Introduced during Ann Demeulemeester’s Fall/Winter 2010 show, the Vitello Olio quickly became an instant classic for fans of the Belgian designer. Sometimes referred to as the “backlace boots” or “corset boots”, the Vitello Olio features a lacing system at the rear of the boot. More than just a novel touch, it gives the boots an incredibly sleek and elegant silhouette in the front and along the top of the foot. The result is a boot that is part combat-part Chelsea, but wholly unique.

A decade after it was first introduced, the Vitello Olio boot still features in Ann Demeulemeester collections and pairs from the early-2010s are now among the most sought-after pieces from the brand’s deep archive. Considering the quality of the leather and the way the boots are laced, the Vitello Olio ages particularly well—which helps explain the interest in older pairs.

Carol Christian Poell’s acolytes may be few when compared to traditional luxury labels, but the avant-garde designer boasts one of the most fervent cult followings in fashion. Footwear has long been central to Carol Christian Poell’s mystique, and key among the Poell offerings are the Tornado boots.

Rather than refer to a single model, Tornado refers to the curving zipper that starts in the middle of the in-step and ends at the top of the boot’s rear, thus creating a clean silhouette when viewed from the front or outstep. As with everything Poell does, the magic is found in the craftsmanship and luxurious leather used for Tornado boots. Over the years, Poell’s Tornado has featured laser-cut leather, the so-called “prosthetic” detailing, as well as Poell’s famous rubber drip; both the traditional heeled-sole and Poell’s more unique U-sole have been used on Tornado boots.

For those who are unfamiliar with avant-garde fashion and looking to discover Poell’s enrapturing creations, Tornado boots are as good a gateway as any.

In similar fashion to the Carol Christian Poell Tornado boots, this is a broader entry. Diemme and Stone Island have collaborated repeatedly over the years. The sneakers the two Italian brands have put out have been solid, but the boots have really stood out.

Diemme’s classic Roccia Vet hiking boots figuring prominently among the archive, but lesser-known models have gotten a chance to shine, as well, like the combat boots—some made of leather, others waterproof fabrics—put out by the Italian duo.

Whether it’s one of the contemporary offerings or a silhouette from the brands’ collective archive—any Stone Island x Diemme boot is worth considering for those looking to tackle cold weather with a modicum of style.

Dirk Bikkembergs’ Bungee Boots are, arguably, the most unique boots on this list and are widely considered to be among the Belgian designer’s most famous creations. Introduced in 1996, the Bungee Cord Combat Boots feature a number of intriguing details. Chief among them is the use of bungee cord for the lacing system, as the name indicates. Another integral part of the system is the metal heel, with a cutout allowing the bungee cord to be laced through the heel, essentially binding it to the boot.

But Bikkembergs didn’t stop at the lacing system, with a split leather tongue giving the boots a unique silhouette when viewed from the front—textured or sleek, depending on how tight the lacing system is drawn over it. Lastly, a squared sole under the rounded toe appears incongruent at first glance, but adds to the Bungee Boots’ mystique.

While Bikkembergs might not be as highly thought-of in 2020 as some of his Belgian contemporaries, it’s impossible to deny the influence and success he had in the ’90s and early-2000s. If nothing else, the Bungee Boots serve a reminder that when Dirk Bikkembergs was good—it was really good.

Guidi sure knows how to make a leather boot. Which makes sense considering Guidi has been making premium leather goods for more than a century. Guidi’s main claim to fame is its know-how when it comes to leather—particularly an embrace of time-honored production techniques. Also near the top of the list when it comes to Guidi’s legacy? Their iconic Back Zip boot.

The boot is aptly named, considering that the zipper up the back of the boot is the standout detail. Barring that, the boots look deceptively simple, with stitching only breaking the pureness of the leather at the heel. Deceptive, because it’s the craftsmanship that set these boots apart, as well as the premium materials that Guidi makes the most of.

It’s a highly-wearable boot, which might be surprising considering Guidi is thought to be among the more avant-garde footwear brands.

Few things are more closely associated with Maison Margiela than Tabi footwear. While the Belgian designer wasn’t the first to riff on the traditional Japanese design element, when Martin Margiela sent split-toed footwear down the runway during his Spring/Summer 1989 collection, he turned it into a fashion statement.

Over the years, countless Maison Margiela footwear silhouettes have sported the split toes, but you could easily make an argument that heeled boots remain the most popular way to wear the unique style.

