Study Hall
2016 W. Chicago Ave. 312-733-4255

My latest trip to Ukrainian Village led me to Study Hall, nestled on Chicago Avenue. Fashion-savvy owner Naoko Nagano said the boutique carries vintage and vintage-inspired apparel for men and women and plenty of nautical- and '70s-style prints. "We're less dependent on trends," Nagano said. Though the sleek store features designers from all over the place, Nagano would like to incorporate more pieces from Chicago designers. "We have a lot of great talent here," she said. The name Study Hall comes from Nagano's idea of exploring new themes in a portion of the store each season. "We hope our collections inspire shoppers to be curious about the world and discover something new when they come to our store."

I had a difficult time deciding on just one outfit. The store carries cozy knits, vibrant sundresses and cheeky accessories—all of which were calling my name—but it all came down to this colorful dress (Tulle, $68). This beautifully draped jacket (Yumi, $120) paired nicely with the warm reds and blues in my dress and quirky tortoise-shell sunglasses (Spitfire, $36) punched up my look. I slipped on a geometrical wooden necklace ($70) from New York designer Erica Weiner to add warmth and interest. Last, my own boots and a cross-body bag (Comeco, $32) tied the whole get-up together.

Where to wear it: Shopping, patio lounging, bar-hopping

Tips:

—Break up a loud pattern with different textures such as wool, leather, metal or wood.

—Boots are a great option for transitioning between seasons.