Last Minute Advice on What to Wear to a First Date

Don't let anyone tell you that it doesn't matter
IMAGE Summit Entertainment

So you've done it, you've ventured into the Battle Royale terror-sphere of dating (don't worry, it'll be fun!) and secured a first date. Good job, but the real works start now.

While a great get-up might not guarantee you that elusive second date (that's what your dashing good looks and scintillating chat are for), you can be sure that a careless outfit won't help your chances... in fact, it'll probably wreck them.

Sorry, but it's true.

In a modern dating world where first impressions are more important than ever, here are the style dos and don'ts to help you avoid the dreaded IRL left swipe.

Don't | Wear a Suit

Ok, there are caveats to this one, because if you have a job that requires wearing a suit and your first date is a few casual drinks after work (which it probably should be), then you won't be able to avoid wearing one; just leave the Prince of Wales check three-piece until at least date number... six? She's going to want to feel relaxed and comfortable in your company, so don't go full #menswear blogger straight away.

No one likes a try (too) hard.

Do | Think About Shoes

Easily the most important element of your first impression outfit, what you put on your feet is a huge indicator of taste in a man. Basically, it's a proven scientific fact backed up by numerous case studies that if you wear square-toed shoes then you will be rude to serving staff and a selfish lover; traits that, like bad shoes, nobody wants to be associated with.


Stick to clean white sneakers, smart and simple derbies or low-key, high-quality boots. Your footwear should make a subtle statement about the kind of man you are...and you are a stylish man.

Don't | Wear a 'Statement' Piece

You might be thinking that we're on a bit of a downer here, but we're just looking out for you amigo. Sure, there'll be some people who greatly appreciate your Prada camp collar shirt, ripped Saint Laurent jeans, and Chelsea boots (we do!), but for the best odds it pays to play it safe in the early stages, which doesn't mean that you can't be stylish... far from in it in fact.

Stick with understated shades and quality pieces that fit well and you are 100% comfortable in. We can guarantee that your date will be more fussed about your body language and the way you wear your clothes, rather than if you're in new season Rick Owens.

Do | Pay Attention to Detail

How's your wallet? What scent are you wearing? Did you floss? Are you wearing a good watch? It's easy to let the little things slide, but if you want to be the kind of guy that she tells her friends about, then attention to detail is a must. You can be the best dressed guy in the room, but when you get a tatty velcro wallet out of your pocket to split the bill (it's 2017, bros) then all of that good work can be quickly undone.

Don't | Wear Shorts

Unless you're going to the beach.

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Do | Wear An Unstructured Blazer

Right, so we suggested against wearing a suit, but that doesn't mean that tailoring in all of its wonderful guises is out the window – you've just got to be a bit more chilled about the whole thing, which is where the unstructured blazer comes in.

Great with chinos, wool trousers, and every variation of shoe. A slim, easy-fitting blazer without formal structure shows care and style, without the intimidation of full-blown suit.

Don't | Wear Lucky Pants

We don't actually believe that Lucky Pants are even a thing, but if you're the one person that this applies to then please reconsider. Even if you don't have lucky pants, make sure you're paying attention to the underwear department (dark, as unbranded as possible). We'd hate to see your chances scuppered because of those novelty boxers from Christmas 2014.

Do | Put Away Your Phone

Not exactly a style point, but the only thing that's going to hinder your chances of a second date more than square-toed shoes is bad manners, of which using your phone at the table is the pinnacle. Unless you're waiting on an emergency call, stick it on silent.

Your Insta followers will understand.

This story originally appeared on

* Minor edits have been made by the editors.

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Finlay Renwick
Finlay Renwick is the Digital Editorial Assistant at
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