A Gentleman’s Guide: What To Wear On A Casual First Date

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The first date is often the most exciting yet nerve-wracking day of a man’s life, and for a good reason. What if the woman you are sharing your time with on that romantic table becomes the woman you will spend your entire life with forever? For sure, that idea puts up a lot of pressure on making your first date worth remembering, and, again, for the right reasons. 

If you think this is the girl for you and want to make her special, you need to dress smart on your very first date. Here is a guide on how to pull off an impeccable dating outfit. 

Wear a Buttoned-Up Collar Shirt

Wearing a T-shirt can destroy your look and, for a first date, a little too understated. Keep in mind that you are on a first date to make a good impression, not to have her run for the hills. So, for a simple yet fashionable style, you must wear a smart buttoned-up collar shirt. Buttoned-up shirts are a classic style when it comes to first dates. For example, you can put on one with a crisp white hue with an elegant touch of navy blue at the collar to look dashing and sharp.

Show Off a Nice Watch

A nice watch is one piece of jewelry that has the power to instantly and effortlessly improve your entire aura. Whatever your style or standing in life, wearing a wristwatch is attractive because it shows that you are meticulous about fine details like accessories and, of course, the time. If you have a Hugo Boss watch, then it’s a plus for you. 

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These watches are for the elite. When you wear a timepiece of such a high caliber, it can say a lot of things about you–your profession, your attitude, your personality, and a lot more. When wearing a watch, make sure that what you put around your wrist is the classic, stainless steel model. Not only will it render masculinity to your appearance, but it also shows that you have a great taste in style. 

Rock Out a Leather Jacket

Forget the stiff blazer and cotton cardigan. Instead, you can rock out a cool aura and make a power move with a leather jacket that will also serve as cover to your woman when she feels cold (an extra point for you, for sure!). Also, a leather jacket shows elegance and masculinity, which is precisely what you need on your first date.

Sport Some Jeans

You will know that wearing trousers on your first date seems a bit too much. Khakis? Well, you will feel that you are like in the office. But jeans will make you more comfortable, calm, and relaxed as you deliver some of the best romantic lines you can say to your date. Just make sure to put on solid, dark denim for a cool yet semi-formal attire on your first date. Choose jeans from stretchy material to ensure comfort and a minimal design which is not too flashy.

Put On Stylish Boots

First dates are always a special occasion, so you shall also make what you wear on your feet suit to the occasion. You might be tempted to put on a pair of sneakers because it is your favorite, but women size you up from head to toe on a first date. So, instead of sneakers, wear a pair of boots. Boots are not only stylish, but they also have good quality and condition, which will make you walk with confidence. 

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Go with a pair of sleek brown or black boots. They are more elegant than kicks but less formal than dress shoes, so it makes for a special occasion like the first date.

Use a Decent Wallet

One of the ways to gain plus points with your date is to pay the cost of your dinner date. So make sure that when you hand the bill, you not only can pay for dinner but also you have a decent wallet.

Women notice the minutest of details, so you must get an upgrade of your billfold. It’s a big turnoff when you get your wallet out of your pocket or bag and it’s all up in stitches. Put your money, for example, into a black or brown leather wallet. Choose the one that is spacious, sturdy, and stylish.

Do Not Forget the Cologne

If there is a weakness in a woman, it is perhaps the whiff of a perfect scent. So, before you go on a date, you must make sure that you know how to apply a cologne without overdoing it. Wear a fragrance that has a warm and lasting aroma. For a classic scent, you can choose pretty much anything from Tom Ford. 


Dressing well on a first date is important because it can either make or break your chances of winning the heart of the woman. Your physical look has so much impact because it is the first thing the woman sees in you. Hence, you must have man knowledge on how to spruce up on your first date. 

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There are many ways to make your first date remarkable, and one of these is to spruce up and dress smartly. Dressing well on a first date is important because it bespeaks respect for your date, and it lets her know that you care about this special day of your life together.

Aside from showing respect to the woman, choosing the right outfit also gives you the necessary confidence as you settle on the table and talk to her. You will walk with your head high and set out to show to the world that you are the right man for this lovely woman. 

You can follow the guide above to get you started. On a first date, do not forget the collared shirt, the leather jacket, the jeans, a pair of stylish boots, a nice watch, a decent wallet, and the cologne. If I forget something on the list, it is up to you to fill in the gap. Good luck with your first date, man!

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