What to wear on a first date (and bag yourself a second)
Words: Zak Maoui
Ah, a first date! Sure, rubbish chat can end a date in minutes. And yes, a bad fragrance (or none at all) can do the same. But first impressions truly do count in this game and a dodgy shoe can end things in seconds, while a good, low-key shirt can score extra points.
There are no two ways about it; choosing what to wear on a first date can be stressful. You’ll want to look as though you’ve made an effort, but trying too hard can have catastrophic effects too, making you look vain and at worst, desperate. Your clothes will of course say something about you, so it’s up to you to make these positive as, again, first impressions matter.
A good rule of thumb would be to keep things simple and pared back, giving you an understated confidence and at the same time, letting their outfit take centre stage, as it should.
So to help you out we've come up with some possible scenarios where your date might take you, and outfit templates that should get you on a second one.
The low-key bar
An eclectic venue and a bit of Dutch courage, what could possibly go wrong? Ensure you look the part. Don't go OTT, but equally don't look like you don't care about a second date, even before it's begun. A dark colour palette - a leather jacket and black, straight-leg jeans - is perfectly suited to the nighttime, and it always works.
The fancy restaurant
One of the more formal of first date destinations, a restaurant requires you to up the ante. Some places will call for a suit, while other will require you to just wear a pair of nice trousers and a slick top. Our advice? Invest in a nice cashmere roll neck (black preferable) which will slip easily under a suit, and can be worn alone.
The big screen
An evening at the cinema is generally a casual affair so it’s important not to overdress, which allows you to avoid looking like you’re trying too hard. This outfit is rooted in workwear, but infused with a sharper edge. Invest in a sturdy, but a comfortable Carhartt jacket, and a pair of YMC trousers for an outfit that will make you look like the coolest person in the cinema (in the dark and out).
The activity date
This is the one where you can have some fun with your outfit. Gorpcore (the old fruit and nutty trail trend) has taken over mainstream menswear in recent years, and this is the ideal opportunity to flex your chops. Grab a pair of On Running sneakers, and pair them with a luxe pair of tracksuit bottoms (we're assuming you're going bouldering or the like). Up top? Simple tee, because you don't want to look like you actually work wherever your date is taking place.
Down at the pub
The pub may be a casual setting, but that doesn't mean you can turn up in your joggers. Ensure you’re suitably dressed in an evening-appropriate outfit that won't have your date calling for last orders. Try going for something with a Scandi feel - minimalist but still in-the-know fashion - comprising a nice Our Legacy shirt and a pair of Acne Studios jeans. You don't want to look try hard, but you also don't want to look like you spend every night in the pub (even if you do).
The alcohol-free walk in a park
These days a date doesn't need to mean one-too-many drinks and a sore head the next day. Instead a walk in the park suffices and probably leads to better decisions - both long and short term. This should be a riff on whatever you feel comfortable in day-to-day (no, joggers aren't OK here). Instead a nice pair of chinos, a simple crew neck and an investment coat are the order of the day.
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