Thinking Outside of the (Shoe) Box

If you read my answers on Whitney's Women Who Work feature, you will have noticed that I'm pretty limited to what I can wear to work. I have to wear pants and closed toed, flat shoes. Since I can't wear cute sandals/heels/wedges, I've been on the lookout for new styles of flats.

I used to wear Sperrys with just about everything while in school (even in the winter, not on a boat). Once I started working I wore my black ballet flats so much that they have holes in the sole.

Not cute. 

I've been trying to branch out to get out of my shoe rut. These penny loafers were purchased a few months ago - they are so soft! Since then I've also purchased leopard smoking loafers and am hoping to purchase these blue oxfords in the near future.

Are you lucky enough that you can wear any shoe you want every day, or are you limited like I am?

Chambray: Old Navy
Jeans: Gap Outlet (similar)
Belt: Forever 21 (similar)
Shoes: Crown Vintage via DSW (similar)
Bracelet: vacation find (similar)