First Date Theory
It’s a Friday in May, the weather has finally turned for the better in New York, and you’ve been invited out to dinner and drinks by a potential suitor. You know where you’re going, but now, what are we wearing? He’ll look “preppy,” at best, from what you can tell by the photos on his Hinge. So, this is going to be more about you and what sort of message you want to convey, as opposed to showing off your fashion knowledge.
Ok, enough hypothetical Bradshaw-isms, this is a situation I’ve found myself in more and more often recently. Not to brag, but I go on a LOT of terrible first dates…so, watch out boys! Anywho, I know I’ll be going into these theaters of romantic combat with my winning personality, incredible wit, and saint-like humility, but what I don’t know is what exactly I should be wearing?
I go back and forth between a few different theories that I’d be happy to walk you through:
Theory 1: Shock and Awe
“Let your plans be dark and impenetrable as night, and when you move, fall like a thunderbolt.” Sun Tzu probably didn’t have the NYC dating scene in mind when he wrote that, but it works well here nonetheless.
This theory, more often than not, is my most preferred. I will say that it hinges on the fact that I love a kooky outfit. I try to show up dressed so me that the only thing I can do is be myself. It makes me feel more comfortable, it’s like an armor.
The effect on your date is similar. It’s sort of like taking them to a restaurant where they have to eat with their hands. It’s disarming and throws them off their game in a fun way. They don’t have the chance to focus all their energy on projecting some sort of image of what you should act like on a first date. Or maybe, even better, they feel more comfortable being themselves when they see that you already are.
Theory 2: Soft Power
So, I know that I possess a CMD (Closet of Mass Destruction), but I also have…a personality. So, as opposed to letting my clothes do the fighting, why not dress softly and carry a big stick?
Subdue the sartorial peacocking for the first date and let my charm do the work for me. Now, I know this won’t work for some of you because, well, I’ve been condemned to a conversation with you. However, for those of you who do have the ability to produce and maintain productive and engaging conversations, I will say this option is something to consider.
This isn’t to say you should be boring or mute yourself stylistically. This is more about wearing a tried and true outfit so that you don’t have to think about it. Unload some of the mental stress of getting ready. Those jeans and that black sweater look great together? Perfect. Let’s go with it.
Theory 3: Tit-for-Tat
It’s 2026. We have the luxury, or maybe the curse, of seeing photos of these eligible bachelors in advance of a date, so why not use that to our advantage?
Sometimes, if I see they lean on the adventurous side of dressing, I’ll go for it with an outfit I think they’d find unique. If they’re more conservative, let’s have a little fun and dress like a blue blood. I find it sometimes gives me the opportunity to wear something I don’t normally find myself in.
A good partner should bring something new out of you, after all.