My colleague Olly Watkins has become more and more interested in traditional menswear and permanent style in recent years. His journey, and the lessons he has learnt along the way, provide interesting perspective for new devotees to permanent style.

Simon: When did you first become interested in clothes?

Olly: Well, it took me a while to get over the bottle-green corduroys my mother made me wear when I was eight-years old.

But by the time I was a teenager I was interested again. And being a child of the eighties, a sharp-cut suit was everything. I didn’t own one for ages but that was the aspiration. I was never terribly interested in casual clothes or in fashion. I just wanted to wear clothes that fitted well and match colours without looking ridiculous.

When I first started work I tried to wear suits and was interested by the idea of tailors. My father used an old City tailor and it was fascinating to talk to him about tailoring and traditional City style.

But that interest remained a minor one?

Yes. I tried to dress well but I never really delved into the kind of questions that were centrally to improving that – why do none of my jackets really fit me? What are the limits to having alterations done? Where could I have one made? It was a frustration with men’s retail really.

And that changed recently?

Yeah, I always used to wear suits, but as the dress ethic in the office relaxed over the years I became more and more casual. Then recently (it may be the onset of old age) I got frustrated and decided to smarten up a little. Like the benefits of a school uniform, I wanted something smart and formal that if anything would take less thought in the morning.

But it really took off when I discovered the whole mini-culture around men’s clothes, the traditions (not rules!), the web sites and the community. It was amazing. So many people talking about something which is largely forgotten today, in an age of high fashion and transient trends – where people walk around in the most terrible outfits just for the sake of looking like other people.

What was the biggest revelation for you?

Just how many people are interested in this area, the whole culture around it. Looking around at people, in whatever city, it’s easy to think that no one cares what they wear at work. I commute in from Essex every morning, and you see legions of men in black, blue or grey suits, with the jacket undone, tie loose and obviously not interested in their attire.

If you look back at pictures of US presidents or other politicians in the past, they are all smart, they all have pocket squares. It was something that men took pride in. That doesn’t happen anymore, so I was surprised to find so many men involved in this area so passionately, that do care.

I really like that niche. It gives you something to follow, in an area that suits me far better than squeezing into a pair of skinny jeans and a t-shirt that isn’t quite long enough.

What’s your favourite outfit?

Probably the thing that fits me best at the moment – my midnight-blue dinner suit that I got from A Suit That Fits. I love wearing it, it fits me much better than anything else and is probably better made as well. I just feel better in it. I didn’t realise that it was almost impossible to cater to my proportions in ready-to-wear clothing, even if altered. [Olly has a 46-inch chest and 36-inch waist: a 10-inch drop that is far above the ready-to-wear standard of six inches. See link here]

I’d wear that with thin-soled, black-calf Oxford toe-caps – I have yet to be converted to pumps or patent leather. And a white shirt, white braces, bow tie and gold cufflinks to match the gold clips on the braces. Oh, and a white silk pocket square.

The cummerbund or waistcoat is essential, I suppose, but I find that the trousers are cut so high that they prevent any shirt showing below the waist button anyway, to the end of the bib of the shirt. It seems a little odd to me to wear a cummerbund that just goes over the trousers entirely. That’s not to say I wouldn’t wear one, just that I don’t at the moment.

Obviously the theory is to cover the waistband of the trousers. But I suppose if the waistband is clean and smart, and the shirt is not exposed, you could argue that the cummerbund’s place has been superseded.

Yes. It just seems a little pointless to me. I suppose it’s a rule that I have learnt how to break, as you describe on the blog. I understand why it’s there and so have broken it sensibly and with full knowledge of the outcome.

To be continued…