I Love Questions!
If I have to start from scratch what are some things I ought to start with?
She goes on to say what her style personality type is, and that makes alot of difference, but in addition one must consider lifestyle. What do you do everyday? If you, like my friend with the little ones, want to wear jeans everyday, well, you had better start there. Why not do the uniform template project this weekend?
(Last May, in Frugal Mom Wardrobe Basics, I described some items which would be first on my spring list. But I took so much flack for the leisure character of my suggestions that I followed up with the well-received Frugal Mom Classics. While these were written going into summer, they may inspire a few going into winter ideas.)
For Fall, I try to work with a uniform template that just combines pieces from other seasons.
So, Mrs Meg, do you like to wear jeans or skirts everyday? Regarding the fit problems you mentioned, some are probably eliminated by skirts. The fabulous Clinton Kelly and Stacy London are big on recommending tailors as well, but then I get the impression you have skills.