What To Wear On Valentine’s Day

You’ve remembered to secure a reservation at the in-demand restaurant, you’ve placed your order at the florist and, after more deliberation than you planned for, you’ve settled on a Valentine’s gift guaranteed to score some brownie points.

Now what the hell are you going to wear?

It’s easy to leave this aspect of a Valentine’s date to the last minute, but V-day is as awkward for dressing as any smart-casual invitation. You don’t want to turn up in a dinner jacket with a rose between your teeth, but nor is this the night for your so-called “tailored” joggers.

Whether you’re going for a Michelin-starred dinner or a simple brunch 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. That’s the clothes sorted – the chemistry is up to you.

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? Seeing as you’ve jumped the hurdles to secure a reservation, you’ll want to match that same effort when it comes to what you wear.

It’s hard to beat some sharp tailoring in this instance, but you’re not off to a job interview and your date won’t want to feel like they’re being interrogated. Loosen it up. Try separates in complementary colours, subtle patterns or a dressed-down double-breasted jacket. Most importantly, leave your shirts in the wardrobe and wear a roll neck or crew neck under the jacket instead. A pair of classic black Derbies or Chelsea boots will chime with what’s going on up top, but maybe add a neatly folded pocket square if the restaurant’s particularly upmarket.

Don’t forget to use the serviette. You don’t want to accessorise with spilt peppercorn sauce.

The After-Work Date

If you’re keeping it casual with a quiet drink or an ever-romantic Netflix/takeaway combination, frankly, we don’t blame you. You can still make an effort with what you’re wearing on Valentine’s Day, though.

Aim for the smarter end of smart-casual to retain some sense of occasion. Start off with a solid pair of winter-weight fabric trousers such as moleskin chinos, selvedge denim, or 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. If you are heading pub-wards, don’t forget a plush overcoat in grey, camel or navy.

We’re not promising anything, but if this combination of textures with a cosy pub corner or romantic movie doesn’t encourage your date to get tactile, then we’re not sure what will.

The Day Date

Whether it’s a day trip to a neighbouring town or city, a visit to a new 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 your best while also regulating the temperature.

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 – 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. Which may or may not be warranted.

The Dance Floor Date

If you’re going out-out, the rules are a little different. Assuming you’ll be in and out of cabs, busy bars and packed dance floors, you can forget about the need to layer up against the conditions and think a little more rock n roll with your get-up.

You’re dressing to be seen, to make an impression, so start with a printed shirt or a lightweight patterned knit. Pick out a sumptuous suede jacket to go over the top and a slim pair of dark jeans down below, then ground the lot with some fancy footwear – Chelsea boots or loafers are our top picks.

Keep the palette dark to give yourself the best chance of coming off like a modern-day Heathcliff. However (in)accurate that impression may be.