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How a Man Should Dress On a First Date

Updated on April 7, 2011

You never get a second chance to make a first impression. How true that old saying is. Unfortunately, many men don’t seem to care what impression they make. That, or they’re just totally oblivious to the importance of how a woman perceives you in those first moments upon meeting.

And it really is just those first few moments. Miss out on those, and you might miss the boat altogether. Don’t worry, I’m not telling you to change yourself, or change your style. I’m telling you to make a good first impression. If you can do that, the second impression can be whatever you want. (Within reason, of course.)

No hats.

Unless you’re a teenager, or want to be equated to one, leave the baseball hats, kangos, derbies, etc at home. Not only do they detract from your appearance, they tell a woman you’re insecure. No, she probably won’t consciously be thinking that last one, but she’ll be feeling it on the inside, cos woman are naturally intuitive. People hide behind hats. Women don’t want a man who hides, they want a man who’s confident and isn’t afraid to show himself. And don’t leave me a comment telling me you wear hats all the time, and it’s unrelated to insecurity. If you wear one on a first date, it most certainly is.

Take your sunglasses off.

Eye contact is extremely important when flirting with someone you’re interested in. Covering your eyes the whole time only tells that person you have something to hide. And, as with the hats, tells them you’re insecure about something. If you’re outside, fine, wear them. But if she wants to talk to you face to face, slide them on top of your head (this tends to look pretty sexy, anyway) and look her in the eye. This tells her subconscious you value the conversation enough to make the effort, and it tells her you’re willing to focus on her. And for God’s sake, do not wear them indoors.

Dress for the occasion.

In other words, don’t over or under-dress. If you’re just going to the movies, you don’t need to be decked out in a leisure suit. If you’re going to a Broadway show, you could stand to wear something nicer than your ratty jeans and a pair of old Chucks. No matter what, though, your date is not going to want to feel like she’s out with a slob. Nor is she going to want to feel like she’s out with the singer in a glam rock band. Dress for the occasion, because she certainly will.

Shine your shoes.

You don’t need to visit the shoe-shine boy at the local train station, but you should clean your shoes before you meet up with your date. It’s unlikely she’s going to consciously scope out your shoes, but if they’re covered in crud, she’s going to notice. Women don’t expect men to be pristine, but we do want to know you take care of yourself to some degree. If your shoes are filthy, her subconscious is going to wonder what else might be.

No wrinkles.

You don’t have to press your t-shirts or jeans – but don’t show up in clothes that look like they’ve been sitting on your closet floor for a week. Yeah, they might be clean, but if they’re wrinkled, they don’t look it. So don’t assume that she’s going to assume they are. Even just running them through a dryer for a few minutes to get the wrinkles out is better than nothing.

You don’t have to dress like a fashion model – and most of us would be a little worried if you put too much thought into your appearance - but it would be nice if you at least cleaned yourselves up before a date!

xx Isabella


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