I don't have too much trouble these days... but it took me years to learn a couple of lessons: 1) Know the difference between clothing and costumes, and 2) always try things on before purchasing them.
I'm with you about Coldwater Creek, and I don't need to try them on to know if they'll fit. But trying them on and seeing how they look ON ME does make a difference.
In my town we have really good thrift stores, and that's where I do nearly all my shopping, because my clothing budget is zero. (That's where I find my C. Creek things.) When you shop that way, you *have* to plan ahead. What I could use in summer I'll usually find in winter. (You're doing something like that at the clearance rack.) So I go for a classic style rather than a trendy one. I have a couple of pairs of dress pants, and I pick up a-line skirts when I can find good ones (because I can't wear straight skirts).
I try to get pieces I know will fit right in the mix and go with what I already have. Right now I'm finding good scarves to use as accessories, too. Sometimes I will put an outfit together and set it apart, not wearing those pieces with any others, so I know I have a whole ensemble ready.
Knowing the difference between clothing and costumes has helped me not to impulse-buy many things that would not work in "real life." It may be beautiful, but it has to be able to go where I go. If it just hangs in the closet looking cute because I don't really have a place to wear it among my friends, why did I spend that money?
So I can usually get myself dressed fairly easily, and I dress up the outfit or not with jewelry or other accessories. The exception to the rule is a really-special-occasion event. My daughter was married last summer, and I spent three hours at a department store trying everything on and spending REAL money for what worked best. I wanted to shine as a mother of the bride, and I think I did! But that dress will also work for someone else's wedding or a fancy party for at least the next couple of years. I try to keep up with style changes, but I love it when I can get away with wearing a piece for years.
When your order comes, fix your hair, put on some makeup, try all your new things on (with more or less the right shoes), and look at them as if the woman in the mirror weren't you and didn't buy them on sale. We can usually be more objective about others. Do you think that woman ought to wear that dress? Does it fit well? Is it "her"? If you try to rationalize for her, send that piece back and hold out for something better. You'll find it.
P.S. You might try changing your everyday habits and wearing something that isn't a T and jeans just to do your errands. It will help you think outside the box and handle your wardrobe better. And it might shock your family, which can be a good thing....