What to Wear: All New Shoes

Jennifer has a fun problem:

I know your list is super long {ed: it is, please wait at little longer to send your requests}, but I’m a desperate woman so I wanted to get in the queue. I recently had a baby (3 months ago). I’ve worked hard to regain my figure, and my old clothes fit again. However, my feet have grown from a size 8.5 to a size 9, and ALL OF MY SHOES ARE TOO TIGHT! I’ve heard this happens sometimes after a pregnancy. It’s weird and it’s permanent. Anyway, I need an entirely new shoe wardrobe. The main workhorses of my shoe wardrobe had been tall black boots and low heeled patent leather black pumps. I need to replace those staples, but I’m also wondering if you had to start all over with shoes… what are the essentials and which ones would you choose? I’d like the choices to be classic, so that all of my shoes won’t permanently date me to 2008.

For money-sense, let’s choose all the classic pairs from one shop (shipping!) and from the sale section:

Flats – I couldn’t get by without a good selection of flats in different colors. My steel gray and wine red pairs are favorites. This green pair would go well with jeans or skirts this spring.
Pumps – A classic black pump is the ideal power-shoe. There really isn’t anything these can’t be worn with. I like one with a bit of a thicker heel, to make your ankles extra slim.
Boots – I only buy pairs that are either flat or with a comfortable stacked heel, otherwise they’ll never get worn. Supplement your tall pair with a flat set that can have jeans tucked in or be worn with casual skirts and dresses. You could hold off until next winter, but there are some good sales right now.
Sneakers – I like Pumas best, but you can rarely find them on sale. These bright chucks are fun for warmer months.

Have fun stocking up!