Outdoors gear is made for out there. As trends take wilderness apparel from the summits to the streets, Highsnobiety is recasting a seminal part of the outdoors for its new home. Trail Mix is a wear-test series by Highsnobiety. Instead of climbing mountains, we put gear through tests that ring closer to home. Is a down coat too warm for the subway? Will mountain boots slip on iced-over streets? Each month, we’ll take on a new category, testing five pieces in the wilds of New York City to answer questions just like these. This month, we’re lacing up trekking boots.

As Spike once said: “It’s gotta be the shoes.”

Whether on a mountaintop or on Mars, footwear matters. Great sneakers might take an outfit up a level. When it comes to the outdoors, however, boots play a more critical role. The right alpine boot means summit or fall. The right backpacking boot means trail or turn back. Forget blowing out a Nike — if a boot fails mid-traverse, it’s game over of a different kind.

Performance-wise, modern outdoors boots make for some of the most impressive gear out there. Lighter hikers combine the agility of sneakers with the stability of a mountain goat. Beefier pairs provide all-conditions security in anatomical designs that still move like Michael. Waterproofing and hybrid shell constructions come standard across both. While they certainly won’t #break2 any time soon, today’s trekkers apply the same level of technology and optimization to pursuits of a different kind. If treated right, some may never break at all.

Shoes made for alpine adventure are certainly built to endure. But in the fashion world, is anything really timeless?

In search of the best outdoors style, Trail Mix reviewed five trekking boots across a range of budgets.

Here are our picks for this season’s best trekking boots for men.

HOKA ONE ONE Kaha GTX ($220)

From Big Sur to Yosemite Valley, California is home to some of the most breathtaking nature on the planet. HOKA ONE ONE, a footwear brand that calls the Golden State home, makes shoes for spending time in it — famously runners, but also boots.

The Kaha GTX is HOKA’s take on a backpacking boot. Named after a Maori phrase meaning “strength and support,” the Kaha combines the brand’s comfort-focused running tech with the stoutness of a hiker. An overbuilt midsole makes it a HOKA. But a GORE bootie, leather upper, and Vibram MegaGrip outsole makes it a bonafide backwoods companion.

Of all the boots in this test, the Kaha was by far the most comfortable. I mean, it’s basically an inch of cushion glued to a waterproof foot cover — what’s not to like? For muddy ascents and fifth-floor walk-ups, the Kaha worked like a charm. There are some durability concerns here, though. I would not, for example, pack the mega-cushioned Kaha on trips that include rocky terrain (abrasion and foam don’t play nicely). But as a crossover piece, the Kaha GTX — a big brother to last season’s uber-popular Tor Ultra Hi WP — earns high marks.

Salomon Quest 4D 3 GTX ($230)

While California might capture more of Hollywood’s attention, the French Alps stir a different fascination. Europe’s alpine areas are steep and treacherous — great for fast winter downhills and fierce summer uphills. Annecy-based Salomon built its name outfitting athletes for the challenges of its own backyard. The Quest 4D 3 GTX is how they do trekking boots.

While HOKA’s Kaha puts its running tech front and center, the Quest 4D hides it behind a more protective shell. The combination of GORE-nubuck upper, thick rubber sole, and rigid toecap amp up Quest’s off-road capability. OrthoLite insoles and the brand’s “4D Advanced Chassis” system make it a comfortable ride — but make no mistake, this is more boot than hybrid.

The Quest would be my pick for vacation hikers looking to get double-duty from the $200 boots they might otherwise wear twice a year. They are incredibly capable, and as fashion pieces, they’re pretty darn great as well (peep the aggressive lines accented by this Grape Leaf/Peat colorway). Urban nomads and techwear enthusiasts will find these reasons enough to cop. If the fashion of function is your speed, make these your Quest.

Mammut Kento High GORE-TEX ($249)

If the French side of the Alps makes rigid footwear, just imagine the Swiss. Mammut (est. 1862) is one of the world’s foremost mountaineering brands. The company got its start making climbing ropes over 150 years ago, and while the centuries (!) since have seen it expand, it never lost its summit-seeking focus. Case in point: the Kento High GTX.

Crampon-compatible and thick like crème fraîche, the Kento High is a proper mountaineering boot. Rubber panels front a GORE-TEX bootie to keep elements out. A sturdy Michelin “Alpine Lite” outsole keeps boot and wearer upright. Clever design touches like 2-zone lacing and a built-for-movement inside keep the whole thing surprisingly wearable. You know, for a mountaineering boot.

Lacing up the Kento High is like stepping into another world. Make no mistake, this is a boot for notching peaks. Durability and capability are foregone conclusions. What is up to question? Wearability. Personally, I enjoyed the Kento. The action sports color scheme and ridiculous lines scored big aesthetic points, and while comfort isn’t its focus, my only discomforts came from banging against the toe on long walks (did I mention it works with cramp-ons?). If you’re an alpinist, try it out. If you’re wearing it as a statement piece, it’s phenomenal. But I wouldn’t walk city miles in it.

La Sportiva Trango Tech GTX ($269)

La Spohr-tee-va. It’s Italian for “the sportswoman.” And in case you forgot that Italy was shaped like a boot, well, here’s your reminder.

Tesero’s La Sportiva has built boots since 1928, a 90-year tenure that’s seen its products take all Seven Summits and a variety of first ascents. The brand’s Trango Tech GTX is one of its more pedestrian products. It’s only a seamless, GORE-infused boot. It’s built to get you up to 6000m. Cramp-on compatibility? Only semi-automatic.

The Trango Tech was my favorite all-rounder in this test. These boots are a true do-it-all hybrid that just looks badass. I loved the race-car looks (black mesh on yellow panels just screams “carbon fiber”) and to-the-toe lacing (a detail borrowed from approach shoes). I also found the lightweight seamless construction to be comfortable and breathable, although there’d likely be some durability concerns around hard scrapes. While the soles are stiffer than a corpse tipping 10 percent, the combo of Lamborghini styling with Dolomite substance made these a winner.

ROA Hiking Andreas ($525)

Italy may have its share of famous mountaineering brands, but that’s not what anyone thinks when they hear “Italian boots.” Mixing high altitude with high fashion, Milan-based ROA Hiking unifies these disparate identities in luxurious, outdoors-inspired footwear. Cue the “elevation” puns.

The Andreas boot (shown here in paint splatter) is ROA’s most famous silhouette. Cut from whole-grain leather that’s been treated for easy-wearing, they are — to put it lightly — not built for abuse. Oversized Vibram soles nod to the Andreas’ functional familiars. But that’s not why anyone blows half a stack on boots from a fashion site.

In fewer words, the Andreas is gorgeous. Like Common Projects with the Achilles, the gift of critical distance allows a fashion-only brand to cast functionwear as art. Here, the combination of thin uppers and exaggerated sole (with retro-inspired ROA logo hits throughout) just works. In all black, it’s a sporty alternative to tech-inspired boots like Prada’s Chelsea. In a multicolored collab context (i.e. ROA x Brain Dead), it’s an all-timer made precisely for this moment.

The Andreas takes the style of substance and carves it hollow — in doing so, it creates a fashion shoe. Just don’t take it somewhere the substance might be needed.

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