5 Essential Men’s Boots for Fall/Autumn

Fall can be a truly wonderful time of the year for menswear enthusiasts–depending on your typical fall climate, that is! Speaking generally, though, autumn is a very enjoyable season to dress in for the classic menswear fan. Neither too hot nor too cold, you get to enjoy the warm golden hues of autumn that enrich the colors and textures of your wardrobe. Today, we’ll share 5 boots to finish off autumn looks!

General Tips for Fall Footwear

We’ve discussed our 11 favorite items for a fall wardrobe before, so today, it’s all about what goes on your feet during this transitional season. First up, we’ll let you in on some expert tips for your fall boot collection before diving into our top five fall boots.

1. Materials make a difference

Depending on what material you choose, you’ll get different qualities of weatherproofing as well as different formalities. For example, there’s a general consensus that you can’t wear suede when it’s wet.

If it’s treated well and looked after, though, suede actually performs better in a downpour than a typical calf leather. A water-repellent spray can be applied to your suede footwear or, indeed, any other suede items you might have and you’re good to go. After all, it’s far easier than applying layers upon layers of polish to your calf leather shoes to give them some kind of weather protection.

As an alternative to suede, take a look at waxed calf leather. The wax used on calf leather provides a greater level of water protection than that of traditional shoe polish, and you get a unique texture with a dull sheen that you can’t achieve with suede.

The downside of both suede and wax calf leather is their more casual nature – great for a dressed-down fall day. But, what about those times when you still want to look sharp and still maintain a bit of weather protection?

This is where cordovan leather really comes into its own as a great fall boot leather choice. It might not be the cheapest, as we discover in this post, but it’s highly prized for its durability and water resistance while maintaining a high shine, fit for dressing things up.

2. Pay attention to the soles

We’ve got our boot uppers sorted, but what about the soles? Leather soles are traditional, and a good leather sole will provide a decent amount of protection. You shouldn’t be wearing them consecutively, especially if they have become wet. They’ll destroy your boots quickly as they won’t have time to rest and dry them between wears. And as we find out on our bespoke shoe series, wet leather cuts easily.

If you have a couple of pairs of leather-soled shoes or boots and you’re wearing them in a rotation, you’re already off to a good start.

To get even more life out of your investment, you can apply a leather sole protection treatment. There is a well-renowned sole guard made by Saphir, which is priced around $20 to $30, which is a small amount in comparison to the huge cost of ruining a pair of quality boots. Otherwise, opt for a rubber sole for your fall boots.

There are a lot of different styles and brands out there, each with a different use. There are studded day-night soles, slim “city” soles, half-rubber-half-leather soles, and chunky, cleated Vibram soles. These types are naturally higher in weatherproofing qualities than standard leather, and will also lend you a greater level of traction, useful for strolling through all those soggy fallen leaves. Of course, the more practical the sole, the less formal it will be.

3. Pick the right boots for your situation

Hopefully, this one makes sense in general terms, but to make things more specific, Balmoral boots aren’t meant for splashing and muddy puddles, and Wellingtons aren’t for the boardroom. Of course, the unpredictable nature of transitional weather means that some days, things don’t go as you’d hoped. But applying these tips to the boots today means you’ll be the most fall-ready you’ve ever been.

Top Men’s Boots for Fall: Chukka Boots

Simple, easy to wear, and comfortable, the chukka boot is a menswear style staple but is especially welcome in a fall wardrobe.

The term “chukka boot” describes an ankle-height boot constructed in a Derby style with two or three eyelets for laces. We’ll go into more detail in a separate guide, but for all intents and purposes, under this category, we’re going to include the desert boot as a great fall boot option as well. The main difference with a desert boot is this crepe rubber sole, which is characteristic to this particular style of chukka boot configuration.

Typically, chukka boots are finished in suede, but you can find them finished in other leathers, too. And just like the classic desert boot, chukka boots look just as gentle when they’re unlined as well as being very comfortable.  We also find unlined chukka boots to give it a little extra freedom to wear thicker socks on a chilly fall day.

In terms of formality, a chukka boot can exist in many different places on the spectrum, based on the last, leather, sole, and color. For example, an unlined, light tan, suede desert boot with a crepe rubber sole is more casual, whereas a black calfskin chukka boot with a slim city rubber or traditional leather sole will be much higher in formality.

Everyone will have different needs for their chukka boots to fill, but if it’s timelessness you’re looking for, you can’t go wrong with the classic chukka boot in a mid-brown suede and a slim rubber or leather sole, whichever is best for the fall weather where you are.

Chelsea Boots

Up next is another stalwart of a classically-styled wardrobe. Being a particularly sleek and stylish item, the Chelsea boot is unique in its ability to cross the realms of casual and formal attire – of course, depending on the exact details. The style is remarkably simple, consisting of form-fitting last, elasticated gussets on the sides, and pull tabs to help you get them on.

Typically speaking, though, the style is best when it’s paired down to simple elegance. Sure, you can find Chelsea boots that support detailing elements, but they look the rest when you opt for the classic, plain-toed variety. What makes them a great boot for fall is how easy they are to wear. Whether it’s a full day on your feet or just a quick visit to the grocery store, a pair of Chelsea boots are quick and easy to slip on, and they’ll pair with many elements of a classic wardrobe.

For further weatherproofing concerns, you can consider Chelsea rain boots and a cross between a Chelsea boot and a classic Wellington boot. The Chelsea rain boot combines practicality with elements of classic style, whereas a tall Wellington boot puts you squarely in the realm of country attire. The ankle-height Chelsea rain boot is a perfect option for a fall wardrobe – just like with Chukka boots previously.

