Chloe, Oak Street in the Gold Coast

Chloe flare CU

Chloe flare half

I already thought Chloe was cool as hell for her off-kilter approach to traditional American prep-school fashion. But when I saw she came complete with accurately monogrammed sweater (CB are her initials), and heard that she even added the feather details to the hat herself, I realized I had come across one amazing individual. If only everyone in Chicago had the courage to take a fashion concept and twist it to make it their own, my job would be so much easier!

Leah, Archbishop Quigley Center

October 26, 2011  |  Gold Coast, Individuals, Rush Street, Streetstyle
Leah

I’m always intrigued by people who manage to make monochromatic looks feel interesting. So often, all black outfits seem tired and boring. By the same token, overly colorful outfits can feel like the wearer is trying too hard. Great style is all about finding the happy medium, and that’s where Leah’s outfit lands. I need to get a hold of some new tights for fall – how cool are her striped ones?

Elizabeth (The Saga of Leather Boots)

October 23, 2011  |  Gold Coast, Individuals, Rush Street, Streetstyle
Elizabeth
Elizabeth’s autumnal color palette could not be more perfect for fall, with a deep pumpkin orange, mustard yellow, and burnished brown leather. Her delicate lace dress contrasts magnificently with the worn boots and braided belt. I love when objects develop a patina from heavy use, or more euphemistically, “love.” Leather boots are especially good at acquiring a record of where we’ve been. Scrapes, scuffs, and stains inevitably develop with time. Battle scars. The marks they earn serve as a record of where we’ve been, and deserve to be celebrated for the personality and authenticity they bring to any look.

This is why I believe every woman needs a pair of perfectly worn in leather boots for fall. Preferably broken-in herself, but a vintage pair will do just fine. Kokorokoko in Ukrainian Village has tons of amazing pairs of high quality vintage leather boots at great prices, so you should definitely check them out.