So I think I may have figured out why it's such a big deal to me that I actually have a jacket, and will be dressed all fancily, rather than just throwing a shawl over my shoulders and saying "good enough". Logically, it would induce less guilt to dress well enough with a new dress than to buy a new jacket AND a new dress to be dressed well.
Now that I have the basics that everyone agrees on, here's where I will start being confusing. I had been really distressed by the idea that I wasn't going to be dressed well. And yes, the fact that I care that much about my clothing is quite sad. I was distressed to the point where I had, for a while before ordering a bolero, been looking for a jacket to wear. And the lace shawl really is ok... I wear stuff like that all the time.
I think that the key idea here is that if you're going to do something questionable, then make it worth while. Yes, normally buying a new jacket when it's not actually necessary is bad. And yes, obviously buying a dress that I might not wear more than once or twice (with that knowledge when I buy it) is obviously horrible. However, while logic might say that doing both is going to be worse than doing either, it doesn't quite work that way in this case. It's as if I was going to buy some fruit from South America. If I buy apples, which are easy to grow and nothing fancy, then that's worse than if I buy a mango, which I can't get any other way, right? (I sure hope so). I'm aware that it doesn't really change the fact that I bought foreign fruit, but at least I got something worthwhile out of it. Same idea with the jacket. Buying it doesn't change the fact that I bought a new outfit (from overseas at that), but it at least means that the new outfit is more worth it than it would be otherwise.
Now, even if this does make me stress less about caring about that, I still have to accept the fact that I am far too concerned over my clothes...