The way in which O'Hara challenges the Status Quo in his poem "Having a Coke with You" is by stating over and over that, amongst all the things in the world that he could be doing, or that he could wish for, nothing at all compares to the feeling that he gets when he is sitting across the love of his life enjoying the simple pleasure of sharing a soda.
Notice how, from the very beginning, O' Hara mentions the hobbies of the rich only to quickly add how little they would mean to them in comparison to being where he is at that point:
Having a coke with you
is even more fun than going to San Sebastian, Irún, Hendaye, Biarritz, Bayonne
or being sick to my stomach on the Travesera de Gracia in Barcelona
He gives a simple and youthful description of his love by offering all the things that he would never rather do in lieu of being with the girl that he loves. In his description he is charming, youthful, funny and imaginative to say the least. Here is perhaps the only time when we see him actually affirming the Status Quo, but he quickly checks himself and goes back to reinstating his predilection for the love of his life.
at you and I would rather look at you than all the portraits in the world
except possibly for the Polish Rideroccasionally and anyway it's in the Frick
which thank heavens you haven't gone to yet so we can go together the first time
In the end he again hints at the things that may be gained in the process of losing oneself to the flash and the glamours of life, but he reverts to how, in the end, having that coke still means more.
it seems they were all cheated of some marvelous experience
which is not going to go wasted on me which is why I am telling you about it
In all, the way in which he stylistically challenges the Status Quo is by contending that nothing that other people might say or do would prevent him from doing his favorite thing, which is to be with the love of his life. As a man, especially as a young man, however, he also hints at affirming the Status Quo by admitting that he, too, would love to have the chance to admire many other things that others admire as well. Yet, being a love poem, he uses his wit and charm to go back to the point of the poem, which is to tell his beloved how happy he is to be with her.