We just got our first snow of the year in Chicago, so I figured it would be a good time to start talking about some of our favorite things that get us through winter.

Growing up with three sisters, Brian has learned all of the BEST things about living with women, including which designer clothing brands are which. He can pick out a Vera Bradley duffel, Tory Burch flats, Joe’s Jeans, and even remembered that the purse I loved at Nordstrom was Michael Kors. He can quote the Babysitter’s Club movie too, but that’s a story for another day 😉

Despite knowing all these brands, Brian HATES shopping for himself, and the majority of his wardrobe is slowly disintegrating. He has worn one single pair of Timberland Earthkeepers for almost 3 years! These boots have served him well, but they need more than just new soles to survive another Chicago winter.

His sweet mom bought him a new pair of the same Timberland Earthkeepers boots this fall, and the side-by-side comparison is just too funny! Brian wears out shoes like crazy, and after trying multiple brands, we’ve found that Timberland and Vans hold up best for his use. We’ve also found some that definitely don’t hold up **cough cough Chrome**

We were laughing so hard when he put the new boot on, we didn’t realize how worn out the old ones were til we saw them next to a new pair! These came just in time too, since we got our first major snow of the year, at least 5 inches and the entire city is covered in a layer of ice. ugh.