Photograph: Nathan Kirkman

1. Paired with a gold-flecked blouse, the voluminous faille bubble skirt by Doris Ruth wears like a dress. The look is feminine and playful-and cocktail-party perfect. Says designer Allie Adams: “It’s a statement piece.” Top, $178, and skirt, $278, at Red Head Boutique, 3450 N. Southport Ave.; 773-325-9898

2. “I was inspired by a dress my mother wore out for a special Saturday night when I was little,” says designer Lindsey Boland. “I can smell the Chanel No. 5 just thinking of it.” Each flutter-sleeved, Empire-waist creation comes with a removable vintage brooch for pinning at the bottom of the low-cut V. $160 at Habit, 1951 W. Division St.; 773-342-0093

3. Leave it to Orlando Espinoza to offer a lesson in understated elegance. What appears to be a simple long-sleeved dress actually boasts folds of ruching that undulate across the bust and the upper back. Says Espinoza: “A dress should not be overembellished or overpowering.” $440 at Malabar Chicago, 1880 N. Damen Ave.; 773-321-6685

4. Lara Miller had tuxedos on the brain when she designed this convertible number that has the “formality of a tux and quirkiness of a bow tie.” Leave the ties loose or wrap them in various configurations: behind the shoulders, crisscrossed in the back, or around the waist like a cummerbund. $368 at P.45, 1643 N. Damen; 773-862-4523

5. Despite Michelle Tan‘s attempts at imperfection-from jagged, unfinished seams to the flip-up bib-her adjustable frock is faultless. It looks best with the apron pulled up and tied around the neck; this style exposes the obi-like waistband and the wide, flat pleats of the A-line skirt. $250 at Michelle Tan, 1872 N. Damen; 773-252-1888

6. No need for a necklace; Shane Gabier has sewnvintagebrass chains into the front yoke of his gauzy tunic. “It can be totally A-line or gathered at the bottom,” says Gabier, who was inspired by sixties communes in California. The result: a look more Edie Sedgwick than counterculture hippie. Wear with leggings and heavy wedge shoes. $320 at P.45