How to Dress For a Date

Dress for date

Dating is hard. I say that as someone from the outside looking in, but it still looks hard. Especially now where the internet has turned a lot of dating sites into “Hot or Not” type lists. I feel for you single people. There are so many things to think about before going on a date. Not only are there the obvious questions about how the person you’re meeting is going to be or look, but how should you look and act and dress.

I can’t offer too much advice on how to date other than to be yourself, which probably isn’t the least bit helpful. What I can offer, however, is a bit of insight on how to dress. It’s something that we overthink all the time in all situations, including dating. There’s that invisible line that marks being overdressed and underdressed; being well-groomed and unkempt. It’s all a lot to take in especially when you’re wondering if you’re about to meet the Next Great Love, or some such thing.

Today I’ll break down how to dress for the right occasion and help you simplify things. It doesn’t have to be that hard and it shouldn’t be something you waste too much time thinking about. If you’re playing the numbers, it probably won’t be your last date so there’s no need to carry the weight of the world on your shoulders. With that said, here are a few of my tips on how to dress for a date.

Dress for the venue:

When we date we sometimes try too hard. While it’s an endearing fault, the result is typically looking like a doofus. As important as you think it is to wear your finest sport jacket, don’t grind that square peg into a round hole. If you and your date choose to go to a casual bar or for a cup of coffee, causal clothing is sufficient. A pair of jeans and a flannel (clean ones) will be sufficient for this affair. Conversely, if you are planning on going to a fine restaurant that serves wine out of bottles and has white tablecloths it might be a good idea to throw that sport jacket on.

People don’t like to be upstaged, and your date won’t appreciate you wearing a suit when she’s wearing jeans. You need to remember that context is important. Your effort will always be appreciated but at a certain point it becomes uncomfortable for the person who isn’t necessarily underdressed, but looks so because you overdid it.

Dress as though you normally would if you were attending that venue, just add a little polish to your look. Do your hair, forego the hat, mix in a shave; little things like that will get noticed. There’s no need to overhaul your look because you have a date. Try and be the best version of yourself.

Clean yourself up:

As I touched on before, be sure to clean yourself up for a date. A little polish will go a long way in ensuring you look good. I realize the term “polish” is a vague and a catch-all, so let’s break that down a little bit:

  • If you’re a guy that shaves somewhat regularly, shave for the date. While some appreciate the five o’clock shadow look, many do not. It’s best to clean that mug up when you’re on a date. You’re trying to make a great first impression and word has is those stick with people;
  • Throw some goop in your hair. I know not all men like to style with gel or pomade or whatever else there is, but in this case it’s best to temporarily suspend your pre-conceived notions and put in the effort. It’s one of those things where your date probably won’t notice that you have styled your hair, but you can guarantee that they will notice if you didn’t. Not styling your hair is lazy and that’s not the message you’re trying to convey;
  • This should be self explanatory but I think it bears repeating. No matter how casual the date and the venue you need to be clean. Even if your date is at a dive bar two minutes from your house you should shower and put on a clean shirt. Again, this falls into the category of not getting noticed when done and absolutely getting noticed when it’s not done.

Simple lessons that need to be followed. The beauty of these rules is that they’re extremely simple and can be easily done by everyone.

Wear confidence:

This falls into the “easier said than done” category of dating but it’s the most important aspect of looking good. I understand that dating is hard and that a lot of people out there aren’t naturally confident, self-assured, or even poised, but try your best. Your date simply wants to get to know you and you want the same from them and yourself. Don’t mumble, look that person in the eye, and for the love of god ask questions about THEM.

The crux of my point is to be yourself and be confident in who you are. Since you’re on a date it will take a little more effort than having a few oat sodas with your buddies, but that’s the whole point. The stakes are a touch higher on a date than other social situations so do your best to rise to the occasion. People recognize and enjoy being around confident people (let’s remember not to confuse confidence with arrogance, shall we?) so do your best to be confident, even if it’s in your own way.

In Closing:

I like to think that none of this is terribly difficult to achieve. I’m not asking you to run out and buy a new tuxedo to impress your date; that would be ridiculous. It’s three pretty simple steps: dress for the venue you’ll be visiting; clean yourself up for the date; and be as confident in yourself as you can be.

The point of all of this is to take away all the barriers that may get in the way of you acting like yourself. You don’t want to be thinking about your shirt or jacket on a date, you want to be focusing on the person sitting across from you. Put yourself out there and be confident and good things will come your way.


Behn Watson runs a men’s fashion blog over at Prior to starting Duck Soup Style, he worked at a local high end men’s fashion retailer as a consultant. For more style inspiration, check out Behn’s instagram account @behn_watson

Written By

Behn Watson runs a men’s fashion blog over at Prior to starting Duck Soup Style, he worked at a local high end men’s fashion retailer as a consultant. For more style inspiration, check out Behn’s instagram account @behn_watson

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