You’ve managed to secure a reservation at that superb restaurant, you’ve placed your order at their favourite florist and, after plenty of deliberation, you’ve settled on the perfect gift that shows just how much you care.
Now what the hell are you going to wear?
It’s surprisingly easy to leave this most important aspect of a Valentine’s date to the last minute, but it’s worth bearing in mind that failing to dress for the occasion after you’ve invested in everything from artisan chocolates to a surprise weekend getaway is about the same as pairing your knackered dirty Converse with your finest tuxedo – you’re simply not doing yourself justice.
But that’s not to say that you should be wearing your Sunday finest to your afternoon brunch date. It’s all about making sure that you dress both stylishly and appropriately for whatever you’ve got planned.
With this in mind, we’re giving you a rundown on what to wear to four common Valentine’s date scenarios.
The Dinner Date
Good choice; how can you go wrong with three courses of masterfully prepared aphrodisiacs accompanied by a few glasses of fine wine? Taking your date to dinner on Valentine’s Day is pretty much fail-safe – and if you’ve jumped the hurdles involved in securing a reservation, then you’ll want to match that same effort when it comes to what you wear.
It’s hard to beat a sharp suit in this instance. Given that you’ve opted for arguably the most traditional type of Valentine’s date, keep your look similarly classic by opting for a two-button, notch lapel style in light grey, charcoal, navy or black.
Remember: your aim here is to appear well-dressed and attractive, not upstage your date and make them feel uncomfortable. With this in mind, round out the look with a simple white button-down shirt or roll neck in a complementary colour, a pair of classic black Derbies/Oxfords and a neatly folded pocket square that sits firmly on the subtle, rather than showy, side of the spectrum.
If a suit is a little too much for you or the restaurant in question, then revert to a foolproof chino and blazer combo. Try a pair of slim- to straight-fit chinos in beige with a navy tweed blazer, blue Oxford shirt and pair of brown brogues or loafers. If you want to add a little formality to mark the occasion, consider introducing a plain coloured knitted tie.
The Cinema Date
We can’t give you advice on what to watch, but we’re more than happy to point you in the right direction when it comes to attire. A trip to the flicks may be a little more low-key than a dinner date, but that’s still no reason for you to slack on the style count.
You’ll want to aim for the smarter end of smart-casual for this one, just in case you end up going for drinks before or after. Start off with a solid pair of winter-weight fabric trousers such as beige moleskin chinos, indigo selvedge jeans, brown/burgundy cords or grey flannel trousers.
Build on your base with a plain cotton, plaid or chambray button-down shirt and a generously sized knit to ward off the chill – a chunky cable jumper or shawl neck cardigan would be ideal – then polish your look off with a pair of smart boots in brown/black.
We’re not promising anything but if this combination of textures doesn’t encourage your date to get tactile, then there’s little that will.
The Day Date
Whether it’s a day trip to a neighbouring town or city, a visit to your favourite museum or a scenic lakeside walk, this option is likely to see you moving in- and outdoors throughout the day, meaning savvy layering is paramount to looking and feeling your best.
Ensure you’re prepared for every kind of weather February can throw at you by teaming a lightweight jacket – think mac, trench, field, unlined parka, etc. – with a mid-weight piece of knitwear, classic crew neck tee and pair of dark indigo jeans or slim chinos.
When it comes to footwear, you’ll want to go for a style that’s both sturdy and comfortable – boots (whether a classic brogue silhouette or worker-inspired style) and leather trainers are your best options here.
If it’s chilly, don’t forget your cashmere scarf and leather gloves – both are luxurious yet understated and will give off a subtle sense of sophistication.
The Home Date
Probably the most intimate option, just because you won’t be leaving your home doesn’t mean your trusty jeans and hoody combination makes the cut. You’ll definitely need to appear put-together, but it’s advisable to stop short of looking like you’ve tried too hard.
Keep your outfit relaxed but presentable. Try a pair of straight-leg jeans or chinos with a shirt and lightweight v- or crew neck jumper, or a knit polo shirt with a pair of nattily cut trousers.
While footwear won’t be at the forefront of your mind, we’d suggest you swap the pool slides or slippers for a pair of tasselled loafers, minimal trainers or desert boots. If you’re a ‘no shoes inside the house’ type of guy, please make sure your socks haven’t got holes in and that they complement your ensemble.
The All-Important Details
Finally, don’t go to the effort of crafting the perfect date – and the outfit to go with it – without making sure your grooming is up to scratch.
Drop by your barber beforehand for a fresh cut so your hair is looking on point and don’t forget to set aside some time for a clean shave or trim – a little manscaping wouldn’t go amiss either.
We’ll say this once and once only: when it comes to fragrance, be sparing with your chosen scent. While a few modest dashes of cologne are crucial for impressing your date, too liberal an application will only serve to suffocate them.