Wearing boots with shorts is no longer just for backpackers, contractors, and two-steppers: this is a verifiable fall weather fit, and you should try it.
Late this summer, I was in Mammoth Lakes during their annual blues festival. After a long hike, my partner, dogs and I decided to grab a beer at Mammoth Brewing and catch some live music. We both had on our hiking boots and Baggies, and we felt a little silly as sometimes is the case when making the transition from trail to town.
Then again, mountain towns contain fashion multitudes.
Case in point: The grooviest thing on the mountain that day was not blues music; no, it was our server’s outfit. We sat outside, and our beer runner had on homemade, rough-cut jean shorts and Blundstones. I’m ashamed to admit how many times I whispered to my partner, “That looks so cool.”
“You’re staring,” she said.
My Go-To Fall Fit

Why I Love This Look
The more I thought about the server’s boots and shorts, the more I realized it was a perfect combo for their job — comfortable, durable bottoms to navigate the sunny temperature swings from inside to out and solid footing with good waterproofing for those inevitable foam-over pours.
Texas two-steppers know this: cowboy boots and short-shorts protect your feet from other dancers while keeping you cool as the floor heats up.
I’m a Wisconsinite originally, where some folks refuse to wear pants when temps are above freezing (seriously). I come from working-class folks; my dad is a welder and pipefitter, and my stepdad is an electrician. Unless I’m on a run or at the beach, most days I am liable to be wearing boots.
I’ve got Danners, Red Wings, Thorogoods, Bean Boots, Sorels, Blundstones, Justins, and, well okay, you get the point. I love boots because boots last. I can wear through a pair of trail runners in a few months, whereas I’ve had some of my boots for nearly a decade.
In the past, I’ve always been sheepish about wearing shorts with my boots unless I’m backpacking or hiking. But I live in Arizona, where huge temperature swings are possible in a single day.
While my extremities are the first body parts to feel cold in the morning, my legs are pretty chill-resistant; accordingly, as the day warms up, it’s a lot easier to pop off a sweatshirt or flannel than it is to change from pants to shorts.
Long story short (ha!), boots and shorts are functional as hell. Steve Irwin was one of the most classic proponents of this hybrid weather hit. Like that beer server, Irwin seemed to understand the value of protective footwear and breathable bottoms for those unpredictable days outside — and we all know that fall weather is notoriously finicky.
So, I am here to tell you that you can — no, you should — wear boots and shorts this season. And better yet, you can look cool doing it.
My Go-To’s

Pull It Off
Stick to the Classics
Consider the Sock
Natural Materials Work Best

Stay in Your Lane
Top It Off
Conclusion
