How To: Dress For A Date


From a first date to the decisive third-date dinner, we roundup three looks that will leave a lasting impression

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It’s not an easy one, is it? Knowing how to dress for a date, especially in the early stages where nailing those all-important first impressions is key. What you wear will ultimately decide the outcome of the date within, say, the first five minutes, so if you turn up in a poorly put-together outfit, well, chances are your date will mentally swipe left and move on.  Whether it’s that self-conscious first meeting or the decisive third-date dinner, we’ve done the hard work and curated three outfit choices below. Because let’s be honest, dating is already tricky enough without the additional worry of what to wear clouding your mind.

The first date

A first date, despite general thoughts on the subject, is quite easy to dress for. Assuming you’ve met through an app – because who chats in bars anymore – the first date will be the first time you meet in person. It’s a cliché as old as time, but making a good first impression matters, especially if you want a second one. You want to look like you’ve made some effort; think a carefully considered “thrown-together” outfit: a bomber jacket (go for a suede option for the touchable factor) awards instant cool points when paired with slim-fit dark-wash jeans and Chelsea boots. Either a casual shirt or a classic white tee can be worn with this look, depending on your mood and how smart-casual a note you wish to hit.

The post-work date

So you’ve made the right impression on the first date. You’ve suggested a second and an after-work drink followed by dinner is on the cards. This time take things up a notch with a more tailored approach. Mix high and low pieces: a suit with a polo shirt and sneakers strikes a cool balance between “I’ve come from the office” and “And I want to impress you”. Bear in mind different textures too; a melange polo suggests softness, giving the outfit a more romantic silhouette. Keep the colours light to evoke a more playful, flirty mood.  

The clincher

You’ve been dating for a while and you’re keen to take things in a more serious direction. A three-course meal in one of London’s top fine-dining spots has been booked. Your attire should reflect this. Smarten up with a double-breasted blazer paired with a sleek shirt. More tonal blues and navies will set the right mood for the evening and opt for a shirt that, to some extent, is in sync with the blazer and trousers. Avoid appearing too formal by forgoing a tie in favour of an undone top button and a relaxed-fit shirt, ideally a printed one to bring interest to the look. When it comes to your footwear opt for sneakers as a nod back to the excitement of those earlier dates.