Hi all: it's been a while!

When I started here back in the dark ages, my everyday work look relied heavily on neat jeans in dark washes — first ankle-length skinnies and then demi-crop flares, both from J Crew, in which I had multiples on heavy rotation. This served me year round: I'd go sockless in the warm weather and shoulder season and then switch to booties in the cooler months.

As pants have relaxed in the past years, I've embraced wider widths and slouchier shapes and have embraced Angie's principle that trendy denim looks elevated. (It's true!)

But as cooler temps are upon us and I'm struggling with a couple of things:

1) What shoes to wear with floor-length and/or pooling denim in cool weather? Is there any kind of boot that can go under a silhouette like this without feeling too heavy?

2) What is the a modern-day equivalent of the neat jean in a dark wash? I've been looking for wider shapes in dark washes and coming up empty. Help!

Posting finds below of old and new styles from my closet.