No matter how hard GM tries to market Buick to a younger crowd, they will always be known as old person cars.
When I was a kid in the 50's most cars had a niche where they advertised and sold to a rather narrow client list. For GM it went something like this:
Cadillac - Top of the line for those who had money to waste and wanted the envy of their neighbors.
Buick - The appropriate car for professionals (doctors, lawyers, accountants, engineers (who didn't want Chrysler products). Buicks eschewed 'responsibility'.
Oldsmobile - Didn't have much defining history. Tended to share client base with Buick until going the performance route in the muscle car era.
Pontiac - For upscale buyers who wanted some 'spit in your eye' performance. Buicks without the culture.
Chevrolet - Transportation on the cheap.
Both Chrysler and Ford had their lineups as well. A few post war independents were also selling to the identical strata and trying to compete with the Big 3. Hudson was at one time the performance machine. Packard tried competing with Cadillac and Buick. Studebaker went after the economy buyer but had some definitely different performance cars in the Hawk line (personal performance?). Imperial was Chrysler's attempt to compete with Cadillac as was Ford's Lincoln. Those were independent car lines then and not just models with sheet metal differences.
Over time the model lines melted together and one car model became pretty much indistinguishable from another. Options like power windows, once the purview of the top of the line models became available on every model. Body parts and trims were standardized and engines became interchangeable. (Remember the big lawsuit by the guy who discovered his Pontiac actually had a Chevrolet engine in it?) Lincoln and Imperial became models instead of brands. Pontiac and Olds, once past the muscle car period, lost their uniqueness among buyers and then lost their reason to exist.
Now there is practically no difference between the various GM brands except the amount of crappy options they can cram aboard to raise the price. Cadillac's frequently wind up below Chevy's on the reliability totem pole because of this. Marketing hasn't changed much though. Chevy's are still marketed to families, Buicks to dual wage earning couples (and notably Blacks) and Cadillac's as the premier and in-your-face marque (Hello Escalade) even though its ratings do not justify it at that level.
American culture has changed so much since WWII that the target demo's are largely no longer clear. When a Youtube "rappuh" can cruise around town dressed like a top movie star of old why would he/she choose a mere Chevy when they can ride in an Escalade? GM would probably love to think that people see its Escalade as the old timey Dusenberg but alas and alack, not even close.