I have to confess, I generally hate clothes shopping. I get overwhelmed by the choices and depressed by the culture adoring disposable fashion and stick-figure thinness. Here's something I did which made a real difference for me.
Figure out a handful of colors that you really like to wear and which look good on you. They don't all have to go together, but they should cluster in a couple overlapping groups so you can make the best use of your wardrobe.
Go poke around in your closets and drawers and note the colors of your favorite clothes. Think about outfits you like that really seem to match up well. (If you're colorblind, have a friend with good fashion sense who isn't help you out with this).
List these colors out and decide on half a dozen you're going to focus on and figure out the ones that can be worn together.
For example, I chose black, red, grey, pale pink and sage green. Black & grey go with everything, including each other. The pink & the green go together well. Red is great with black or grey.
Now when I'm shopping, I'm looking for my colors first. It makes it really easy to scan a rack (or a catalog) and zero in on just a few things that might suit me. It's then very quick to flip through things eliminating things I don't like about the fabric or details ("Too synthetic & shiny", "Too busy a pattern", "Too many fiddly lacy bits around the cuffs"). When something does connect and it's in my price range, I check the sizes and try a few on to find which one for this manufacturer is flattering to me.
Over time, as I do the "turn the hanger around backwards, put it back the normal way after wearing it, and 6 months later get rid of the backwards stuff" trick, I find my closet has largely settled into my chosen colors with a few exceptions, most of them dresses or suits for special occasions, rather than the mix-and-match outfit ingredients.
Shopping for clothes is still not anything close to my favorite activity, but it's a lot more tolerable now.
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