To my opinion the combination of his name Winston Smith is very funny, he has an 'expensive' first name, and a rather common surname, I find it pretty funny, but in his society his function was really insignificant!
The name "Winston" comes from the name of a village in County Durham.
The village came to be known as Winston from the old english words "win"(Wine) and "stan"(stone).
The name "Smith" is derived from the Anglo-Saxon word 'Smite' which means 'To Strike'. It came to stand for specific trades. Thus who worked with Iron (Strike iron to give it shape) were called Blacksmiths those who worked with gold, striking and beating it to make jewels were called Goldsmiths. And rom the trade came 'Smith' became a family name.