Wearing a Pocket Square on a First Date: Stylish or Overdressed?

Going on a first date with the woman you like is one of the most exciting things. But, I know that it can also be quite nervous since first impressions are always important. You want to introduce yourself properly while managing to impress her on a first date. That’s why, deciding on where to meet, how to act and, especially, what to wear can be tricky. First date outfits are always a big deal for men. Because you want your outfit to look stylish while it truly represents you. You may righteously seek the help of accessories like a watch and a tie to find the perfect outfit combination and to add a nice touch. Another little helper is a pocket square to complete your look. But, when it comes to wearing a pocket square on a first date, the concern of whether it is too much or too formal, arises. Despite the common belief that pocket squares are worn only in formal occasions, you can actually wear one on your first date and it will help you give the right impression. Hear me out to find out why. 

Traditionally pocket squares are linked with formal attire or black tie dress code. However, there is no such a rule that limits your use of a pocket square. You can dress quite casual, yet wear a pocket square. And, if you are using pocket squares regularly, why shouldn’t you wear one on an occasion as important as a first date? It is true that  trying so hard to leave a good impression doesn’t look good, but a simple yet elegant touch of a pocket square hardly gives your outfit  that kind of a vibe. It only shows that you are a man who pays attention to details and loves to put effort and women enjoy men who takes his time to look his best and appreciate their effort. There is nothing wrong with showing that you have dressed to impress. If pocket squares are a part of your daily outfits, which it should be by the way, wearing one on a first date might be one of the best decisions. A pocket square doesn’t signal you are overdressed. If anything, wearing a pocket square will make you look like you respect both yourself and her enough to wear an accessory that stands out. So, pocket square is always a nice touch. 


However, you should just be yourself on a date. So, if you normally never wear a pocket square, then it may not be wise to wear it on the first date as she will never see you again wearing a pocket square and you won’t feel comfortable wearing something you are not used to. But still, there is no reason why you shouldn’t be experimenting new things that might breathe into your style. If you feel eager to try something new and open the door of unknown in fashion to impress your date, don’t overthink about it. Just find a pocket square in good quality that fits your outfit, and be proud of your courage. Square fold or puff fold will be the best if it’s going to be the first time you are wearing a pocket square. 

Always go with a pocket square that compliments your overall look and fits the place you are planning to meet. It will just point out you are different from the rest of the men, because not every man she sees out there wears a pocket square. It also shows that you have a good taste. You don’t want to look regular on your first date. On the contrary, you want to look sexy and strong. Remember, she is most probably going to spend hours to get ready for the date and try to look beautiful as well. There is nothing wrong in putting a little effort when you are meeting with someone important for you for the first time. Wear a pocket square, try to look your best, and have fun!  

Don’t hesitate to wear whatever you want, including a pocket square. Just chill and try to have some fun, even with your outfit. Don’t worry about looking overdressed or anything. It’s not every day she sees a confident man who knows exactly what he needs to wear, after all. Just enjoy your style and date!