HOW TO DRESS FOR EACH AND EVERY DATE NIGHT POSSIBLE

So, your first date is locked in. Good for you! Now, it’s time to make sure this winning streak continues by getting your date night outfit in check. Generally speaking, guys either put in way too much effort, or not enough at all. We get it. You’re either very into this solid 9/10 and want to impress, or you’re very into this solid 9/10 and want to act like you couldn’t give less of a fuck. Either way: that’s cool.

As is the case in most menswear issues, finding the in-between is the difficult bit. You want to make a bit of an effort, but not too much; you want them to know you’ve taken an interest in their Hinge prompts, but not that you’ve already found them on LinkedIn; you want to be presentable, but still cool and louche and laidback.

We’ve got you. This GQ guide is here to inspire your next date night outfit. Whether you’re just grabbing a quick flat white or hitting up that ridiculously overpriced ‘small plates’ restaurant with a six week waiting list, here’s how to dress for every date night possible.

What to wear on a coffee date

What to wear for a first date drink

What to wear to a fancy dinner date

What to wear when going for a walk with a date

What to wear for an activity date

What to wear for a date at home

The coffee date

The coffee date is probably the most Hallmark of all dates. It’s just you and your new fave person with your fave drinks in your fave spot. It’s casual, the least committal, and all very laidback. But just because you’re in a comfortable setting, it doesn’t mean you should, y’know, feel too comfortable.

With that in mind, you can’t go wrong with wardrobe staples like a black or white T-shirt, some straight-cut jeans in a dark wash (for the love of all that is holy: no distressing or ripping please), and a pair of sneakers. You can tell a lot about someone by the state of their kicks, so keep them marginally clean. Finish off the fit with a solid jacket that cuts a fine shape: slightly broader shoulders, nice neat lines. No need for big branding, either: it’s your name and your name only on the billing today, buddy.

A date in a bar or pub

Bars and pubs can be vastly different places depending on where you are in the UK. But if you want your second date to lead to a third, and your third take to lead to a fourth (and so on and so on), keep your date night outfit smart-casual on both occasions. We’re talking solid shirting, decent trousers, and a pair of chunky Derbys or Chelsea boots.

If this sounds a little too formal for your liking, a striped tee and a light overshirt could work too. The latter can be in any style that you want really, but if you’re feelin’ lucky, you should opt for something that’s understated without any wild, wild graphics. No obscure ’80s cartoon prints. None.

The fancy dinner date

Going to a big restaurant is the ultimate way to impress your date. Not only will it feel like a proper event, they’ll also get to know your water choice (still, sparkling, or tap?). It’ll also show them what you look like when you’re all dressed up.

You could go for a suit, but that might come across as too interview-y. Maybe that’s a little too dressed up. The last thing your date wants is to be asked when they went above and beyond in their previous role. Instead, slip on a rollneck jumper. Polo shirts are also a good shout (long-sleeved only), but if you really want to spice up your menswear, get you a knitted polo. Oh, and don’t forget about your watch. There’s nothing more icky than whipping out your phone in the middle of a convo, even if it’s just to check the time.

A walk in the park date

While meeting up for a “walk in the park” sounds like it could be code for something else, most of the time, a walk in the park is genuinely just… a walk in the park. Your date night outfit is dependent on the weather. If it’s feeling extra chilly, a sweater made of merino wool or maybe even cashmere will definitely keep you warmed up. Layer this with a coat or a puffer jacket and you should be all good.

If the weather feels warm enough, a short-sleeve shirt and some selvedge denim will look hot. If you’ve got particularly long hair, a baseball cap will keep your locks at bay and bode well for both fits. And for extra points, meet them with their fave coffee already in-hand.

The activity date

Heading to the cinema to watch the latest Scorsese film or attending a pottery class is obviously very different from something like going for a hike or even Zorbing. So if you’ve got an activity date pencilled into your calendar, it’s always worth knowing exactly what’s planned.

You want clothes that reflect who you are (a real man of integrity), but also clothes that you don’t mind getting bashed. The pottery class will give you an apron, but short sleeves on a classic T-shirt are preferable to something fancy. Go for beat-up, reliable jeans that look good, but not too good. And if it’s an indoor climb, show the world what the squat rack gave you with some solid workout wear.

The at-home date

It shouldn’t come as too much of a shocker, but sometimes at-home dates are the best kind. Perfect for those nights when you’re both feeling extra introverted and you don’t want to interact with other people, cracking open a bottle of wine, turning on Netflix and enjoying low cost quality time is one of life’s few luxuries.

But, even though you’re dating from home (DFW?), you still shouldn’t feel too comfortable. Grab yourself a nice oversized cardigan and some slacks. You should also think about investing in some brand new crew socks. If you really have to go down the loungewear route, you can’t go wrong with hoodies and sweatpants from more premium labels like Aimé Leon Dore, Fear of God, and Kith. Maybe leave the Crocs in the box until at least the 500th date, though.