What to wear on a first date - besides confidence

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06.06.2018 2504

There are not many situations that are as nerve wracking as going on a first date (okay, maybe having to give a presentation in front of your entire department or taking a pregnancy test when your period is late). Especially if your date is someone you are highly interested in, you’re probably trying to make sure you leave the best impression possible. I’m not going to judge you for stressing out about this - I’ve been there and I get it. And when you start thinking about what could go wrong, it’s not even that unreasonable to get nervous: Where should you go? What if the conversation dries up even before the food gets to the table? What if you run into your ex, who happens to live in that part of town?


One thing you shouldn’t waste your time on worrying about though, is what you’re going to wear. It’s definitely one of the things that are absolutely under your control.

While it’s neither the Oscars, nor a job interview, there are a bunch of “rules” out there regarding the do’s and don’ts of an appropriate wardrobe for a first date. It’s difficult to distinguish which of these “rules” are actually worth following and which you’re best off ignoring. As an example: after just ten minutes of internet research on the topic, I’ve read both that wearing flip flops on a first date is a big no-no, and - in a different article - that they’re actually really cute with a nice summery dress. Essentially, the single one golden rule is: wear whatever makes you feel confident and like the best version of yourself. That being said, there are a few tips that might help steer you towards whatever that best version looks like for you.

    • Make yourself comfortable

    The number one thing to focus on and a prerequisite for looking stunning is making sure you’re relaxed. After all, you’re going out on that date to enjoy your time, so wearing something that makes you feel uneasy will be a waste of your evening. On top of that, your date is probably going to (consciously or unconsciously) pick up on how you’re feeling and you don’t want to set yourself up for the unnecessary awkwardness that follows.

    Now, don’t confuse feeling comfortable with looking sloppy. There’s nothing wrong with dressing up a bit more than you do in your day to day life and your date is going to feel flattered when he sees you made an effort. It just means that if you’re the type of woman, who usually stays away from makeup, the first date probably isn’t the best occasion to try out that new bright red lipstick. Instead, choose the look that makes you feel like yourself - which in return is the best premise to looking marvelous.

    • Avoid anything that could be described as “too much”

    Be careful to not go overboard in either direction - on whichever dimension that might be: too short, too long, too transparent, too modest, too loose, too tight, too expensive, too oversized… - you get the idea, right?

    Let’s take jewelry as an example: instead of hanging your face full of chains and risking looking like a rapper, who compensates his insecurities with outrageous bling bling, pick out one classy piece that makes you feel good. Same with exposure: it’s a well known rule of thumb in fashion that when it comes to showing skin, it’s safest to pick one body part - your back, legs, shoulder or cleavage. Show off that part of your body and cover the rest.

    Whatever it may be - makeup, heels, color, size, transparency, … - don’t exaggerate it.

    • Wear something that fits

    Ever been at a party and not been able to concentrate on the conversations because your shoulder straps kept sliding down? Had to stop dancing halfway through the night after your gorgeous new pumps gave you blisters? Or not been able to take a step without that cute tube skirt riding up? Yep, then you know how irritating clothes feel that don’t fit very well and you will probably agree that that’s not something you’d want on a first date. Don’t wear anything you can’t walk in, eat in, breathe in!

    Just in case you still find yourself having to readjust your outfit during your date: be discrete about it! Excuse yourself and do it in the bathroom instead of pulling a boob scoop in front of your date and the entire restaurant.

    • Dress for the occasion

    Sitting in your little black dress on a picnic blanket in the park feels just as awkward as having to walk past a bunch of elegant snobs in your baggy jeans and crop top. To avoid unpleasant situations make sure you know where you guys will be going and what you’ll be doing. Or how about you suggest an activity and place for your date?

    • Don’t wear something out of your hamper

    I get it - you love that pair of jeans. But no matter how amazing they make your butt look, if you’ve been wearing them all week, don’t make them part of your outfit for a first date. Not only do clothes collect smells and stains, they also lose their shape when having been worn a couple times after being washed. Grab something fresh out of your dresser!


    Now, before you pull everything out of your closet in an effort to follow all these tips: relax! Wear whatever makes you feel confident, empowered and like yourself, even if it goes completely against something you just read. Think of these tips more as a guideline in case you’re feeling completely lost and trust your own instincts. Your date is going to evaluate you’re guys compatibility based on your humor, your conversation and on what you have in common anyway - not on what you’re wearing. And if he does, then you’re better off without him anyway.


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