I said previously I never wore socks with ballet flats (all true!) but I have to confess I've been wearing socks with my mary jane flats - http://www.zappos.com/keen-sie.....fee-liquer

Eep! Please don't kick me off the forum! :-P

That being said - I have two dressy pairs of ankle boots - almost stilleto heels, and not suitable for a normal day at home with the kiddies. Can anyone suggest a good ankle boot/sharp loafer to wear with socks and bootcut jeans?

I have difficult feet (bunions, etc) and I don't mind investing in a pair of high quality boots/shoes.

Here are my thoughts:

http://www.zappos.com/frye-car.....-burnt-red
in burnt red or tan

http://shop.nordstrom.com/S/30.....72&P=1
love these in blue

http://shop.nordstrom.com/S/28.....73&P=1
in tan

Couldn't find loafers I liked - but on a completely different - but still casual note - Converse!

http://www.zappos.com/product/7576767/color/1114

(I don't know as these fit the more polished image I want to project, but they're kind of neat, and apropros for the playground)

In general, I'd like to steer away from 'sporty' and aim for funky, tailored, urban chic. Whatever that is! :)