L.L.Bean Vest, Flannel Shirt and Boots (SO comfy b/c of the tumbled leather. Here’s my winter pair.) / Ponte Seamed Leggings (My go-to pair!) / Emma’s Sweater, Cords, Boots and Barbour Jacket / Mitch’s Flannel Shirt and Similar Barbour Jacket (Here’s mine!)

Mitch here!

Kelly can’t drive. To be fair, she technically has a license… but for the safety of Chicago residents, she shouldn’t. While I love her to death, Kelly behind the wheel is like the T-Rex from Jurassic Park emerging from the brush. There’s mass destruction, everyone runs away, she can’t see anything, and she has very small arms. It’s not her fault, though. She moved to the city right after college, so the last time she drove on a regular basis was in 2006. (Fun fact: contrary to everything I just said, Kelly is excellent with manual cars. Back in New York, she learned how to drive stick in no more than five minutes, and drove our roommate’s manual car up and down the FDR on her way to the Bronx for several weeks while I had jury duty. Got her back in an automatic and was a disaster again. It doesn’t make sense.)