Fashionably fashionable

I'm not fashionable, by any stretch of the imagination.  It's not that I don't want to be fashionable.  I would like to look put together and not like a complete slob.  I've been sporting that look for many years, and it's time for a change.  There are two roadblocks on my path to fashion.  1) I'm notoriously cheap.  I would say "frugal," but that puts a positive spin on my condition.  I feel ill if I pay full price for clothing, even if I need it.  Intellectually I am aware that you get what you pay for.  I still have great difficulty paying more than $10 for a T-shirt.  2) Body shape.  I'm not trying to be a size-zero-runway-model.  I'm fine with being a size 10.  My problem is my middle.  This is where all the extra weight congregates and invites extra weight from other people to hang out and play Bunco.  Because of this, I don't feel comfortable wearing close-cut clothing (say that five times fast!).  Then I'm forced to buy baggy clothes, and now we are back to the slob look again.  To be trendy, one has to be on the thin side.  I saw a woman today, rocking the super high wedges with skinny jeans and a plaid fedora.  Her issue: muffin top.  Confidence is part of rocking an outfit.  My muffin-y goodness does not need to be seen by the world, and hence, I have no desire to be trendy.  I do want to be fashionable.  I want timeless pieces that look good on me and just look good.  If I can find some way to reconcile my two issues (comfortable clothes at a reasonable price), I would be a happy, less-slovenly woman.