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Women of Style 2018

By Ariel Cheung, Laura Hine and Jaclyn Jermyn

Portraits by Kevin Penczak | Styling by Kelsey Oenick | Shot on location at St. Jane Hotel


These five Chicago mavens are ready to take on the world—and they look endlessly chic while doing it.

This design master started her luxury shoe line, Kendall Miles Designs, at 21 years old. Now she’s walking tall, splitting time between her native Chicago and New York City.
My first big fashion splurge was... a pair of white patent leather Manolo Blahniks that I bought with money I saved when I was 14. Those were probably about 4 inches. From there, the heels only got higher.
When considering a purchase... I gravitate toward higher-end things because the silhouette matters, and that just takes a certain level of expertise. I think Tom Ford does a great job with that.
I can’t wait for an occasion to wear... a Christian Lacroix piece that my dad bought for my mom many years ago, which she gave to me. It’s really a jacket but it hits me like a short dress, and it’s so beautiful. It’s such a special piece to me.