Written by Menswear Style in Tips & Advice on the 26th May 2021

Whilst it’s true that when it comes to dressing for that first date it’s all about making an impression, you should always be aware that less is more. A first date will always have a certain amount of nervous tension about it and the last thing you want to be doing is making too much of a fashion statement, so much so that you are constantly worrying if you’ve bitten off more than you can chew. Men sadly often go too far in one direction than they should. Either they’ll dress down to such an extent that it looks as if they couldn’t care less. Or, they totally misread the situation and dress as if they are going to the Met Gala. The truth is that somewhere in between is where you should aim if you want to impress on your first date, here’s a few helpful tips.

Dress Neutral 

Don’t go for an abundance of colour, keep things neutral and simple. There’s no need to arrive for your first date blaring like a siren. Be understated and stylish and that way the date will be less about any ‘brave’, potentially disastrous, fashion choice you decided to mistakenly make.

Accessorise, Wear a Watch 

You’d be surprised by what signals wearing a watch can make. In 2021 it’s fair to say that a large percentage of the population don’t wear a watch, opting instead to use their phones to keep them aware of the time. However a watch gives off a vibe of sophistication, organization and awareness. If that watch happens to be a nice stylish watch, but not one that’s garish and blingy, then all the better. 

Dress for the Occasion and the Location 

Increasingly, to avoid ruining a perfectly good evening or to help manage expectation, a first date might just as easily entail a coffee in Starbucks or a simple lunch downtown. However, that doesn’t mean you should put zero effort into your appearance, so dress according to the situation. Keep to simple colors, black or navy blue and if the date is a small affair then make sure your outfit is sharp if not dramatic. 

Great Underwear 

If you’ve got a pair of ‘lucky’ underwear that’s been worn far far too often, think again. Wear clean and simple boxers, after all you may not be the only one who sees them. Again this is about having the confidence that you are making an effort without any of your clothing decisions becoming the subject of conversation.

If the Weather Permits, Layer 

A good way to show that you are a good catch is if you look as if you have prepared for the season and the elements. If it’s a brisk cold day, then this is your chance to layer with confidence. A sporty bomber jacket on top of a nice shirt and vest will give the impression of a man who is prepared and ready. In many ways the colder the weather the more you have to display in your wardrobe. 

Go the Extra Mile With Your Shoes 

If there’s one part of an outfit that men pay way too little attention to, and women vice-versa, then it’s shoes. If you have followed our advice thus far by dressing in an understated and neutral manner, then the shoes are the chance to impress. This doesn’t mean you should wear an extravagant pair but a pair of Chelsea boots or similar, polished and spotless of course, will go down well. 

Be Prepared 

Now a successful first date is, clearly, more than just a case of dressing well. You need to be in the right frame of mind and ready to impress on the whole. You’ve already secured the date you’ve been waiting for, maybe via a great dating app, and you can find more info about these here, now you have to focus on the occasion itself. Hopefully your fashion decisions will set your mind at ease and you can then look to make an impression on your date. Firstly, put your phone away (and resist the urge to retrieve it from your pocket), be on time (maybe even a little early) and have in mind some conversation starters. Above all, be yourself. This may sound a little trite but if the date is working well you’ll soon forget any pretence you have about reinventing yourself to dazzle your date, and then the sky's the limit.

Dress Neutral, Wear a Watch, and Wear Great Underwear are all recommendations in this guide to What to Wear On that All Important First Date.