That’s certainly an insightful monologue but I don’t understand why the audience is laughing. Maybe I’ve lost my sense of humor in my old age 
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I would argue that youth culture arose as a reaction to the cultural conformity of the mid century. Far from being its creater or driver, consumerism just cashed in on it. Maybe it was/is frivolous, but that was a backlash against the clean cold logic of the modern experience. Intelligence & experience got us two world wars and the brink of extinction. After that, we could all use some good goofs (which this person should stick too).
Anyway, the reason the cool kids wear the same shoes & drink the same beer as years ago is because we live in a deterministic world where the past leads directly to the future. No time for the present. This gives them control over the past, and the sillier, the better.
I’m surprised nobody has made mention of Geico. Take a look at their two very separate advertising schemes:
The gecko, a cute cuddly mascot who relies on dry humor reminiscent of 70’s British humor, definitely marketed to a more adult crowd. I know my parents and even my grandfather love the gecko.
Then they have the whacked out “whose watching who” commercials with the googly eyed dollar bills. I’m fairly certain these are aimed at the younger, internet generation who is used to seeing crazy, nonsensical things all the time. Everyone I know from my parents’ generation who has seen these commercials has a hard time understanding what they’re even advertising… despite already knowing what Geico is.
Clothing is something that you can make your own through customization. There is a very different look between wearing a Polo shirt that is three sizes too large vs. wearing the same shirt a size too small. Technically it’s the same product…
It is very interesting to see what luxury car companies are doing now, especially the upscale brands of bigger companies like Cadillac, Lexus, and Acura. BMW and Audi seem to have stuck with the no-nonsense classic approach, whereas the aforementioned companies are all getting a bit more youth-y and abstract (especially Lexus with their new IS-C ads).
It’s been done before and here’s how:
It all depends on how you play to the new consumer group. What do they want from X product as compared to the original group? How do you play to these attributes of association? Is there a difference in functional need or aesthetic desire?
The job is easy if both consumer groups have the same functional need (i.e. they like the same flavors of ice cream) but are buying based on aesthetic desire (packaging). Brands can drastically alter their aesthetic equity while delivering the same product to a new group. Of course, if prestige is a large part of overall brand equity, then any deviation may be seen as abandonment of purpose by management (such as when Porsche came out with their SUV).
L’Oreal for Men shampoo is an excellent example. A simple color scheme shift is all it took to open up a whole new demographic to the product. They offer a shampoo of little to no increase in investment in a bottle that required no new tooling or manufacturing infrastructure and increased their market by at least 25%.
Geico has a third campaign too–the “its so easy a Caveman can do it” ads.
All three campaigns are definitely sending a different message, which would obviously resonate with different groups.
Gecko = General brand awareness. They pull him out when they have a specific message to communicate.
Googley-Eyes = Saves you money
Caveman = Easy to use
I can’t speak for generations Y or Z or whatever the youth market is known as, but everybody I know above the age of 30 thinks the dos equis guy is pretty great.