Confession: Style-Challenged

The last couple of items on my list got me to thinking. And thinking got me headed towards a harsh truth. And that truth is that I really don't know how to dress myself.

I mean, I don't think it's What Not To Wear time here, I don't wear acid wash or tapered jeans or horribly age-inappropriate clothing. But I certainly do dress in a boring, generic, somewhat blah and ill-fitting manner.

I think part of it was getting stuck in the "interim clothes while I lose weight" trap, and then plateauing. Because now all my clothes are either way too big or don't fit quite right, but I didn't want to spend any more money until I could buy a smaller size, and so on and so on. So I think I need to suck it up and buy some new clothes. Probably Value Village clothes, but clothes that fit me.

I also don't think I know very much about style. I mean, I know when other people are stylish, but I get overwhelmed trying to figure out how to put things together and what might look good on me.

Any recommendations on blogs/online thingies, magazines I should read? Here's what I like/have realized:
1) I appreciate it when curvier girls rock it out, and would like to learn how to do that.
2) Not everyone who's a size 2 looks good. Not everyone who looks good is a size 2.
3) I love vintage styles, but not looking like I'm wearing a costume
4) I love colours and bold prints
5) I need to learn how to accessorize
6) I love clothes that are a little quirky, or that stand out without looking like they're trying too hard
7) I don't own nearly enough shoes

So I think I'm basically trying to build a wardrobe from scratch. Hopefully my sewing escapades can help with this. But I feel lost.

And can we talk about makeup? I have no lipsticks. Well, I have lipsticks, but none that I wear regularly. I got stuck on the idea that with my big eyes, strong lips make me look a little clownish. Whether or not that's true, now when I wear lipstick, it's all I can see, so I don't know if it looks good or not. I'm pretty unskilled at makeup application to begin with, but am determined to learn.

I want to look pretty, dammit! Anyone have any suggestions on where to begin?