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Walk on the Style Side: A Lived-In Review of the Best Direct-to-Consumer Boots for Men

* We wear-tested five direct-to-consumer men’s boots
* Five unique styles mean there’s something for everyone
* Shop these brands online to cut out the middleman 

Online shoppers are usually looking for a deal, and they never think it’s a good one unless it’s a steal. If you’re in the market for high-end men’s boots, you’re in luck. New brands are forgoing typical distribution through big box stores and boutiques, choosing instead to go direct-to-consumer. By cutting out the middleman, designers can offer the same merchandise to customers at a much lower price than you’d pay at a traditional retailer.

The only problem with buying anything online — especially shoes — is that you have no idea how they’ll fit or feel once you try them on. We scoured the internet to find the most popular D2C men’s shoes and put them through our lived-in review process to uncover the five best boots you can buy online.

Best Value: WOLF & SHEPHERD Onyx Chelsea Blitz

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I’ve never been a huge fan of Chelsea boots. They’ve always looked a little too polished for a guy with Rust Belt roots who adjusted quite easily to SoCal casual style. Five minutes with Wolf & Shepherd founder Justin Schneider completely changed my mind. “He’s a winner,” the former Notre Dame decathlete enthusiastically tells me, describing his customer. I want to be a winner, too — I was dying for those boots.

The magic isn’t just in the branding. Before launching Wolf & Shepherd, Justin designed athletic shoes for Adidas. Now he applies athletic technology to classic men’s footwear. For example, replacing the standard wood heel and nails with an EVA running sole and carbon fiber shank makes the Onyx Chelsea Blitz a full pound lighter than its counterparts.

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I decided to try them out on a trip to New York. Now, since these boots are crafted for professional men who wear dress shoes from the early morning through the evening, they’re also built to last, with a leather upper that breaks in slowly. The idea is to replace the sole when it wears out, but keep the boots.

It probably wasn’t smart for a California boy who goes through life in hippie slippers to break in a pair of durable boots in the city that never stops walking, but that’s just what I did. Suffice it to say that I fought the boots, and the boots won. They look great and they’re incredibly well made, but you’d do best to break them in slowly. By the third time I wore them, they felt perfect.

Styling-wise, the Onyx Chelsea Blitz has versatile appeal. You can wear them as an alternative to dress shoes, with slacks and a button down. They also do wonders to polish your off-duty denim looks. They’re perfect to pack for business travel, as they work just as well on the street as they do in the office.

Overall, they offer the best value for their versatility and durability. You can wear them with almost anything, and the slow break means slow wear and tear.

Most Comfortable: ARVEE NYC Sahara Chukka

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When a shattered foot hobbled Arveena Ahluwalia’s fashion game, the then-financial professional was determined not to follow the doctor’s orders and wear orthopedic shoes. With the style sense of a dyed-in-the-wool New Yorker, Dr. Scholl’s were a Dr. Don’t for her.

A mission for stylish footwear that provided comfort led the civil engineer-turned-investment banker to find a new passion – this time, making her own shoes.

When she finally returned to work, the guys in her office hit her up with requests for comfortable dress shoes. From that first batch of clients, Arveena built what became Paul Drish shoes. Now she’s launched her namesake brand. It has a new name, but keeps the same focus on comfort and style.

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The Sahara Chukka is crafted from hand-brushed suede into a classic silhouette with minimal detailing. They look great, but the genius lies in the technical components. The leather sole is infused with thermoplastic rubber to make walking easy, while the stacked leather heel absorbs shock.

The simple design focus on comfort has definite appeal for the Southern California crowd, especially considering it’s one of the few markets where boot season doesn’t include much precipitation. I paired them with dark wash skinny jeans and a printed shirt. They work best for dressy casual looks.

These boots win “Most Comfortable,” as they’re lightweight and soft to the step.

Best Style: PAUL EVANS Newman Chukka

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Fine Italian craftsmanship meets the direct-to-consumer market in Paul Evans footwear. The online shoe brand produces all of its inventory at the same family-owned factory in Naples, Italy, where skilled artisans have been making shoes for generations.

The Newman Chukka is handcrafted from calfskin using Blake stitching, the preferred method of Italian shoemakers for its ability to create lightweight, flexible footwear. Blake stitching is also durable, meaning that with proper care and maintenance, these boots will last a lifetime.

While they fit like a dream and feel great throughout the day, my favorite thing about these chukkas is the hand-painted finish. The Aged Cognac colorway is flashy enough to catch the eye, but not so over-the-top that it dominates your look. Striking the perfect balance between polished civility and rugged masculinity, they put the strut in your step.

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Italian shoes run large, so when ordering from Paul Evans, be sure to order a full size down. If your new shoes don’t fit, it’s no sweat returning them. Just use the prepaid return label for an easy exchange.

These boots get “Best Style” because they earned lots of compliments — strangers were stopping me everywhere to say how great they look.

Best Break From Your Routine: M. GEMI The Piega

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Keeping with the theme of Italian craftsmanship, M. Gemi’s namesake founder, Maria Gangemi, is a native of Sicily. The brand recreates for online shoppers the quintessential Italian boutique experience, where shoppers could find a selection of locally-crafted, reasonably priced merchandise that was always being updated with new designs.

The Piega ups the ante with sacchetto construction, a method of shoe making in which the lining and insole are stitched together as a single piece. Sacchetto construction eliminates the need for an insole, meaning that The Piega is incredibly lightweight and flexible. The vamp laces-up quite tight, offsetting the soft flexibility of the suede upper with strong support and a glove-like fit.

A suede upper means they don’t go in the rain or snow, which eliminates winter for these boots. Even without precipitation, they’re so lightweight that your feet would freeze in low temperatures. Fortunately, they’re as comfortable as summer slip-ons, making them perfect for dry days in the spring and early fall.

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The navy blue colorway offers a fresh break from typical black or brown boots. Navy is a neutral, so you’re not limited in styling options. I wore them with gray wash jeans and a modern striped button-down to a dinner party with the DTLA fashion kids. They garnered a decent amount of attention, especially when they barely missed being doused by falling glass of Cabernet. It’s a good thing they’re so lightweight; otherwise, I might not have been quick-footed enough to dodge destruction.

These boots are the “Best Break From Routine” because they give you an option other than black or brown. Blue Suede Shoes may be a hit song, but most guys stick to the basics. Wear these babies to shake things up.

Best Balance & Support: JACK ERWIN Carter Wingtip

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If you’re looking for a dress boot that beats the elements, look no further than the Carter Wingtip Boot from Jack Erwin. The durable Goodyear construction is reinforced with a storm welt along the seal between the upper and outsole, making for weatherproof style that won’t let you down.

Handcrafted in Spain, the Carter Wingtip’s journey begins at the Du Puy tannery in Chadrac, France, where the full-grain calfskin leather is prepared. The thick leather upper allows these boots to break in over time, making them better with age. Additionally, a cork lining molds to your foot with wear, increasing both comfort and durability.

Speed hooks at the top of the shaft make for easy on-and-off dressing, although the laces do tend to come loose from the hooks at least once throughout the day. It’s annoying, but no more so than a shoelace coming untied.

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These boots are casual enough that you can wear them on the weekend, but moderate brogue detailing gives them a classy feel that’s perfect to swap out with dress shoes at the office during the winter months.

They win “Best Balance & Support” for the unexpected orthopedic benefits. Full ankle coverage provides extra support without pressing the tendons and causing inflammation. A slightly exaggerated sole distributes weight and impact with each step, promoting balance and absorbing shock.

If you buy something because we told you about it, we may receive compensation from retail partners.