What to Wear on a First Date to Actually Get a Second One

Image via Complex Original

The devil is in the details, and impressing your date is really going to live and die by the little things. Whether this means clipping your nails on the day of, or hitting the barber shop beforehand, you should put some effort into your appearance before you rendezvous. If you're the type of guy who rocks a beard, trim it up. While studies have shown that ladies don't generally like bearded guys, keeping your facial hair neat will earn you fans regardless. It's the smallest details that will leave the biggest impression.

Yes, much like a job interview, you're planning on making a good impression. But unlike a job interview, you're not trying to woo an employer (though we got your job interview style tips right here). Relax. Most guys want to approach a date with the level of formality that goes with an interview, but on a date, dressing like that will have you looking like you're trying to meet the parents on date one. 

While any advice on formal dressing depends entirely on where you take your date, we suggest keeping the sport coats and ties at home, and going more casual than dressed up. It's not the best to wear jeans and a T-shirt to an interview, but a pair of slim denim, a minimal T-shirt or button down, with a leather or denim jacket would do wonders on date night. We know you're probably nervous, but showing up in a tux isn't going to do you any favors.

It's basically a cliché that women are “crazy for shoes,” and while not every woman you meet is like that, you'll do well to keep your footwear on point. Of course you're trying to impress your date, but that doesn't mean you need to pull out the dress shoes. A clean pair of classic sneakers (be it Vans, Nike, or adidas) will almost always do the trick. The emphasis though, is on "clean."

There's no doubt that most ladies won't care so much about the style of your sneakers, as they do their cleanliness. It's not that your kicks need to be spotless, but if you look like you just hit a climbing trail, or have visible holes—those may not be the shoes to wear. You don't have to go out and buy a brand new pair of sneakers before your date, just grab a Magic Eraser, or toothbrush, and go to town. At least if the date goes sour, you still walk away with cleaner kicks.

Date night denim shouldn't be difficult to decide on. In terms of what you should avoid: anything with crazy holes, anything baggier than a slim straight, or jeans in a color that isn't black or a shade of indigo. If you're an absolute beginner, dark indigo or black denim is a no-brainer. They walk the line between dressed-up and laid back and can be worn with a T-shirt or leather jacket as well as a button-down and unconstructed sportcoat.

Of course, for guys with more advanced style, the sky's pretty much the limit. Jeans are the pizza of first date outfits. Once you nail the basics of fit, it's hard to mess up. Jeans with some slight fraying or a couple well-placed rips (crotch blowouts are always forbidden), go for it. Light wash? Why not. Stacking is permissible as well, as long as your denim is still tailored enough to look tapered as it stacks up. As always, avoid anything that could even remotely be called #NTDenim. Keep it tailored, keep it simple, and your denim problems will vanish.

We're all about keep things casual for your first date, and you should be comfortable. Sweatpants are not the way to do this. We've shown you how to wear sweatpants to work, and we're certainly aware of their flexibility in the modern man's wardrobe, but when you're trying to impress someone, they're just not the pant to lead with. 

Chances are that you own a pair of trim jeans or trousers, and they're better for a few reasons. While sweatpants are casual, it comes across as a lack of effort if you meet your date with a pair on. Wearing actual pants shows you actually tried. Of course, if your first date is at a fitness class or SoulCycle, that's an exception to the rule.

Putting on a watch is acceptable for a date. It doesn't even have to be flashy or expensive, but adding a timepiece not only makes you look like you know how to accessorize your look, but also ensures you'll actually be on time. When it comes to other accessories, you should exercise caution. Despite what pick-up artists tell people who've actually wasted money on their advice, the whole "peacocking" thing is for dudes who have no personality and therefore nothing to actually talk about on a date.

Earrings aren't necessarily terrible, but should be minimal (if worn at all). Chains are fine if the links are small and don't distract from the kit you've carefully put together. Let's put it this way: While you may want to flex your wealth with a chain, or two, nothing looks cornier than a guy who wears too much jewelry. Beyond the obvious shine, keep pins to the lapel of your jacket (if you have one), sunglasses for outdoors, and scarves to winter outerwear. A good rule to remember is to throw on everything you think you want to wear, and then take off one or two things.

No matter what happens, the success of your date night will hinder on your cleanliness. It doesn't matter if you're coming from work, or the gym, or your grandparents' house: You need to clean up before your date. Ideally, you should shower, but washing your face, taming your hair, and an application of deodorant will go a long way.

In terms of cologne: a little bit goes a long way. If it's a scent you wear regularly, you should know well before date night how strong it is, and more importantly, how much to apply. You want your date to associate you with a faint scent that leaves a little to the imagination—so like a good conversation, don't come on too strong. Don't buy or try a new scent on date night either. If she's agreed to go on a date with you, and you've already met before, it's likely that she's cool with your current cologne. You should be clean and smell great, but you want your date to smell you if you're lucky enough to get up close and personal, not from a yard away.