I own a lot, like 20+ pairs, and I just got rid of several pairs. Your post is making me think about them critically though instead of just leaving them on the rack in the back of my closet. I need to get rid of some that I never wear. But I have about 5 pairs that I wear regularly:

1. Black leather waterproof boots get worn 90% of the time between fall and spring
2. Black leather oxfords for fairer weather
3. Blue New Balance trainers, "classic" style for more casual wear
4. Birkenstock Gizeh sandals for warm weather
5. Gym shoes, right now they're New Balance but I like Converse for lifting too

Shoes I wear sometimes:

1. Green pumps for dance
2. Blue strappy pumps I picked up in Italy
3. Blue sparkly pumps, my wedding shoes that still get worn out occasionally
4. Fluevog wedges
5. Black leather booties
6. Sorel boots for snow/ice days
7. Super tall strappy platform sandals required for a couple of maxi length dresses so they don't drag on the ground

Shoes I should probably get rid of:

1. Pink Fluevog "Lover" boots
2. Blue Fluevog pumps
3. Strappy silver pumps that are incredibly uncomfortable
4. Brown leather Fluevog oxfords
5. Vintage brown leather boots
6. Knee high Cole Haan boots. I never wear them, they're not comfortable enough to walk to work in.
7. Black Badgley Mischka pumps that are half a size too small and just downright painful
8. Sorel rubber wellies. Not comfortable enough to walk to work in, too heavy/clunky, so they kind of defeat their own purpose of being waterproof rain boots.