Arming yourself with a wardrobe packed full of winter-ready threads is, perhaps, the sole joy to come from bidding farewell to summer. But it’s not just warm, waterproof layers you need to consider: it’s time to address your footwear for fall, too.

Here, we examine five boot styles that will see you through the season with pure, unadulterated flair.

1. Hiking Boots

Have you been spending your weekends training for a forthcoming trip up Kilimanjaro? If the answer’s no, then you can be forgiven for overlooking the humble hiking boot as a viable footwear option for the season ahead.

Regardless of your outdoorsy aspirations (or lack thereof), hardy hiking boots have established themselves as a foul-weather footwear essential over the past few years – especially among sharp men who prize a shoe’s ability to face down all manner of meteorological nasties in style.

We’re not experts in adventure sports, so we’ll leave recommending boots for seriously tough terrain to the professionals. What we can do, though, is suggest designs that are ideal for navigating city streets, heavy dog walking sessions and the occasional trip to a countryside pub.

You need a pair that offers untold levels of comfort, ankle support and other orthopaedic box-ticking features such as full-leather linings and cushioned footbeds. Diemme, Fracap and Red Wing are the leaders in the field, offering durable and practical options that don’t compromise on aesthetics.

In terms of styling, stick with the outdoors and pile on clothes constructed from suitably robust fabrics – think thick flannel shirts set against raw selvedge denim and, heck, even a gilet if you have one lying about.

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Key Styles

  • River Island Lace Up Hiker Boots In LeatherRiver Island Lace Up Hiker Boots In Leather
  • Walk London Trail Hiker BootsWalk London Trail Hiker Boots
  • He By Mango Leather Hiker BootsHe By Mango Leather Hiker Boots
  • Aldo JoiAldo Joi
  • Trekker Hiking BootTrekker Hiking Boot
  • Dune Champion Tan Leather BootDune Champion Tan Leather Boot
  • Red Wing 8131 Heritage Work Moc Toe BootRed Wing 8131 Heritage Work Moc Toe Boot
  • Diemme Roccia Vet BootDiemme Roccia Vet Boot
  • Fracap M120 Cristy Vibram Sole Scarponcino BootFracap M120 Cristy Vibram Sole Scarponcino Boot

2. Chelsea Boots

The Swiss Army Knife of your shoe rack, the Chelsea is by far the most versatile boot you can buy; the right pair looks just as good worn with a suit Monday to Friday as it does a leather jacket and shredded skinny jeans for a gig at the weekend.

While suede Chelsea boots are having a moment right now – thanks to A-list advocates like Kanye West and Harry Styles – it’s a delicate material that can be hard for us mere (stylist-less) mortals to keep pristine.

So if you can’t be bothered with the regular cleaning, brushing and applications of protector spray required to keep suede versions looking their best, then opt for easy-wipe leather instead. As it happens, a pair in smooth black leather is much closer to the iconic original anyway.

Details to look out for include autumn-ready rubber soles and the classic heel pull, a practical feature that many modern iterations don’t have (but should), as well as contrasting coloured or patterned elasticated side panels, which lend a contemporary feel to your boots.

As this is a British classic, it will come as no surprise that our homegrown brands produce some of the best Chelsea boots on the market. Look to the likes of Grenson, Church’s, Ted Baker and Paul Smith for smart and sophisticated options that can be dressed up or down on your say-so.

Want something a little more rugged? Adelaide-based brand R.M.Williams continues to handcraft durable and handsome Chelsea boots designed to cope with life in the Australian Outback, so it’s a dead cert they’ll deal with whatever Mother Nature throws at you this season.

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Key Styles

  • Ted Baker Camroon Leather Chelsea BootsTed Baker Camroon Leather Chelsea Boots
  • Dune Leather Manderin Chelsea BootsDune Leather Manderin Chelsea Boots
  • Reiss Tenor Chelsea Boots BlackReiss Tenor Chelsea Boots Black
  • Dr. Martens 2976 Originals Black Chelsea BootDr. Martens 2976 Originals Black Chelsea Boot
  • Allsaints Nash BootAllsaints Nash Boot
  • Grenson Jacob Brogue Chelsea BootGrenson Jacob Brogue Chelsea Boot
  • R.m. Williams Leather Chelsea BootsR.m. Williams Leather Chelsea Boots
  • Cheaney Godfrey Leather Chelsea BootsCheaney Godfrey Leather Chelsea Boots
  • Churchs Beijing Leather Chelsea BootsChurchs Beijing Leather Chelsea Boots

3. Brogue Boots

If, like us, brogues don’t just form the backbone of your formal attire, but your casual wardrobe too, then the impending arrival of the colder months probably has you wondering what the hell to wear on your feet. After all, with leather soles and a low-rise silhouette, brogues are hardly known for their winterproof properties. Step forward, the brogue boot.

This cold-weather iteration is perfect for gents who want to retain an element of sartorial tradition, but who also covet the benefits of a robust pair of boots. Reaching higher up the ankle and featuring heftier, rubberised soles, a pair of brogue boots boasts the chill-beating and water-resistant properties required to get on with things in the cold – while looking boss.

As with Chelsea boots, they can be worn as part of a smart or casual outfit. Team them with flat-fronted chinos, a blazer and crisp Oxford shirt for days at the office, and when you’re going off-duty, pull them on with your favourite jeans – hems carefully turned up to show the details, of course – and some oversized knitwear.

In terms of colour, keep it classic in tan, brown or oxblood leather. If you’re feeling daring, look out for a pair in a patent finish, though these can be harder to pull off if your style isn’t already on the bolder side.

