Wes

Wes

Wes is rocking the grassroots trend to wear sneakers without laces. This trend actually led one fashionista into a run-in with homeland security police on the CTA Redline. According to ChicagoNow, the police identified the man as a “security risk” because recently released prisoners often wear shoes without shoelaces, which are classified as a dangerous tool by jails and prisons. Chicago police detective Andre Watkins discussed the new style, saying in the article that the suspect “brought a fashion trend to my attention.” No need to worry about Wes, he was on his way to Lollapalooza and performs with a local band.

Rachel

Rachel_Crop

Rachel is wearing square-framed glasses, original Sperry Top-Siders, acid wash denim shorts, woven leather belt, plaid short-sleeve button-down shirt, feather charm necklace, and a long strap leather purse. I photographed her outside of the Gold Coast Urban Outfitters.

Tyler

Tyler

Tyler’s eloquent style instantly caught my eye. He is wearing freshly polished dark leather boots, gray tailored pants, and a sheer jersey tee shirt. He is also carrying what looked to be a handmade leather backpack. His look captured my attention because he is so present while looking stylistically as if he belongs in nineteenth-century Chicago. If he were a literary figure I’d place him somewhere between a Charles Bukowski poem and an Upton Sinclair novel. This, the presentation of a character, is what great style is all about.

The style pendulum is swinging away from the lazy and causal looks favored by the Boomers, for whom a status symbol is to wear jeans in their professional workplaces (see Steve Jobs), towards the tailored and fitted looks popular before the cultural revolution of the 1960s. Many of the designers (Marc Jacobs at Louis Vuitton) presented collections inspired by more “conservative” eras like the 1950s. Although they’ve been calling it the “Mad Men Effect,” emphasizing the top-down direction of this trend, trendsetters like Tyler have been leading the move towards the tailored aesthetic on the streets for several years now.