When a tailor turns to cycling: meet Ollie Trenchard

In Interviews, Products by Claire

When a Savile Row tailor turns his hand to his first love of cycling, good things happen. Ollie Trenchard is one of the Row’s young tailors, a pattern cutter who has a tendency to make his own outfits when no one else is making them just right. With an obsessive collection of white t-shirts and a love for things ‘just so’, Ollie’s launched his new creation: a foray in to the world of cycling gear with onenine9teen.

In the corner of Rapha’s central ‘cycle club’ cafe is a man in absolutely no Rapha gear. Grinning, he waggles his feet – he’s wearing slick silver Giro cycling shoes and has been waiting for a crisp day with zero chance of rain to take them on some Regents Park laps. They are very shiny. “I’ve nicknamed them ‘The T-1000s’” (after The Terminator) he says and laughs. Then: “I’m very sweaty,” which ruins the polished look.

Ollie Trenchard is an interesting combination of cyclist, runner and Saville Row tailor. This year he’s brought it all together to create his own line of cycling caps. Made by a stylish tailor who makes what he can’t find in shops, they’re as sharp as you’d expect.

The first time I meet Ollie is through Run Dem Crew, running lightening quick around some of London’s backstreets. A year later, we are cycling the west’s backstreets on a very dark night a couple of years ago to cheer friends running a 100km race, which finishes up by west London’s Regent Canal. As we ride, his toes in the straps of a fixie, he tells me how he’s busy finding his feet with a brand new job, cutting on Saville Row. It’s the start of a story about someone changing their life and going for what they want. Getting an illusive apprenticeship on Savile Row is no easy feet, but he tells the story casually.

Ollie Trenchard

“When I left school and went to university, it was probably the furthest thing from my mind. I went to university in Manchester and studied accounting and finance. I absolutely hated it and dropped out in my first term before Christmas. Getting up on a Monday for double economics lectures was grim. So I stayed up in Manchester for a bit and dabbled with the idea of doing a fashion course at Manchester Met. I was like ‘err, not sure’ so delayed it.

I came back to London and worked a job I absolutely hated. So I was like ‘alright, enough of this. Enough of bad decisions. I need to actually think about what I want to do.’ Strangely enough, I watched a BBC documentary about Saville Row. It was a three-part series and I was fascinated by it. I was glued to the screen watching it. I knew that was what I wanted to do. It just appealed to me. It’s something that hadn’t changed in a very long time, it was more about style than fashion, it was based around a craft – using my hands, to some degree. It just hit me!

One day I was cycling around London and I was near Saville Row. I popped in to see Patrick Grant who’s the owner of Norton and Sons. He’s a fellow cyclist – I saw that on the documentary that he used the cycle in to work. He seemed kind of approachable – a younger guy. So I went to ask him how I get involved. I went in, all scared, up to this grand door. I tapped on the door, all sheepish. He was so nice. He sat me down and just explained what all my different options for getting into tailoring were. The route that I chose was to go to Newham college in London, a specific tailoring college. It was all from scratch. The first day we were taught how to hold a thimble. It was really from the very beginning.

The day I found out I’d got the [Saville Row] job I was on my bike and was cycling down the road from my Dad’s in Dulwich when none other than Patrick Grant actually cycled down the road past me. I cycled up to him: “Oh hi there, I don’t know if you remember me.”
He was like: “Yeah yeah! I remember you.”
“I got the job!”
”Incredible, well done!”

It was a nice full circle.”

Ollie’s tale is a huge story of change with any inevitable tough moments glided over, looking upwards enthusiastically. He first told me the story when he was still halfway through the process, and even then he told it with a laugh. In the cafe it’s accompanied by shiny shoes and even more smiles, but I can’t help but be wowed by anyone who’s brave enough to make big choices about what they really want to do in life.

Ollie Trenchard with bike

Talking to Ollie makes The Row seem less shrouded in snobbery and more like a street of skill that it once did at the height of its fame. There’s a relief in knowing that good people like Ollie are entering The Row, which can feel like – and perhaps prides itself on being – one of Britain’s most archaic industries.

Months later, we’re riding the Dunwich Dynamo through the night with an intimidatingly quick group of messenger cyclists. Toes strapped into the same fixie and gunning it down the country lanes, the only way to get them to pause for a breath is the lure of a 4am bacon sandwich. “Oh my god. Dunwich Dynamo was one experience and a half” Ollie remembers, laughing.

Ollie’s world of cycling opened up through his Dad. Ollie talks about how he first got in to cycling, as kid riding mind-blowing journeys into the city. “First of all, from about the age of seven, eight and nine, my Dad used to take me out. We used to go on epic journeys into London. That was my first experience of actually cycling on the roads. Prior to that it was in the park, but for road trips it was with my Dad on my old mountain bike. We’d venture up into central London, grab a bite to eat – that kind of thing. That was the first experience of actually exploring with my bike.

‘One of my cool mates said ‘you need to get that fixed’… Then I was riding around scared for a week and a half in fear for my life.’

Falling in love with cycling as an adult was a different story. Forget epic rides, Ollie first got back on a bike for function before giving in to the allure of knee-jolting fixies. “I was working in Victoria at the time and I had a company car and I had a Vespa. I wanted one mode of transport that I could use to get to and from work, and I started riding a bike. That was a single speed and a few months later one of my cool mates was like ‘you need to get that fixed’ so I got it fixed. Then I was riding around scared for a week and a half in fear for my life. I remember one incident when I was riding down Farringdon Road and I took my feet off the pedals and they were just spinning round. I was thinking ‘how am I going to stop this thing?’

“The first day I felt comfortable riding fixed was when I was late for work. I was riding down Embankment, past Big Ben, and I just wanted to get there. I had suddenly gotten to work and I’d been riding fixed and I hadn’t even thought about it. It felt natural. That was the start of my fixed gear adventure. That was probably seven and a half years ago now.

“It’s kind of progressed from there. I’ve tried some track racing and I’ve done some sessions at Herne Hill. Dunwich Dynamo was one experience and a half. It kind of broke me in a way. I rode fixed and completely destroyed my knees. It kind of affected everything else: my running, I didn’t really cycle much after that, and I thought ‘right, let’s get a road bike and look after my knees a bit more.’ That was the transition in to road cycling. It was less about looking cool and more about being efficient.”

Ollie cycling cap onenine9teen caps

Finally the three have collided, and the love of fine craft, riding and tailoring have come together. The caps hark back to his fixed gear obsession, fuelled by a trip to San Francisco.

“I’m an obsessive about these things. I’m very particular about certain pieces. I’ll wait for six months to find that perfect one.”

“I was at the beginning of my fixed gear adventures and took a trip to San Francisco with a friend. San Fran’s got a massive fixie culture out there – like Mash SF are huge. I went into a few shops and found a beautiful navy cycling cap. I loved it… and it was getting worn out. I approached a guy to buy another one but he wasn’t getting back to me. I emailed him, I called him and messaged him. So I thought ‘okay, I could probably make one of these..’ I had my sewing machine at home and cobbled together a cap, trying different caps, adjusting it, trying different fabrics. Eventually it worked and I wore it all the time. [It’s made from] the fabrics that would be used to make a suit.

“One of the nicest things about my job is that I don’t ever have to look at a computer screen. When I’m most comfortable in my work, is when I’m stood at my boards just chopping cloth. It’s such a nice feeling. You just get into a groove. Just striking out with a piece of chalk, then you get your shears and you’re just chopping away. It’s just really relaxing. I’m quite content with living in 1950.”

“I liked cycling caps. I’m not a big hat person but I found something that became my signature amongst my friends. Then it went from there.

Ollie Trenchard image

“I tend to stick rigidly to colours and colour combinations. Very plain palettes. I love navy blue, I love pops of white, whether that be a shirt or a white t-shirt. I guess it’s influenced by growing up in the city, with blacks and greys. I tend to keep it very simple. I’m an obsessive about these things. I’m very particular about certain pieces. I’ll wait for six months to find that perfect one.

“My tailoring enabled me to have the confidence to put it together.”

The tendency of a tailor to make his own clothes when he can’t find the right ones in shops can only mean good things. The search for the perfect merino cycling cap is over. Ollie, a fan of the black/navy/white wardrobe, admits that he’s often running late because he can’t choose the perfect simple white t-shirt to wear. You suspect this frustration with clothes must be a frequent occurrence. Good thing he’s only made two hats. They come in black and navy, with plans to experiment in the future.

ClaireWhen a tailor turns to cycling: meet Ollie Trenchard