Yeah! Free Shoes! Now what do I get?

I am having a shoe conundrum. It is well known that I am a very thrifty person (which is a nicer way of saying that I'm a cheap bastard) and recently I recieved a $100 gift card to Zappos.com from the wonderful Manolo the Shoeblogger.

Now comes the question of, what do I buy? Originally I thought I would buy a pair of shoes that were just fun, but now the other half of me (that thrifty half) is telling me to go on the cheaper side and get two pairs of shoes that I would actually wear. I think I have narrowed myself down to a sensible shoe (I do not own any black flats, and I think that needs to be rectified) and a more fun, but still wearable shoe (maybe a fun color? interesting cut?).

Here are some of my initial ideas for my new shoes:

The practical:

Dr. Scholl's - Step Up $72.95

The self improvement shoes:

Earth - Allure $112.95, MBT - Sport Low $248.95

The If-I-wanted-to-treat-the-gift-card-like-a-$100-off-coupon shoes:

(left to right) Cesare Paciotti - 9380101 $485.95, Sigerson Morrison - Belle $308.95, Ruthie Davis - DAVIS $283.00