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Congrats on the "new" job Kelly! The shoes in #1 look like they work fine with the straight legs; also like Angie's idea to try a low cuff as well. I've basically abandoned all straight leg pants for exactly this reason, unless they are cut very slim and end on the ankle or above.
The culottes are fab! I'll get you in those culottes with tall boots yet, that'll be a sweet winter look for you dontchaknow
(Oreo is adorable! Love the little pompom bit on that sweater.)