HAROLD TILLMAN glides from his office to greet me, clutching a copy of The Sunday Times. “Just checking you look like your photo,” he grins, proffering a hand.

Tillman, a long, elegant man with courteous manners, avoids giving me the up-and-down, for which I am grateful. Anyone looks scruffy next to him in his pin-neat, hand-made suits and impeccably coiffed grey hair. “Actually, it needs a cut,” he says later, patting the back of his head as he composes himself for the photographer. This is after he has dashed from the room with a grooming case to “sort himself out” as soon as he sees the camera.

A vain man? Undoubtedly, but appearances are important to Tillman, and many rather like him for it. Veteran of the rag trade, early mentor to Sir Paul Smith and a risk taker who has been up and down in various clothing businesses for nearly 40 years, Tillman is as resilient as a rubber ball.

He made a mint supplying Carnaby Street with hipsters in the late 1960s, went bust heading Honorbilt in the early 1990s, and has floated three different clothing companies in between. That’s when he wasn’t running menswear in America and dabbling with cocktail bars and restaurants over here.

In his time, he has made a lot of money, and lost it too, which makes him a controversial figure. But God loves a trier, and Tillman, in rag-trade folklore, has been there, done that and wholesaled the T-shirt. Last year, aged 57, he emerged as the new owner and chairman of Jaeger, the famous British clothing brand that has floundered in recent times.

He is also chairman and 37% shareholder of BMB, the trading group (current sales £170m) that supplies clothing to J Sainsbury, and sells brands in Allders, Debenhams, House of Fraser and Selfridges. And if he is looking rather pleased with himself when he steps from his black Bentley at the Grosvenor House’s Retail Trust ball tomorrow night, the highlight of the fashion trade’s winter season, that is because, with Jaeger under his belt and BMB worth nearly twice what he bought it for, Tillman is on a roll again.

Good to be back? “I was contemplating retirement last year till Jaeger came up,” he says, in his slightly languorous drawl. Tillman, it transpires, has been contemplating retirement since he made his first fortune in the late 1960s. But he has never stopped because, like most entrepreneurs, he could never resist another money-making opportunity.

He took faded giant Jaeger off the hands of Richard Thompson, the former QPR chairman who had bought it from Coats as part of a bigger deal. Neither side will give figures for the transaction. What Tillman will say is that, backed by GMAC Bank, he has injected £10m of capital, and bought the lease of Jaeger’s flagship store in Regent Street for £25m, and provided Thompson with “several million pounds worth of profit”.

For that outlay at Jaeger, Tillman gets a famous brand, £120m of worldwide sales, the leaseholds on 52 stand-alone stores in Britain’s high streets and a clutch of licensing deals. Tillman clearly thinks he got a bargain. “You couldn’t establish that for £100m,” he says.

The key question, of course, is would you want to? Jaeger lost £11m in its last accounts after trying to modernise its image as the brand for the “maturer” lady. It hired hip designer Bella Freud to produce a line of groovier gear. But emulating Burberry, which overhauled its fusty reputation to become a trendsetter with a market value of £1.9 billion, proved tougher than many thought.

Now Tillman is going to give it another crack, with a different approach. Not so much Notting Hill this time, “more Wimbledon and Harrogate”, as he puts it. “We are not going young. We are aiming for the mature customer, but with a fashion twist. And we are getting a lot of younger interest in it. So you can say we are looking after our 60-year-olds, but catering for 35-plus, too.”

Tillman is also keen to expand the menswear. “I think there is a need in the market for a suit to challenge Hugo Boss, around the £500 mark.” And then there are opportunities in home furnishings, fragrances, shoes, the chance to build a restaurant in Jaeger’s Regent Street store, six more UK outlets he wants to open. Maybe even floating the firm. “It depends on the new licensing deals I am working on. We’re finalising stuff in Japan and also in discussion with China...”

Sitting at the glass-topped table in his double-roomed office overlooking London’s Cavendish Square, the garrulous Tillman is not short of ideas. It was ever thus. Born an only child to south London parents who ran their own clothing business — his dad trained at Montagu Burton — Tillman was borrowing money and cutting deals while most of his peers were still looking for job opportunities.