5. The flat
Example: Dr. Scholls "Habit"
"I still care about looking cute, but god DAMMIT I will be comfortable."
4. The winter boots
Example: Target tan $20 boots
"God DAMMIT I'm going to be comfortable, even if I look unprofessional."
3. The high heel with pointed toe
Example: Claret by Big Shoes
"I'm super feminine, have a great sense of style and I'm going to show it."
2. The high black boots with chunky heel
Example: Siena, by Chic Petite
"I'm going to look cute, be comfortable and be authoritative!"
1. The high-heeled-high-black-boots
Example: Black Suede by Hattie and Mag
"I'm going to be chic, look sexy, not be comfortable, and attempt to be authoritative."