Think like a merchant – Treat your wardrobe like you are trying to sell it.
The way most stores present their collection to shoppers is that all the items on one wall or fixture should work together backwards and forwards. The shopper should not have to search throughout the store to find things that go together. There are basics and then usually a fun key piece which makes the outfit pop. Your closet and outfit should work the same way. Do the items hanging in your closet make sense together and do you have enough fun pieces that make it pop?
Go through your current wardrobe and identify the pieces that "pop." These are the items that drive your personal style.
If you have too many "pop" items, time to go back and make sure you have the basics to pull an entire outfit together. If your "pop" items are from last year, are they still in style this year?
If you have too many basics, then time to add some "pop" to your wardrobe. Do not mistake pop for trend but maybe start by picking one particular trend you kind of like and start there.
For those on a more limited budget, a simple statement accessory can do the trick usually for under $25.
A "pop" item I am loving that can go with jeans or black pants, pumps or flats:
Large and in-charge yet both affordable and versatile accessory: