For Men

What to wear on a date: the psychology of men's fashion

June 30, 2017
▪ 5 mins read

The psychology of men's fashion: what to wear on a date

I’m fashion consultant Ollie Pearce and I want to make sure you know what to wear on a date. The night of the big date and all the effort of the painstaking chase seems to have finally paid off. She is primed, receptive and ready for you to sweep her off her feet. Well, you hope so at least! You leave work with a spring in your step optimistic about a night of good conversation, flowing wine and hopefully romance and rapport. But one questions eludes you; what to wear on a date? It's been nagging on your mind a little bit but you have decided your trustworthy favourite shirt, smart shoes and a douse of manly aftershave should do the trick! Anyway, it's you who she is interested in. The clothes aren't that important... Are they? The answer is most definitely yes!

Let's break it down a little.

Women and men alike form that all-important first impression within minutes of meeting a new person. This is only amplified when meeting a potential love match. If you dress and have a cool style then you will automatically be registered in the subconscious as a "cool stylish guy". When dressing in a plain, boring manner you will be received as a "plain, boring guy". If you dress in an uncool, bad manner... I think you can see where I'm going here. You are what you wear! It's a cliche I know but one that has been relevant since the dawn of time. Even William Shakespeare adhered to this unwritten social law! In Hamlet, Polonius uttered the brilliant statement; "clothes maketh the man". We can go back even further in time and look at other unlikely historical fashion victims. Every high-value male since the dawn of time has used their style to transmit their status and prowess. Let's think Celtic warriors painting their faces blue. American Indians with Mohican hairstyles. Maori warriors covered with tattoos. Even pirates had dreadlocks large earrings and eye make up. These were all fashion statements which were saying, "Hey check me out I am confident and cool! And I have high social status and deserve the attention my style is giving me".

Find your style

This is not to say you have to make an extreme statement like these ancient fashionistas. However you have to look good and especially be aware of what is current and congruent with your age, type and personality to be viewed as a cool guy. Alpha males and men who are used to female attention and know-how to command it realize that their image and thus their sense of style is an immensely important element in transmitting there high social status, sense of self and in simpler terms making them 'cool'. Which is why I want to tell you about why what to wear on a date maybe more important than you think.

The female frame of mind

If you are even uttering the words "I'm not sure what to wear on a date?" to yourself, then you may need to rethink your style. Get out there and get a new wardrobe. If you just don't have a clue what you should be wearing and just feel a bit lost then "I'm not sure what to wear on a date?" Or "what should I wear to attract women?" is probably plaguing your romantic existence. If you’re that guy, then seek advice from a pro! One thing I have learnt from an extensive career as a stylist is you never regret investing in your appearance. It opens doors and gets results in the battlefield of dating. So those were some of the implications and ramifications of a good sense of style. It is also definitely worth thinking about the female mind frame. Women are extremely aesthetic creatures. In general, your average women puts a huge amount of time, money and effort into looking her best. She enjoys fashion and loves to look good. Your average guys don't. He thinks that if he looks ok and feels ok then that is enough. Why should he put any more effort into what to wear on a date? If you want to attract more women then you must reciprocate these values on even the smallest scale by knowing you look good and adhere to basic current trends. Leave it to chance and you’re extremely likely to put her off without even opening your mouth. Or have her thinking, "hmmm he doesn't dress very well" and is thus "not my type". Which means you had better have amazing social skills and the ability to entrance her with your wit because you are going to be playing catch up from the get-go.


Women want to be proud of the man they are dating, they want to love his style and show him off to there friends. Now be honest do you think that tired old shirt and jacket are something a desirable woman is going to be keen to "show off" to her buddies? Men tend to base attraction on sex. It doesn't matter if a woman is dressed in a bin liner! If she is sexually attractive then most guys ignore her style as long as it's passable and focus on her physical nature. Women are the opposite. It is image and appearance, and thus fashion, that makes a guy sexy: so what to wear on a date becomes an important way to communicate attraction. It is his sense of self that’s transmitted through his style which makes him a good prospect and "the type of guy I go for". When a woman says "my type" she isn't referring to his ethnicity, body type or any other physicality's, she is referring to his fashion sense. It's his fashion sense, which situates him in society and makes him a cool fella and a good prospective choice of partner at best! More likely a desirable woman deems a good style as the absolute minimum for a guy to even be considered and given any chance whatsoever.

Your style, your holy grail

The tiny percentage of men who know how to command a style which eludes "cool" and social status are laughing at these guys who are missing the dating holy grail of a killer image. It's this tiny percentage of men who are the ones who get all the chicks! They are used to attention used to being treated like a cool guy and thus they pay close attention to this central element, which makes them "that guy". If you want to be a more successful player with the fairer sex then make sure you look the part! If tonight or any other night you are wondering "ahh dammit I don't know what to wear on a date? The regrettably you will learn these lessons the hard way! Good luck! Ollie Pearce


Ollie is a professional stylist and image consultant and works with Hayley Quinn helping men to achieve the look thatwomen respond too. He also runs a YouTube channelwith an abundance of great fashion tips hacksand suggestions to cater to any man's identity.

Hayley Quinn smiling profile
About the author

Hayley Quinn is a leading dating and relationship coach, with 3 million views of her TEDx talk and 18 million YouTube views. She is spokesperson for Match, a columnist for Cosmopolitan, a regular contributor to international media, and has been published by Harper Collins (“The Last First Date”, 2022) and Simon & Schuster (“Do This, Not That: Dating”, 2023).

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