Simon Cundey says he really doesn’t mind whether or not his two 20-something sons follow him into the family business – “I’d never push them,” he says, “because I never was” – but perhaps there’s just a hint of concern that they might choose some other path.
After all, Cundey is already the seventh generation to run Savile Row tailors Henry Poole & Co. And not just any Savile Row tailors but, approaching its 220th birthday, the Row’s oldest. It was back in 1806 when James Poole established himself as a military tailor outfitting officers over the 12 years of the Napoleonic Wars – even if it was his son, the more hobnobbing and dandyish Henry, who got to put his name to the family business.
“When you consider your company history, it brings a kind of reality check of your core values back to you. It unifies your thought processes and makes you appreciate the importance of having a long-term vision,” says Cundey, as he preps for an arduous US trunk show tour. “It’s that history that brings so many customers to us, the sense they have of Poole as much as an institution as a manufacturer.”
It’s a point Cundey has spent recent years driving home by committing £100,000 to the on-going restoration of the company’s 120 dusty and often decrepit order books, dating back to the 1840s, ones that the British Museum, no less, would occasionally remind him were historically important. “I remember moving all these old order books as a 16-year-old, only to see the metal shelves they were put on later collapse,” Cundey recalls. “Health & Safety people would have had a field day with them”.
Pages have subsequently been cleaned and covers rebound – at least for those volumes up to the 1950s. Being able to read them again has brought some revelations, not least that US Civil War general and later President Ulysses S Grant, ‘Buffalo’ Bill Cody and Bram Stoker were all customers.

Jonathan James Wilson
Not that Henry Poole can’t provide a litany of establishment figures that have graced its parquet, among them Irving Berlin, Rex Harrison and John Hughes; Frank Lloyd Wright, Serge Diaghilev and Emperor Hirohito of Japan – whose tailoring envoys first coined ‘sabiro’, after Savile Row, for the Japanese word for a suit.
Then you have the statesmen, the likes of General De Gaulle, Muhammad Ali Jinnah and Winston Churchill – whose patronage was marked last year through special edition cufflinks in collaboration with the Churchill Society.
Whisper it, but Cundey recalls his father, in a bid to help the (Second World) war effort, recycling the paper patterns for the bespoke suiting of one Benjamin Disraeli. Don’t tell the British Museum.
“I think the people who come to us love a bit of that heritage,” says Cundey. “It’s a talking point for them, something that’s beyond the craft of their garment.”
And yet, he adds, he is also wary of singing the same old song. “You can overwork the heritage story and apply it to too many aspects of business – some brands just go too far with trying to draw out those things which belong to history. It’s like brand extension. Look at Pierre Cardin. He started out as this incredible designer and ending up doing pencil cases.”

That’s why, while Savile Row has something of a reputation for being rather stuffy, he’s keen to push Poole’s aesthetic forward into the kind of clothing that the company somehow forgot that it used to make. There’s an ideal line, Cundey suggests, between being above fashion and being oblivious to it, hence why the Row needs the periodic freshness injection of a Tommy Nutter or Richard James
The time was when Poole would outfit a gent for every sartorial need, not just formalwear. It was this that, in part, allowed Cundey’s ancestor – Samuel Cundey, a cousin of Henry Poole – to lead the tailoring house to expansion abroad, opening branches in Vienna, Berlin and Paris, and making it the largest bespoke tailoring business in the world by 1900.
“The dynamic of our core construction has seen a major shift,” Cundey explains. “It’s still a Henry Poole cut but much lighter than anything we made, say, ten years ago. It’s the kind of thing people might have looked to Italy for before, but it’s well within the capabilities of a tailor [like Poole] that outfitted customers for the tropics. The fact is that we live in a more mobile and more comfort-driven world and there’s a demand for a more performance-led garment consequently. It’s true that some Savile Row brands aren’t ready to change – yet. The knowledge is there. They just need the right teams to make it happen.”
This demand for a still sharp but simultaneously more relaxed garment keeps the cutters on their toes too. Cundey concedes that he misses the kind of customer that might come in ready to pioneer their own garment, for it can be these who can end up introducing a new future staple to the menswear canon.
In 1865, Edward – then Prince of Wales and future king of England – asked Henry Poole to fashion an evening coat in the deepest blue for wear at informal dinners. (Well, informal for royalty, at least.) And so, the classic dinner suit, effectively co-invented by Poole, was the result.


“It’s the characters who have a vision as to what they want who are often the most interesting to work with, providing it’s within the bounds of good taste, of course. But I’d love someone to come in and say, ‘I have this idea…’” Cundey enthuses. “Even the heritage brands have to come up with new ideas, but that tends to be generation by generation. The pace is slower”.
Of course, perhaps Cundey thanks himself lucky that anyone is still wearing a suit at all, at least not one that’s matching grey marl hoodie and sweatpants. “My great-grandfather and father took the business through two world wars, my father had to contend with the three-day week [of the mid-1970s] and I’ve had the pandemic,” he laughs. (Easier to do, now that his business has survived it.)
“We’ve all had to knuckle down. At least we could take the hit because we’re not owned by shareholders. And we certainly did take a hit at the time”.
That came with an awakening – and rapid response – to what was perhaps the final straw to break the tradition of dressing formally for work, even in the more straitened worlds of law and banking. While staff cuts were made, it also came with a new appreciation for the company’s apprentices – who Cundey decided not to let go, even with so little for them to do.
“I’m very glad of that, because we’re so busy now,” he says. Besides, Cundey says, discussion of tailoring, and Savile Row especially, tends to be overshadowed by consideration of the craft. There’s a tendency for the outside world to remember that, as with the other tailors, Henry Poole is a business, fighting to find staff, to keep on good terms with landlords.

Jonathan James Wilson
“There’s serious investment in the next generation of tailors and cutters – after all, it takes three to five years of training, costs a lot of money and tends to be disruptive,” explains Cundey. “And, of course, we’re always competing with the allure of the glamour of the fashion industry too.
“But actually the job security we offer has been a real selling point – like many jobs in craft now, being an upholsterer for Rolls-Royce, for example, they’re something a talented person could typically be assured of doing for the rest of their lives.”
As for those landlords? Cundey says that, post-pandemic, they too now seem to better appreciate that, if it’s not squeezed too hard and given the necessary space to do what it does, Savile Row is a long-term safe bet. It remains, after all, the global byword for excellence in men’s tailoring.
“This is not Bond Street, however, which is more like a game of chess, with constant movement,” says Cundey, “but nor can Savile Row be a working museum. We have to stay dynamic.”
See more at henrypoole.com