Ask a Girl: What Should a Man Wear on a First Date?

Our friends over at StyleList want to help you out. So, instead of just assuming you know everything a woman desires, why don’t you listen to the editors at the premiere fashion site on the Web and make sure you are doing the right thing when it comes to the opposite sex. This week: first date attire.

There’s a lot of decisions that can go into a first date. And while we’ve already discussed your behavioral dos and don’ts (remember, we aren’t a petting zoo) we’ve yet to dive into the world of your wardrobe.

We’ll start by clearing the air and saying, yes, your outfit actually does matter. Not only is it a representation of your dress choices in general, but also the clothing decisions you might make when meeting our parents for the first time (and, yes, we think about that too).

Our recommendation is to dress with effort, but don’t make your outfit so elaborate that it becomes a conversation piece (we’re sure you think the same thing about our outfits). Imagine this: the equivalent of you in a suit on a first date is a girl in sky-high heels and a mini dress. Yes, it sounds nice and looks good from afar, but all you’re thinking is “why are they wearing that?!” and “I can’t wait to tell my friends how over the top you look.”

Most likely, your first date is drinks or dinner, so your best bet is a fitted collared shirt, jeans or khakis (depending on the venue), and a pair of shoes that are nicer than your typical weekend sneakers, but not as done-up as your dress shoes. Nothing fancy, just something to show you care about how you looked when taking us out for the first time. It’s the perfect middle ground between casual and sophisticated, and it’s exactly what most girls want to see.

Now, there are always a few exceptions to this rule. If you’ve planned a day-date that involves a casual activity, by all means throw on the jeans and a t-shirt. But that doesn’t mean it’s ok to wear basketball shorts and a ribbed white tank (this isn’t Saturday basketball with the boys). And if your job requires you to wear a suit and you have to head right from work to your first date, your suit is always acceptable. But one piece of advice would be to lose the tie; it’s the perfect way to make you and your suit seem even cooler.

A few things to NEVER wear on a first date: jerseys (even Bradley Cooper’s character looked silly in one in Silver Linings Playbook), tie dye, anything stained, and Tevas. Just never wear Tevas.

If you’re still looking for exactly what to wear on your first date, we’ve put together 9 essential items for a foolproof first date outfit sure to impress.