What To Wear On Valentine’s Day (Even If You’re A Cynic)

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What To Wear On Valentine’s Day (Even If You’re A Cynic)

Words by The Daily Team

2 February 2017

The clothing you need to make a good impression this 14 February – whether it’s a big date on the town or the sofa.

Valentine’s Day is one of the more divisive dates in our annual calendar. Some people choose to ignore it, while others actively slander its existence, muttering darkly about a conspiracy invented by evil card companies and PR agencies. Some people buy into the whole thing – literally and metaphorically – and use it as an excuse to turn into hopeless romantics for one day every 12 months in a bid to impress their other halves. If you’re single, it can be a striking reminder of said relationship status, and therefore represent the darkest day of the year. Or if you are single and happen to have a hot date on 14 February, then it is a golden opportunity to reverse the solitary existence that society so cruelly frowns upon. However you intend to treat Valentine’s Day this year – whether you’re a hopeless romantic or downright cynical – below, we have come up with some tools (or, clothes, rather) to help you deal with it. Love, MR PORTER.


You absolutely love being in love. And, second only to Christmas, Valentine’s is your favourite time of year. You spoil your other half as if they were an Egyptian queen, and treat the day with a kind of reverence usually reserved for weddings and funerals. Either that, or your partner feels this way and, since they caught you chatting to your ex on Facebook the other week, you need to make amends and well and truly meet them in the middle “for once”. Whatever the situation, you are playing the hopeless romantic and only a smart suit will do for the sophisticated and thoughtful activities you have planned. A smart, black Paul Smith suit, with a flash of red from this Brunello Cucinelli pocket square. It’s what Saint Valentine would have wanted.


You might have a long-term girlfriend, or perhaps you’re single – whatever your relationship status, you actively detest Valentine’s Day. You are the Valentine’s Day Cynic, and nothing will change your mind. Sure, you wear your heart on your sleeve, but only insomuch as you talk freely (and often) about your hatred for this corporate, twee festival of vanity. The only proactive thing you’ll be doing on Valentine’s Day is gluing your letterbox shut in an attempt to thwart any postmen thrusting sickly pink cardboard through it. As such, you will make no effort in what you wear. Sweats it is, then. This sweatshirt from Beams + Champion and minimalist John Elliot sweatpants will do nicely.


We are imagining that you are someone who harbours mixed feelings about Valentine’s Day. There’s no real problem with it, you’ve never really celebrated it as such, but perhaps you happened to match with someone on Tinder who thought it would be funny and quite charming to have your first date on this special day of love. And you absolutely want to impress this person. But you also do not want to look like you’ve got too into the whole thing. You’ll buy them a drink, for example, but there’ll be no cards and flowers. So, leave the suit-wearing to other Romeos and instead plump for a failsafe combination of a classic blue blazer (which shows you totally understand style, particularly when purchased from Prada) and good old Dries Van Noten Derbies (which represent your strength of character and robust nature). Or something like that.