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How to Dress on a First Date (For Men)

Updated on October 30, 2009

First dates are a big deal to many people, and rightly so. And even if they aren't, I'm sure everyone can agree that you simply don't get a second chance to make a first impression. While most women aren't going to write you off because of your clothes, most will definitely take them into account when first meeting you -- and they will definitely take them into account on your first actual date, because your appearance will tell her an awful lot about what you think of yourself and also her. (This is true whether you or not in you insist the opposite, so don't bother trying!) The following tips are intended to help you make the most of your first date and ensure the best odds of landing a second date.

1. Make sure your clothes are clean.

It's amazing how many guys will pick a shirt up off the floor, stick it in the dryer for 10 minutes to get the wrinkles out of it and then put it on. Guys -- no matter how much cologne you spray on that sucker, it's still going to smell like old clothes. We probably won't mention it to you, but we will notice. This also applies to things like socks and undies, especially if there's even the slightest chance you think we might be seeing them at some point.

2. Make sure your clothes are wrinkle-free.

You don't need to have creases in your jeans (and hopefully you won't!) or ironed socks, but you shouldn't be picking us up in your rumpled t-shirt and wrinkly khakis, either. If you look messy we're going to assume you don't know how to take care of yourself, and most of us are looking for a man, not a toddler.

3. Make sure your clothes fit.

Unless you're 13 and spend all of your time in a skateboard park, your britches should know where your arse is. If they are lost and hanging down to your knees, you look silly. And we'd rather you didn't look silly. Conversely, you should not be sporting t-shirts that are three sizes too small in the hope we'll notice your six pack.

4. Make sure your clothes aren't offensive.

Some women will think a t-shirt with various, er, positions, on the front of it is funny. But if she hardly knows you, you would be a fool to show up on your date in this kind of getup. The same goes for obscene quotes, phrases and other inappropriateness. Good rule of thumb: if your mum would smack you for it, don't wear it on a first date.

5. Make sure they smell like Tide and not Drakkar.

I do not know why so many guys spray cologne all over their shirts but this is really silly. It's meant to go on your skin and it's meant to be subtle -- if you spray your shirt the smell is likely going permeate your personal space and this may well make her want to keep out of it. Do not drench your clothing in cologne unless you're 13 years old and don't know any better.


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