Date Night For The Gentlemen: What To Wear

By Olivia Kaiser on March 31, 2014

So, you finally asked her out on a date–or, maybe she has more nerve than me and asked you. Regardless, you landed the date, now what should you wear? It’s generally a lot easier for men to find outfits than it is for women. Men grab a pair of pants, a shirt, and they’re on their way. However, if it is your first date, or even a night out with someone you’ve been in a relationship with for quite some time, it should be obvious that you put some effort into getting ready for the big night.

There are men who dress better than others; that is just the way it works. But just because your date sees you in sweats or jeans and a t-shirt every day in class, it doesn’t mean that this is okay for a date–in fact, it is in no way, shape, or form okay. If you want your date looking like a million bucks, then you should know they want you to look good too.

Now, this doesn’t mean that you have to wear a suit (though who doesn’t love a man in a suit?), but it does mean that you should look like you put some effort into getting ready. And really, all you need is to consider a couple of aspects as you get ready.

The first thing you should consider is where you are taking her. A nice restaurant or a pizza joint? Dancing or bowling? Indoors or outdoors? Wherever you two are going for a fun romantic evening, it should be the first thing you think about when choosing an outfit.

Photo courtesy of tsbmen.com

If you’re going for a night out on the town, go for a sleek, classy look. Try a nicely tailored jacket in a dark neutral fabric, paired with a printed collared shirt, a dark-wash jean or even a white jean (as shown in the photo). Perhaps the date calls for a more casual look because you’re going on a walk or to the movies. In this case, try wearing a dark wash jean and a fitted hoodie with a collared shirt underneath.

The second thing you should think about is what tone you want to set and what her personality is. Now perhaps the latter is unfair–if it’s a true first date chances are you don’t know a lot of about her personality yet (hence, the date).

But you can tell a lot about a person by what they wear and how they act when you’re around them in class, at work, or wherever. So if you’ve heard her mention how it drives her insane when a guy wears an Affliction t-shirt or other shirts with random sayings, I would recommend avoiding those.

Photo courtesy of tsbmen.com

You need to know your style, how you’re complected, what colors look best on you. Not into that because you’re a manly man? Well … at least avoid the color orange. No one looks good in orange.

Layering is always a good look for men. But you have to be careful, because it can either help slim your figure or make you look larger than you are. So make sure you buy the right fit or get it tailored to fit you. Not to mention it will come in handy when you walk her home and she’s freezing because she “forgot” her own jacket.

Some good, general rules for guys for what to wear on a date are dark wash jeans, a button-up collared dress shirt and nice shoes. As an Esquire article points out, women can tell a lot about a person by their shoes, so pick a pair that is appropriate for where you’re going and leave your work boots or tennis-shoes at home. You don’t need to over exaggerate your sense of style or lack of for that matter. It is a mistake a lot of men make.

It’s a good idea for you to prep your clothes the day before. Maybe that sounds crazy, but it won’t be when you are rushing out the door with your shirt wrinkled and halfway untucked. Is your shirt wrinkled? Iron it. Is it a hopeless cause? Find an alternative. Can’t find your belt? Borrow one from your roommate. By finding what you need before you actually need it, you will feel less rushed and calmer by the time you ring the doorbell.

Finally, don’t overdo it on the cologne. Yes, us women love the smell of men’s cologne, but only in moderation. It should seem like it’s just the way you smell, not like you went swimming in it.

Overall, women love it when they see men dressed nicely. It’s attractive to see men who care enough about the date that they upgrade their everyday appearance.

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