Three jeans-loving editors had their attempts at workwear critiqued by Cerato Boutique stylists and the head of a consulting office. Tip No. 1: easy on the leopard print. Groupon’s editorial employees wear a lot of jeans to work. It’s fair to say we’re more “casual” than “business casual.” However, we know that for most people, dressing for work is a unique fashion challenge. To investigate the intricacies of “business casual,” we performed a simple experiment: first, three editorial employees put together outfits they felt represented traditional workwear, each dressing for a common workplace scenario. Then we asked office-fashion experts to critique the outfits. Our Panel of Experts: The Boss: An anonymous power player who runs an office of a large, international consulting firm Tracey Glibowski: Owner of Cerato Boutique (3451 N. Southport Ave.), a boutique CBS named one of the best places in Chicago for office wear Sarah Hinman: Assistant buyer at Cerato Alyssa Petersen: Personal stylist and founder of Cashmere & Wit Amelia, Dressed for a Regular Workday of, Like, Eating Faxes in a Cubicle Fort Amelia’s outfit: J.Crew cardigan and necklace; Banana Republic sheath dress; Payless flats; Kate Spade earrings; BonLook glasses. Amelia: “I have a box in my closet labeled ‘alternate-universe business casual clothes.’ ... This box is very small. It mostly just holds this gray dress.” In general, Amelia recoils at the idea of businesswear. “Mostly because I hate ironing.” The Boss: “For my office, this would be a perfectly appropriate outfit for every day.” Her only caveat: try to wear “real shoes, by which I mean not flats.” Even a low heel adds polish, she says. Sarah Hinman: Sarah says pieces that mix and match easily, like Amelia’s sheath, are the cornerstones of any work wardrobe. She thinks leopard print might be a bit too bold, though, and recommends a cardigan in a solid bright instead. Amanda, Dressed for an Important Presentation about Business Things Amanda’s outfit: Rachel Comey booties; A.P.C. skirt; Madewell sweater and jacket; her trusty water glass. “I overheat like an old laptop when I get nervous, so I always have water around in high-pressure situations,” she explains. Amanda: “I genuinely like this skirt, even if it’s a little out of my comfort zone.” (She usually works in skinny jeans.) Also, she didn’t blow-dry her hair. “I don't do that ever, not even for pretend business presentations.” The Boss: Although this outfit is built from classic pieces, the Boss thinks the skirt looks stiff and a little too short, creating what she dubs a “schoolgirl-y” vibe. She suggests a skirt that’s 2–3 inches longer, in a more flowing fabric. She also notes that “the stacked heel on her boots makes them more informal than boots with a matching [covered] heel.” Alyssa Petersen: She agrees that the skirt could be longer but commends the blazer for its comfortable fit. To add visual interest, she recommends a not-too-sparkly pendant necklace, like those from local jewelry houses Susan Elizabeth Designs or Ali’s Collection. (Both have pieces available at Cerato.) Michelle, Dressed for a Job Interview with an International Paper-Clip Holder Magnate Michelle’s outfit: Zara pants and button-down; Guess pumps; necklace from Goods; vintage rings. Michelle: “I'm a creative, so I didn't want to walk into the interview looking like I'm going to a funeral or to court.” She hopes the color-blocked button-down and pumps are enough to keep it professional. The Boss: She likes the shirt and shoes but recommends adding a blazer. “If in doubt, wear a suit,” the Boss says. “You cannot go to a professional environment for a job interview (consulting firm, law firm, accounting firm, bank, large corporation, for example) without covering your hips. I don’t know why.” The pants, however, are a little too informal for her taste—she would prefer pants tailored to a cropped length, rather than cuffed. Tracey Glibowski: She agrees that a blazer might make this more appropriate (she recommends Cerato’s selection of blazers by BB Dakota). She loves Michelle’s pant color, though—“It's a beautiful blue that's refreshing to the typical black interview outfit”—as well as her simple jewelry. A Few Final Pro Tips  Keep it covered every day: “You want to make sure your clothes cover your shoulders,” the Boss says. “Neither your undergarments nor any lack of undergarments [should be] on display.” Minimalist jewelry is best: Tracey loved Michelle’s simple accessorizing but warned that something like a sleeve of bangles can result in “too much jingle.” Don’t dress for anything other than work: “You [shouldn’t be] attired to participate in a sporting event, barn raising, or ballet recital,” the Boss says. Wrinkles are your nemesis: “As a general rule of office attire, I would encourage everyone of all genders to purchase an iron and learn how to use it,” says the Boss. Photo: Mae Rice, Groupon