Why would I carry a cute bag when I have a frayed backpack?

OK.  Here are some potential positive aspects of the project to dress me:

I am not poor and am willing to spend money on clothes.  (This will be more true after I put a new roof on my house.  Once that is done, I'll be able to spend money again.)

For someone who wears entirely neutral clothing, I actually have a strong aesthetic preference and am not afraid of color.  You asked about shoes.  I like maryjane-esque shoes and I like shoes with dots.  I don't like pointy shoes because my toes are not pointy.  I can't wear a narrow heel because I'll roll my ankles.  I love piping in general, don't like fussy fastenings.  I have definitely not solved the boots problem.  I looked at the flat boots on that site and the boots with the two elastic sides, and both are ridiculously narrow for my calves. 

Jewelry.  Actually, I quite like jewelry, although I never wear it.  I'm in the habit of taking off jewelry to work out, and then I never put it back on and then I never put it on in the first place.  But I like it and have some earrings and necklaces that I'll put on when I do wear girl clothes.  I either get jewelry in the Garment District in Los Angeles or, oddly enough, at farmer's markets.  That makes it sound like hippy jewelry, but it is more like craft fair booths are making an inroads at some of the different markets I go to.  I don't have any good jewelry, of course.  But I do have sparkly earrings.

Handbags?  I have some, and they are better than no pockets.  But they aren't as good as pockets.  They're so prone to being left behind.

That will have to start you off, hon.  The concept for the rest of it is vague, and by vague I mean hidden in a deep fog on an island far out in an ocean I've never been to.