When it comes to clothing, these men know their stuff. Who better, then, to talk us through the latest outerwear?.

We’re reluctant to make gender generalisations, but, regardless of their area of interest, men do seem to favour the deep dive. Whether our passion lies in the late 1980s New York hip-hop scene, the narrow-gauge steam railways of India, stainless-steel Rolex sports watches of the 1970s or mid-1990s supercars, we’re all about the rabbit hole. And so it is with style. We don’t like tailoring, in general. We like soft-shouldered southern Italian tailoring, or Japanese takes on mid-century American workwear, or Californian hiking brands. This makes sense, of course. Menswear is relatively understated, and not so much about sudden sea changes in colour and silhouette. Instead, it tends to be about the details, the brand, the provenance and the history. The experts, therefore, tend to be somewhat stringent in their preferences.

To explore this phenomenon and showcase some of this winter’s cult outerwear, we sought out five men who, when it comes to style, share a passion that runs deeper than mere aesthetic. They are interested in the why, as well as the what, of fashion, the films and music that influence design, the subcultures that gather around certain looks and the things that our clothes say about us. They are a disparate group, from a laid-back Mancunian who’s seen it all and seems to have nothing to prove to a status-aware south Londoner who, thanks to his background, remains acutely conscious of the image of success that he projects. Each has a unique point of view and the necessary eloquence to express it.

Londoner Mr Nick Love, 48, is the film-maker behind Goodbye Charlie Bright, The Football Factory and Sky One TV series Bulletproof. When he was a young man in south London, he was at the cutting edge of casual fashion, and retained this “geezerish” image into the early years of this century. His tastes may now be elevated, but his love of clothes remains undimmed.

How would you describe your look?

Upmarket casual.

How did you get into fashion?

I remember my mum buying me a stripy red and white Lacoste T-shirt when I was 11. I wore it to school and they treated me like a king.

What’s a typical outfit?

My favourite designer is Brunello Cucinelli. I’ll wear a Brunello blazer with jeans and trainers. I have sports jackets from Brunello and I’ll wear them with Stan Smiths. I literally live in Brunello. It’s pretty amazing.

What is it about this look that appeals?

Because not many people can afford it, it’s about exclusivity. And I’ve always loved Italian clothes, right back to the Paninaro era in the 1980s. I found Stone Island through magazines such as The Face and Arena, and I got my first Stone Island jacket in 1986. I was into labels so young. I remember getting fake Lacoste T-shirts in Deptford Market when I was nine.

Are your clothes specific to where you live?

I live in London, but if I go to Florence or Rome, I feel very comfortable. Men really make an effort in Italy. I grew up in a working-class area of south London and everyone would put all their money on their sleeve. Now I’ve got aristocratic friends, and they dress like tramps in moth-ridden sweaters. And I’ll turn up in a £2,000 jacket.

What other style signifiers do you like?

I’m wearing a Patek Philippe Aquanaut, which is a low-key watch. It’s not like a gold Rolex. Pateks are for people who know. I loved Panerai when I was younger. A watch is the only thing you can wear inside a building that shows your worth.

If you could transport yourself to go shopping, where would you go?

In 1984, the best shop ever was Nick-Nack on Wardour Street. It sold Fila, Sergio Tacchini and Ellesse. It was tiny and it was run by this nice Pakistani family, but it became the epicentre for London soccer casuals buying and stealing clothes.

Mr Elgar Johnson is fashion director and deputy editor of the British edition of GQ Style, and he’s as interested in sport as he is in clothes. He sometimes demonstrates his affinity for 1990s lad culture through his taste for Oasis T-shirts and, perhaps more shockingly, baggy jeans that puddle on top of his shoes. He has a powerful affection for Liverpool Football Club, and has styled fashion shows for brands including Philipp Plein and celebrities including Mr Anthony Joshua.

How would you describe your look?

A bit of north and a bit of south, and appropriate for someone who could be watching football at all times.

Would you say you’re obsessed with style?

No. I’ve never been overly excited by clothes. I’m more about what happens to people when they wear them. How the personality changes. I find that much more fascinating.

What is your typical look?

A full navy tracksuit by Brunello Cucinelli, Sunspel boxers and T-shirt, a Stone Island jacket and white trainers.

What is it about this look that appeals?

This is a look I’ve grown up with. It’s not changed a huge amount, except the brands maybe have become more high-end. I don’t think there’s anything wrong with dressing casually in streetwear, as long as you evolve with it.

Is this look affected by any cultural influences?

My style is based around sport, because I’m a huge football fan. And by truck drivers, because that’s who I grew up around in the 1990s.

If you could transport yourself to go shopping, where would you go?

I would go to Hyper Hyper in Kensington in the early 1990s and Mash, which used to be on Oxford Street.

