Should I Wear a Pocket Square On A First Date?

First impressions are powerful things. They take a matter of seconds to form… but their impact can last for a lifetime. If you’re heading out on a first date, then this is surely something which will be crossing your mind several times as you spruce yourself up in the mirror, making sure your hair is looking great, your clothes are stylish, clean, and neatly pressed, and as you’re splashing yourself with some tasteful eau de cologne. After all, as you walk through the doors of the bar, restaurant, or club at which you’re meeting your date, you want her eyes to light up in excitement, and not fall in frustration and disappointment at yet another man who can’t be bothered to make an effort.

In this article, we’re going to be looking at whether or not wearing a silk pocket square on a first date is a good idea, and whether or not such seemingly small men’s suit accessories can make all that much of a difference. The world of dating and courtship has changed so much in the fast-paced world of dating apps etc, it can sometimes be hard to tell whether old-fashioned sophistication still has an impact. Do women even notice handmade pochettes, beautifully folded in a jacket pocket? What kind of impression do pocket squares make on the opposite sex? Can pocket squares be worn with relatively casual clothes? We’ll be answering all of these questions and more besides.

So, without further ado, let’s dive right into the world of dating and pocket squares, and start considering the impact these stunning silk accessories for men can have, and what that can bring to that all-important first impression. The course of romance may never run smooth… but that doesn’t mean you can’t give yourself a head start, with an elegant image which speaks volumes about your character.


What Women Really Want

One of the things so many men fail to realise when it comes to first dates is just how much effort most women go into, in order to make sure they put across the right image, and to make a powerful impression on the man they’re meeting. A lot of time, money, and energy goes into each first date… so imagine how frustrating and irritating it must be, to turn up on time after going to such lengths, only to find one’s effort hasn’t been reciprocated in the slightest!

What women look for in a man is a question with more potential answers than we have time or space to write in this editorial. However, one thing is more or less for certain; on a first date, they want to feel as though their time has not been wasted, and that they’re meeting a gentleman who has put some real effort and thought into his appearance and how he comes across. In this sense along, wearing a beautiful pocket square in your jacket pocket is definitely, undeniably, and unquestionably a good move.

When you opt to wear a pochette, and learn how to fold a pocket square properly for maximum impact, you’re doing much more than just decorating your jacket with a stylish accessory. You’re sending out a clear signal as to the kind of man you are. You’re somebody who understands the power of a positive first impression. You’re an individual unafraid of showing off your personal sense of style. You’re a man who likes to look good for his lady, and who goes the extra mile when it comes to preparation. It’s hard to understate just how impactful that can be!


The Mark of a True Gentleman

Few items scream sophistication quite like a handmade pocket square. Here at Robertto’s, we make all of our beautiful pochettes from high quality Como silk, in order to achieve the very utmost in elegance and urbane beauty. However, it would be a mistake to think of pocket squares as only appropriate for wearing with formal wear. Indeed, modern pocket square wearers have shown that these stylish jacket accessories are more versatile than you may have realised.

Why is this relevant? Well, because first dates nowadays are unlikely to require any kind of formal wear, unless you’re taking the bold step of arranging your first date at a society dinner, a movie opening, or a night at the opera (and if you are, we take our hats off to you!). You can wear a pocket square with a sports jacket of blazer, thrown over a smart t-shirt and a pair of jeans, and make the kind of impact that will have her blushing with excitement as you swagger through that day. In fact, there’s something doubly dashing and elegant about matching up the vintage elegance of a stylish pocket handkerchief with somewhat casual attire - it shows you’re a man who knows how to rock the latest trends, while also keeping one foot in the world of timeless and retro style.


Inspired By (The Right Kind of) Stardom

‘Where have all the real men gone?’ is a question which regularly features in women’s conversation regarding dating, and is the kind of thing you’ll see plastered across the covers of women’s lifestyle magazines in any given month. What do they mean when they say ‘real men’? Well, they mean the kind of smooth-talking, sharp-dressing gents that used to dominate the silver screen, back in the days when men were men, and knew the alluring power of a folded pocket square in their jacket pockets. The enduring appeal of such characters was reinforced recently, with women worldwide swooning over Don Draper in the hit serial Mad Men - a gent who was rarely without a pocket square in his impeccable office attire, or without a beautiful lady on his arm.

Wearing a pocket square on your first date immediately lets your lucky lady know that she’s meeting a man who really gets this. Pocket squares aren’t about slavishly following the latest transient trends, or preening like a peacock and fussing over every tiny aspect of their appearance. Instead, they signify a powerful sense of confidence and self-awareness, and a willingness to align oneself with an aspect of masculinity and masculine style which, let’s face it, isn’t particularly commonplace anymore. Knowing how to fold a pocket handkerchief is more than just being willing to look great; it’s a mission statement, a way of letting your date know exactly what sort of style icons you aspire to, and the perfect way to inject some real personality into your outfit. Everyone’s a winner!


Rarified Skills For Modern Men

Here at Robertto’s we’ve worked tirelessly to offer you a wide range of coloured pocket squares, and pocket squares emblazoned with creative designs and patterns, in a range of beautiful tones and hues. Now, if you’re able to purchase a pocket square which you can pair perfectly with your outfit, you’re going to make the kind of impression that really makes an impact.

It’s no secret that overall, women are considerably better than men when it comes to pairing their accessories, working with colour coordination, and coming up with outfits that really catch the eye. However, if you’re a man who can show that you’re able to wear a coloured pocket square that contrasts or harmonises perfectly with your blazer, your shoes, your belt, or your tie etc, you can be sure that she’ll be deeply impressed at your dress sense and your style skills. As mentioned, it’s not exactly the most common trait among modern men… so pulling it off with great panache is something which will go a long way, and will easily show that you are quite the catch.

All in all, it’s more than fair to say that wearing a hand-rolled silk pocket square, such as those made by Robertto’s, on a first date isn’t just a great idea… it’s a great idea which is sure to bring about impressive results. You’ll make yourself memorable, you’ll create an unforgettable first impression, and you’ll clearly demonstrate that you’re a man of action with a sense of style which cannot be beaten. What could possibly be better than that?