Peri, I have trying to use a seasonal approach to some of my variety and also "seasonal discipline" (well, discipline is a stretch, but it's a concept, at least).
For my figure type, winter mostly means not-very-tapered pants, and hemming them long enough to wear out over booties and shooties to get a longer legline so I don't look so schtumpy, and similarly concentrating on several good pairs of comfortable ankle boots in my basic colors.
I can experiment with ankle or tapered pants in the summer.
Yes, I like the fun look of tweed ankle pants, but that is more seasonally confused for my cold-natured self and also a huge footwear challenge.