He came, he saw, he conquered, he lost everything, and then he conquered all over again.
The young Harold Tillman inherited his innate passion for design from his tailor father and milliner-mother. As Tillman himself recollected to The Observer, “My father, a Yorkshireman through and through, taught me tenacity, while my mother gave me style.” Leaving school at 15, Tillman revolutionised the London College of Fashion’s recruitment policy by being one of the first male students to study there in 1962.
At 19, Tillman became an apprentice for wholesaler Lincroft, a company known for conventional attire and stiff suits. However, Tillman, by now a fully fledged retail-junkie and honed opportunist, used the recognised brand to get his own designs on the rails, styling Carnaby Street in Shea jackets and hipsters. Within a year, he was outshining - and outselling - the established old guard.
Aged just 24, the fledgling investor was the youngest person to ever float a company on the stock market

George Best
In 1967, Lincroft’s owners retired and the headstrong Tillman took out a £5,000 loan to acquire the business, although he was unaware just how lucrative the buyout would prove. Aged just 24, the fledgling investor was the youngest person to ever float a company on the stock market, which proved to be a gateway to a series of acquisitions, including Kilgour French and Stanbury. Consequently, the deal reinvented Tillman’s business which came to be known as Lincroft Kilgour.
Soon, Tillman was making history for the third time in his relatively short life by brokering the UK’s first celebrity endorsement. Tapping into the birth of celebrity culture, Tillman employed his friend, the footballing genius George Best, as his brand’s ambassador. “I simply took his name and put it on shirts. It was a great success. It was a young whim of mine – but a great whim,” Tillman affirmed.
With a hawk-like eye for designers, Tillman also groomed the talent of a young Paul Smith, introducing him to Saville Row’s guild of fine, bespoke tailors. Working as a designer at Lincroft Kilgour, Paul Smith took classes by night in tailoring and in 1970 he opened his first haberdashery business, only three years after Tillman gave him his initial break.
Millionaire
Tillman, a veteran rag-trader at 30, sold Lincroft Kilgour to merchant bank Cannon Street, valuing his net worth at over £1 million. Covenant not yet compete, Tillman left the style-frenzied streets of London to experiment in New York. Literally dripping with inspiration, the business mogul broke new ground on his return, opening the UK’s first cocktail bar, Rumours.
While the 80s whirled by, Tillman proved to be a living King Midas yet again; everything he touched turned to gold. In an interview with The Guardian, Tillman reflected, “Over the years I owned several clubs and restaurants - bought them, sold them, enjoyed them. The things that I look at are fashion related, hence the restaurants. It's hard to explain. But it's got to be related to being in the fashion industry.”
Honorbilt
We can forgive Tillman’s presumption that he was bulletproof, but the high-rolling entrepreneur did not foresee Black Monday. In 1987, Tillman bought the loss-making division of Austin Reed, Honorbilt, with visions to apply his ‘Lincroft-technique’ to the ailing tailor. Hungry for prosperity, Tillman’s coup was cut short by the global stock market crash.
“It was a very, very bitter lesson,” Tillman confided to the Evening Standard, adding, “It was a reckoning of the mind. It taught me that I don’t walk on water.” In short, Tillman’s entire portfolio was wiped out in an afternoon due to the foundations of his core business being built purely on its FTSE status, and the management team he had placed in charge could not patch up the haemorrhage caused by Black Friday.
In an interview with Growing Business Tillman described his mindset post-crash. “You’ve got to turn these things into a positive experience” he said, “keep your eye on everything and don’t believe that everything goes on forever. If you have a car accident you’ve got to drive more carefully next time.”
In 1990, the Department of Trade and Industry called a court hearing to sentence Tillman to a director’s ban for life, but negotiations saw this reduced to three years. Tillman was filled with regret for placing dangerous levels of belief in his management team as he scrambled to keep hold of anything he could.