Tommy Roberts: Designer who dressed Swinging London and pioneered the 'retro' look

Tommy Roberts is a character out of an Ealing comedy, a jovial, lovable creature, a really brilliant icon of London," said the late Malcolm McLaren in 2009. Outsized and funny – everything he did seemed permeated by his surreal sense of humour – Tommy Roberts was an often unsung hero of British design and underground culture. "In Italy he would be an elder statesman," the historian Catherine McDermott wrote in 1987. "Tommy Roberts represents that part of British creativity which is able to delight and surprise."

Living perpetually in the gap between life and art, Tommy Roberts was an indelible influence on British fashion and design over the last 50 years. In 1970 he had a weekly slot on the BBC TV magazine show Nationwide, providing fashion news. He was even an early "foodie": at his restaurant Mr Feed'Em, in the basement below his state-of-the-art boutique Mr Freedom, he would serve blue mashed potato; in each bowl of soup floated a plastic fly.

Born in 1942, Roberts became a teenager as rock'n'roll arrived in Britain. Even at the age of 13 he sensed the zeitgeist: with his school-trousers tapered to 14-inch bottoms and having acquired a black-flecked off-white drape jacket, he became a junior Teddy Boy. When Blackboard Jungle showed at Catford ABC, he danced in the aisles; his skill on the dance floor soon earned him local legend. Dancing in 1964 to the Dudley Moore Trio at a Bromley nightspot, he met Mary Brookes, who became his first wife.

Leaving Catford Central School for Boys, Roberts entered a foundation course at Goldsmiths' College of Art, becoming a follower of the newly popular trad jazz. But this was soon replaced by the more advanced modern jazz as Roberts transformed into a "Modernist", replete with scooter and an American college-boy look.

As though playing the role of the archetypal South-east Londoner, he took a job after leaving Goldsmiths as a second-hand car dealer; his own pink convertible Vauxhall Cresta signified his status. In 1964 he set up a Camberwell-based car dealership specialising in exotic classic marques.

Soon, however, sniffing the wind, he followed his family's rag-trade tradition: in 1966, at 10 Kingly Street, parallel to Carnaby Street, he opened Kleptomania, specialising in, as Roberts defined it, "weird bits of junk" – "camp", as it was then defined. The opening stock included original Gladstone bags and Chinese opium pipes, Victorian red guardsman's jackets, even a penny-farthing bicycle. "Such pieces," wrote Paul Gorman, Roberts' biographer, "along with busts of General Gordon and Queen Victoria and Edwardian statuary, prefigured Roberts' future direction: the marketing of lifestyle."

In terms of that marketing, Kleptomania's location above the hip Bag O'Nails nightclub, where Jimi Hendrix made his UK debut, could not have been more convenient. Onstage Hendrix wore a Kleptomania frilled shirt; Pete Townshend and Keith Moon also wore Kleptomania clothing; then the Yardbirds' guitarist Jimmy Page became a particular aficionado of the store, and friend of Roberts, buying a What The Butler Saw machine.

A pioneer of what later would become known as "retro", Roberts recalled how he "woke up to the fact that anything wearable was snapped up: old riding boots, cravats, gloves, hats and embroidered shawls, black moleskin fedoras and naval officers' wasp-waisted frock coats."

At the end of Kleptomania's first year Roberts sensed another cultural shift: he became an active participant in the new hippie culture, eagerly consuming psychedelic drugs at UFO and the Roundhouse, and growing shoulder-length hair. Now the Kingly Street shop could have been in San Francisco's Haight-Ashbury, West Coast acts sailing out of stereo speakers; fringed gypsy shawls were on sale, next to psychedelic posters and "grow your own" pot kits.

Losing interest, in the summer of 1969 Roberts opened Mr Freedom at 430 Kings Road. Mr Freedom was a tribute to the bold, bright colours of Pop Art, in which the influence of Andy Warhol and Roy Lichtenstein was clearly discernible – bold-coloured vests and tops bore such slogans as ZAP! And POW!, alongside items bearing the images of Mickey Mouse and Donald Duck and prototype platform shoes. Soon Mr Freedom had become an international fashion force. The stock available in the new Kensington store, which opened before Christmas 1970, was stunning. Among the items were PVC seats fashioned as oversized sets of false teeth; red bed linen featuring hammer-and-sickle pillows; pouffes in the colours and shapes of Liquorice Allsorts.

Performing "Brown Sugar" on Top of the Pops, Mick Jagger wore a Mr Freedom cap and T-shirt; on Elton John's early American performances he was clad in Roberts' clothes: a yellow boiler suit with a piano appliqué and a pair of winged boots. Across the US, department stores and boutiques stocked Mr Freedom lines.

By the beginning of 1972, however, it was apparent that the expanded Mr Freedom had been over-ambitious. In financial confusion it closed and Roberts opened the City Lights Studio boutique, selling upmarket idiosyncratic clothing, in the then rundown Covent Garden: Bowie's double-breasted suit on the cover of Pin Ups came from City Lights. But trade was not good – the shop was hard to find. Early in 1975 City Lights went into receivership.

In 1981 Roberts opened Practical Styling, near London's Centrepoint, a celebration of modern design. It was succeeded by TomTom, a store in Soho, selling high-end eclectic design. By 2000 he had a new shop, at 2 Columbia Road in Shoreditch, selling 20th century art and design – the location indicated that Roberts' antennae were still lined up to coming trends.

The ever ebullient Roberts fell ill to cancer four years ago. At the launch at 2 Columbia Road this summer of Paul Gorman's biography of him he was clearly not well. A more abiding image of him was furnished by the designer Paul Smith, writing in Gorman's book, recalling Tommy Robert's favourite – and motivating – catchphrase: "Come on, let's get going!"

Thomas Steven Roberts, designer and entrepreneur: born Bradford on Avon, Wiltshire 6 February 1942; married 1965 Mary Brookes (marriage dissolved; two sons), 1993 Jane Sharratt (one son); died Canterbury 10 December 2012.