Stop don't do it. Outfits, or head to toe looks are not even sorta cool, besides it really does age your look.  Don't walk into a store and buy a complete outfit, instead mix it up it's much more fun and much more interesting. Here is an example. Take a simple sweater paired with a skirt or pants, add some amazing accessories such as a big statement necklace, a pair or attention getting earrings, or a vintage handbag, then strut your stuff. Try mixing a cheap t-shirt with an expensive skirt or pants, then add pearls and a cool handbag. Think out of the box, ask yourself what a woman in Paris or New York would  do. Never be afraid of mixing items you love, chances are you will feel comfortable and confident that way and others will feel it too. Don't take clothes seriously have fun with them.