Dress To Impress: How To Dress Up On a Casual First Date

June 22, 2021

It may be a casual date, but if it’s the first one you know very well that you can’t be casual about the way you dress!

Men have forever been tagged as lazy and outside the realm of fashion. But, if you take a look at any men’s fashion segment, such as tuxedos, blazers, and jackets, or dress shoes for men; you will find a sea of luxury options. So, it is upon us, the new generation of men, to put these options to use and flip the script. And what can be a better occasion than a first date!

Right from your haircut to your shoes, everything matters on the first date! People may tell you that first impressions don’t matter, but that’s not true. How you view yourself is as important as how your potential partner will view you. So, if you don’t have a strict sense of fashion and are wondering what really to wear on that first date, here’s the perfect article to help you out!

We have divided it into three neat sections – how to pick the right clothes, how to pick the right shoes, and everything else you need to know.


So, let’s get started!

Choosing The Right Clothes

They say clothes define a man, and even if that’s not true, it’s going to be true on the first date. On one hand, you can pull off a casual date look by wearing a pair of baggy pants, a white tee, and some sneakers. On the other hand, if you wear a casual shirt, matching trousers, and a pair of polished shoes; you leave an elegant first impression.

This is not to say that any of these two styles are better than the other, but you will end up presenting your persona through your clothes. 

Any fashion style that resembles your persona is a good choice. So, it’s important that you present yourself in a way that is comfortable to you. Don’t try to be someone you are not on the first date. But, at the same time, since there are going to be implications of the way that you dress on your date, it’s better that you choose wisely!

Another aspect to keep in mind is the venue of your date. If it’s a club, then you don’t want to appear in a tuxedo, and if it’s a high-end restaurant, you don’t want to wear something too casual. Sure, dressing casually top-to-bottom may not be your best game, but you also don’t want to make the other person uncomfortable on the first date. So, make sure to blend in but also have your own uniqueness in there.

Lastly, make sure you are looking sharp and presentable across all styles. You may be wearing the most casual of clothes, but they need to send out the message that you care about what you wear. You don’t want to turn up to your first date with the most formal suit and tie. Just slip on a good suit and a pair of formal elevator shoes and your date will know that you are a man of elegance!

Choosing The Right Shoes 

Sneakers? Boots? Sandals? As always, the answer can be any of them. But, if you really want to show that you are someone who pays attention to their sense of fashion, then dress shoes for men is a great option. Not only are they easy to pair with your attire, but you also have a huge collection of these shoes available online in various styles. 

How to style formal elevator shoes?

Something that men usually have a problem with is their body image, and this starts with their height. An easy fix for this is a pair of height-increasing formal dress shoes, commonly known as elevator shoes. Now, if the word formal is something that throws you off you don’t necessarily have to pair them with a tuxedo. These shoes come in various styles, both formal and semi-formal. Also, with the right choice of clothes, you can wear semi-formal elevator shoes with a pair of jeans, a tucked-in white shirt, and a great pair of sunglasses!

Formal dress shoes for men have always been a great hack for those who feel unconfident about their height and if you feel the same way, it is more common than you think. With the advent of social media and the race for the perfect body image, this phenomenon has increased even more. But, if you have the right shoes you don’t have to feel this way anymore. It is extremely important that you feel confident about yourself on your first date.

So, browse the web, jump on to JENNEN Shoes and find a pair of men's formal dress shoes to increase height. You will definitely find one that matches your style and when you look in the mirror those few inches that you always thought were missing will be right there!

Topping It All Off

A date is one of the most important occasions in a man’s life. Society has given it upon us to find a partner, and not the other way round. So, we need to ensure that we are prepared when this occasion arises.

