Very cute! I think Lindy Bop is a great company for those who are interested in trying the vintage style or wanting to start slowly. They are affordable and have a nice size range! I end up referring a lot of people there who are starting out.
You could start slowly with a fit and flare style. You don't have to be a size 8 anymore to wear them and look good. I'm like a 14 and it works well. In some cases, these dresses have a lot of heavier fabric that hides lumps, over a light jersey. Do research on your shoes 1st and match to them. For example, I think wedges are 1930s or 40s. Rounded toe (I trip over pointy toes in my size 10 shoes!) with a moderate heel that's neither stiletto nor very blocky granny heel. There's some ideas that don't need to look vintage, necessarily. Short sleeve button down shirts, for example. That can go either way. Don't overlook having things made for you. There are sweaters from Italy and heartmycloset on Etsy. It's not expensive in general and it'll look great.
Very pretty items. I have written to LB to collaborate, they told me to write back in the Fall. So if you have any tips....You looked wonderful in everything.