I'm rather frugal (student budget!), but was told I needed a pair of good real leather boots to survive my first Iowa winter (originally a Cali girl) because the salt they put on sidewalks after it snows wears synthetic materials quickly. Debated a lot whether to buy these boots (which I wanted SO bad) because of the price, but now that I have them 100% worth it!!
1) I get compliments on them constantly from strangers and friends, alike.
2) Since it's real leather, any scuffing easily comes out with basic brown shoe polish (look brand new after some heavy usage).
3) VERY comfortable for walking all day.
4) Casual enough to wear to class, nice enough to wear out on the town.
5) I followed reviews and ordered a half size up (7.5) and was initially upset that they were so loose. However, now that it's actually winter, they fit PERFECTLY with thermal boot liners (try Steve Maddens knitted ones for the best look). Since their intended purpose was for winter, I guess I can handle a lit extra room in the toe during spring/fall in order to accommodate extra layers in the winter. Even debating buying a second pair (another +$200?? gasp!) in a different color (size 7, this time) to wear more comfortably with thinner socks during warmer weather.

For the same price you can buy 3-4 pairs of synthetic boots that will likely wear out after one year of heavy use or you can invest in a classier pair of real leather FRYE boots that will last much longer and look/feel SO much better. I went with the latter and have never been happier with a purchase!