7 Boots to Invest in This Winter

It was about two years ago when I realized that being an adult means wearing seasonally appropriate footwear. Like people who drink iced coffee in the winter, I’d opt for flats in even the most impractical weather; my feet would get soaked in rainstorms, and numb from a wind chill. Aren’t your ankles cold? I’d hear on-repeat––and they were. 

But to me, an alternative didn’t exist. Sneakers made an outfit look too casual, and heels didn’t make sense for everyday—especially if lots of walking was involved. The practical replacement would, of course, have been a pair of boots, but I was stubborn: I always found them to be too clunky and tough to style with my usual rotation of cropped jeans and long dresses.

That is, until I found the ones: Phoebe Philo-era Céline ‘Country’ ankle boots bought off TheRealReal (though I get most of my clothing on consignment, shoes are a tough secondhand buy; these, luckily, were brand new). The purchase was motivated by pure superficiality—I was spending most weekends in Connecticut and needed to invest in footwear that could handle tougher terrain without compromising on style—but I quickly realized they were actually comfortable, too.

When I think about what the pieces I’m drawn to say about my psyche, it’s clear that longevity reigns supreme. Unlike flats, whose soles can be flattened after just a few miles, boots have staying power. From materials that can handle the elements to styles that can withstand trends, the seven pairs below are more than worth the investment. 

Kaya Boot in Moss, Brother Vellies ($650)


Brother Vellies’ take on a traditional Chelsea boot, the Kaya, feels as good as it looks—on the outside and inside. With a slightly tapered front, stamped, mossy leather, and a 2” heel that gives just the right amount of lift, the pair is sleek enough to be dressed up, but cool enough to be styled down with jeans and a chunky knit.

Founded in 2013 by Aurora James, the brand has maintained its commitment to traditional African design practices; James sources materials from local farmers and works with artisans and craftspeople across the globe. Plus, they never put their products on sale—”Their value is assigned based on materials and fair labor practices,” says the brand, “which are unaffected by the traditional commercial consumption cycle.”


Slalom Boots in White, Nomasei ($590)

Inspired by the outdoors, these boots are all parts practical—a rubber lug sole, an extra-padded upper—without compromising on style (a white patent leather exterior isn’t what we’d expect from a pair of hiking shoes, but it’s exactly what we want). 

Meaning “Six Hands” in Italian backwards, Nomasei operates its business on five pillars of responsibility, a byproduct of the founders’ time at Chloé. From offering high-end products at a fair and sustainable price and providing customers with total transparency to working with local Italian craftspeople (a.k.a. no outsourcing) and partnering with organization 1% For The Planet, Nomasei is “committed to creating fashion that’s sustainable and respectful of the environment.”


Ranger Boot, Rafa ($350)

Made-to-order items can feel intimidating, but Los Angeles-based label Rafa makes getting custom pieces more attainable. Handcrafted by a local group of 20 artisans, Rafa uses 100% vegan, eco-friendly materials (which limit the amount of water, chemicals, and waste used to make each item). 

The brand’s Rafa boots, made from their signature ultra-suede, which is crafted from recycled water bottles, are timeless. The back lace-up detail gives the pair a special touch without feeling too trendy, and the flexible, sock-like construction (and double-lined orthopedic insole), means comfort is at the forefront. 


The Weekend Boot in Sage, Alice + Whittles ($200)

Following a successful Kickstarter campaign in 2013, Toronto-based Alice + Whittles sought to create a brand with one purpose: to reduce waste through simple and versatile design. Made in a family-run factory in Portugal, functionality is a primary design-driver, but not at the cost of sustainability, comfort, or style. The Weekend Boot is the essence of all four—it’s crafted from 100% vegan and virgin plastic-free, its upper is water-resistant (and made from repurposed marine plastic), and its 100% recycled synthetic wool lining is temperature-controlled. In short, you’ll never have to worry about your feet getting wet or cold.

The Classic Combat in Black, Essen (€289)

Biker boots are often clunky and toughen up an outfit, but this pair does the opposite. ESSEN’s Classic Combat Boot offers a more delicate take on the style—the chunky sole may be utilitarian, but the slim cut and lace-up front keep things soft. Plus, the back metal zipper makes taking the shoes on and off seamless. 

Handcrafted in Portugal, ESSEN wants to create a new fashion cycle: By offering new styles through a pre-order model, ESSEN doesn’t produce more than necessary. The versatility and quality of their pieces, too, encourage shoppers to invest in items they can wear in any weather, in any season, for years to come.


Mira Boots, Rejina Pyo ($568.03)

Though London-based Rejina Pyo is best-known for feminine dresses in pretty pastels, these chunky ankle boots from her Fall/Winter 2020 show prove she has range. With a cleated sole and elasticated side panels, the Mira Boot is tough in all the right ways.

From people to packaging, sustainability is an ongoing process for Pyo; on her site, she even suggests that, after you’re done with one of her products, you gift it to a family member or friend or sell it on a luxury resale platform. That’s advice we can get behind.

Beia Boot in Hazelnut, Zou Xou ($325)

Zou Xou founder Katherine Theobalds saw first-hand how much waste the fashion industry was creating  when working as a designer in New York City. That experience led her to create her own label of well-made, practical and comfortable shoes that go easier on the planet. “A good shoe has a distinct character and captures an emotion. That’s why I only design what I love and have use for. Through the years, I’ve realized that taking this approach to almost anything I consume makes me want less and ultimately feels more satisfying,” she says of her Buenos Aires-designed brand

The Beia Boot is the epitome of a good shoe. A mid-heel boot with a ‘90s-inspired shape, it’s stylish, simple, and no-frills: Just a super-soft leather with a rounded square toe, and classic block heel. 

Photo Credit: Brother Vellies

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