Bar the suit you’ll pick out for your dream-job interview or the one for your (eventual) wedding, no outfit should be more thought through than the one you’ll wear on that all-important and utterly nerve-wracking first date. The goal here is to go for something that plays up your best qualities, conveys confidence and provokes interest – all while looking like you haven’t tried too hard. (No easy feat.) Our advice: crack out the BODE jacket, which will mark you out as a man of taste and, more importantly, provide a guaranteed point of conversation. And why not show off a little more of your style nous with a sprinkling of Bottega Veneta – namely its intrecciato tote bag and brilliant glossy Derby shoes? That said, you don’t want to appear to be a victim to the trend cycle, so bring things back down to earth with wholesome casual pieces such as a visvim flannel shirt and some chinos. Altogether you’ll exude a level of innate, pared-back style that won’t be impossible to recreate should you proceed to the next round.

Helicopter rides, five-star suites, the best seats at the ballet – no romantic gesture is too lavish. (His partner deserves it, after all.) If that sounds familiar and you’ll be the one pulling out all the stops – maybe even a ring – for your date night, you’ll need a head-turning outfit that mirrors your efforts. A sumptuous navy velvet tuxedo jacket by the always-tasteful Brunello Cucinelli will nod to the sense of occasion – and be irresistible to the touch. Elsewhere you can stick to the formula with a classic Canali evening shirt and straight-fit tuxedo trousers. For finishing touches, sleek patent-leather SAINT LAURENT boots and a studded silver ring by Pearls Before Swine are guaranteed to infuse an eveningwear look with a rock’n’roll edge.

Perhaps you’re one half of a cosy, long-term couple that prefers to keep it low-key. Flashy proposals and public displays of affection? No, thank you. A cosy meal at your favourite local or a walk in the park is more than enough to keep the spark alive. Let’s be real, here: at this point, your life partner has likely seen you at your absolute worst, but that doesn’t mean it’s not worth keeping them on their toes every so often. Start with a laid-back jeans-and-sweatshirt combo (CHERRY LA’s jersey and wide-leg denim by DIME should do the trick), which you can jazz up with smart layering. Try Needles’ undeniably cool bomber jacket juxtaposed with soft-pink Oxford. Then, finish off with a functional tote (roomy enough for the gift that you promised not to buy) and streetwise accessories for an outfit that makes them take a second look – but not burst into laughter.

Whoever decided the “hottest” night of the year should fall in mid-February clearly had a sense of humour. In other words, no judgement from of us should you opt to spend yours hunkered down with your partner in the warmth of your own home. However, much like a three-course slow-cooked dinner over candlelight will offer an upgrade from every other night in, it pays to invest in a first-class loungewear look that’s a far cry from the slouchy sweats they usually see you in. JW Anderson is on hand with an adorably snug Jacquard hoodie, which you can pair with cotton-poplin trousers by Dries Van Noten. Also consider swapping out your granddad slippers for a pair of faux raffia mules from Marni, which will hold their own should you choose to pop out. Finally, what could possibly be dreamier than wrapping up a romantic evening in with a snuggle on the sofa? LOEWE’s impossibly soft mohair blanket will no doubt make it one to remember.