I'm going to deviate a little from my list when it comes to handbags. For year one I will have to aquire two of them, one brown in reptile skin and one black in suede. As it is I have a very nice handbag from the forties already, but it is green.
Green is the colour that hat, belt, scarf and clip are going to be, to combine with brown, so instead of a brown bag I will use my green bag and choose accessories to match it. As for the black suede bag, I plan to sew it myself. I have a very nice book for that purpose, Making Vintage Bags: 20 Original Sewing Patterns for Vintage Bags and Purses by Emma Brennan.
There are patterns and descriptions for bags for four decades, the twenties to the fifties and though there are only five from the forties, I quite like them all. I have made up a few bags as gifts and found the book very instructive and the patterns easy to follow.