If some cruel twist of fate forced me to choose only one outfit to keep–say, my ne’er-do-well roommate fell asleep with a cigarette and set the apartment ablaze–I would grab my Momotaro jeans, a Henley shirt, and, most urgently, my favorite boots. Like well-loved denim, boots can feel like an extension of the body, a wearable relic of memories from hikes, travels, and unforgettable nights out. As does the boot-clad cowboy, explorer, or soldier, I feel primed to tackle whatever the world throws at me with sturdy rubber and leather under my heels.
Boots are a versatile sartorial workhorse. They endure punishment yet are capable of adding dash and edginess to almost any outfit. They pair as well with jeans as brand-new sneakers and as handsomely with corduroy pants or chinos as dress shoes. Even after the abuses of muddy hiking trails or grimy urban sidewalks, boots look like a million bucks after a scrub and polish. Granted, high-quality boots are an investment, but they’ll last for years with proper care–far longer than sneakers or loafers.
Whether your summer adventures entail trekking through national parks or carousing about town as a sharp-dressed bon vivant, good boots will serve you well every step of the way–even in the warmer months.
Amberjack Obsidians
Footwear designers often grapple with the conundrum of balancing comfort and aesthetic appeal: lean too far into comfort, and boots resemble geriatric footwear; sacrifice comfort for design, and they become onerous as medieval torture devices. Amberjack has nailed the secret sauce of marrying exquisite comfort with unimpeachable design. Like the founders of Vineyard Vines, Amberjack’s CEO, John Peters, transitioned from a corporate background to pursue a more creative and entrepreneurial path. I became a devotee after buying the brand's Chelsea boots, a pair of chestnut-brown slip-ons that I practically live in during the summer. While Amberjack’s Chelsea boots are perfect for summer barbecues and cocktail parties, the delicate suede is not designed to withstand mud and water. When the trails beckon, grab a pair of Amberjack’s flagship boots. These brawny lace-ups are crafted from rich, durable Portuguese leather. Avant-garde memory foam composes the soles, molding to wearers' feet for extra comfort and arch support. With a pair of these bad boys, you can hike all day without sore feet, and they’ll garner compliments when you hit the bar for a post-trek refreshment.
Buy: $209
Red Wing Iron Rangers
Red Wings have maintained a cult following among boot aficionados for over a century. Founded in 1905 in the Great Lakes port city of Duluth, Minnesota, Red Wing initially designed workwear for longshoremen undertaking the arduous task of unloading cargo ships in the winter. Each pair of Red Wings is still crafted by hand in Duluth, and the leather ages like fine wine, developing a lovely patina over the years. The Iron Rangers’ beautiful design makes them as appealing to an urban flâneur as a blue-collar hired hand. The boots are tough enough to withstand any abuse short of running them over with a steamroller, and when time and mileage thin down the soles, just take your boots to a Red Wing store for resoling. The brass speed hooks, designed for quick lacing and unlacing, are another brilliant touch, adding a subtle flair to the handsome leather body. One caveat: Iron Rangers require a couple of weeks to break in. Wear them around town before embarking on a long hike or camping trip.
Buy: $349.99
Vasque St. Elias Hiking Boots
Vasque Footwear also hails from Duluth, and the founder, W.D. Sweasy, grew up as loyal to Red Wing as a Lake Superior dockworker to the Minnesota Vikings. But while Red Wing designs work boots, Vasque’s target market is hikers and outdoors enthusiasts. Vasque meticulously sources superb leather, rubber, and metalware, and the fine craftsmanship is obvious even from a glance. Vasque’s St. Elias boots are lined with GORE-TEX, a breathable and waterproof fabric that keeps trotters dry and toasty even after fording streams or trekking through snow. I wear my St. Elias on the wettest or snowiest days of the year in New York City, and they trump my Bean Boots for keeping out the wet. With crenulated soles and snug ankle support, St. Elias boots are ideal for the most strenuous treks. I recently took mine on a hike through Yosemite’s notoriously treacherous Half Dome. While Vasque’s ethos evokes mountain trails and campgrounds, St. Elias’ sleek leather shell is comely enough to wear out to business casual events (especially when the weather turns foul).
Buy: $230
Thursday Boot Company Captain Boots
Based in New York City, Thursday Boot Company crafts footwear fashionable enough to pass muster at Manhattan’s hippest haunts yet rugged enough to hold up against the abuses of the city’s less-than-pristine walkways. In addition to boots, Thursday crafts dress shoes and sneakers aligned with the same goals of blending aesthetics, durability, and accessible pricing. With a capped toe and speed hooks, Thursday’s Captains are reminiscent of Iron Rangers, but Thursday’s design is dressier. Captains are showstoppers for business casual parties and tough enough to wear on light hikes. That said, if trails are wet and muddy, grab a more water-resistant pair like Vasque’s St. Elias boots Like Red Wings, the leather gets better with age, and you can resole the boots every couple of years to keep them in shipshape. For my taste, solid black Captains are the sharpest boots on the market to rock with dark jeans.
Buy: $199
Taft Rome Boots
Taft’s Rome Boots, festooned with acanthus-leaf and paisley motifs etched into the leather, are as eye-catching as a burgundy smoking jacket. The gradually fading color pattern, darker at the toe cap and lighter around the ankles, brings to mind a vintage Gibson guitar with tobacco sunburst hues. If you have a penchant for flashy boots, Rome Boots are the ne-plus-ultra. Taft does not skimp on craftsmanship in favor of glitz, and each pair of Rome Boots is hand-cut and painted from exceptional European leather. You can customize Rome Boots in vivid colors, but I prefer them in dark brown for alternating use between hiking and socializing.
Buy: $295
Brunt Marin Boots
An apt analogy for Brunt’s Marin boots would be a hands-on landscape architect with an advanced degree from Harvard’s School of Design. Like Carhartt jackets, Marin boots are rugged enough for the gnarliest jobs—even working amidst electrical hazards—but the design bespeaks sophistication and thoughtful taste. The leather is waterproof and coated with a gloss resistant even to oil or corrosive chemicals. On the spectrum of boots best for hiking and boots best for dressing up, the Marin boots skew towards the former; however, for a confident dresser, they look dapper paired with dress clothes.
Buy: $139
