What to Wear: Shoe Challenged

Jessica struggles with finding shoes for a couple reasons:

I was hoping you could help me out with a wardrobe problem of mine. I would love to get some new, winter friendly shoes (I have about a ton of ballet flats, but they leave my feet frozen!). I’ve been going to stores and wanting to buy some great boots, ankle boots, etc. but I can’t seem to find much of anything that is right. I need some things to wear with jeans, skirts, dresses, slacks, etc. Here’s where I run into trouble: I am 5’5″, a size 6, wear a size 11 shoe (so anything remotely chunky is out of the question), and due to foot injuries I can only wear flat shoes. My budget isn’t gigantic (I’m a newlywed college student!), but I really need something.

A couple tips before we get started: Payless is a great source for affordable shoes in sizes above 11. And don’t forget that you can wear trouser socks with those flats for extra warmth. I understand the injury situation, I have had to wear flats and wedges ever since my back problems started. Here’s my suggestion:

Boots – J.Crew goes up to a size 12 online. A sturdy pair of flat boots will serve you well for many years. It’s an investment (Christmas present?), but one that pays off. Great with skirts, pants, tucked in jeans. Try them on in person and compare with boots at Nordstrom, Target, etc to find your perfect pair.
Sweater – From Old Navy. I have this sweater.
Tank – Mine has silver beads around the neckline for a little extra flair.
Jeans – A nice dark pair.
Bag – From Nine West on sale.
Earrings – Little beaded drops from Anthropologie for $28.

Stay warm out there Jessica!