ETA: M., your SWH was one of the best I've read in a while! (Usually, posters get yelled at. :) ) I'm so glad some of us could help and give you ideas. And you know, if you really like to pick up those fifty-cent items at garage sales, do so-- and then donate them to a women's transitional housing/shelter which serves women and their families. Those children--boys and girls--are in desperate need of 'nice' clothes...some of them leave their homes with next to nothing.... Good luck on this new way of doing things!
Mama, time to take control.
When you shop, pick out her clothes for her. Kids are very mercurial and will like something one day and reject it the next--- even favorite things. This way, you will not be frustrated with her not wanting to wear clothing she's chosen. (By the way, I don't remember getting to choose any clothes until I was about 8 or so, so this may be more than she can deal with.)
If it were me in this situation, I would have her do one of the following:
1.Pick out the following day's clothes EARLY the day before. Before bedtime, before dinner if possible. This is to avoid any 'prolonging bedtime' situations and frankly, by the end of the day, none of us are at our best.
2. Have her pick out the outfit and wear it to bed in lieu of pajamas. It's already on, no fussing in the morning. Even if it's wrinkled, it's not a big deal. She'll wake up dressed and you will avoid a conflict you don't want to have. (I let my son do this, by the way, and it works wonders!)
Here's the thing: adults sometimes have perceptions about things that children simply do not have. Pretend her closet is a well-stocked pantry... you are likely not going to be in the mood for everything in that pantry all the time. I say this lovingly, but kids are weird (from our perspective) when it comes to clothing. My son will pick out fleece sweatpants on an 80 degree day because that's what he 'wants' when he looks in his drawers.
If you think your daughter has too many clothes, then pare down. I like the idea of offering two choices, personally, for tops or bottoms. Kids don't really need more than 6 of anything if we're doing laundry often enough. Some kids do want to wear the same thing daily, and sometimes that means buying two of something, sometimes that means they must cooperate and change into other clothes earlier in the day so what they are wearing can be washed. Considering she's going into kindergarten, which is a big unknown, I would choose the option that works for both of you in regard to autonomy for her and a certain level of housework for you.
Lastly, just because I noticed this in your post, be sure to find other things about your daughter to enjoy besides her being cute, and share them with friends. Too often, girls are raised with an inescapable emphasis on 'looks'. I'm not saying that you, personally, are going overboard, but when we used to get a lot of 'he's so cute' comments about our son, I tried to change those conversations to reflect areas *he* was proud of: his interests, progress or accomplishments. Here's something from Mama's On Call worth reading... it might be worth sharing with family that dotes on your little girl.
http://mamasoncall.com/2012/06/how-to-talk-to-girls/