J Shoes wool and leather shoe 225$.

Chukkas, or desert boots are the perfect daytime shoe for weekends. They’re comfy, easy to pair with multiple outfits, and their clean design will look good for season. This fall, J Shoes mixed wool and leather together (a big footwear trend this season) for a new and lower-cut take on the classic desert boot.

Sperry chukka $120.

Sperry brings us a classic leather chukka in a perfect earthy colour. They’re lightweight and comfy, a perfect daytime shoe.

Sperry boots $160.

Nobody likes moving their boat shoes to the back of the closet and moving the boots forward. Sperry has a solution: a low rise boot that looks more like a boat shoe. On rainy days or cooler fall days, this wool and leather boot will keep you warm and dry without looking like like a boot. When spring comes, these will protect your feet from the mud and rain while still looking seasonally appropriate.