Just remember, your body touches your bike in only three places--butt, feet, and hands. I find it a good investment to protect those, in that order. Poorly made, poorly fitting shorts are no fun and not worth the $25 spent on them. I buy one pair of Pearl Izumi shorts per year, and they last 4 years. After 4 years, they get a bit transparent, but I still wear them with regular shorts over them. PI's label indicates the year. When mine get too "showy" I mark them with a laundry pen so I don't mistakenly wear them without regular shorts. The chammy's still good! I buy one pair of good cycling shoes every 10 years--my Shimano shoes lasted 10 years, and I replaced them last year. Gloves are not that big a deal (important, but not expensive)

The other thing I spend money on is a HELMET and I replace it every three years (I ride 30 miles per day commuting, so I sweat alot). I don't look at the price, I just buy the one that fits the best. It happens to be a Bell Ghisallo, which is $100, but if I was happy with the $40 helmet, I would buy it. If I crash, I replace it immediately after the crash. This has only happened once, and the helmet broke in three places--better the helmet than my head. They do make helmets with ponytail holes, but I can't remember the name if it (Bell model, I think).

I don't know how far you are riding, but the essentials for me are a helmet and good shorts. If you don't have clipless pedals, sneakers will work for shorter rides. Gloves can be found for cheap. Invest in the important things and don't fritter away on the non-essentials. Eventually, you will build up a collection by finding out where the deals are to be had.