What to Wear on a First Date for Men

It’s your first date with a new woman and you want to make the best possible impression. So what do you wear? After all your clothes will be one of the first things she sees so you need to make sure you get it right, so you need to get it right.

Here are some tips on picking the right items to wear on this all important date so that you can start the evening with the right impression.

Choose your sizes carefully

This should go without saying, but if something feels or looks too big or too small – no matter how much you like it – leave it at home. You should always make sure you pick items that fit you perfectly.

Baggy tops don’t do you any favors and can make you look a little immature, not a good start, don’t do it.

Stick to simple clothing

Don’t try to overcomplicate things. Pick a nice shirt and trouser combination for example, instead of trying to find a waistcoat to go with them. Go for plain clothing instead of trying to match up a patterned and eye catching shirt with trousers that won’t clash.

It’s all too easy to overthink, especially if you are nervous – remember, it’s a date, not a fancy dress party. You don’t want to walk in wearing your work scruffs, but equally, looking like you robbed a fashion store on the way over is probably best avoided.

Remember to pick nice shoes

Most women love shoes so don’t spend ages choosing the rest of your outfit only to slide on an old pair of scruffy shoes at the last minute. You should pick a pair that complement the rest of your outfit and don’t look dog eared.

However don’t choose your date night to wear one particular pair of shoes for the first time. If they hurt – which they are almost bound to do – your mind won’t be on your date.

Stay smart – avoid crumpled t-shirts with slogans on them

There are plenty of men who buy those t-shirts with the big and bold slogans on them. Maybe you’re one of them. If you are, you need to be sure you leave them in the cupboard.

Even if you iron them and they look pretty smart, most women would be turned off by an aggressive or smart opinion emblazoned on their first date’s t-shirt, so make sure you don’t fall into this category.

In fact, don’t wear a t-shirt at all; this should really go without saying, but a nice shirt will go a long way. You need to look like you’ve put in a little effort here.


Most first date clothing rules are common sense. Looking smart and making sure you are presentable are the main two, but as you can see from the above tips there are also some lesser known faux pas you can make.

The trick is really to plan ahead and not leave it until the last minute to choose your outfit. With the right preparation you should definitely look the part when you meet your date for the first time… Good luck!