What To Wear On A First Date (And What Not To Wear)


Knowing what to wear on a first date can be a stressful experience. You want your date to leave thinking they don't need to change anything about you – including your dress sense. In general, there are two possible mistakes a guy can make; not dressing up enough or overdressing. Sounds about as easy to master as Beethoven's 9th Symphony right? Well, it's not as hard as you might think and it's worth making the effort to get it right because first impressions still matter, even in this post-Tinder world. So here are some key pieces and tips for what to wear on a first date with a few hints on what not to wear thrown in for good measure.




We'll begin with something you should never ever wear on a first date. Yes, a well-tailored suit will always make you look sharp but on a first date a suit – especially if it looks like a work suit – can feel stuffy and make you look as though you couldn't be bothered to go home after work and get ready for the date. Ultimately the whole experience should be fun and, if possible, you should feel (or at least appear) relaxed. If it's a weekday date and going home to change beforehand is not an option then avoid looking career obsessed and making your date feel underdressed by making a few adjustments before leaving the office.


You can totally change the look and perception of a suit with a few small changes. A smart t-shirt or a crew neck jumper to replace the shirt and tie and a pair of smart white trainers will transform you from overdressed to cool and casual. If the date is in a fancy restaurant or the theatre (you're trying too hard but that's a whole other article), look to separates – a sharp blazer with tailored trousers – and ditch the tie.




A clean and simple button-down shirt in a subtle colour strikes a perfect balance between too smart and too casual and any guy who can cut a dash in one is worthy of a second date. You can play around with colour, textures and prints but two things are essential: fit and fabric.


Make sure it's slim (not skinny – button strain does not look good), sits square on the shoulders and drapes naturally down towards the hips (leaving room for any paunch you may have acquired while single). Fabric-wise, go for breathable cotton so as to limit the first date sweats. The button-down shirt can also provide a way to sidestep any overdressed/underdressed dilemma by simply tucking it in or not tucking it in.


If you'd rather wear a t-shirt then keep it simple and free of ‘hilarious' slogans or political statements. Any image or slogan that has to be justified with the words, "it's only a bit of banter" or explained by a discussion on politics or religion is probably not going to make for a great first date. These are things that will be important when moving in together but not first date fodder.




The next piece of the first date puzzle is a nice pair of jeans or chinos. If you opt for denim then look to straight cut or slim fit that are roomy in the thigh but tapered from the knee down. Mid-Weight denim (10-12 oz) is your ideal fabric as its weighty enough to drape like trousers but not so heavy that it's stiff and bulky. No rips, no dad jeans, no embroidery and definitely NO BOOTCUT.


A lot of guys these days will go for a cropped ankle look by rolling up the cuff. It gives a nice colour contrast but it only really works if you're baring that ankle flesh and that can be divisive on a first date. A bare ankle is likely to conjure up one of two images of what lies beneath an invisible sock – a piece of clothing that can never be described as sexy – or that you're actually sockless. Given that it's the first date and they have no idea how good or bad your personal hygiene is, it's best not to call that into question by conjuring up images of smelly toes. So save the mankles for future dates.




Your choice of shoe has the power to give and take away from your outfit. A sneaker will tone the formality of separates or a smart shirt and trouser combination, while Chelsea boots or brogues will lift the casual nature of a jeans and jumper outfit. When picking your shoes, adhere to the dress code of where the date is taking place first and foremost. Then consider the overall aesthetic and match your trousers to your shoes. Finally, go for comfort – meaning don't break in a pair of new leather shoes on a first date. Wincing and limping isn't all that attractive.




We've all seen the ads where a man emerges from an asthma-inducing fog of a certain body spray to be greeted by a harem of beauties. In the real world, too much aftershave or deodorant is more likely to have the opposite effect and will leave your poor date coughing and spluttering as they ask for the bill. Your first date grooming needs to be subtle. Overdoing it on the fragrance can also send the message that you couldn't be bothered to have a proper shower.


You want your date to lean in closer and catch a whisper of your fragrance, not force them to breathe through their mouth for the whole date. Choose a subtle scent that you like yourself and apply a spritz to each wrist and around the collarbone.

Patrick McLoughney