The collection runs from the hip length Halsted jacket to the knee length Southport, the calf length Mag Mile overcoat, the full length Dearborn trench, and the Oakley Swing Coat. All are cut from the same 100% RWS wool, so the choice comes down to length and shape.

Start with how cold it actually gets where you live and how much coverage you want under that. A hip length jacket like the Halsted works for milder days, while knee length and longer options like the Southport, Mag Mile, and Dearborn hold up once temperatures really drop. Our coat length guide can help you find the best length for your lifestyle.

A higher wool percentage holds its shape and heat longer than a blend cut with cheaper fiber. Our guide on how much wool a coat should have breaks down what to check before you buy.

Most of The Checkroom's coat collection is rated 5°F to 35°F, which holds up through a real Chicago winter. The Halsted jacket runs warmer weather only, rated for 30°F and above.

Black is about the easiest color to build outfits around, since it looks just as at home over tailoring as it does over jeans and a sweater. Try it open over a suit for a sharper line, or belted and buttoned up for a cleaner silhouette on colder days. Our wool trench coat style guide has more outfit ideas for both casual days and dressier ones.