Street View is a fashion series in which Isa Giallorenzo spotlights some of the coolest styles seen in Chicago.

Dressed up or dressed down Zachary looks equally dapper, thanks to the fit of his garments and his kempt beard. Plus the dude can accessorize, starting with those charming hats. Recently I was leafing through Esquire and came across these New Rules of 21st-century style. Here are some that Zachary has down pat:

—The upper-left-hand quadrant of your torso is your sartorial sandbox. Lapel pins, pocket squares, et al. are all toys for the tinkering.

—Potential upside to clothes that actually fit: instant five-pound weight loss.

—A well-tended beard is not any more kempt or unkempt than a clean-shaven face. It is a matter of comfort and ease.

—Men who wear ties to the office even though they don’t have to are three times as likely to run the office someday as those who don’t.

—Rather than shine or width, the new breed of power tie has texture and depth.

—There is a difference between looking like you care and looking like you are trying. You want the former.

—Stop thinking about what you should wear and start thinking about who you want to be. Your clothes will fall in line.”

(Excerpts taken from Esquire, written by their fashion editors.)

  • Isa Giallorenzo

See more Chicago street style in the Chicago Looks blog.