There are few times when the average man cares about clothes as when date night approaches.  For good reason, too. Your date is a chance to make a whole new first impression and what you wear and how you wear it is going to play a huge role in making that impression. For this article, we’ll look at what different choices say about you, how to use them, and the important factor of dressing contextually for a date.

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The shirt

Whatever kind of shirt you’re wearing, whether it’s a tee or a button-up, is going to play a central role in your outfit, especially if you’re wearing no jacket or an open jacket. For one, one thing you should never wear on a date is a graphic t-shirt. It doesn’t matter how casual the setting is, those logos and supposedly funny quotes don’t make you look like an interesting man. It makes you look like a teenager. Simple tees are best and best accentuated with a casual jacket to add a little contrast. As for button-ups, if you want to rock the shirt untucked look, make sure the hem doesn’t dip too far below the belt-line. If it does, it will just look like you’re wearing a shirt too big for you.

The sweater

It takes a lot of guys quite a long time to realize what role the sweater plays in their choice of outfits. When you’re too young, they make you look a little older. If you want to give off the impression of maturing, a casual simple sweater like those highlighted at is a good choice. They don’t have to be worn too formally, either. If you’re on a casual date, think about rolling the sleeves up a little. Sweaters need to be a good fit, too. You don’t want them hanging off of you. If you work out, then they can give a subtle hint at the definition of your body which will catch some eyes without egotistically shoving it in their face.

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The suit

Not every date is going to be appropriate for wearing a suit. If it’s a dinner date, however, don’t think about wearing anything else. There are different levels of suit, of course. Unless the place is particularly up-market, you’re not going to need the full formal approach. A blazer over a simple tee and a pair of chinos can be enough. Going too formal and over-dressing compared to your date is going to make them self-conscious. Regardless of what parts of the suit you wear, however, make sure you’re following a few essential rules. Keep the tie darker than the suit. Match the belt to the shoes. Don’t sit with your suit jacket buttoned up.

The jacket

The jacket makes a good addition to most kinds of outfits. You just need to find which jacket fits the occasion. If you’re sitting in a restaurant, then a blazer is the ticket. If you’re sitting in a bar or going on an adventure date, then the jacket can me more of a personality indicator than a part of the formal dress code. For instance, if you want to go for more of the rugged look and show some classy masculinity, then a good earth-toned jacket can do the trick. If you’re wearing leather, make sure it’s high-quality, however. The whole subtle masculinity look can be ruined by squeaking every time you adjust yourself in your seat or move around in general.

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The watch

That’s the top part of the outfit done. Before we move below, we’re going to talk about an essential of forming impressions that it seems the majority of men have forgotten. Remember accessories? They have a purpose. In particular, the old favorite of the watch plays a very particular role that it has served successfully for hundreds of men. Women look at your wrist to see if you’re wearing one. If you’re flashing something classy like those from then it immediately communicates to them. It communicates the idea of a man who has success on his mind. Watches are about class, so this means that, no, your Star Wars piece isn’t a good idea. It needs to not be flimsy, but to have a certain solidity and prestige to it.

The pants

Your choice of pants is just as contextual as all the other choices mentioned in the article thus far. But there are a few rules to keep in mind no matter what context and what kind of pants you’re wearing. Pleated isn’t a good idea, for one. It has a distinctly suburban dad look that is very rarely the kind of image you want to go for. Making sure they fit and stick to the right level is even more important. You don’t want your pants going higher than your navel, but you definitely don’t want them dropping and showing your boxers. Slovenly isn’t a good look to any woman.

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The shoes

Shoes are just as much of an accessory and another one of the first places that a woman will look at to get an idea of the man who has asked her out. Context is essential, of course. If you’re wearing a suit, then you need a good pair of leather shoes or classic brogues. If you’re going casual, then be a bit more minimalist with shoes. Shoes are another signifier of class. But they’re also a signifier of how well a man takes care of his appearances. Spend time polishing shoes and getting rid of any scuff marks before you go on your date. Sites like can tell you more about what exactly women look at when they’re looking at your shoes.

The facial hair

Some women love facial hair. Some women hate it. There’s no ‘yes’ or ‘no’ rule. What there is, however, is a rule about making sure that you take care of it before you head out. If you’re not growing a beard or you can’t, then get yourself shaven clean. Don’t make any wrong assumptions about the fluff on your chin. The scruffy look is not the rugged look. If you are rocking a beard, then take care of it. Get it trimmed uniformly so that it’s not sticking out from your face but framing it. If a woman loves your beard, there’s a good chance she’ll want to touch it. Using proper beard oil gets it feeling and smelling a lot better if that’s the case.

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The cologne

Yes, you need some. Deodorant isn’t enough. Women expect you to wear some kind of scent and if they realize none is there, it doesn’t say anything good about your hygiene practices even if you don’t particularly smell. But don’t drench yourself in the stuff. You need a single spray for two heat areas. A light spray on the wrists, one for the neck, one for the underarms. Cologne isn’t something that you’re meant to spray on you like antiperspirant. You spray it on the heat areas and the scent tends to cover the whole body. Also, for the few guys do it, do not spray your crotch with cologne. Use powder spray if you want to take care of yourself down there.
With the tips above, your style should be ticking all the right boxes on your next date. You’ll look good and you’ll feel confident, which is just as important if not more so. From there, it’s all about dazzling them with wit and humor. Good luck out there.