It’s Your First Date, And He’s Looking A Little Underdressed

I can’t believe that we’re finally meeting, after a good three weeks of exchanging text messages. After all, I spent the whole morning and the better part of the afternoon setting my hair and going through my closet with my bestie to select my attire for tonight. Longer… if you include the trip to the manicurist and for the long-delayed facial. I want to present the best version of myself on this unforgettable first date. Except that when he showed up… He was dressed in a faded workout shirt, and a pair of short pants…

A man and woman dancing on their first date
First dates can be stressful, especially if you don’t know what to wear. Relax, sit back and continue reading for some easy tips on how to dress to make a good first impression on your dates.
Photo by Allef Vinicius on Unsplash

Most Women Want To Look Their Best For Their First Date

What you have just read was my personal account in May 2019. I was a woman excited at the prospect that my first date would turn into something exciting. We had chemistry chatting online, and he checked all my boxes. He had a stable job, a dog and most importantly, he was available. So, disappointment was all I felt when I saw him showing up on our first date in a faded workout shirt, and a pair of short pants. All the more so when the venue was a classy bar in Kuala Lumpur, Malaysia called Shelley Yu’s. I was devastated and frankly, exasperated that I had put in so much effort to ensure the date would go well, but he didn’t. I never did call him back for a second date.

Dressing up for your date shows that you respect her. You can’t control whether your date will like your personality; you can, however, make a conscious decision to put an effort to look your best. Your date must have spent a considerable amount of time to look presentable for you. The least you can do is to return the favour. It’s simply a matter of treating another person as you would like to be treated. So, how would you impress your date?

Look More Presentable On Your First Date

Generally, most women will put in extra effort to look more presentable on their first date. This is perhaps our innate feminine quality. However, what can a man do to look more presentable for his first date and to make a good first impression?

Two people sharing a meal and enjoying themselves on their first date.
Make a good first impression on your first date by putting a little more effort into your own appearance. Image by Sasin Tipchai from Pixabay

It’s really not rocket-science. Imagine you’re attending a job interview. What would you do? Definitely, you would be sure to cover the basics: showering, shaving, and spritzing on a little cologne. After all that is done, you would pick out your sharpest outfit to make sure you stand out from the rest of the candidates. Similarly, apply the same steps on your first date.

After all, it is almost like a job interview, but instead for a job, you are looking to make a first good impression to a prospective significant other to love and cherish you.

The Many Different Styles To Make You Look Your Best

Dressing up for a date can be as easy as 1, 2, 3. You don’t have a wear a suit and tie for every first date. It is better to have a more casual approach but do remember that casual means comfortable, not sloppy. What matters most isn’t how much money you spend on your clothes, but how well they fit on your body. You don’t want your date to be distracted by your sloppy and baggy getup, do you? Typically, a fitted (but not skin-tight) silhouette—where your clothes hug but not constrict your body—is the way to go. Look for items like a tailored sport jacket, straight-leg jeans or slim button-down shirt. It’s all about wearing the clothes versus letting the clothes wear you.

Here are some styles or look you can consider for your next date:

1. The Business Casual Look

Business casual is loosely defined. If you want to add a little more pizazz to your outfit, consider a good pair of trousers and a classic button down shirt. That’s all you need. This attire would be perfect for a first date in a classier restaurant. If you want to go the extra mile, a nicely fitted sport jacket could give this look a much more polished touch.

A typical business casual outfit characterised by a Glen check cotton sport jacket. Here it's match with an off-white solid shirt medium grey flannel trousers, finishing touch with a casual knit tie.
For a more polished look, you can even pair your sport jacket with a pair of trousers. The best part is the pattern does not have to match. Perfect for a first date in a classy restaurant! A typical business casual outfit characterised by a Glen check cotton sport jacket. Here it’s matched with an off-white solid shirt medium grey flannel trousers, finished off with a casual knit tie.
Image by Jonathan Woo, courtesy of Solarex Imaging

2. Dress Down Stylishly

There’s a common myth in the men’s style world. Style is three-piece suits and perfectly creased trousers. In other words, style means dressed up and this common misconception is probably why we don’t see men dress up as much as women do. Remember that you don’t have to go all out on a date. Even wearing a clean pair of jeans with a button down shirt or a turtleneck is sufficient. Not to mention comfortable. This is the perfect outfit for a casual date, be it at a dive bar or a walk in the park.

