The Paloma 03 Waterproof by Josef Seibel is another quality entry into the Chelsea boot arena. Robust nubuck uppers are lined with a faux fur to keep cozy on those cooler fall days, and an inside zipper helps get them on and off relatively easily. A waterproof membrane also promises to keep you dry on those damp fall days. A combination PU and latex rubber outsole adds chunky style and solid fall weather grip.

Available at Glebe Trotters.