New Look founder Tom Singh must have hoped that, aged 62, he could look forward to putting his feet up and enjoying his millions rather than being back on the operational frontline of fashion retail.

But that’s where he finds himself after the ousting of New Look chief executive Carl McPhail and the departure of chairman John Gildersleeve in the wake of poor trading at the one-time trendsetting retailer.

For Singh it must feel like a shopkeeping Groundhog Day as he confronts again similar challenges to those he overcame to make his £515m fortune in the first place by building New Look.

Only a year ago, New Look’s owners - private equity houses Apax and Permira as well as Singh - hoped to float the business. Public investors wouldn’t buy it, and that decision looks smart today.

The irony is that New Look has been a financial success story for its owners - it has returned more than twice the original cost to them and increased profits year after year.

But in more recent times, New Look has not been a retail success story. The reasons are partly understandable - they are the same reasons that have affected others.

But those shared difficulties are only part of the story. New Look has really gone off the boil, partly it seems for losing a feel for product - a deadly retail failure. A staff move from Dorset, with the associated disruption and loss of people, was one contributor. The likelihood is that a strong product person will fill McPhail’s shoes.

New Look’s present difficulties are also a reminder that questions that were posed at the time of the IPO attempt remain unanswered today.

The idea at the time of the private equity buy-out was to turn New Look into a British Inditex, but international growth has been stuttering.

To that now add trouble at home. Even last year potential investors were asking how long New Look could continue to expand here given its historic growth. New Look has made some advances online, and that remains an opportunity, but the fundamental questions are more urgent.

Last year potential investors were worried that there would be little left on the table for them after any float. This week’s developments will reinforce that view. It’s up to Singh, and McPhail’s eventual replacement, to convince people otherwise.

george.macdonald@emap.com