Similarities exist mainly in the fact that with both Winston and the proles, the party has determined their quality of life. They both suffer from the rationing, the fact that wealth and luxury are withheld from them, and that the party is the one that is in control, running the show. They are both subject to the party's propoganda also; they are trained to be war-loving party patriots. They live rather poor, destitute lifestyles, and have the party to thank for that.
One big difference between Winston and the proles is in the amount of freedom that they have. Winston is watched like a hawk; everywhere he goes, his movements are analyzed. The proles, for the most part, are free to go wherever and do whatever--the party doesn't really consider them a threat. Winston oftened wondered why the proles didn't just rebel, because if they did, they could overwhelm the party with sheer numbers. The party's philosophy on the proles though was that
"It was not necessary to know much...Left to themselves,...they had reverted to a style of life that appeared to be nature to them, a sort of ancesteral pattern...to keep them in control was not difficult."
They were complacent and apathetic in their lives, so didn't need to be controlled or watched as closely as Winston did. So, even though both the proles and Winston have miserable lives, Winston's is worse because he has to be careful about every single thing that he says and does.
One last difference is that Winston is more aware of the lies that the party cranks out on a regular basis, because he is the one who helps to create them. The proles have no access to such information. Winston knows that the party manipulates information to better their image and control the minds of the population; this knowledge makes his life even more tortuous, because he's aware of the fact that he's being had in an elaborate hoax against mankind.
I hope that those thoughts helped; good luck!