What guys need to know about dressing for that first date

It’s an age-old question, one we still panic about sometimes. What to wear on a first date? If you never think about what you wear when you are going out for the first time, then we should probably smack you upside the head, as you probably have no clue to what you are doing. It is possible, of course, that you are one of those people that are just naturally fashionable, but we can generally bet our rent money for the next year that is not the case. So here are a few things to know about what to wear for that first date that will take some of the stress out of it and give you your best presentation.


Once you know where you are going, and trust us when we say you better know where you are going before you go, as well as have a backup plan of where to go if the first place didn’t work. Once you know where you are going, you can choose what to wear, whether it’s jeans and a t-shirt (not a graphic tee please) or jacket and tie occasion, you will have a starting point. It is also good advice to let the lady know what the dress code is so that you will both be on the same page. 

Bump it up one level

Whatever you think is appropriate to wear for the date, bump it up one level. We don’t mean wear a tuxedo. We mean just dress a little higher level than you think. Wherever you are going, think about what everyone there will be wearing and just dress a little bit better. You want to impress your date, so when she looks around, you will be better dressed than most and be showing some style. Again, just a little bit, if you wear a suit and tie to a beer festival, you have completely missed the point.


Women notice shoes. You might only have 2 pairs but she probably has a few dozen shoes in her closet and thinks that is a minimum. Most women love to shop for shoes, so if you think they aren’t’ going to notice yours, you are very much mistaken. Get a good pair of shoes that are comfortable and classic. Whether leather oxfords or canvas sneakers, make sure they are clean and in perfect condition. Make sure they are comfortable or you yourself will not be comfortable and it will come across. 


Accessories are nice, but don’t get carried away. Make sure the belt matches if you are wearing one. Don’t wear too much jewelry, a ring and a necklace is about it, maybe a subdued earring. Keep it simple. 

Clean and ironed

Make sure that everything you wear is clean and ironed. Everything you wear should be stain free and in good repair. Women notice these things. I hope we don’t have to tell you as well, that it should be the first time you wear whatever you are wearing since it has been washed. Don’t do a sniff test and think its fine, it won’t be. Smell is very important on a first date, so make sure your clothes smell great, use a dryer sheet if you have to.  

Dress like an adult

If you are over 18, dress like an adult. No graphic t-shirts, no torn jeans, no “cool” anything. Just wear something appropriate for where you are going, and keep it simple and classic. It is a good idea to learn to wear things like that normally anyway so you will feel comfortable in them. Being comfortable in what you wear is important. There is a story of Sean Connery when he was first in the James Bond movies. The director made him wear the suit all of the time, no matter what he was doing. They joked that he even needed to sleep in it. The point being that Sean Connery looked great and rocked that suit, as he was comfortable wearing it after that. 


This might sound silly, but get your clothes tailored. A good tailor can take you to the Sean Connery level of James Bond. Even if it’s a t-shirt and jeans, if it fits perfectly and enhances you, you will see and feel the difference. For your first date you want to look as good as you can, and trust us when we say a good tailor is worth every dime to make that happen. 

Don’t wear makeup

These days a lot of guys wear makeup, whether it is a little eyeliner, etc. There is nothing wrong with this, but for a first date, avoid it. Keep it simple, it will not enhance you on a first date. Unless you are a master at it, she will spend half the night examining your makeup and wondering why you are wearing it. 

Keep it simple

The best thing for a first date is keep it simple. We all want to create some amazing date and look fantastic, but in all reality, the opposite usually happens. So keep it simple, wear classics, be well groomed, and again, keep it simple. Less can go wrong. 

A first date can be a terrifying experience, but remember that there are 2 of you there. She is just as worried as you are and is probably going through more outfits for what to wear than you ever will. Follow our tips here and they will do you no wrong. You will have the best chance to make a great impression and hopefully a second date where you can relax and shine. We wish you the best and remember there is no hurry, just relax and have a good time.