The irony of this advertisement is intensely potent, though the creative strategy is rational and easy; needless to say, this campaign ran well after the death of the now revered beatnik writer, who passed from this world with nothing, not even a strong reputation, the likeness sold to the corporation by some desperate descendant. Despite being born and raised in one of the principal preppy dominions, Baltimore, I have never exclusively associated khaki slacks with the lacrosse-playing, summer-home-reveling prototype, a connection so many others forge. For me, there has of course been that uninspired look of a corporate drone, or that carefree rich kid of the creamy upper echelon of socioeconomic strata, but there is also a sort of sense of rugged adventure, one with more abandon than that traditional denim dungarees. A sort of escape; strangely, a sort of irreverence for pragmatism, simultaneous and contrary to the very pragmatism they are also connote.
Romantic, without being disgustingly sentimental or too flagrantly overt, I would imagine this served the company well; Kerouac, like the khakis he dons here, is a familiar and recognized name, without being typical or mainstream. A sort of safe risk. Unfortunately, this artfully developed and marketed bode of confidence for the ever-classic khaki will not sway my dear filmmaker; fortunately, he is like Kerouac in that respect, refusing to fetter himself to commercial, mass produced expectations. I prefer that attitude, exuded in a subtle and untouchable exuberance in this photograph, something that, unlike the slacks, Gap cannot produce and cannot sell.
(image taken from Open Culture)