A very casual unbleached linen sport jacket, draped over a mock turtle neck, completed with a less dressy medium wash jeans.
This is a simple, relaxed style that pairs the flattering shape of a suit jacket with the casual feel of denim. Perfect for a casual first date look. Perfect for a casual night out in town, but will still stand out from the rest of the crowd. A very casual unbleached linen sport jacket, worn over a mock turtle neck, completed with a less dressy medium wash jeans.
Image by Jonathan Woo, courtesy of Solarex Imaging

3. Sporty Casual For A Picnic In The Park

Sporty casual is ultimately activewear. For example, you wouldn’t wear a sporty casual outfit to an event that calls for semi-formal or cocktail attire. But you can wear this for a picnic in the park or even a funfair date (I love funfair dates the best). This typically means a dri-fit shirt, training pants or pull-over hoodie, you’re good to go!

Sporty casual is the best type of outfit to wear for picnic dates.
Sporty casual is the best type of outfit to wear for picnic dates.
Photo by Jane Sundried on Unsplash

4. Home Casual

Now, this is the type of clothes you DO NOT WEAR ON A DATE! These clothes are basically worn in the comfort of your home: short pants, worn-out t-shirts and joggers. These are also not appropriate to wear on your first date just as how it wouldn’t be appropriate for a job interview.

A pair of shorts and a t-shirt would be perfect to snuggle in your bed .
Home casual is the type of clothes you would wear in the comfort of your own home. This usually consists of a pair of shorts and t-shirt. Not recommended for a first date.
Image by Jcomp from Freepik

How To Make Any Outfit A Date-Worthy Outfit

Any outfit you wear could be easily enhanced with a dashing sport jacket on top. But, you’re probably wondering, “Why a sport jacket and not a blazer?” Well, because of the flexibility of a sport jacket. A sport jacket is an odd jacket that can go well with anything, which is why it is perfect. You can mix and match it with any of your outfits without the worry of looking out of place.

 A blue pattern sport jacket on top of a white button down shirt.
Any outfit could be two notches better with a fitted sport jacket. Perfect for your first date, job interviews or business meetings.
Photo by Luigi Estuye, LUCREATIVE® on Unsplash

You can find a sport jacket even with fast-fashion brands such as H&M or Zara. However, before making your purchase, keep in mind that sport jackets aren’t suppose to stretch. The fast-fashion industry mass produces ‘standard’ sizes that don’t seem to fit everyone, as we all come in different shapes and sizes. It is hard to fit our body in moulds that the fast-fashion industry assumes that we are in. Therefore, do consider a bespoke sport jacket and one place where you can tailor a quality sport jacket is from Gent’s Props.

Gent’s Props tailor Sky Ng will ensure your sport jacket will be worth the money you pay for it. Saying that he is a good tailor would be an understatement as he is not only a skilled tailor but also an experienced one. Sky Ng was an apprentice in his father’s bespoke tailoring business before branching out on his own.

Don’t Be Nervous On Your First Date! You Got This

A date in a classy restaurant with wine
Perhaps the most important point to remember is that success in dating, as in life, doesn’t come handed to you on a plate. If you want your first date to work out, you need to put in the effort and why not start with your outfit.
Photo by Alev Takil on Unsplash

First dates are a pretty big deal and everyone wants to score a second date. So, don’t let your outfit be the reason your Facebook status still shows that you’re single. If you have no clue what to wear, just throw on a sport jacket on top of what you’ll normally wear. This is a perfect way to not only make a lasting positive impression but also to show respect for your date.

If you don’t already own any sport jacket, get in touch with Gent’s Prop via Facebook or call them directly at +6012-280 0182. Every man should have at least one sport jacket in his closet, for those days when you need to spice up a casual look. For example, with a little attention to colours and patterns, you can look stylish and sophisticated without sacrificing comfort or utility. And if you’re still wondering what exactly is a sport jacket, come back for the next episode. We’ll dive into the origins, and why it’s the most versatile garment you’ll ever wear.

What's your go-to attire for a first date?

About Preveena SIVAKUMAR

Engineer, teacher, and a published author, Preveena is one friendly and bubbly character. Travelled all over Asia in search of muse and inspiration for her writing. After all, the more you've experienced the world, the better the perspective of your stories will become.

One Reply to “It’s Your First Date, And He’s Looking A Little Underdressed”

  1. Pingback: Sport Jacket: The One Garment To Spice Up Your Style - Espoletta

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