With a prime location in the River North district, Andy's Jazz is a piece of Chicago history. Formerly a '50s hangout for the local newspaper employees, Andy's is known as the spot for authentic jazz music. Not a place for quiet conversation, this place has all the roar you'd expect from a hopping night of live music — and the baby-back ribs to go with it.
Channel Andy's '50s roots with a denim romper and slip-ons, but add a statement necklace to keep it current. Since Andy's is loud already, go for an understated outfit — but with a pop of nail color. It is summer, after all. This outfit will keep you comfy and cute in this busy, sometimes standing-room only venue.
Andy's Jazz Club, 11. E. Hubbard St. (at N. State Street); 312-642-6805.
Clockwise from top left: Rag & Bone Dumont Denim Romper, $275, available at Otte; Marina Fossati Statement Necklace, $211.70, available at Farfetch; Dior Vernis Nail Lacquer in Rosy Hot Pink, $24, available at Sephora; ASOS Clutch Bag With Metal Plate Fitting, $30.55, available at ASOS; DV by Dolce Vita Gulliver Slip-On, $59.95, available at DSW.
Photo: Courtesy of Andy's Jazz Club
If walls could talk, we'd definitely want to listen to the ones at Green Mill. Patterned after Clark Monroe's Uptown House in Harlem, Green Mill offers a sophisticated atmosphere and a rich history of heavy-hitter clients: The jazz bar is Al Capone's former haunt. If you're looking for a more classic jazz experience, definitely check out this Uptown spot. And since Green Mill is strictly booze, it's the perfect after-dinner activity.
Since Green Mill allows for a more feminine look, it's the perfect time to pull out your floral-printed dress. Can't you just see it swaying while you dance? Add the perfect pair of heels, jeweled earrings for an extra touch of elegance, and a bright, coral lip to seal the deal.
Green Mill Jazz, 4802 N. Broadway Avenue (at Lawrence Avenue); 773-878-5552.
Clockwise from top left: Dorothy Perkins Petite Floral Fit & Flare Dress, $29, available at Dorothy Perkins; Wanderluster Snowdrop Stud, $110, available at Wanderluster; Josie Maran Argan Love Your Lips Hydrating Lipstick in Coral Delight, $22, available at Josie Maran; Forever 21 Iconic Quilted Crossbody Bag, $19.80, available at Forever 21; Rupert Sanderson Ivory High Heel Sandals, $295, available at Rupert Sanderson.
Image: Courtesy of Green Mill Jazz
The big kahuna of the Chicago jazz scene, Jazz Showcase is a must on your local bucket list. Since 1947, the Showcase has been home to some of the biggest names in jazz, not to mention some of the best nights out on the town. We recommend getting your tickets in advance.
Since Jazz Showcase is the big leagues, it's the perfect opportunity to broaden your horizons. Combine a sleeveless button-up and fedora for a menswear-inspired look that doesn't scream zoot suit. The silver oxford also gives a sartorial, but feminine, nod to the men's wardrobe from which you're pulling. And since you won't be needing an arsenal of supplies for a night like this, stick with a clutch to keep things simple.
Jazz Showcase, 806 S. Plymouth Court (at W. Polk Street); 312-360-0234.
Clockwise from top left: Mossimo Women's Open Front Blazer With Faux Leather Trim, $29.99, available at Target; Elizabeth and James Jayna Sleeveless Shirt, $202.13, available at My Wardrobe; Forever 21, Woven Fedora, $14.80, available at Forever 21; Anna Sui Lace Eyelet Shorts, $255, available at Stylebop; Candela Perf Diado Oxford Flats, $127, available at Saks Fifth Avenue; Zara Three Flap Crocodile City Bag, $79.90, Zara.
Photo: Courtesy of Jazz Showcase