Jack Wills has previously ridden the wave of soaring demand for its preppy clothing among Middle England teens and university students, boosted by endorsements from the popular boy-band One Direction.
But the fashion retailer, which has 80-plus stores, appears to have hit choppier waters and two senior executives are leaving the chain that also has a presence in the US, Middle East and Hong Kong.
Paul Woolf, the finance director, has already left the private equity-backed retailer, while Liz Hall, its head of UK stores, is to exit early next year.
The departures follow the decision to axe sister brand Aubin & Wills and 11 stores in the autumn, although a few may be converted into Jack Wills. In a further setback, the retailer sunk to a loss of £4.75m over the year to January 31, which it partly blamed on a rapid international expansion.
Fashion industry sources said that it has suffered subdued trading in the UK this year, suggesting the appeal of its polo shirts, hoodies and sweatpants has waned. However, sources close to Jack Wills suggested its like-for-like sales were in positive territory recently, adding that the chain had not yet started its Christmas discounting sale. They also added that online sales continue to grow strongly.
Mr Woolf is to join Virgin Active, the gym group, as group finance director in January. It is unclear if Ms Hall has another role to go to and Jack Wills declined to comment.
Former Vodafone director Wendy Becker was appointed chief operating officer in August to strengthen the chain, which was co-founded by Peter Williams and Rob Shaw in 1999. The pair still own 70 per cent, while private equity firm Inflexion owns the rest.
Total sales grew, by 32 per cent to £120.1m last year, driven by 29 new shops across the world.