Former team-mate Jacques Villeneuve once famously dismissed him as just a 'boy band member' while Scottish racing legend Stewart was more wounding in his assessment.
Only last month he said: 'In my day we were committed, dedicated and professional. We didn't have the distractions you have these days with parties and girls. Jenson does not need the distraction; it's hard to focus if you're going out a lot. He needs to concentrate. He needs to win a race.'
No doubt about that. But is the playboy tag warranted?
Button said: 'People are very opinionated. Reading something in the paper from a past driver who knows nothing about your private life, who comments on it, and says you're doing things wrong -- it's just not for them to comment on.
'I work bloody hard and it's fair enough to be silly every now and again. I have to be careful where I do it, of course. I just have to do it behind closed doors as much as possible.'
The young brunette is sitting at the table behind, peering under her lashes, waiting and hoping for a flash of recognition to come her way at the glamorous ceremony.
It does not take long. Button, giggling and giddily entangled with one of his mates, breaks away for a moment and flashes her his look, the look. Job done. Now all he needed to do was try to stay sober enough to remember her later on.
As he wanders through the starstudded line-up at the Royal Opera House, Button is open, polite, cocky and charming and in an utterly relentless chat-up mode. If only results on the track came as easily as they do at glittering events like the GQ Awards.
It is the least you would expect from a recently-unattached grand prix driver with a yacht, an apartment in Monaco and an annual income of around £10million a year. This penchant for the high life is not exactly a new phenomenon either.
Even when he was just an F1 fledgling, Button's behaviour provoked concern from the permatanned Flavio Briatore, a man who has had more than a few supermodel dalliances himself. The Benetton boss thought the young Englishman on loan from Williams allowed his eye to wander too far from the track. And it comes to something if a character like Briatore is worried.
It centred on Button's antics on his boat 'Little Missie', which quickly became notorious along the Monaco pit lane. Matters became somewhat strained when Briatore also discovered the harbour master had placed his own yacht on a worse berth to this brash young driver's and worsened when the girl group Atomic Kitten arrived for the race, attracting the paparazzi like moths to a flame.