Best High-End Men's Clothing Store

This Gold Coast shop runs a no-frills website: The sole description is “George Greene is a men’s clothing store.” The clothes, on the other hand—Missoni, Chrome Hearts, Yohji Yamamoto—are for the rare peacocks among men who are decidedly unafraid of frill. The three owners work with clients all day, every day, fitting them in slender … Read more

Best Men's Clothing Store for the Money

If you want to look sharp without being mistaken for a Eurodude, zip to sisters Sarah and Amy Blessing’s Bucktown boutique. The expertly curated mix of smart-casual clothes—slim John Elliott sweatshirts, Thom Browne tapered trousers, chunky Maison Margiela crewnecks—will nudge you just far enough outside your comfort zone.

Best Running Shoe Store

This chain’s innovative shoe-fitting system gives it the edge. After a computer analyzes your weight distribution and arch height, a staffer will watch your stride on a treadmill, then recommend the right shoe. Road Runner stores the data, the better to serve you next time.

Best High-End Hair Color

For natural-seeming highlights, the pros at Maxine are worth shelling out for. They’re masters of balayage (from $200), a technique in which color is hand-painted on individual strands, leaving you looking sun kissed, not streaky. The sleek white space feels as luxe as the Kérastase products they’ll massage in during your postdye blowout.

Best High-End Haircut

With 11 years of experience styling guests and performing makeovers for The Oprah Winfrey Show, Ingrid Trevino now has one of the most coveted chairs in the city. She can create red-carpet-ready long layers, of course, but she’s equally masterful with short, precise bobs (from $155). A killer blowout from a recent visit lasted for … Read more

Best Men's Waxing

Hair on your back, chest, nether regions—whatever you need removed, this is the place to have it stripped off. Men’s Health and Bravo have named the chic salon in Lake View one of the best in America, no doubt for its (almost) painless hair removal and friendly staff. Waxing runs $25 (abs) to $300 (full … Read more

Best Mani-Pedi For the Money

As SNL’s Stefon might say, this studio has everything: vegan-friendly polishes, 500 no-chip hues, technicians who specialize in durable tips and toes, and free wine. (Repeat: free wine. If they don’t offer it up front, just ask.) Walk-ins only. Manicures start at $18; pedicures at $35.

Best Pet Supply Store

Snow boots for cats, the world’s strongest catnip cigar, $112 sterling silver dog tags: This place is easy to poke fun at. But owner Alice Lerman matches frippery with function by stocking healthful foods and heuristic playthings (see the line of Swedish-designed interactive “enrichment puzzles,” more or less Rubik’s Cubes for dogs). 

Best Place for a CrossFit Workout

The first gym in Chicago to offer CrossFit, the full-body workout that draws from weightlifting, plyometrics, gymnastics, and pretty much every other fitness trend out there, this one reigns supreme. Why? Its 75-plus classes a week (more than anywhere else in town), thoughtful one-on-one assistance (goal-setting sessions, nutritional education, body composition analysis), and slow, safe … Read more

Best High-End Tailor

This 54-year-old family business specializes in bespoke suits and other garments in the world’s most luxurious fabrics (Dormeuil mohair, Loro Piana cashmere). Balani’s obsessive attention to fit has attracted such clients as celeb chef Graham Elliot and former Chicago Bear Israel Idonije. Prices range from $125 for a custom dress shirt to $30,000 for a … Read more