So you’ve swiped right and received a flurry of come-hither emojis – or maybe gone old-school and had a ‘yes’ to your brave face-to-face “Fancy a drink?” gambit.
But getting someone to agree to sit across from you at dinner is just half the battle – next you’ve got to select a suitable venue and choose the right attire to ensure you’re dressed both a) attractively and b) appropriately for the time, place and occasion. It’s the latter that’s your main priority – because, really, if you’re sinking serious cash into a meal, it only makes sense to go with a different look than, say, if you’re meeting for a Sunday pint.
Fortunately, we’re on hand with some expert advice on what to wear, wherever the date may take you.
1. On A Casual First Date
You’ve probably seen the meme positing “A well-tailored suit is to women what lingerie is to men”. True dat.
For a casual meet-up like an after-work cocktail, a change from your boardroom best isn’t always necessary. But remember that, while the silhouette-enhancing structure of your tailoring might play to your advantage, not all suits are created equal – so plan ahead when getting dressed in the morning and opt for one that’ll transition seamlessly from office to bar come clocking-off.
The “well-tailored” bit above is key – fit has to be spot-on. So, if you’re the kind of guy who skips the basic rules of suiting on account of wearing one as uniform, you might be better off switching kits before your rendezvous.
As for cloth, nix broad banker pinstripes and stick with classic solids in grey and navy. Need inspiration? Take your cue from Suits’ Harvey Specter – you know, the guy who is always decked out in peak-lapelled Tom Ford power tailoring. In fact, buy a Tom Ford suit if you can afford it. If not, try one of these more affordable alternatives and get your tailor to do the rest.
Just as important as a sharp suit, however, is the shirt you wear under it. So swap the pit-stained one you’ve been powwowing in all day for a freshly laundered substitute. There’s pheromones, and then there’s downright offensive.
2. On A Movie Date
If, for some bizarre reason, you don’t want to spend your date getting tanked up on Dutch courage, then try something a little more cultural instead. Like seeing a film or checking out an exhibition. (And then getting tanked up.)
Wardrobe-wise, you can play it pretty cool for this one with something that reads smart-casual. Think dark selvedge jeans, neutral chinos or tailored trousers teamed with a button-down shirt worn under a knit jumper or sweatshirt. You’ll look put-together without overstepping the mark.
And unless you’re planning to Uber your date from A to B (good move, sir), there’ll be some walking involved, so steer comfy with your footwear choice and opt for a pair of unfussy trainers – clean white styles come up trumps this season.
3. On A Dinner Date
Considering there’s a two- to three-hour feast ahead of you, assuming things are going well, comfortable clothes are key; but given the surroundings, it’s only right your sartorial choice show respect for the chef, fellow diners and your date too.
For a foolproof separates combination that any man can pull off, try teaming a navy blazer (double-breasted is a wise choice for concealing that post-meal bloat) with straight-fit grey flannel trousers for a look that cuts the mustard in its formality, but won’t give you indigestion.
Keep it classic underneath with a crisp white shirt and accessorise with a woven silk tie that’s plain or subtly patterned. Then, step your look up with some quality leather shoes like black or dark brown Derbies, monk-straps or loafers.
As the well-worn phrase goes, your choice of footwear is the first thing many people notice and a deciding factor in whether you ace or flunk a fine restaurant’s dress code. Don’t let what’s on your feet make you fall short of your date’s expectations. (Or worse, get you refused at the door.)
4. On A First Date For Drinks
This applies to all dating scenarios, but it’s especially pertinent in the case of a casual Sunday afternoon pint, a time when – slightly absent-minded and bleary-eyed – you might be tempted to let standards slip a bit.
But as anyone considering getting their kit off with you will tell you: hygiene and grooming are everything. Three-day stubble is fine – desirable, in fact – but what’s non-negotiable is arriving at the pub scrubbed up, deodourised and lightly scented, with Colgate fresh breath, nails clean and trimmed, and nasal hair in check (who knew, but studies show unruly nostrils are a major deal-breaker for potential mates).
And no almighty hangover, either. Sure, it’s Sunday and it’d probably be weirder if you showed up having stayed in on Saturday night, but turning up bloodshot with vodka breath isn’t exactly an aphrodisiac either.
The only thing rough and rugged about you should be your artfully dishevelled style: think Steve McQueen, outdoorsy Ralph Lauren, worn denim and leather, boots and aviators – fresh from a little weekend woodwork or motorcycle maintenance (or so you’d have them think).
5. On A Dancefloor Date
Regardless of which brand of beats you’ll be treated to in the club or at the gig, it’s hard to steer wrong with a look infused with rock ‘n’ roll.
Distract them from your two left feet with a disarmingly simple combo of a plain white or Breton tee, black leather biker jacket and slim-fit black jeans – but not so slim as to stop you from breaking out your best moves without, you know, actually breaking something.
Your choice of footwear is dependent on your dancing prowess. Tony Manero-level lords of the dance should look to round out their look with a pair of black leather Chelsea boots, but the rest of us stand a better chance of staying upright in a pair of Vans Old Skools or clean leather Chuck Taylors. Easy as 1-2-3.