If you buy through our links, we may earn an affiliate commission. This supports our mission to get more people active and outside.Learn about Outside Online's affiliate link policy

Women's fall boots that will take on the trail and look good doing it. (Photo: Courtesy Forsake)
The season of thick flannels and protective leather boots is on the horizon. Prepare early with these essential women’s boots, perfect for chilly fall days.

These boots got an upgrade this year with the addition of a fully waterproof and seam-sealed upper. The leather is paired with vulcanized rubber soles to keep you firmly planted on city streets when the weather turns icy.

The Cataluna proves that Chacos are no longer just for dirtbags. To create this stylish option, Chaco paired its plush sole with a full-grain waterproof leather upper. A molded TPU midsole, heel zipper, and bamboo heel complete the look. Wear them on a date or even just to dress up an oversize flannel.

If you’re looking to channel your inner lumberjack, then these will do the trick. Easily the burliest of the bunch, the Round Toe boots give a nod to Red Wing’s century’s worth of experience making men’s work boots, but in a slightly more refined package. They’re made from full-grain leather that will only look better as the years go by. The women’s fit has a narrower last to help your foot feel more secure while you walk around.

Going on an after-work hike? These fully waterproof boots look good enough to wear to the office but feature Vibram outsoles to keep you from slipping on ice or rocks. Plus, the gusseted tongue and taped seams prevent water and debris from entering your boots through the lace eyelets or the space between the tongue and the upper.

Perfect for around town and your workday, these boots have steel plates in the midsoles for extra durability and structure. The outsoles also resist motor oil, acid, organic fat, and heat up to 284 degrees Fahrenheit.