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Comfortable Women's Boots

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Has anyone else noticed how uncomfortable women's boots (the ones that look nice and not like hikers) are?

I want to find a good, fashionable, ankle high pair that is weather proof (or at least weather resistant) and also offers support that you can walk all day in.

Any suggestions? I'm having a really hard time with this one. I tried LLBean and they have hard soles. No room for insoles either.
My trip to Amsterdam and London is coming up and I want to be able to break them in before I go.
I'm all ears (or in this case, eyes).
Thanks!

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