Preschool teacher Diane Lena, 38, has a fair-size vintage collection–mostly mod–but she likes to mix it up with current pieces from new and independent designers. “I feel like I’m a patron,” she says. She breaks out the more radical stuff after hours, when she plays synth and sings with the electroacoustic rock act Istvan & His Imaginary Band. Here, while she admits the pairing of Undesigned’s black bamboo bubble skirt with a black top from Cyndi Chan’s ORi’EN may seem basic, “on a closer look you’ve got these interesting details,” like a keyhole neckline and gathered hem. Likewise Lena chose ORi’EN’s gold trench with magenta lining after noticing some intricate pleating on the back. The necklace, by Objets d’Envy, is agate with a yellow crystal in the middle; Lena bought the hat, by Claudia Skoda, and the vintage shoes last summer in Berlin.

Where to buy

Skirt, $144, at Pivot

Top, $99, at Casa de Soul and Malabar Chicago

Trench, $320, at Casa de Soul and Malabar Chicago

Necklace, $75, at

Art accompanying story in printed newspaper (not available in this archive): photo by Saverio Truglia.