As style industry backstories go, Mr Dan May’s is somewhat unorthodox. He now works as a fashion director who curates effortless, textured ensembles for the likes of Port Magazine, Man About Town, The Telegraph and brands such as Giorgio Armani, Dunhill, Tommy Hilfiger and MR PORTER, where he is a contributing fashion editor. However, his youth was defined not by fittings and fashion shows, but by cold mornings, muddy boots and sweaty scrums. Imagine.

“My style definitely evolved from my background, which is sport,” he says. “I went to Loughborough University to play rugby and I used to play for Bristol. So, my early teenage years and my twenties were very much about comfort and tracksuits and sweats.”

From there, it was a circuitous and felicitous route into the world of styling. While working as a personal trainer in London, Mr May was scouted as a model, which led to photoshoots, which led to a passion for photography, which led to a course in photography and styling at London College of Fashion. There, he says, although the idea was to learn how to take pictures, “I ended up loving the styling and the art directing a lot more.”

Styling has been Mr May’s mainstay since then, but in 2020, he’s adding another string to his bow, as creative director of new menswear brand SMR Days, a co-venture between Mr May, communications guru Mr Adam Shapiro and industry veteran Mr Gautam Rajani. Thanks to the small matter of a global pandemic, SMR Days’ debut collection – a dreamily relaxed selection of holiday-appropriate menswear that’s also designed to stand up, style wise, to city use – will be launching a little later than expected. (Look out for the MR PORTER exclusive in October.) But Mr May is fairly philosophical about it. “We took the positives from it and just said, look, we’ve got an extra six months,” he says.

He’s been using the time well, filling the SMR Days website with plenty of warming editorial features, including a set of charming postcards from fashion photographers, including Mr Matthew Brookes, Mr John Balsom and Ms Linda Brownlee.

Anyway, back to those tracksuits. These might have been the Alpha and Omega of Mr May’s style, but, just as his career has evolved over the years, so has the way he dresses. Today he explores the joys of athletic clothing – comfort, tactility, informality – through his love of workwear, which, he admits, has become “a slight obsession”. It’s a look – and one which Mr May describes straightforwardly as “workwear meets sportswear” – that focuses not just on honest, functional pieces such as chore and trucker jackets, straight-legged fisherman’s trousers, military-inspired overshirts and the odd pair of sweatpants, but also a marked appreciation of flexibility and softness when it comes to fabric and construction.

A typical outfit from Mr May will feature washed denim, thick, tactile knitwear and loose-fitting clothing, with a bit of stretch to it if possible. He likes texture and depth, shops by touch and always makes sure, whatever he’s wearing, that he’s free to move. You’ll never, for example, find him wearing a heavy coat or a structured blazer.

“If it’s stiff, it just doesn’t work for me,” he says. “I kind of feel anxiety when I have to wear a suit. It feels like I’m being put in a straitjacket.” The overriding quality he seeks from his clothing is comfort. He has learnt that feeling good is often the first step to looking good.

“Having styled hundreds of people, especially celebrities, you don’t know what you’re going to put them in until you meet them,” he says. “You put somebody in something they don’t feel comfortable in and you’re going to see it in the picture.”

Putting this particular thesis to the test, in our own small way, MR PORTER visited Mr May (and his dog, Buddy) at his home in West Sussex, a place for which he has a newfound appreciation after isolating there and battling through a particularly nasty case of Covid-19. (His four-word summary? “It was brutal, mate.”)

Thankfully, he is now back on his feet, which meant he was able to take us on a jaunt to the beach, called Climping (which sounds painful, but is actually rather lovely), and a tour of his own place while taking us through the tenets of his personal style.

“This is just me taking the dog for a walk – track pants, good New Balance trainers,” says Mr May. “I love a stripy Breton top. It’s such a go-to. And I really like the Mr P. stuff, too. This simple chore jacket almost has a shirt quality to it. It’s a good layering piece. And I’ve used the denim jacket almost like a blanket. It’s just an extra, easy underlayer for me. The track pants are the Brunello Cucinelli wool ones. They’re super comfortable and I’ve got a couple of pairs. But I also like wearing my regular old Nike ones, which are a classic, easy grey marl. I’m not so rarefied that I need everything to be wool and cashmere.”

“This is a LOEWE workwear jacket with a contrasting patch pocket. It’s a really nice piece. I often start an outfit with this kind of workwear jacket. I’ve probably got about 40 variations of the same thing. Whenever I bring one home, my husband’s a bit like, ‘Uh, you’ve got five of those already.’ And I say, ‘No, this one’s slightly different because, if you look at this collar, it’s got a lining.’ And he just like looks at me as if he’s thinking, ‘I can’t even...’ I don’t actually know how I pick one out for each moment. It’s weather-led, I guess.”

“I’m not a big coat person, but I do love a gilet. It’s an easy thing to put over a workwear jacket and you don’t lose the sense of the outfit, in a way. You can also just keep a gilet in your bag in case you need it. I love the visvim one I’m wearing here, and I also love the Moncler ones. Then I’ve got a TOM FORD cardigan on. I hate big logos and stuff like that, but if you give me a cardigan from Brunello Cucinelli or TOM FORD I’m going to love it. The quality’s amazing, but you don’t necessarily know where it’s from. For me, a personal sense of comfort is much more important than other people knowing what I’m wearing.”

“I love a heavy overshirt that also works as a jacket. This one is from Outerknown. I buy from a lot of surf brands and this is a cap from Pasadena Leisure Club, which I’m really loving at the moment. I’ve bought a lot of their T-shirts, but their caps are super light for the summer. The shorts are from visvim. I like baggy shorts. As I mentioned, one thing I don’t like is anything tight. Even if it’s shorts, or T-shirts, or trousers, because of what I do usually – I’m bending over, I’m running around, I’m lifting things – I have to be comfortable and it has to be practical.”

“There’s always an element of blue in my outfit, either the jacket or the trousers. It’s definitely my safe colour, my go-to colour. And I love the colour of this shirt. I think of it as Bill Cunningham blue. It was what he wore the whole time he was taking photographs. It’s a really comfy workwear jacket, in a linen-cotton mix, so it’s super soft. I wear the glasses just for reading. They’re Izipizi. The watch is a Swatch. I love watches and I have a bit of a collection. I’ve got a couple of Rolexes and a Panerai and so on, but just before Christmas I was going abroad on a job and decided I didn’t want to wear a Rolex walking around. I ended up buying a Swatch at the airport and I kind of prefer it. It’s just so light and easy.”

“These are Mr P. workwear trousers, which are a lovely shape with a straight leg, and then a visvim chunky cardigan. And then there’s a rugby shirt, which I love still. I was really happy at the rugby shirt coming back into fashion. I’ve got a couple. I find them in vintage stores – I particularly love the old Ralph Lauren ones. I didn’t wear my rugby shirts for ages and I ended up giving them to my brother. And now I’m like, ‘Oh, Tim, can I have those shirts back please?’ I much prefer wearing them to a more formal shirt. And it’s definitely a nod back to the fact that I was wearing rugby shirts for 20 years as a kid. As for the Birkenstocks, I have a long relationship with them and it’s got more intense during lockdown.”