like you’re looking for, they are easy on the eyes. You make the decision that you’re going to go out and get it because you’ve been locked up in the house and single for too long. Like Beyonce said, “Put your freakum dress on.” Now men, don’t take that literally. While we are strong advocates of gender expression, we mean that more a euphemism. Put on those “get laid” clothes. Show off the assets.  

Honestly, there aren’t that many rules for this date option. A man in a sharp dress suit is just as much as a turn on as a man in a tight black t-shirt and some grey sweatpants. Women you can literally put on your come freakum dress, come on….I know you have one. Short and backless. The hallmark of dressing for this type of date is to wear something that makes you feel sexy as hell. When you feel sexy, you invite sex; it’s a confidence thing. But let’s be honest, if your going out with this mentality, your clothes most likely won’t be on the long…

This the time when you can wear all those big patterns: cheetah print, deep V necks that show off your chest. Put it all on the table because let’s be honest this isn’t about Mr. Right, so does it matter if your clothes make them think you have a big personality because you parent never loved you? Nope.

There you have it. Go forth into the world and swipe, tap, like and be confident in knowing you will be prepared to dress for the occasion. These don’t just have to be for the first date… maybe you’ll pull out the come freakum dress on the third date, maybe it starts as a fling then you get coffee? Can you ever predict these things? Nope! All you can do is be prepared for what may lay ahead.

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