As with most things Margiela, there’s no shortage of options when it comes to Tabi Boots. There are more conservative, half-inch lift black leather boots, or there are three-inch lift painted white ones—and, of course, there are plenty of options in-between. It’s the split toe that brings them together. Given the Tabi is avant-garde by nature, it’s an easy way for men to dabble with more than an inch-lift. When you’ve got cloven-hoof boots you might as well swing for the fences!

Introduced as part of Prada’s Fall/Winter 2018 collection, the Brixxen was available in a number of colorways, but the ones that really stood out were those that took advantage of the three distinct parts of the upper to create a color-blocked Chelsea boot. The all-white crackled leather version also earns a mention!

The Brixxen enjoyed almost immediate popularity in 2018, thanks to the growth of the normcore and gorpcore movements, within which the [boots sat as a kind of elevated take on Blundstone’s classic 500 boot](grailed.com/drycleanonly/best-chelsea-boots). It’s an example of high-end designers getting referential design right—offering something familiar with a luxe twist that warrants the higher price tag.

While new versions of the Brixxen have featured in Prada collections since that Fall/Winter 2018 debut, the original takes remain, arguably, the best and most sought-after.

At first glance the ROA Andreas doesn’t look like your traditional designer boot. However, in just five short years, the Italian footwear brand’s signature model has become something of a mainstay in fashion circles.

The Andreas features a standout Vibram sole, with an aggressive tread, and typically uses a combination of leather, ripstop nylon and rubber for the upper. Though the in-line, classic ROA models are stocked by high-end retailers, what’s really allowed the Andreas to explode in popularity has been collaborations with the likes of Brain Dead, 1017 ALYX 9SM and Fragment Design.

Despite the high-profile high-fashion collaborations, the Andreas remains a robust boot, equipped to handle harsh climates or actual hiking—a gorp-ier, less techwear-adjacent alternative to Salomon’s trail sneakers.

Saint Laurent Paris owes one of its most successful pieces to former creative director Hedi Slimane—though, if we’re honest, what doesn’t the modern incarnation of Yves Saint Laurent’s brand not owe to Slimane?

The Wyatt debuted during Saint Laurent’s Fall/Winter 2013 show and draws inspiration from a Frye boot of the same name. A harness, which wraps around the ankle, is the main similarity between the boots, with Saint Laurent’s version being markedly shorter, skinnier and longer in the toe.

The Wyatt was a smashing success from the off—a perfect distillation of Slimane’s part glitzy-part grungy rock-inflected offering. So popular has the Wyatt been that, well after Slimane’s departure from Saint Laurent, it has remained central to Saint Laurent’s core footwear offering, season after season—always available in black leather or brown suede, in addition to seasonal exclusives.

If you’re looking for a pair of boots to pair seamlessly with a suit, there’s no reason to look any further than Thom Browne’s Wingtip Boots. The American designer is well-known for his throwback (and shrunken) approach to tailoring, but Thom Browne footwear is nothing to scoff at.

The Wingtip Boots are essentially an extended version of Thom Browne’s classic dress shoes, with beautifully pebbled and robust leather used throughout and intricate broguing at the toe, heel and collar. There’s also the tell-tale tricolor grosgrain pull-tab used at the heel collar.

Thom Browne is wont to pair these with his high-water trousers or even the short suits that he’s helped normalize. In colder weather, the Wingtip Boots are great to pair with a traditional inseam length, too. That makes these supremely versatile—good for those looking to spice up their tailoring, or for those going for a more traditional look. The choice is up to you.

Virgil Abloh is such a towering presence in the industry that he’s entered the rarified air where nothing but a first name is enough for people to know who you’re talking about. But once upon a time, the utterance of “Virgil” without anything else, made a select subset of the fashion crowd think about a boot—rather than a designer.

The boot in question is Visvim’s Virgil, an artisanal take on the traditional work boot, with a Vibram outsole, cushioned cork insole and rubber cap on the lateral heel.

As with everything Hiroki Nakamura does with Visvim, the Virgil blends in to the untrained eye, looking like a pair of vintage Americana boots. It’s the small details that elevated Visvim, as a brand, and the Virgil is no different—from the naturally-tanned and dyed leathers and suede to the superior craftsmanship.

The Virgil is incredibly versatile, but looks best when paired with well-worn denim to round out a rugged look.