What To Wear On A First Date

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As the old saying goes, “you only have one chance to make a first impression”. Never is this saying more accurate than during those first few moments on a first date; when a pair of “what-are-thoooose” shoes could mark the end of a beautiful love story, or a nice clean, ironed shirt could ensure you a second date. I’ve been asked this question a lot lately (probably because I’ve started doing a dating podcast), so to help you -the reader- to ensure you make a good first impression, here is a guide on what to wear on a first date.

Tinder Date at a Pub

Let’s set the scene. You’re at home on a Friday night, you check the info button to see who’s on ‘The Late Late’ and ‘Graham Norton’, you have no interest in the Minister for Health or the cast of ‘Mamma Mia 2’, so you pick up the phone and log into your Tinder and promptly fall in love with the first person you’re matched with. You commit to a date and plan to meet in the local pub the following night. When Saturday comes, you then have to figure out what to wear to impress Lucy/Luke. The solution? Keep it simple and low-key, but also like you’ve made some bit of an effort; like you want to impress, but not go overboard. Think slim-fitting jeans and clean trainers with a textured crew neck jumper or a slim fit polo shirt. Have a shave and style your hair but, again, don’t go overboard. Think bed-head rather than job interview.

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Dinner at a Fancy Restaurant

A tricky one, as I usually deter people from going to dinner on a first date (especially one you can’t really afford), but the reality is that sometimes to get the girl (or guy) you have to go the extra mile. If you’re heading to a fancy restaurant, then my advice would be to suit up. The way you’ll make an impression is by playing around with it (the suit that is). Think double-breasted blazer or oversized pinstripes matched up with more traditional trousers. Finish things off with a long pair of navy socks with chestnut or oxblood Derbies and you’ll look like you made the effort. This is also a look that can be put together without spending a fortune if you head to the high street. You’ll need those extra pennies for the lobster and champers, daaaarling.

The Coffee Date

We’ve all been there. You’re chatting to someone on Tinder or DMs or whatever app and they ask you out on a date, but you’re a little bit.... meh. So rather than suggest going for a drink, you make a coffee date to suss them out first and see what they’re like before you commit to a ‘real date’. So, do you dress to demonstrate your lack of interest? No, because what if you get there and find out that they’re actually pretty amazing (but have terrible chat game on digital platforms) and now they think you’re a bit of a douche and THEY don’t want to go on a ‘real date’. So, refer back to your Tinder-date-at-the-pub attire or, if you want to hedge your bets and wear a tracksuit, then make it a pair of matching Ralph Lauren or Tommy Hilfiger sweats. You can always play the “let’s get takeaway cups and go for a walk” card so that your athleisure look makes perfect sense.

The Walking Date

This one scored highly in my First Dates guide. Wear a decent pair of trainers so you can sprint away if you don’t like the look of them! All joking aside, the “let’s go for a walk” date is the only one where you can rock up in a tracksuit and a hoody and it doesn’t look like you’ve made no effort or are being intentionally disrespectful. Bear in mind that if the walking and chatting goes really well you might want to grab a drink or a bite to eat, so don’t rock up looking like Damo from ‘Damo & Ivor’ or they won’t let you in anywhere.

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The Friend-Zone Pizza Date

You’ve been friends for years and you’ve always had a thing for them, but the reality is they’ve only ever seen you as a friend. So you convince them to go for a one-on-one pizza away from the rest of the friend group, which you hope will elevate you out of the ‘friend-zone’. What you’re looking for here is confident and masculine, without looking like you’re trying too hard. Opt for a nice bomber jacket with a nice, clean white t-shirt and smart jeans or chinos. Make sure you pay and be patient. It might take a few of these low-key departures from the friend group before they start to see you as boyfriend material. 

General Advice

The late Sir Hardy Aimes famously said, “a man should look as if he had bought his clothes with intelligence, put them on with care and then forgotten all about them”. So, look like you’ve made the effort, but not too much effort because no girl wants to date a guy that looks like he’s spent longer getting ready than she has. Same logic applies to fragrances; pick a good one (I’ve suggested plenty in the last few years) and spray conservatively on your chest and on your hair (as well as neck and wrist) to give them an incentive to get closer. Invest in a decent wallet, because nothing will kill momentum quicker than pulling out your velcro, fold-over Liverpool crest wallet to pay for the drinks. And finally, get some decent underwear, because you never know and, as Roy Keane says, “fail to prepare, prepare to fail”.

Patrick McLoughney