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.
The pair of shorts and pair of boots I most often combine are my Patagonia All-Wear Hemp shorts and Blundstone 550s in the Rustic Black (really more of a gray color). I loved the way the Blundstones looked with shorts on the Mammoth Brewing server, and I love the way they look on me. Chelsea boots are the sandals of boots. Quickly slipping on a pair matches the more casual vibe of wearing shorts.
I tend to wear shorter inseams when I’m pulling on boots, as I feel like the height of a boot effectively eats up some of the leg space that would otherwise be present with a shorter short and a lower shoe.
While everyone’s body and style are different, playing around with the boot height, shorts length, and sock height ratio to suit yourself can add a lot to this look (Steve Irwin was a master of this ratio).
Pull It Off
While wearing boots with shorts is already familiar in the outdoor world (see: backpacking) I argue that it has much broader plausibility, especially during the fall season. Even the high-fashion world is starting to acknowledge boots and shorts as a verifiable move. Here are a few practical tips to make it work for you:
Stick to the Classics
Have a great boot? Show them off. In my experience, wearing shorts actually draws attention down to the boot, as there is less covering them up. Recognizable, respected boot silhouettes stand out: this is your time to feature those Danner Mountain Lights or Doc Martens that you spent good money on.
Consider the Sock
I’ve learned in styling this fit that the sock plays an important role — it’s where you can create harmony. I opt for something mid-weight that rides an inch to a couple of inches above the boot height in a muted color. This helps bridge and blend the gap between boot and short. Anything too thin or too low leads to the boot looking out of place.
Natural Materials Work Best
Fast-drying synthetics are great on the trail or in the gym, but fall weather is all about being cozy. Cotton or hemp shorts, wool socks, and leather boots play really well together in this look.
Stay in Your Lane
Personally, I’m pretty conservative in my style. I’m not one of those high-fashion HOKA folks, and so I wouldn’t likely don a bright chunky alpine boot or big baggy JNCO shorts. I do, however, hike a lot, so I feel perfectly natural in a pair of Billy Goats and Mountain 600s. Stick to your style, and you can’t go wrong.
Top It Off
We cannot forget the top: boots and shorts may be a match made in heaven, but they love a pullover or fall jacket. Great style is often tucked in layers, brought out by juxtaposition. A fleece, flannel, or sweatshirt can help emphasize the expectation a boot creates while the shorts interrupt that convention.
This may all sound slightly goofy, but when you live in the West, slightly goofy is mostly the norm. So if you trust me, no-pants-November (no-long-pants-November?) should make your fall fit list. Show your shins! Free your knees! Join me in the pleasure that is boots and shorts!