I think I am the "winner" (she said dubiously) of this category: I have over 40 dresses.
Now, I am also between sizes and my seasons range widely, so there are always at least a dozen that can't be worn at any moment.
On the flip side, I own 2 pairs of pants (one is part of a suit), 2 pairs of jeans, and 3 skirts (two of which are too big).
April, I didn't own ANY dresses before I joined YLF either. Funny thing what a good style site and losing significant weight will do!