Alice, by the Historic Water Tower

Alice"
TopShop Employee 2 armparty2
Alice necklace

Forget leopard print, how about dairy cow print? And add in a bright red collar to keep things quirky yet fashion-forward. I love all of Alice’s woven bracelets too; they’re a nice contrast to the metal necklaces around her neck.

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?