This may sound a little off, but if you know each piece of clothing front to back, you'll be so much better off. You should know the following things about each individual item in your closet:
The fabric and designer.
- Colors it looks best paired with.
- What style of clothing it looks best paired with (long, short, fitted, loose).
- The right accessories and shoes with it. This knowledge will help you know what your wardrobe is lacking and what your most-valued pieces are. It will help keep your wardrobe organized. Keep the information on record and in order with pictures, sketches, lists, or a database.
If you're really set on looking great day after day (and you're willing to put quite a lot of effort into it) I suggest planning ahead and keeping track of your daily ensembles. This works great during school-months or for planning vacations.
Get a notebook or calendar that can be solely devoted to describing and recording outfits. This eliminates trying to remember when you wore an outfit last ("Did I wear this the other day? Last week?)." Instead, you'll have written records to look back upon.