The You Bet! Tailoring Challenge

1995: 30 fittings in under 3 minutes on National Television

“Oy mate, what size am I?” was a question I grew used to hearing people shout out in the streets of London in 1995. It was often asked by complete strangers as I passed them by to work. I’d just laugh it off and carry about my business which was booming, after taking centre stage on Saturday night national television and completing a tailoring challenge few thought doable. 

In the early to mid 1990s, I’d been beginning to make a name for myself at a big-name London tailoring house. I’d been in the industry for just under a decade, which is no time at all in the tailoring business. Much like any craft, it takes decades to become a “master”, and even then it’s a perpetual learning experience. 

Ever keen to become the very best at what I did, I’d take on all challenges and projects. In peak seasons I’d fit up to (and above) one hundred people in a single day. After all, there’s nothing like putting in the time early in your career to build up your eye as a tailor and prove your capabilities. Suffice to say, the younger me had something to prove. 

That’s how I came to find myself running around the stage with sweat lashing down my brow and fear surging through my veins in front of a packed audience, rolling cameras, and some of the UK’s best known celebrities. 

Measuring Up To The Task

The challenge laid down was to fit fifteen different people, all of varying sizes and physical quirks, for top hats and tails, in under two and half minutes. The time limit meant that I’d have to fit them all pretty much by eye, not with the luxury of a measuring tape. As for my success or failure, that would be judged by Ron Morby, an eminent tailor who had in fact fitted my great grandmother, an actress, for her role in the 1964 film My Fair Lady

The idea came from the producers of You Bet! one of the UK’s most popular TV game shows at the time. 

For those who don’t remember, the basic concept of You Bet! involved members of the public trying to complete difficult challenges in a limited amount of time. A revolving panel of celebrities would place bets on how they thought they would perform, as would the studio audience, and the victorious panelist would donate their winnings to a charity of their choice. 

The people behind You Bet! had their fingers on the national pulse, and after seeing the massive success of the British film Four Weddings and a Funeral, sensed that an episode based on formal wedding dress would capture the attention of the public. 

That’s where I came into the picture. Ever keen for some good publicity, the marketing director of my company asked if I’d be up for the challenge? The way he saw things, it was a chance to showcase why we were so highly regarded in the tailoring industry. 

I was young, bold and confident enough to agree immediately. But thinking back, failure or embarrassment would have been a huge blow to my company, and a disaster for my own career.

The Biggest Challenge to Overcome

The time limit was one thing, the pressure of a live audience and celebrity panel was another, and the knowledge that I’d be broadcast onto millions of televisions the country over cranked up my nerves the closer I came to filming day. 

But the biggest challenge to overcome was the technicality of the fittings themselves: While an experienced tailor has a great eye for body measurements, Morning Tails aren’t so easy to measure as they need to fit elegantly. Hats, meanwhile, are a different ball game altogether. They’re extremely tricky to fit by eye as a tailor must accurately visualise where it’ll sit on the wearer’s head, which is a tough ask. Add in the fact that things like glasses, voluminous hair and head shape all throw the eyeline off. Let’s just say I’d begun to doubt myself a little. 

I also had a sneaking suspicion that the fifteen random people would have been selected specifically to be pretty varied in shape and size, and boy was I right. 

Filming Day, Trial Runs & False Starts

Many of you will remember Matthew Kelly — he was everywhere back in the 1990s and early 2000s. But before becoming the host of Stars in their Eyes, he was on You Bet! (having replaced Bruce Forsythe, in fact). Matthew, ever the gentleman and professional, popped into my dressing room twenty minutes before I went on, just to wish me luck and to share how impressed he’d been by my skills during the trial runs that day. That made a big difference for me, calming me down no end. The truth was that the trial runs hadn’t gone at all well; the magnitude of the studio environment had been a big shock to me, as had been my need to work around all the camera men and lighting fixtures. But come the final trial, I realised that I’d have to make some strong demands for how things needed to be filmed so that I wouldn’t get distracted.


I could hear the chatter of the audience, which crescendoed into a wall of noise when the entrance music played and Matthew took to the stage. And just like that, I became calm and focused.

Walking out on stage was like an out of body experience. I let the noise of the crowd and the glow of lights wash over me, and cast my eye to the celebrity panel of Dale Winton, Rugby star Gareth Chilcott, wine critic Jilly Goolden, and actor Liz Dawn (better known as Coronation Street’s Vera Duckworth. 

Their presence actually calmed me further, as I knew Gareth Chilcott pretty well. I’d fitted him many times over as a customer, and took heart from the fact that he immediately bet that I’d complete the task successfully. 

And so it began. Fifteen men lined up before me, each more different from the last, and all well beyond the parameters of “regular” in size and shape. To be honest, the two and a half minutes of the task are a complete blur to me. All I remember is the audience laughing at something and worrying that I’d messed something up. But there was no time to stop and think, I just had to keep calm and carry on. 

One hundred and fifty seconds, fifteen people — ten second per person, five seconds per fitting, just my eyes, my experience and my instinct. When the timer ran out, a roar of congratulations went up in the studio and a wave of relief flooded over me. Somehow I’d done it. I’d helped raise a ton of money for charity, I’d shown why my company was the best tailoring house in the business, and by extension, that I was one of the best tailors in the business. 

When I got home that evening, exhausted and elated, my answering machine had more than forty messages from people I hadn’t heard from in years, all of them congratulating me, and quite a few seeking out my tailoring services. If he could do the job well in ten seconds, they reasoned, imagine what he could do in a proper fitting?

However, tailored clothing is an investment that pays off in both the short and long term. Sure, it takes time to make and fit just right, but once perfected, it will last for years and years without its lustre diminishing. And even if you gain or lose a few pounds as time passes, a good tailor will always be happy to readjust, refit or tidy up their own creations. 

The Tailor in Demand

No sooner had the episode had aired than my company launched a huge marketing campaign to celebrate my success on You Bet! 

My name and face appeared on one hundred shop windows throughout the country, hailed as the tailor who’d beaten the You Bet! Challenge. By today’s standards it might not be stellar sophisticated advertising, but back then it was effective. The company’s sales received a big boost, I became the most in-demand tailor there, and I had my fifteen months or so of fame.

Would I do it all again? I doubt it, but I’d encourage any young tailor — any young professional of any kind indeed, to take on some kind of challenge to test their limits and prove themselves under pressure. Maybe not on national television, mind you… 

It was a huge risk, but the reward was just as huge.  

Share :

Make an appointment

Getting started takes only a click.
Make an appointment, when you’re ready.

More Articles

The British Summer Social Season is just around the corner, believe it or not. To give you plenty of foresight on the events you might need to dress the part for, we’ve put together a rundown of the key dates. 

Take proper care of your tailored suit by following these easy steps.