The Highsnobiety Fall Fit Toolkit is your manual for dressing well this season, from wellies to weather-ready running gear.

We get it. It can be hard to loosen your grip on an all-sneaker rotation, especially if that's been your only set-up thus far. But good style demands experimentation and variation. Streetwear and luxury continue to become increasingly entwined, with some form of smart tailoring seen on the runways of pretty much every label at the moment. And let's be honest, a formal pant requires something a little more refined when it comes to footwear.

Of course, we'll always reserve an area in our collection, as well as our hearts, for sneakers but there's a time and a place for everything. With colder weather on the way, boots are the best place to start the seasonal wardrobe switch, and we’ve rounded up eight footwear options that take things a little more adult.

Shop our favorite boots for Fall 2021.

ROA Andreas Boots

Andreas Boots

Andreas Boots

$414

ROA

Buy at Slam Jam

Your wardrobe deserves a solid pair of hiking boots, regardless of your extracurricular activities this Fall. Here, ROA has blessed us with a shoe with all the functionally of an outdoor staple, equipped with luxurious materials. The Italian brand has crafted the shoe using lizard printed calf leather, overlaid reinforcements across the toe, and a handy-dandy, durable Vibram® sole. It's a boot that will turn heads — on and off the mountainside.

Salomon S/LAB XA-Alpine Advanced 2

XA-Alpine Advanced 2

$290

Salomon S/LAB

Buy at Highsnobiety

Personally, I feel Salomon makes some of the best Fall and Winter shoes. The brand's functional footwear is designed to withstand even the most unpleasant of conditions while trail-running. Your suede 990s and all-white Air Force 1s couldn't really hold up against a puddle. The S/LAB XA-Alpine is one of Salomon's most advanced sneakers. The boot-sneaker hybrid boasts a protective gaiter to keep your shoes free from debris and unwanted elements, all while rocking an all-terrain Contragrip outsole. These boots can handle almost anything that you throw at them.

Moncler Lir Boots

Lir Boots

Lir Boots

$825

Moncler

Buy at Slam Jam

Olive is one of the year's winning colors. We've seen it just about everywhere. No surprises here, Moncler's Lir boot is another shoe that effortlessly mixes functionality with style. The boot's massive off-white midsole contrasts beautifully with the shoe's green leather upper — a feature that will keep your feet dry even on the rainiest of days.

Thinsulate™ Duck Boot

Thinsulate™ Duck Boot

Thinsulate™ Duck Boot

$100

Sperry

Buy at Sperry

Sperry kicks are designed for being on the sea, so they should be a go-to on your search for the perfect winter boot. Take this pair of Duck Boots, for example. Lined with Thinsulate™ fabric, they're wildly warm and you're in no danger of dampness thanks to the fully waterproof upper. What's more, their utilitarian aesthetic is bang on-trend in all-black.

Maison Margiela Tabi Bianchetto Chelsea Boots

Tabi Bianchetto Chelsea Boots

$1110

Maison Margiela

Buy at Highsnobiety

Margiela has elevated the classic Chelsea boot. The shoe's painted look, 15th-century Japanese inspiration, and high-heel make this one of the brand's strongest footwear offerings from its Fall-Winter collection. It might be a little out-there, but it’s about time men got a little braver in their footwear choices.

Bottega Veneta Tire Rubber-Trimmed Chelsea Boots

Tire Rubber-Trimmed Chelsea Boots

Tire Rubber-Trimmed Chelsea Boots

$1100

Bottega Veneta

Buy at Mr Porter

Bottega Veneta's Fall boot is a playful reinterpretation of the iconic Chelsea boot. The shoe's bright and stacked rubber sole is the boot's best feature, protecting you from the weather while giving you a few style points this season.

visvim Canoe Moc II-Folk Boots

Canoe Moc II-Folk Boots

Canoe Moc II-Folk Boots

$1020

visvim

Buy at Mr Porter

If there is anyone who can rival Bottega Veneta's approach to quality, it's going to be visvim. It wouldn't be too hyperbolic to say that Hiroki Nakamura creates some of the best clothing in the world. Every garment is made using carefully sourced, high-quality materials and is designed with an exceptional level of expertise. The Canoe Moc II-Folk is handcrafted using vegetable-tanned full-grain leather. It's a shoe with a story — a great investment piece.

Raf Simons Cylon 22

Cylon 22

$540

Raf Simons

Buy at Highsnobiety

Raf Simons did something here. We don't know what exactly, but we love it. Another Fall must-have from the designer, the shoe mixes athletic footwear and luxury boot design effortlessly in a futuristic silhouette. The shoe's combination of suede leather across the upper and chunky rubber outsole somehow work. You are going to be seeing a lot of this boot this season.

HOKA One One Sky Kaha

Sky Kaha

$255

HOKA One One

Buy at Highsnobiety

HOKA ONE ONE is quickly becoming one of our favorite go-to footwear brands. Beyond just running shoes, the brand designs comfortable, trek-ready boots. If you are really about that life, the Sky Kaha has got your feet covered. The shoe is weather-proof, thanks to its water-resistant leather upper and GORE-TEX midsole. Those uphill climbs just got a little bit easier.

Our Legacy Camion Boot

Camion Boot

$575

Our Legacy

Buy at Highsnobiety

Not every boot has to be super-functional. A classic leather boot can do wonders for your Fall wardrobe. Why? Well, the look is timeless, easy to dress up and dress down. If you are on the hunt, Our Legacy has got you covered. Its Camion Boot is made from the highest quality leather and is equipped with a sleek but sturdy Kilger leather midsole and outsole. It's the perfect boot for those of you who prefer to spend time trekking urban landscapes.

Salomon Quest 4D GTX Advanced

Quest 4D GTX Advanced

$275

Salomon

Buy at Highsnobiety

A GORE-TEX body? Debris-free protection? Contragrip? Yes. Salomon has blessed us with a Fall boot that could handle even the most extreme adventures this season. However, its khaki colorway will look just fine on casual, fit-conscious explorers.

Dr. Martens Vintage 2976

Vintage 2976

$255

Dr. Martens

Buy at Highsnobiety

What can you expect from Dr. Marten 2976? It's an iconic Chelsea boot made from top-quality leather in the brand's historic factory. The 2976 features the brand's iconic stitching and bouncy soles. Dr. Martens take a while to break-in, but once you do, they are yours for years.

Want to keep browsing? Head to the Highsnobiety Shop for more products that we love.

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