The best date night fits are simple but not basic, cool but not try-hard, easy-going but show effort. It’s a tightrope walk that’s harder than getting a Valentine’s Day reservation at the best restaurant in town.
To save you from overdressing, underdressing or worse—randomly throwing on any unironed garment within reach—we’ve broken down four date settings and the ideal outfit for each. To make sure they strike the right chord, we’ve pulled inspiration from four modern heartthrobs to create looks that will definitely get your date’s heart racing.
The best men’s date night outfit formulas
The wine bar after work
There are some essential things to know before arriving at the hip local wine bar: the share plates are the size of your palm, the natty wine tastes like salad dressing (but you’ll love it), and the crowd is a combo of cashed-up boomers and It-girls taking 0.5x zoom selfies. Somehow, all these elements combine to create the perfect date spot—good food, good booze and plenty of over-the-top characters to inspire conversation.
In terms of dress code, the modern wine bar sits in the grey area between dressed up and easygoing. Not as casual as a pub, not as formal as a restaurant—but still cooler than both. There’s nobody who nails this exact vibe better than Paul Mescal. The Irish actor has hit his stride recently by perfecting smart casual fits, mixing well-fitting basics and classic tailoring to create results that make the internet hyperventilate.
Take a page out of Paul’s book by tucking a Henley shirt into tailored trousers and finishing the look with black leather shoes or your cleanest retro sneakers. Undo just the right amount of buttons, and you’re all set to swirl your wine glass like you know what it does.
The lowkey (but special) dinner at home
Let’s face it, with the cost of living the way it is, a big night out (or any size night out) might not be on the cards right now. Thankfully, cooking for someone—or at the very least plating their favourite takeout—can be just as romantic (bonus points if their love language is acts of service).
Avoid the urge to overcompensate by trying to make the evening something it’s not. There’s no point putting on a suit just to eat at home; it’ll read as corny. Instead, embrace the beauty of making the everyday extra special.
The Bear taught the world about the power of a simple, well-fitting white T-shirt, and this is your chance to tap into that thirst. In fact, why not lean in and go full off-duty chef cosplay, white tee, loose workwear pants, clogs and all. Tuck a tea towel into your waistband and embrace your inner Carmy, but with more focus on his style and less on his emotional terrorism.
When they walk in and see you looking your casual best with the table set, flowers arranged, candles lit, and wine ready to be poured, they’ll be swept off their feet so hard they’ll forget all about Jeremy Allen White’s Calvin Klein campaign.
R. M. Williams script cap
Uniqlo 100 per cent Supima cotton crew neck T-shirt
The fancy restaurant dinner
You did it; you’ve secured a table at one of the fanciest restaurants in town (c’mon, forward-thinking!). Tonight, you’re going big. We’re talking about cocktails on arrival, multiple courses, don’t look at the price, “let’s get both” kind of night. It would be a shame to ruin such a lavish evening with an undercooked outfit. Now is the time to raise the bar and pull out something slick—it’s time to wear a suit jacket.
The key here is to tap into tailoring while keeping it modern and avoiding anything too fuddy-duddy. Wearing a tee or tank underneath your favourite black suit is a great way to nod to dressing up while adding some youthful energy. There’s a reason it’s become a go-to move in Charles Melton’s impressive style playbook. You can’t steal his bone structure, but you can steal his look.
The chill sunset picnic
Surely you had to know that, at some point, Jacob Elordi would show up on this list. As the internet’s number one babygirl, the Australian actor has won hearts with his impressive acting chops and even more impressive personal style. Elordi’s outfits are always on point, but they’re particularly strong when mixing casual tailoring and slouchy knitwear—the perfect combo for a chill sunset picnic date.
A pair of classic straight-leg jeans, a knitted polo sweater and polished black boots will show your date you care about nice things without coming off as a try-hard. It’s a picnic-appropriate outfit that says, “I just threw this together and happen to look like an off-duty Hollywood heartthrob.”
But the most crucial garment to have with you on the picnic date isn’t actually for you; it’s for them. Repeat after us: bring a jacket. When the sun goes down and the temperature drops, you can pull out a jacket (or, even better, slip it off your back) and drape it around your date. Trust us, it’s what Jacob Elordi would do.
