When did I become obsessed with the low boot?  Last summer’s stacked-heel desert boot was a gateway shoe, and from there it was the low biker boot for winter, the low scuffed boot for spring, and now the low cowboyish boot.  And of course I am obsessing over the classic desert boot for fall, but enough has to be enough at some point.
Anyhoo, I am rocking these from Madewell all the time these days and recently spotted a woman wearing them to perfection with a Proenza Schuler-ish shift and a big old sweater — pushing a stroller with a Birkin bag thrown on the handle, no less!  This would be my (more budget-friendly) version of the outfit.
Madewell booties 
Zara Tunic Dress

Anthropologie Cardigan
Lanvin sunglasses

Banana satchel
Bugaboo Bee stroller