As the co-founder, creative director and buyer for streetwear retailer Oi Polloi, 52-year-old Mr Steve Sanderson – now designer of his own brand, Wyse – has seen it all. From the 1980s and 1990s music scene in his native Manchester to the frenetic contemporary menswear scene, the breadth of his experience gives him a rare sense of perspective on the world of style.

How would you describe your look?

Pretty casual and relaxed. I’ll be in canvas trainers, such as Converse or Vans, or Wallabees or Birkenstocks with socks. I wear a lot of OrSlow trousers, a drawstring version of fatigues or a beach pant. Pretty soft, unstructured. I like knitwear. I like Margaret Howell – it’s relaxed and super-comfy. It’s quite low-key. None of it’s heavily branded.

What is it about this look that you like?

After wearing jeans and workwear for a long time, I want something comfier. Now I’m after cashmeres and brushed cottons. I don’t want to look like I’m trying too hard. In this game, because you see so many people trying so hard to make labels and brands that stand out, you want to go super-simple.

What’s the fit like?

It’s not tight, but it ain’t baggy. On the bottom half, it’s about the joy of an elasticated waist, especially if you’re travelling a lot. I don’t think full-on sportswear is the place to go at my age, but a looser, slightly tapered trouser shape is good.

What influences your look?

Everything comes from culture. Everything I’ve ever been into has come from music references or film references. It just gets into your brain at a very young age, probably pre-teen.

If you could transport yourself to go shopping, where would you go?

I’m happy enough with today. I don’t need to collect old stuff.

Mr Ollie Olanipekun, 34, is creative director of the agency Superimpose Studio, which helps brands including adidas and Burberry communicate with elusive millennial and Generation Z consumers. He’s developed a functional look that’s influenced by his childhood in Coventry.

How would you describe your look?

It’s a classic silhouette but peppered with African flair. It’s quite peacocky. There might be a loud patterned shirt in there, but the silhouette’s traditional.

What’s a typical outfit?

adidas Campus trainers, Stan Ray cargo pants, a hoodie, a cap and a Rolex. It’s a Datejust 1601. Entry-level, but it’ll do me. The flair could be a heavy-duty pink hoodie, bought from an army surplus store.

What is it about this look that appeals?

It’s durable. With all my outfits, I like to be able to chase after the bus if it goes past me. That’s my approach to everything I wear. Could I run after the bus? Could I chat up a girl? Could I be comfortable at my desk?

Is there a cultural influence on your wardrobe?

It’s music, 1990s-era hip-hop and the New York skate and hip-hop scene of the late 1990s. The Beastie Boys are probably my style icons.

If you could transport yourself to go shopping, where would you go?

New York in the early 1990s and late 1980s. The era captured by the photographer Jamel Shabazz of people in Cazal sunglasses and big sheepskin coats. Imagine the outerwear you’d be able to buy.

Did you enjoy the shoot?

I was wearing classic Prada trainers. I love that they’re having a resurgence, because I was there first time around. I remember saving up to buy them and battling with bouncers who wouldn’t let you in because you were wearing trainers.

Mr Andrés Branco, 29, planted the seeds of London-based fashion label Wavey Garms in 2013 when he set up a Facebook group for fans of late-1990s sportswear. He now has a shop in Peckham, south London, and Wavey Garms is starting to produce its own designs inspired by Mr Branco’s deep affection for rave-inspired sportswear from the 1980s and 1990s.

How would you describe your look?

Sophisticated chav.

Do you think of yourself as a style obsessive?

I’m into what the working-class people of England are wearing, what real people such as the young rudeboys of Peckham or the Essex boys I see at festivals are wearing. Also, I get obsessed with designer jackets. I search eBay for weeks to find vintage Stone Island pieces.

What’s a typical outfit?

A full Lacoste tracksuit or a boxy-fit Cav Empt jumper. But if I’m feeling lively, I’ll put on a Moncler or Stone Island jacket, a pair of trousers and my Gucci loafers or Prada trainers. And I can’t miss out my old-school Moschino and Versace. I’ve been collecting them for years.

What is it about this look that appeals?

All these looks come from the scenes I’m involved in. Graffiti and raving are two massive things in my life, and fashion is a huge part of both subcultures.

Are there cultural references that inform your look?

Early-1980s English football casuals’ fashion is amazing. The 1990s and early-2000s drum and bass and UK garage were so original and vibrant. I love the film La Haine and Nick Love’s film Goodbye Charlie Bright.

If you could transport yourself to go shopping, where would you go?

To 1997. The drum and bass scene was popping and the London graffiti scene was big. My older cousins were wearing full Moschino outfits with Reebok Classics. The go-to shop was Proibito on Bond Street. Going back further, to around 1989, 1990, I would love to visit a shop in the now-defunct Kensington Market called Sign Of The Times.

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