Ah, so it has finally happened. You met her in that class you took once and bonded over the really boring lecture. She’s cute, she’s smart, she’s funny and when you asked her out on a date she actually said ‘yes’. Congrats. I’m proud of you. I really am. But do you have any idea what you’re going to wear?
You should always try to dress well when you go out on dates. Actually, you should always try to dress well all the time. It says a lot about you and the type of person you are. I know we’re not supposed to judge people on how they look, but I will judge you. If you’re dressed badly, I will assume you’re an idiot and chances are, so will your date.
So you’ve decided to take your date out on a nice, relaxing, casual date. A movie? Sure, why not? Now, there is a time and place for certain clothes. Do not wear a suit to a movie theatre. You will look out of place and it will show your date that you’re not exactly the sharpest tool in the shed. ‘Then what should I wear?’ Great question. If you don’t already own a pair of dark jeans, I suggest you go out and buy a pair. Chinos work well too! One thing to definitely keep in mind when buying pants is that they should fit. Don’t buy pants that are 8 sizes too big and don’t buy pants that don’t let your best friends breathe (you know what I mean).
Try to grab a nice button up shirt. Something that goes with the shirt and shows off your personality. Again, fit is really important here too. You don’t want to wear a shirt that can double as a parachute. Unless you’re going sky diving – then it’s okay. Get a tailored shirt. Shoes are probably the most important part of your outfit. Everyone notices your shoes. You know when your date gets a little awkward and she looks down and notices your favourite pair of kicks that are a little too lived in? That’s when she’ll notice them. So make sure you wear a nice clean pair of shoes that match whatever it is you decide to wear. And for christ’s sake, make sure your belt matches your shoes!
You sir are a fancy man. Spending the bucks to take your date to a classy restaurant. Nice.
No, Kelsey’s is not a fancy place and neither is that Asian place you go to for lunch with your buddies.
Wear a blazer jacket. Seriously, you can’t go wrong with that. Blazer jackets make you look more masculine. They also make you look like you’re important, when chances are, you aren’t. Follow this up with a fitted dress shirt that is tucked in. Do not leave it untucked. I cannot stress enough how sloppy you will look. And again you can either go with dark jeans or chinos. It really all depends on what blazer jacket you wear.
If I wanted to, I could go into details about colours and all that jazz, but I won’t. I’m lazy and I’m not here to do everything for you. I’m just trying to give you guys a guide. Some inspiration. The most important thing to remember is to dress comfortably. If you feel weird wearing what you’re wearing, it will come across and she will be sure to notice that. You do want things to go well right?
Dressing really well on dates doesn’t mean you should look like a completely different person. It’s really about being the best possible version of you. You’re selling yourself to your date and you want her to buy. Dressing well won’t magically make your date go well if you’re not being yourself. Remember there’s a reason why she said yes to you in the first place.
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