What Women Want: What Men Should Wear to Impress a Date

When it comes to dating, wearing a perfect outfit is essential to making a good first impression. In fact, you have about a seven-second window to do so, whether you’re out on a date or going for a job interview. This means that you have to pack a lot of non-verbal communication into that window of time, starting first and foremost with your outfit and how well-groomed you look.

Something else to keep in mind: It only takes someone a 10th of a second to form an impression of you just from the look on your face, according to a series of experiments by Princeton psychologists Janine Willis and Alexander Todorov, which appeared in Psychological Science. So not only do you need the right outfit for a first impression, but you need a smile on your face or some other pleasant expression when you first meet your date. And if you hit the impression button on the nose, then a second date just might be in the cards.

So gentlemen, if you want to keep yourself in the game, then you need to first impress your date. Don’t worry, The Cheat Sheet has you covered. Here are a few great outfit ideas that we know will help you score a second date.

1. The after-work outfit

A man who's dressing to impress a date

A man who’s dressing to impress a date | iStock.com

If you’ve got a date right after work and you know you won’t have time to change beforehand, keep it simple by wearing your normal work attire — with a little bit of an edge added into the mix. If you don’t feel like wearing your “date outfit” to work, just bring it with you and leave your other clothes at work to take home another time. Go the traditional route and opt for a darker color palette. All black is always a good call, but if you want to switch it up a little, try a black pair of slim fitting chinos with a neutral color button down, a fitted grey tweed blazer, and a pair of black or dark brogues. You’re going for comfortable chic, but it’s also a good chance to convey that you’re a professional.

2. The relaxed outfit

a stylish man

A man wearing a relaxed outfit | iStock.com

You may not be going on an overly romantic date, but you should still look your best. For a relaxed or chill date, you can be a little freer with your outfit choices. If you want to go a little more “cool guy” opt for a moto jacket instead of a blazer — unless you’re going to dress the blazer down. Try a black or dark pair of jeans (it’s OK if they’re a little ripped because it adds to your “cool guy” vibe), but just make sure the rest of your outfit is up to speed with a fitted dark short or long sleeved T-Shirt and a nice, chunky cardigan over it.

A cardigan still says you’re relaxed but at the same time respectable. Don’t forget to opt for a pair of boots, which will not only give you a little extra height but will make you stand up straight. It’s sophisticated, yet still has a non-committal cool vibe.

3. The day date outfit

A man wearing a leather jacket

A man wearing a leather jacket | iStock.com

The day date can entail anything from going for coffee, brunch, or even an easy stroll through the city just enjoying each other’s company and taking in the sights and sounds. You can visit a flea market, a gallery, or grab a day drink at a new, hip spot. It’s a day meant for exploring and spending time together, and this means you want a look that’s fitted and comfortable. It also means that you’ll be throwing on a nice pair of stylish kicks, but not so dressed down that if you happen to go to a fancier place you’re not wearing something that looks beaten up. Opt for a pair of comfortable slim-fitting dark jeans, your choice of a plain or striped T-shirt (to add a little extra appeal and interest to your outfit), with a moto leather jacket, lighter denim jacket (if you wear black chinos or jeans), or a classically cool bomber jacket.

Just remember, even when you’re dressing down, you always want to look your best — aim for the just-walked-out-of-an-H&M-catalog look. Good luck, gentlemen!