Key brands that offer a killer line of brogues include traditional Northamptonshire shoemakers such as Tricker’s, Grenson, Church’s and Cheaney, along with outdoors heritage labels like Barbour.

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Key Styles

  • Dr Martens Affleck Brogue BootsDr Martens Affleck Brogue Boots
  • Asos Brogue Boots In Tan Leather With Back PullAsos Brogue Boots In Tan Leather With Back Pull
  • Ted Baker Sealls2 Leather Wingtip Brogue Ankle BootsTed Baker Sealls2 Leather Wingtip Brogue Ankle Boots
  • Davenport Brogue Lace BootDavenport Brogue Lace Boot
  • Grenson Fred Triple-welt Pebble-grain Leather Brogue BootsGrenson Fred Triple-welt Pebble-grain Leather Brogue Boots
  • Dune Errignton TanDune Errignton Tan
  • Trickers Stow Brogue Derby BootTrickers Stow Brogue Derby Boot
  • Barbour Billingham Derby BootBarbour Billingham Derby Boot
  • Aldo LarewielAldo Larewiel

4. Leather Desert Boot

With the exception of sports luxe-inspired looks, there’s scarcely an outfit that wouldn’t benefit from the addition of a pair of desert boots. We’re not going to get bogged down in the history of this iconic silhouette here (suffice to say, its design was inspired by some highly, and unintentionally, chic shoes sold at Cairo’s Khan el-Khalili bazaar back in the day), but it’s a style that has versatility and simplicity at its core.

We all know spring/summer calls for desert boots constructed from buttery soft beige or tan suede. But as we segue into autumn and winter, it’s time to consider leather as the more seasonally-appropriate alternative.

The classic Clarks Originals model still sets the bar for desert boots. Not only are they expertly made and beautiful to look at, but they also come in a plethora of finishes, colours and materials. And, if you have your finger firmly on the sartorial pulse, you’ll know just how awesome the brand’s collaborations with other labels can be – take this year’s Clarks x Herschel love-in, for instance. Keep your eyes peeled for new team-ups as we enter AW15.

If your budget doesn’t stretch to the real deal, there are plenty of high street retailers that can equip you with a pair that look and feel almost as excellent as the original. River Island, Topman and ASOS all offer styles with the iconic crepe sole and waxed leathers and, arguably, provide even more bang for your buck.

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Key Styles

  • Asos Desert Boots In LeatherAsos Desert Boots In Leather
  • Clarks Originals Leather Desert BootsClarks Originals Leather Desert Boots
  • River Island Desert Boots In LeatherRiver Island Desert Boots In Leather
  • Reiss Coster Leather Desert Boots Ox BloodReiss Coster Leather Desert Boots Ox Blood
  • Clarks Tumbled Leather Desert Boots In BlackClarks Tumbled Leather Desert Boots In Black
  • Ted Baker Torsdi2 Classic Leather Derby BootsTed Baker Torsdi2 Classic Leather Derby Boots
  • Aldo KedaonAldo Kedaon
  • Dune Cactus Lea TanDune Cactus Lea Tan
  • Clarks Originals X Horween Leather Co. Desert BootClarks Originals X Horween Leather Co. Desert Boot

5. Derby Boot

“Derby boot? What kind of fresh hell is this?!” we hear you cry. Well, friend, like Nike’s sneakerboots and the aforementioned brogue boot, it’s another footwear hybrid made to kill two birds with one stone, and one set to help you slay your style this season.

As you might be aware, Derbies are the shoes you pleaded with your mum not to make you wear when you were a kid, but are now the footwear du jour for well-heeled, stylish men about town. Traditionally, they are round-toed, open-laced (meaning the eyelet tabs are attached on top of the upper) shoes in polished leather; the boot upgrade shares these design features, but has an elongated silhouette.

While they can, of course, be worn with black skinnies and a patterned shirt to the pub, the main reason for owning a pair of Derby boots is to winter-proof your more formal looks. Keep an eye out for those crafted in pebble or grained leather that work particularly well with textured flannel or tweed suits, as well as styles with mixed uppers (think leather and suede), patent finishes and burnished toes.

When it comes to colours, timeless tan, chocolate brown and black will never fall out of style and can be combined with both your professional and off-duty attire with ease. That said, those that want to stand out could consider warm, autumnal hues such as burgundy, navy or grey – any of which will add a contemporary edge to this smart and sophisticated silhouette.

From high street to high-end, there’s a pair of Derby boots out there to suit every budget. Look to Russell and Bromley if you want a pair with enduring appeal and quality.

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Key Styles

  • Reiss Arnold Grained Leather Boots BrownReiss Arnold Grained Leather Boots Brown
  • Asos Lace Up Boots In Black LeatherAsos Lace Up Boots In Black Leather
  • Ted Baker Musken Leather Derby BootsTed Baker Musken Leather Derby Boots
  • Portobello Toe-cap Lace BootPortobello Toe-cap Lace Boot
  • Dune Calvin Boot BlackDune Calvin Boot Black
  • Aldo LaudiasAldo Laudias
  • Oliver Spencer Grained-leather BootsOliver Spencer Grained-leather Boots
  • Cheaney Pebble-grain Leather BootsCheaney Pebble-grain Leather Boots
  • Paul Smith Shoes & Accessories Fillmore Leather BootsPaul Smith Shoes & Accessories Fillmore Leather Boots

Final Word

Don’t get left out in the cold; look to add one or two of these hard-working boots styles to your footwear collection instead.

Which of these boots bowls you over? And how will you be wearing it this season?

Comment below to let us know.