Estelle

Outfit details: ASOS jeans, Rag & Bone Newbury boots (snag a size 8 on consignment here!) , cashmere sweater, Everlane bag, Céline sunglasses, vintage belt.

When you don't know what to wear, sometimes you can have great luck with a monochromatic outfit. It can make you consider pieces you would normally never pair together, and head-to-toe color is quite striking.

I'm channeling either Andrew W.K. or a santeria inductee, whichever you prefer. Top it off with a cozy cashmere crewneck and trusty heeled booties and you're good to go.