Sitting down to a pot of tea in a Brick Lane coffee shop, Kevin Rowland is pleased when I point out to him that there are plenty of young Shoreditch kids dressed just like him these days. Today, the Dexys singer is wearing a pair of box-fresh white Converse Chuck Taylors, Levi's raw denim 501XX jeans with a two and a half inch turn-up, and a vintage Breton-style knit from a Covent Garden second-hand shop. Looking out the window, his vintage-led retro style is mirrored by people half his age milling about outside. But there's one major difference compared to most of them – Rowland's got soul, and he's got swag.

Rowland's intrinsic sense of style is at one with his emotionally charged lyrics, and his songs about true love, obsession and heartache. The way he moves, the way he talks and sings; it's all about attitude and it's a lifestyle defined by Rowland's dress sense. Lots of us can whack on a fly outfit, but for Rowland, with his music and clothes feeding off each other, it's a way of life. "What I wear is an expression of how I feel. The times when I was the happiest, I had a really good look going on, but it wasn't the look that made me happy, it was a reflection of how I felt. Everything felt alright inside. The periods when you don't feel great, you look lousy."

At 58, often rocking immaculate vintage suits, Rowland is a dapper man by any account. For anyone who's seen him perform songs from One Day I'm Going to Soar, the band's first album in 27 years, the importance of dressing the part is obvious. At a recent Shepherd's Bush Empire gig, wearing high-waisted trousers, a sleek 50s workwear jacket, kipper tie and a broad-rimmed fedora hat, Rowland impressed nearly as much with his confident stage outfit as with his newly written songs. Because, having nurtured a public interest in clothes ever since the days of Come on Eileen in 1982, he's never looked better than today. "I really do feel that I look my best now. I think back at those years and I wouldn't want to wear any of the outfits I wore back then," he says. Those outfits may have been questionable to some at the time but they would also appear to be very prescient. The Mean Streets donkey jackets and rolled-up woolly beanies from the Searching for the Young Soul Rebels album in 1980, and the Ivy League outfits of the mid-80s Don't Stand Me Down era are all trademark Rowland looks, are staples on the streets of London today.

It's funny to think it hasn't always been sartorial bliss for Rowland. You can't really discuss clothes and style with the man without going back in time to My Beauty, the 1999 covers album that saw him dress in drag on the album sleeve and perform at Glastonbury festival wearing a dress. The album was panned by the press, and it wasn't just criticism that was hurled at him; at several festival gigs that summer, the crowds pelted him with bottles. Secure in his choices, Rowland openly discusses the episode: "In the mid-90s, I saw a Thai waiter in Covent Garden wearing a sarong, and it just jumped out at me. I couldn't understand why women, and not men, wore skirts – it seemed bizarre to me. The idea matured with me for a while and then I started wearing sarongs in 1995, two years before David Beckham did the same. And then I began painting my nails." Rowland then took it step further and started wearing leather kilts and black mountaineering sandals that looked like something the ancient Romans would have worn. "Later, the idea of wearing a velvet dress came to me. It was a phase I went through, I don't like that way of dressing now, but at the time it was me. It totally expressed how I felt; I had a desire and a need to wear soft fabrics, like velvet and lace, fabrics that are mostly in the domain of women."

Rowland is a perfectionist when it comes to both the music and his wardrobe: "Every day is a new opportunity to put on a new look, maybe even several times a day for me. Sometimes I'll have an afternoon shower and change outfit." His earliest fashion memories are pre-puberty, so impressing girls had nothing to do with it: "From the age of seven, I was combing my hair and wanting to wear shirts, and when I was about 10, I wanted cufflinks for my sleeves and [liked] getting done up. I remember dreaming about a sky-blue button-down shirt with a navy sheen to it. I'd seen mods in north-west London wearing them." And it was definitely the mods and not the rockers who Rowland looked up to. "Yeah, I was on that side of the fence. I thought they looked fucking great. I got talking to them; I was about 11 and they were 17 or 18. I was fascinated by them. I didn't like the rockers. They were old-fashioned; they were the past. Mods were contemporary; they were cutting-edge while rockers were dirty looking, and that's never been appealing to me. I like it clean cut. I don't like rock festivals, always walking around in the mud. I want to have a shower and look clean."

So what's Kevin Rowland's position in terms of contemporary high-end fashion? With a style so associated with vintage, is he at all interested in the Paris and Milan menswear catwalks? "I don't care about Bond Street but I do go to Jermyn Street to get my underwear and socks. I'm into bespoke tailoring; I like tailors like Mark Powell and brands like Mister Freedom. My motto is 'never not shopping'. I'm always looking for stuff. I have been meaning to go to Dover Street Market for ages. They sell Thom Browne suits that I really like the look of. But I wouldn't buy clothes just because of what brand it is. I can't stand that way of thinking. Although, if a pair of trousers were absolutely amazing, if they fitted me perfectly and it was a stunning material, then I would fork out."

The irony is that, according to Kevin, the music press gave him a harder time for his preppy Ivy League look in 1985 than they did for his My Beauty dress in '99. Like all trailblazers, like all people who dare take a stand and show the world a vulnerable side, Kevin Rowland has paid a price. But now, in 2012, as a man in his late 50s walking down Brick Lane in vintage workwear and tailor-made suits, people turn around to look at him for all the right reasons. His sartorial wilderness years seem to be done and dusted.