I have found that getting my clothes ready in advance, like the night before, saves me all the stress of feeling like I have nothing to wear. I stand in front of my closet and pick not only one outfit, but like 3 to take along with me because I stay at my boyfriend's house some days and then have to jett off to either of my jobs that require different types of dress. But I never get that feeling that I wish I could just get rid of everything and start over again.
The accumulation in my closet has grown to where by the time I do my next load of laundry, I rediscover things I sometimes haven't work in weeks. I try to wear out all of my things before the next load of laundry. This allows me a limited amount of clean clothes to wear and to choose from.
In the past year I have been weeding out my closet because I found that many of the clothes (dresses in particular) were not my style anymore or didnt fit me (mostly vintage). I have sectioned off part of the floor by my bed for things that will be sold on ebay, and have now begun specifically buying for ebay (things that I adore but dont fit, that I know someone else will love). This makes things in my head much clearer for if I would buy a certain thing for myself or someone else.
But because I have started working retail, I feel I have finally been paying attention a little more to seasonal trends. Especially after moving away from Southern California where it feels like there are no season changes sometimes. I put away my winter clothes to make room for my closet. Because I used to laugh when I would read fashion magazines, and people would speak about how they need to get new things every season. Which I still think is slightly ridiculous (just use some of the things you already have). But now I understand that feeling of what you have not fitting in with the rest of your clothes. Especially when I have to wear clothes from my store in mixed seasons/years.
I have learned through becoming older, how to control my compulsive shopping. I tell myself every single time that if I do not instantly fall in love with said item, I will absolutely not purchase it. Because after starting to finally earn my own money (as some of you will see in life) it becomes so easy to want to buy something just because. You should not do that. I think this is what creates the whole feeling of not having anything to wear. Sometimes you are blinded by the things you dont want to wear, you miss the things you could.
On the other hand, I found that organizing my closet space and wardrobe by color also helped a great deal. This helps me by not wasting time rummaging through drawers and hangers for something that will coordinate. I can tell you I only have three drawers, one is for intimates, one is split between white and light color tops, the last is split between black and dark tops. My closet goes from dresses, skirts, pants, jackets. I know where everything is and it saves me time putting things away. Granted that every week or two most of it gets unfolded or mixed. I dilligently put it all back together on a lazy afternoon.
It takes work to get out of the funk. But instead of just piling more things on top of what I dont want, I trade it out. I am just relieved that getting dressed has become easier over the years. I will try to remember this the next time the feeling sinks in!
This is why I have so many black tops ... I've bought only a couple since I started planning my wardrobe, all the rest predate the current era 
I've practically doubled my wardrobe in the past year because I keep buying buying and buying.
