Instead of assuming pipe and slippers and retiring as planned in 2003, Brixton-born Tillman, now 64, snapped up womenswear brand Jaeger. He is thought to be worth an estimated £295m and counts Sir Stuart Rose and Philip Green among his friends.
How did he make his millions? Fashion is in Tillman's blood (he started in his parents' clothing business). But he's ballsy too: within three years of joining clothing supplier Lincroft, he bought it and took it public soon afterwards at just 24. He has, however, been known to sail close to the wind: earlier in his career, he had a tussle with the DTI that resulted in a three-year ban from directorship.
The secret of his success? Tillman is known in the trade as a 'man who can't say no'. Since buying Jaeger from entrepreneur Richard Thompson, Tillman has transformed it from ailing British warhorse to cutting-edge fashion house. Only time will tell if he can pull off the same trick with most recent purchase, Aquascutum.