Suppose you were a struggling farmed up there in SD and your neighbor sent you photos of him zipping around on on his brand spanking whatever John Deere whatever. Wouldn't you feel that that was a bit pretentious????
Kinda like some run of the mill bartender inheriting the lottery and then popping back into the bar showing off the bling……people don't really dig that all that much. It's showing off…and it doesn't always sit too well.
Michelle O is the perfect example of having "it" without coming off pretentious. She carried herself beautifully on numerous magazine covers (not sure if she was on VF or not. I'm not a reader).