Jersey- up to $100 if I found a really nice one I thought would last for years, but I usually pay no more than $60.
Bibs- up to $300 if I found a sweet pair that were incredibly comfortable and would last at least a few years. Usually spend about $120.
Shoes- up to $300 but they should last at least 5 years or longer and be insanely comfortable and stiff.
Glasses- up to $250 but must be high quality and last for several years. (I wear contacts so glasses are very important to me)
Notice the bibs, shoes, and glasses are what ill spend the most on because those can make the difference between a sweet enjoyable ride and misery. The jersey isn't nearly as important in my opinion unless its for cold weather and keeps you out there riding.
It is all about what you think is worth it and if you have the money to spend.