Retail entrepreneur John Kinnaird, whose shoe chain Dolcis went into administration last month, made a bold comeback this week with the acquisition of struggling clothing chain Style Menswear for a token sum of £1.

It begs the question, why is Kinnaird going headlong into another business when the dust has not settled on his last venture? Kinnaird has made no secret of the fact he wants to buy back a pruned version of Dolcis and so it is likely that, if he is successful, he will merge the shoe and clothing businesses. But if Alexon – which previously owned both Dolcis and Style Menswear, which consists of retailer Envy – could not make either business work, why does Kinnaird think he can do any better?

Kinnaird’s retail career is chequered with both successes and failures. He made his name and fortune as retail director of Sir Tom Hunter’s Sports Division. Hunter, a well-respected retail entrepreneur, has created several budding protégés and anyone given his seal of approval is likely to go on to greater things.

Yet Kinnaird has had his fare share of hiccups. In 2002, he tried to turn around the fortunes of struggling chain Warner Bros Studio Stores, but failed. The chain, which he ran and part-owned, went into administration in 2004. He also lost out to Sports World boss Mike Ashley on a deal to buy Original Shoe Company early last year.

And then there’s Dolcis. Kinnaird had grand plans for the struggling chain and hoped to take it into profit next year. He overhauled the product and stores and tried to position the brand at a slightly higher price point than it had been known traditionally.

The fruits of his labour were seen at its first new-format store in Glasgow and it certainly looked enticing. Gone was the dusty, drab Dolcis of old, replaced by a fashion-forward brand that was relevant in today’s competitive shoe sector.

Kinnaird also hand-picked his management team and pulled in several footwear stalwarts. Dolcis’ fortunes seemed to be on the up until its investor, Epic Private Equity, pulled the plug at the end of last year.

Epic’s departure left Kinnaird in the lurch and he worked hard at securing new investment. When this failed, he was left with no choice but to put Dolcis into administration.

And, while Kinnaird must be credited with trying to save some Dolcis stores and staff, he is not going to do this without renegotiating terms with landlords and suppliers. If he does resurrect Dolcis, it will be at their expense. And, while landlords can probably take the hit, the same can’t be said of suppliers.