Victory Gin, Victory Cigarettes
Discontented with his life, Winston turns to vices as a means of escape and self-medication. In Winston's case, it's alcohol and cigarettes. He drinks gin to sedate his paranoia, like that time he downs a shot or two before finally writing in his journal. He smokes cigarettes for a similar reason: to calm himself down. These common vices help Winston check his doubts and paranoia at the door.
OK, sure, that sounds great - but it's really not that simple. Once again, we see some irony here. Winston's "vices" aren't personal decisions, nor are they small acts of individuality or rebellion. Rather, his vices have been assigned to him. Which kind of defeats the purpose of vices altogether. There was a Simpsons episode where Marge tells Bart he can't have vegetables until he finished his ice cream. The result? Ice cream is not so enjoyable anymore. Same deal here.
The Red-Armed Prole Woman
Winston sees this woman as a symbol of freedom. Party members never sing, but hearing her song through the window of his rented room fills Winston - and soon, Julia - with hope for the future. What is this hope? That the proles will become cognizant of their plight and rebel against the Party. After all, Winston reasons, the Proles constitute the only group capable of success because of their sheer size (85% of Oceania population). Unfortunately, as Winston and Shmoop note, the proles aren't smart enough to get their act together. Thwarted again.
But that's not all. Winston and Julia also acknowledge the Prole woman as a symbol of reproductive virility, and thereby, hope for the future. They see her as "beautiful" because of her wideness, largeness, and toughness - all indicating her ability to give birth to future generations of rebels intent on overtaking the Party's rule.
The paperweight, the old man in the prole bar, St. Clement's Church
The paperweight and St. Clement's Church have SYMBOL written all over them. These items are remnants of the past that, because of the Party's control, no longer have any basis in "reality." By surrounding Oceanians with propaganda, party doctrine and contradictory "facts," the people of Oceania no longer have a past. Their memories aren't even reliable because, after all, what would you think if you distinctly recall X, but X is nowhere to be found in dictionaries or historical documents. Even your friends give you are "are you crazy?" look when you ask them. Thus, in Oceania, it becomes impossible for people to question the Party's authority. Not to mention that whole threat-of-torture thing.
Fortunately, some remnants of the past do remain, and the "useless" paperweight fascinates Winston. He buys it as an attempt to reconnect with the past. Same deal with the old man in the bar - yet another attempt to get in touch with history. The old picture of St. Clement's Church hanging in the room? Singing the song with Julia? Again, more representations of the past.
Notice a blatant and rather non-subtle artistic device: when the Thought Police come to lead Winston and Julia away, the glass paperweight is shattered on the ground. Hmm. It's almost as if Winston's chances at recovering the past are shattered, too. Funny how that works out.
The ubiquitously placed Telescreens
With their dual ability to blast Party propaganda and to view and hear the exact goings-on in a room, these telescreens are a visible symbol as well as the direct means of the Party's constant monitoring of its subjects. They also symbolize the tendency of totalitarian governments to abuse technology to further their own ends instead of to improve living standards.
BIG BROTHER IS WATCHING YOU. Scared yet? Big Brother is the face of the Party, the leader behind the great power. The best part is that we never come to confirm his actual existence. He might not even be real. Maybe the Party just hired an intimidating-looking male model to make those posters. The face of the Party, Big Brother acts as reassurance and a trustworthy entity for many (his name is warm and fuzzy and easy to embrace). Yet, he is also your biggest enemy and threat - if you are one of the criminals (he is watching your every move).
So about his name. This is more irony. "Big Brother" should be a nice guy that, even if he gives you wedgies once in a while, still has your back on the playground. But since war is peace, freedom is slavery, and ignorance is strength, Big Brother is also a controlling and not remotely brotherly guy.
The ultimate symbol of opposition to the Party, we are not sure whether Goldstein actually exists. Publicly, he is known as a Party enemy, but he actually serves the Party's purposes as a scapegoat. Every time something goes bad or wrong, the Party attributes it to Goldstein - conveniently. Could Goldstein be a device created by the Party? We wouldn't put it past those guys.
Julia's Scarlet Anti-Sex Waist Sash
This represents a citizen's devotion to Party doctrine and Party cause. A symbol of chastity in the book, Julia's sash actually represents her duality. A devout Party member by appearance, Julia uses the sash to disguise her true actions (she has sex all the time).
Appearing only in his dreams and memories, Winston's mother represents better, pre-Party days when life was safe and not quite so oppressive. As the novel progresses, however, we also come to see that she represents Winston's intense sense of guilt. If Winston didn't actually kill his parents (and we're leaning toward this), then Winston's mother is the epitome of a pleasant past colored by the lies and manipulation of the Party.
The Place Where There Is No Darkness
This phrase first comes to Winston in a dream, when he imagines that this is where O'Brien wants to meet him. Heavy foreshadowing here, because he does indeed get here eventually - at the Ministry of Love, where the lights never go out. This symbolizes Winston's ultimate, doomed fate. It's also more of Oceania's ironic use of language. The place of NO darkness is metaphorically the darkest and gloomiest location. Unless you think rats and torture are all sunshiny and happy.
Winston's Varicose Ulcer Above His Ankle
A thing that swells and itches, and after you scratch it, flakes. Sounds gruesome, right? So is sexual repression. Have you noticed how the ulcer seems to bother Winston most in the mornings? How about when its symptoms subside after he starts seeing Julia? Or how it becomes engorged again when Winston is separated from Julia? Exactly.
These were only briefly mentioned in the novel, but that doesn't mean they are unimportant. Memory holes are those things in the ground that the Party insists any scraps of paper get tossed into. They lead to a furnace. Let's think about this for a second. Memory...furnaces...memory...are memories being burned here? Why yes, they are. By destroying paper, the Party destroys documents and therefore evidence of the past. Which, given all the thought control going on, would seem to be the only real link left to history. Well, it was, anyway, until it got sent to the furnace.