A few extra things that you definitely need to keep in mind:

  • Stay well-groomed. You may want to rock a beard or a stubble, but it should not look unruly. Sure, the unruly look can appeal to some, but it’s not something you want to go with on the first date. Staying well-groomed sends the message that you are someone who puts in the effort behind yourself, and this will always go down in the good books.
  • Don’t rush things. Take your time, but at the same time don’t leave everything till the last moment. Pick your clothes and shoes in advance, decide upon a venue and groom yourself for the occasion.
  • If you think that there’s a piece of clothing or a pair of shoes that you would like to buy, order them online beforehand or else you will regret not having them on the big day. This is a common mistake, so make sure you don’t fall into the lazy trap.
  • Keep the occasion in mind. The colours of your attire and your dress sense should match the occasion. It’s great to stand out, but the degree of standing out should be in control. If you stand out like a pear in a basket of apples, that’s not a good thing. Stand out by being the shiniest apple!

Final Thoughts

So, there you have it. These are perhaps the best tips you will find on the internet on how to dress up for a casual first date. Keep in mind that the date is as much about you as it is about the other. So, the effort you are putting in is not merely about pleasing your date, but, it is also about feeling good about yourself.

If the clothes you have picked or the shoes you have bought do not make you feel good about yourself then you are probably not making the right choice. As stated before, you need to ensure that you have the perfect balance between being formal and being comfortable, and this can only happen if you are not compromising on being who you are.

Now, you are ready to go out there and have the best date of your life. Remember, clothing is only half the battle won. The rest is your personality!

Men's Shoe Size Guide

FOOT LENGTH (MM) EURO SIZE AUS / UK SIZE US SIZE
235 37 4 6.5
240 38 4.5 7
245 39 5.5 7.5
250 40 6 8
255 41 7 8.5
260 42 8 9
265 43 9 10
272 44 9.5 10.5
280 45 10 11
288 46 11 12

Measure the length of your feet in mm, with your heels against a wall. 

For increased accuracy, ask for assistance when measuring. 

If you have broad feet, we recommend selecting one euro size larger than your measurement.

It's common for one foot to be slightly longer than the other. For example, if your results are: right foot (254mm) and left foot (257mm), then we recommend size 42.

If unsure about sizing, we recommend ordering one euro size larger and a set of 1.2cm Ezylift Insoles. These shoe lift insoles can be inserted into your JENNEN Shoes if there is a little extra room inside, or into your regular shoes for extra height and cushioning. 

Women's Shoe Size Guide

FOOT LENGTH (MM) EURO SIZE AUS / US SIZE UK SIZE
212 35 4 2
220 36 5 3
229 37 6 4
237 38 7 5
246 39 8 6
254 40 9 7

Measure the length of your feet in mm, with your heels against a wall. 

For increased accuracy, ask for assistance when measuring. 

If you have broad feet, we recommend selecting one euro size larger than your measurement.

It's common for one foot to be slightly longer than the other. For example, if your results are: right foot (229mm) and left foot (231mm), then we recommend size 38.

If unsure about sizing, we recommend ordering one euro size larger and a set of 1.2cm Ezylift Insoles. These shoe lift insoles can be inserted into your JENNEN Shoes if there is a little extra room inside, or into your regular shoes for extra height and cushioning. 

Shoe Size Guide

MEN'S SHOE SIZE GUIDE

FOOT LENGTH (MM) EURO SIZE AUS / UK SIZE US SIZE
235 37 4 6.5
240 38 4.5 7
245 39 5.5 7.5
250 40 6 8
255 41 7 8.5
260 42 8 9
265 43 9 10
272 44 9.5 10.5
280 45 10 11
288 46 11 12

WOMEN'S SHOE SIZE GUIDE

FOOT LENGTH (MM) EURO SIZE AUS / US SIZE UK SIZE
212 35 4 2
220 36 5 3
229 37 6 4
237 38 7 5
246 39 8 6
254 40 9 7

Measure the length of your feet in mm, with your heels against a wall. 

For increased accuracy, ask for assistance when measuring. 

If you have broad feet, we recommend selecting one euro size larger than your measurement.

If unsure about sizing, we recommend ordering one euro size larger and a set of 1.2cm Ezylift Insoles. These shoe lift insoles can be inserted into your JENNEN Shoes if there is a little extra room inside, or into your regular shoes for extra height and cushioning.