Guys: Here’s how to choose a go-to fall boot
A go-to fall boot is like a good pair of jeans: They’re comfy, versatile, and practical. With all that going for them, you might wear them most days. A leather boot can take you from hop festivals on through to St. Patrick’s Day shenanigans—and you’re going to be returning to them every fall, for years to come.
But that’s a lot of pressure: how do you decide which boot to buy? Don’t worry! We got you.
We’ve gathered up our favorite men’s casual leather boots and called out their top features to help you choose. And while only you can really decide whether you’re a chelsea boot guy or a lace-up guy, hopefully this guide can point you in the right direction.
(And while this is a guide to our men’s boots, anyone can rock these boots, it’s just the sizing that comes into play.)
How to choose your fall boot
We know it and you know it (hopefully): our shoes, boots, and sandals are all about versatility. We want to go peak to pub without changing our hiking boots—and we want our casual shoes to do the same. Just having an “outdoorsy vibe” doesn’t cut it. We want the performance to match the style, so you can keep your after work plans open.
That’s why the boots listed below offer a lot of the same outdoorsy-friendly features, like seam-sealed or waterproof leather uppers, cushy insoles and supportive outsoles for going the distance. And all of our leather boots feature durable construction and premium, environmentally preferred leather (more on this at the bottom).
All of this might leave you with one question: How do I choose? Here are four specifics to consider:
1. Lace-up up or chelsea boot: Across the board, the lace-ups fit more snugly (seeing as you’re in charge of the laces), but our chelsea boots are also designed to hug your foot. A chelsea has a slimmer profile, can be slipped in quickly, and has a bit more of a stylish feel to it. However, depending on the boot, each offers quite a different style and fit.
2. Style: Each boot’s style can be interpreted differently, depending on your perspective. What might look like a combat boot to us might look refined to you (sorry, it’s science). So, when you’re looking at the boot, consider and compare color, shape of seams, appearance or texture of the leather, and the overall shape of the boot.
3. Brown or black: Brown is a great everyday choice and looks good with just about anything. Black can look more professional and is dressier for a night out. So ask yourself where you normally go (the barn or a cool downtown bar called, “The Barn”?), think about what you normally wear (brown corduroys? dark wash jeans? a black utilikilt?) and choose accordingly.
4. Performance: Each boot offers a different type of outsole (think lugs vs. a sneaker sole) and level of weather-readiness (insulation, seam-sealed construction, waterproof leather, etc.). Consider what fall looks like in your neck of the woods—and whether you’ll be venturing into those woods.
Think you know what you’re looking for? Read on and explore our durable, rugged styles with weather-ready features designed to conquer the chilly season ahead.
Ames: The versatile moc boot
What makes it different: Limited edition; moc toe
Performance features: Welted design; luggy outsole
Where you’d wear it: Acing that second job interview, taking a ruminative river walk, and then reliving each interview question over dinner with friends.
The Ames Moc boot is rugged-meets-classy-casual—and it’s a limited edition. It’s the classic moc toe (that U-shaped seam around the toe box) that sets this boot apart visually. It’s purely a style preference.
But as the headline says, this boot is about versatility. The welted construction boosts stability and durability while the luggy, rubber outsole takes it into off-road territory. However, with the detailed stitching and the soft, super rich leather, this boot cleans up nice for a dinner date. In short, the Ames Moc boot is perfect for a spontaneous schedule. Its brother, the Ames Chelsea slip-on boot, offers the same details and fit, but skips the moc toe in lieu of a more streamlined look.
Eastin: The feel-good boot
What makes it different: Our most consciously constructed boot ever
Performance features: Water repellency; seam-sealed construction
Where you’d wear it: Volunteering for the environment, catching the game—any game—and then taking a date to see the sunset from the bluffs.
The Eastin 8" Lace might just be the last fall boot you ever buy. Seriously. We made the Eastin boot super durable, using Million Step Quality construction—a fancy way to say, we tested it for over a million steps and it kept going. What’s more, we built it in a way to reduce its impact on the planet. It repels water without PFCs, uses Eco Anti-Odor, and features premium, American hide leather from LWG-certified tanneries. The cushy, sneaker-like KEEN Luftcell outsole reduces materials and creates a lightweight, comfortable ride.
And that’s just about the planet. It’s handsome to boot, with hand-finished leather, smooth lines, and herringbone lining. The seam-sealed construction makes it great for fall—in fact, this has already become a top KEEN employee pick (breaking the third wall: this writer can actively see three pairs at this very moment). The collection also includes an Eastin Chelsea boot.
The 59 II: A smooth classic
What makes it different: Classic looks for mild weather
Performance features: Breathable mesh lining; welted design; luggy outsole
Where you’d wear it: Walking the streets of East London, swinging by your favorite motorcycle club, and then catching a rock show at the pub.
The 59 II boot has been a KEEN staple for years and offers a more refined style than the others on this list, with a smooth, premium nubuck leather upper and equally smooth stitching. This classic is great for days when the temperature starts dropping or in climates where fall and winter stay fairly dry and mild. This update from The 59 original features a more secure fit and distinctive toe-cap.
The boot’s name comes from The 59 Club in Britain, a now global club that brings together motorcycles, music, and friends—exactly what this boot aims to do (motorcycles optional). With its shiny, dressy upper and grippy outsole, this boot is up for anything and is as rugged or refined as you want it to be.
The 59 II Chelsea boot is a great option as well.
The Slater II: Built to—and for—chill
What makes it different: Classic looks for cold, wet weather
Performance features: Water repellency; KEEN.WARM insulation; welted design; luggy outsole
Where you’d wear it: Traveling home for the holidays, hitting your old haunts, and digging out your childhood friend’s car after it got buried by a snowplow.
The Slater II (above left) is actually part of a larger collection of similar boots that includes The 59 II. Each boot in the collection offers different features designed to conquer the weather in your distinct part of the world.
The Slater II offers up two distinct weather-kicking additions: KEEN.WARM insulation that’s rated to -4°F/-20°C and a PFC-free water-resistant upper, making it the perfect fall-to-winter-to-spring boot. If the cold isn't your issue but rain is—hello, Portland!—check out The Rocker II (above right), a waterproof version without the insulation.
This whole collection—insulated, waterproof, chelsea, and all—is great in that it never feels overdressed or underdressed. It’s all about embracing that hardcore versatility and gaining a work-to-weekend edge. The hardest part is choosing which color to get.
That environmentally preferred leather
Tanning leather is a dirty process, which is why we source our hides from Leather Working Group-certified tanneries. The closed loop water treatment reduces water use and eliminates wastewater pollution in the tanning process. Learn more about our process.