Heading into the great outdoors is a wonderful way to get to know someone better, but canyoning or white-water rafting may be best kept for a later date. Instead, opt for a walk somewhere nice with beautiful views. The only catch can be the weather, so bring a brolly and tool up on good garms. A warm coat – a shearling bomber by Paul Smith, maybe, or an easy-wearing shell jacket, such as that by Danish brand NN07 – and some sturdy boots or hiking-friendly sneakers, but a pair that look as good as they feel.

Then it’s about layering up with great texture and hard-wearing fabrics. Find a good flannel shirt for full outdoorsy vibes and trousers that you can actually move in. AGOLDE has a great pair of wide-leg pleated jeans that are good for vaulting over country stiles, but won’t have you looking like you’re getting ready to summit K2.

Finally, invest in some cosy accessories that you can reach for if the wind picks up. Or better yet, kindly offer for your date to wear. “No no, really, I insist…”

A slicker option than the walk, so your outfit should be slicker, too. Think tailoring, smart separates, leather shoes, a proper overcoat, etc. And if you do opt for a suit, keep it soft and slouchy. This is a date, after all, not a business meeting.

New York brand The Row has a corduroy suit that would be perfect – the matching pleated pants give that voluminous, 1990s Richard Gere silhouette – or you could go slightly more casual with a layered look, topped off with a great jacket, courtesy of Mr P.

A look like this needs to be finished off with the right watch, which is where this stainless-steel IWC Schaffhausen Ingenieur automatic comes in. Like the suit, it seems low-key, but is in fact beautifully made and deceptively smart. If your date asks, tell them about its black “tapisserie” dial and the 120-hour power reserve, and that IWC was in fact instrumental in the steel sports watch boom of the late 20th century… Or maybe just ask them about their favourite movies.

If you’re stuck for ideas, there’s always the pub. The great British boozer will never let you down. In fact, it might just serve as the venue for the greatest date of your life. Pints, games, grab bag of crisps split open on the table – what’s not to love?

Dressing for the pub date, though, can be tricky. It’s a brilliantly informal place, but that doesn’t mean jeans, battered sneakers and a grubby T-shirt will necessarily cut the mustard. You want to keep it low-key, but still allow your sense of style to come through. So, why not indulge in a little modern prep? We’re talking straight-leg blue jeans, such as these by Acne Studios – distressed, but not destroyed – a comfy cardigan and suede lace-ups. John Lobb has a pair of rubber-sole Derbies that would fit the bill perfectly. The kind of thing one of those square-jawed Harvard guys might have worn in 1968.

You don’t need a tie, necessarily, and a blazer might be a bit much, but a great pair of glasses wouldn’t go amiss. And the right belt – steel-tipped and suede, by Anderson’s, perhaps – is crucial.

You want to dress like the kind of bookish guy you might find in the corner of a cosy Dublin pub, reading Yeats and nursing a pint of Guinness. Who could resist such a man?