Dressing yourself well is kind of like cooking—some people have a knack for it, other people need a cookbook or they'll burn down the fucking kitchen. There's no shame in needing a little guidance and if sartorially challenged men are willing to ask for help, they'll have a new best friend in Trunk Club, a personal styling and delivery service that picks out clothes that are likely to work for a particular guy (based on his specifications) and sends a box of them to his door at his request. Really crazy: it's free. A flesh-and-blood stylist puts together each "trunk" at no cost. Even the shipping is free. And guys send back what they don't want, no strings. Launched by Bonobos cofounder Brian Spaly in 2010 and operated right here in Chicago, Trunk Club isn't just for the clueless; it's great for guys who are just really busy and guys who actually like to shop, but don't like the undressing and redressing in a hot three-by-three room part.