Megan on Break, Milwaukee Ave

October 24, 2011  |  Close-ups, Individuals, Streetstyle, Wicker Park
Megan

Yesterday I was walking down Milwaukee Avenue in Wicker Park, surveying the streets for someone to photograph when I spotted Megan sitting on the stoop. She was relaxing with a newspaper during her afternoon break. The saturated red lipstick against her fair skin with the black spray painted door was simply begging to be photographed. Plus, taking a great picture is always easier with a naturally beautiful subject.

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.

Cuffed & Camoflauged at Lincoln Center

Lincoln Center 1
I realize I often neglect men’s fashion in favor of women’s. I have to admit, I’m clearly biased in favor of the girls. One might even say prejudiced, but the first step is always to admit there’s a problem, right? I can’t help that I think men’s fashion is, well, boring. Sorry guys. I’m learning to appreciate the subtleties thanks to the boys over at MidweStyle.

This dapper young gentleman has elevated the cuffed pants trend to new heights. With these stylish jeans, the inside is as important as the outside. If you know which clever designer produced these pants, tweet at me (@ChiStreetStyle) so I can add it to the post.