Male Guide On How To Dress On A First Date Based On Your Personality

Sharing is caring!

First dates can be daunting. Especially when you have to factor in keeping confident, finding the best place for the date, and most importantly making sure you are going with the right person. You want to come across as the best version of yourself and you should be fully transparent so you don’t waste time with the wrong person. One of the underrated ways of communicating your personality to your date is to dress like you. We know this sounds like an obvious statement to make, but too often some men overthink the clothing part and force themselves to feel uncomfortable in something they would not typically wear. Realistically the best thing you can wear is confidence, so if you are dressing true to yourself and feel good in it, confidence will shine through and you will feel like the perfect man.

Of course, the occasion is a huge factor to take into consideration. You should not wear a comfy tracksuit to a dinner date, even if you wear a tracksuit most of the time and you wish to reflect the fact you are a laid-back guy. Be smart when planning the date in this instance, don’t plan something you know you wouldn’t enjoy. Like we said you need to be authentic to yourself. If you are laid back, keep it casual and agree to meet up at a local pub. 

We have made a generalization list for types of guys and what we think you might try to wear on your first date. If you think you fall under one, two, or even three groups, work with it. Mix and match your styles and dates to show your ability to adapt to different situations, and let your personality shine.

The Gentleman 

Now if you are a gentleman, you will care very much about your appearance and the latest trends to be followed at the time. You will not often be seen out of the house in a pair of sandals, shorts, and a stained white t-shirt and if you were seen, you would be completely mortified. You might always have a fresh haircut and the maximum time you can go without a fresh cut is 2 weeks. Assuming you fit under this category, you are going to want to reflect your attention to detail and style in your outfit. 

Starting with the bottom half of your outfit, you need to make sure your shoes are clean enough to eat off! Leather or suede can allude to your specific taste, just make sure if you go for loafers you wear invisible socks. Pants-wise, tailored ones with a bright leather belt will always win. Keep them dark, and pair them with a crisp white shirt or bright polo top. 

The Cool Guy 

A cool guy is often happy to spend a lot of money on a normal t-shirt as long as it says a luxury brand’s name. Men’s designer t-shirts with a pair of skinny jeans or cargo trousers are a day-to-day for them. They might spend more on a pair of trainers than they do on their energy bills and enjoy spending money on the finer things in life that are trendy. whilst they look for the love of their life they spend their weekends in the club with bottles on the table. If you think you fall within this category, we have a few recommendations.

Firstly, if you are looking for a genuine partner who is not money orientated, now is the time to ditch the in-your-face designer clothes. If you want to still portray the fact you can admire luxury, express that through the quality of your clothing. You might go for a pair of designer jeans that aren’t explicitly high end, and pair them with a couple of smart trainers. Include jewelry, but do not be too flashy. Keep it simple with a small chain or pendant and a watch. A little can do a lot.

The Laid Back Guy

If you fall under the laid-back guy category, you probably aren’t too bothered about what you wear either way, but you want your date to be impressed so you are searching for a little advice. You are happy spending the weekends in the pub with a pint, or going to different food spots and enjoying the simple things in life. Your wardrobe probably consists of only a few items you are very happy to keep on wearing for years to come.

If you are looking for an outfit that shows you want to make an effort whilst reflecting on your chilled-out self, the best look to go for is comfy smart. Perhaps you take your date on a pub date or somewhere else you feel comfortable with, your outfit should reflect that. Hoodies and sweaters can look smart despite their general purpose. Wearing some comfy jeans, smart cargo trousers, and some clean trainers will do the trick. Emphasis on clean trainers because dirty trainers will not get you any points!

Overall, these are just a few pointers on how you might consider dressing if you are clueless about what to wear, but you still want to reflect your personality. There is no right way to dress and honestly, most people are not superficial enough to decide whether they like a man based on what they wear. 5 Basic men’s outfits that can never go wrong will also be a safe move. It does help you express your personality in more ways than one, and you should try your best to dress to impress yourself as well as your date.