Top Five Men's Boot Styles for Fall/Winter

It's no secret Fall is the best season for menswear.  Jumpers, sweaters, and flannels replace your polos and Ts. Linen moves out and wool moves in. Rich, earthy tones pop like the leaves around you. It's nature's fireworks display! Most importantly, though, we get to break out the boots.

This article reviews our top five men's boot styles for Fall/Winter and shows how you can incorporate them into your complete wardrobe. 

The Leather Wingtip Dress Boot

This should be the first boot in your wardrobe. It's the perfect balance between "dressy" and "casual."

The sleek profile of the upper means you can dress it up. While we wouldn't suggest wearing it to a Power lunch, this boot can be paired with heavier-weight flannel and tweed suits. 

The decorative perforations on the toe (called broguing) make the boot easy to dress down, too. Pair with dark denim and a sports jacket for a Friday night out, or with moleskin pants and a flannel shirt for running errands on Sunday afternoon. 

We'd recommend a medium to dark brown for you first pair.

You can find our take on it here. 

The Suede Chukka Boot

Our second pick is a chukka boot. Originally developed for polo play and named after the 'chukka', a period in the game, this the quintessential casual boot. 

You can find them in smooth leather, waxed leather, and suede- and we'd recommend the last one for your first pair. 

While the last can vary between an elongated, Italian-style and the stumpier, American type, the chukka works beautifully for a range of casual styles. 

Pair with a T and some denim, or throw on a safari jacket to spice it up a little. 

Dark brown, caramel, tan, or even grey are great options for you. 

You can create your own model here. 

The Chelsea Boot

Our third recommendation is the Chelsea. Designed and introduced by Queen Victoria's personal shoemaker, it's a close-fitting, laceless, ankle-high boot characterized by a sleek last, low heel, and an elastic strip on the shaft to help the boot slip on and off with ease 

Materials also come in smooth calfskin and suede- though for your first boot we'd recommend the sleek leather. 

The model has gone in and out of fashion throughout the decades, but we find the style to be perfectly timeless.

Dress the boot up with a smart business suit if you're inclined to a "mod" style, or dress it down with slim jeans. For the most flattering and streamlined look, we'd recommend a tapered trouser here.

While the Chelsea comes in a range of colorways, we'd recommend dark brown or black for your first pair.

For our take, the Escobar, have a look over here.

The Combat Boot

The Combat boot is your 'ready for anything' boot. 

Characterized by a higher heel and a higher shaft that fits snugly when laced properly, this has a military heritage. 

When deciding on a combat boot to get you through rain and show, it's especially important it comes with a Goodyear welt. The welting process waterproofs the boot and protects your feet from the elements. 

For more on the Goodyear welt, you can check out this article here. 

The combat boot is inherently more casual in nature, but it will serve you well on weekend errands or coffee dates. 

Pair with denim, flannel trousers, or other casual combinations. 

As for colors, we'd recommend dark brown or black for your first pair.

We're still working on this model here at IDRESE, but stay tuned!

 The Jodhpur Boot

With our basics covered, we can introduce a wildcard for our final pick: the Jodhpur. This boot is similar in shape to the laceless Chelsea save a few key differences. 

First, the heel is often a touch higher than the Chelsea. This is done because the boots were originally designed for riding and polo play. The rider needed to keep his feet in the stirrups!

Second, the boot has an ankle strap and buckle fastened around the shaft. This was originally implemented to keep the boot on during intense play. But, the application is really more form than function in the present day. 

So, how to wear the boots? With confidence. They can work with odd jackets and chinos or with jeans and a leather jacket. These boots will make a statement and you will get noticed, so we'd recommend keeping the rest of your outfit subtle to allow them to speak for themselves. 

Colorways can be whatever your heart desires, but medium tan and lighter brown options are great places to start. 

For our model in black, you can look here. 

Wrapping Up

Boots are an essential part of any well-dressed man's wardrobe, and we hope this article has armed you with the knowledge to make a great selection. 

With these boots in your closet, you'll be prepared for any situation. 

Thanks for reading!

Yours in Style, 

Tony