The choice of materials plays a big part in how dressed up or relaxed your Chelsea boots look. Once again, black calfskin is the way to go if you want to pair your Chelsea boots with business wear, but brown tones will allow you greater versatility.

As we’ve already suggested a mint brown, suede chukka boot for your fall footwear collection, go for a pair of Chelsea boots in a darker, waxy calfskin. Not only will they provide a greater level of weather protection, they’ll also provide a greater variety of choices when it comes to fall-appropriate footwear. There’s going to be a time when you want to be formal in fall.

Balmoral Boots

A Balmoral boot is the absolute must-have boot if you’re a classic style enthusiast. With its origins in the 19th century, the Balmoral boot was actually the everyday footwear choice for men, with everything from work to weddings happening in a pair of Balmorals.

Previously made in the Regency Period, such as Beau Brummell would have worn tall boots every day, similar to a pair of riding boots. The Balmoral boot was the next evolution as men started to wear their boots under instead of over their trouser legs. And we strongly recommend you don’t try wearing tall, leather boots under your trousers.

The ability to wear a boot under your trousers is essential for fall, as there are bound to be days when you want to look smart but still maintain a practical edge. After all, on a cold autumn day, having an ankle-height boot under your trousers keeps you nice and warm.

Balmorals can certainly elevate casual clothing, but they look their best when paired with sharper attire. Of course, this does mean a trade-off in terms of practicality as the Balmoral boot is typically constructed from an elegant, polished calfskin as well as any potential contrasting leathers on the upper portion of the boot. Although, it’s possible for the whole boot to be made of the same leather.

This also means that Balmorals are rarely seen with rugged or chunky soles as the elegance of shoe-like upper benefits from a coherent design that follows through to a slim and stylish sole. This means that you’re more likely to find Balmoral boots with leather or slim rubber soles.

With all that in mind, your Balmoral boots should be the opportunity to smarten things up in your fall footwear. So, go for classic dark colors and a smart calfskin. Blacks, grays, reds, and browns are all great choices here.

Derby Boots

If you love the look of a Balmoral but want something for those in-between days, go for a Derby boot. Granted, this term might seem similar to that of a Chukka boot. This style is also somewhat broadly defined. So, let’s break it down to what sort of thing you should be looking for: at or just above ankle height, Derby construction, robust lacing system. It can certainly be very easy to find yourself in the realms of combat or commando boots when looking for a Derby boot, and it’s because of that open lacing.

It offers you the greatest range of adjustment, which is perfect for a boot worn in transitional seasons. If it suddenly turns into a warm fall day, you can open your laces and let your feet breathe or, if it’s a cold one, the Derby boot will be more forgiving for a pair of warmer socks worn underneath.

To set your Derby boots apart from the modern military styles, go for full- or pebble-grain leather. The texture helps the leather develop a unique patina over wear, and choosing a leather in a rich deep brown will make the boots surprisingly versatile.

Derby boots are also a great opportunity to experiment with additional details, such as a cap-toe, a wingtip, or broguing. A great sample of an alternative to a rich brown, pebble grain leather would be these wingtip Derby boots with broguing in the classic, rosy brown, cordovan tones.

Jodhpur Boots

Finally, we have a more unique boot style, but certainly no less stylish. A Jodhpur boot is similar to a Chelsea boot, boasting a simple and elegant design. But, instead of an elastic gusset to hold your foot in, you’ll find a buckle and strap.

As its name suggests, the Jodhpur boot has equestrian roots, with this and the Chelsea boot both originally being used for horse-riding pursuits. Before moving to the mainstream fashions in the 1920s, a taller variation of the Jodhpur boot rose to prominence in the 1950s, known as the “engineer boot.” The style was worn by cinematic bad boys like Marlon Brando and James Dean, creating particular intrigue for leather boots sporting straps and buckles.

While the engineer boot is still available today, the shorter Jodhpur boot still retained a lot of its sartorial elegance, being uniquely appreciated by those with a flare for the extraordinary. After all, Jodhpur boots aren’t super common nowadays; that makes them all the more special as an addition to your fall wardrobe.

Naturally, Jodhpur boots will always work well with traditional country clothing, but as we’ve discussed before, a transitional season like the autumn months provides a great opportunity to indulge in leather jackets. So, whether it’s the Trialmaster from Belstaff or the iconic Perfecto from Schott, a pair of Jodhpur boots makes a wonderful addition to these outfits.

The reason a Jodhpur works so well here is it echoes the classic pairing of two utilitarian garments. But, the boots aren’t as rugged as the engineer boots, which possess a chunkier sole and boxier toe. Indeed, the refined round toe and slim sole of the Jodhpur boot are what elevates the Jodhpur boot into the realm of elegance.

When it comes to choosing leather for your Jodhpur boot, classic calfskin is king here. You can certainly find them in a range of different materials, but a slick pair of well-polished Jodhpur boots will set you right for many fall days to come.

Conclusion

Whatever stage you’re at in your fall boot collection, we hope you enjoyed our suggestions for these essential styles.

Are any of these boots new to you, or are you a fall boot fanatic? We’d love to hear from you in the comments.

Outfit Rundown

Today, I’m wearing a camouflage, casual, long-sleeve shirt with a pair of dark denim, shadow stripe Fort Belvedere socks in brown with light blue stripes, and a pair of brown suede Chukka boots. Check out the Fort Belvedere shop for socks like these.