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Mark Remillard is a journalist and podcaster based in New York.
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As great as the summer is, fall might be my favorite time of year. The weather cools, the humidity drops, and the warmer clothes that spend the summer in my closet finally make their return. There is so much to love about men’s style during the fall, but I constantly find myself thinking most about one specific component.
Alongside lightweight jackets and sweaters, one of the first items to make their way back into my wardrobe are my boots. From the all-weather necessities to the elevated dress boot, here are the five best boots to add to your repertoire this fall.
Chelsea Boots
Chelsea boots date back to the Victorian era but remain a staple of men’s style even 150 years later. These distinctive boots are easily identifiable by their lack of laces that are substituted with an elastic ankle, making them easy to slip on and off.
Versatile and comfortable, Chelsea boots are a must-have boot style for every man’s wardrobe.
In the 1960s, Chelsea boots became staples of mod subculture, breathing new life into the shoe. They were famously worn by icons like the Beatles and Rolling Stones.
60 years later these boots still do make you look and feel like a rock star. They’re excellent additions to a man’s wardrobe and since they’re commonly found in a variety of colors and materials, they’re one of the most versatile boots available.
With a full suit you can ditch the oxfords for a pair of leather Chelsea boots in black or brown, to add a bit of distinction and character. To go even more casual, you can even forgo the tie in place of a turtleneck or long-sleeve shirt – a great look for fall weddings.
Despite the ability to dress them up, Chelsea boots may feel most at home in your everyday weekend wear. Because of their slip-on/slip-off nature you don’t have to put a lot of thought into them. Match a pair of suede Chelsea boots, like the Thursday Dukes with a pair of chinos and a bomber jacket for heading out to the movies, or switch back to leather Chelsea boots along with cuffed jeans and a peacoat when you’re headed to the bar with friends.
Chukka Boots
Chukka boots are another riding boot brought to the U.S. by way of British influence (the term ‘Chukka’ stems from the term “Chukker” in polo). The lace-up boots were popular among British polo players in India prior to the country’s independence.
Similar to Chelsea boots, Chukkas should definitely be a part of your everyday rotation in the fall. Usually made of leather, but also often found in suede like the Church’s Ryder III Chukka boot, these shoes have either two or three eyelets, making them a close second to the Chelsea boot in terms of grab-and-go capability.
Church’s Ryder III chukkas were made famous by James Bond in “Quantum of Solace.”
Think of these as your everyday walking boot. A good pair with a quality welt, such as the Allen Edmonds Chandler Chukka boots, should last a long time. Plus, if the upper is made from a good leather, you’ll find that they start to form to your foot.
Chukka boots are no doubt on the casual end of the boot spectrum, so look to pair them with chinos or jeans anytime you’re out and about. And hey, why not wear a polo shirt with them to keep it in the family?
Dress Boots
Dress boots are a loose category of boots that are perhaps better defined by their materials than their cuts. A highly polished leather, usually calf, helps elevate these boots from something more rugged to something more refined.
You’ll often find these boots with some ornamenting features, such as broguing in the style of a wingtip—like these Allen Edmonds dress boots. Or find them with a cap toe like these Farfetch Scarosso boots, which have a stitch of leather running horizontally along the toe box. Ideally, the soles of a dress boot should be leather, though rubber soles with minimal treading would still fit in this category.
These are the boots to wear if you’re looking to go formal but might be worried about some slick walkways. Treat these shoes well and keep them with a good shine and you’ll have a great pair of boots to wear under a suit for most occasions.
You’ll find that while standing in a pair of dress slacks, the fact that you’re wearing a boot is hardly noticeable as the heel and toe look quite similar to any other dress shoe. It’s only once you sit down and cross your legs that your cuffs ride up and reveal your sartorial secret.
All-Weather Boots
As you may have noticed, the first two boots mentioned have British lineage and there’s good reason for this. As Alan Flusser notes in his seminal work “Style and the Man,” English shoes and boots were meant to deal with cold, wet climates. Inclement weather is a top reason to choose a boot over sneakers or dress shoes. Enter: The all-weather boot.
A Menswear Library Must-Have
The higher ankle provides better coverage, keeping dirt, salt, snow, and water out. This broad category could cover everything from mock-toe boots (more on them later) to combat boots.
So, what to wear when the weather isn’t great but you’re not storming the beaches of Normandy? Try a leather boot that has a more natural finish. Let the shoes develop some character as you wear them in harsh conditions and they start to patina. Check out boots such as the Timberland Originals 6-Inch boot. Avoid leather boots with a high shine on them or you’ll be bringing an emergency shoe-polish kit everywhere you go.
As for style ideas, the weather might determine how you plan to wear them but given their utilitarian purpose, keep it casual. Try it with some cuffed jeans, a turtleneck, and a bomber jacket if the weather’s decent, and if it’s not, try swapping the jacket with something more protective to stay dry.
Classic Moc-Toe Boots
Distinguishable by the unique stitching across the top of the toe box, the moc-toe boot derives its name and style from moccasins. A quality pair will have uppers made from leather and a sturdy welt, such as the storm welt found on a pair of Red Wings Classic Mocs or the Goodyear welt on the Grant Stone Brass Boot, that will help keep out the elements.
You’ll also find these often come with distinct braided nylon or rawhide laces. The soles are typically rubber and come with a wedge sole instead of a heel.
These are perfect shoes to wear with a cuffed pair of blue jeans, light or dark, and a long-sleeve flannel shirt. They’re the right boots for working in the yard cleaning up those piles of fallen leaves, or for an evening at an outdoor sporting event. Casual and distinct.
Considerations
Just as there are numerous types of boots, there are also a wide range of colors in which they come. If you’re just getting your collection going, it’s probably best to stick with colors that will suit a variety of clothing choices. In most cases, that’s going to be a pair of brown boots. You really can’t go wrong with them.
For some of your more casual boots, such as the moc-toe or the Chukka, virtually any shade of brown should work fine. Your dress boots should stay on the darker end of the spectrum. Unless you are adding to a collection, avoid black and other colors as they’ll have less utility.
As mentioned, materials and welt are important. Full-grain leather with a Blake or Goodyear welted construction might be more expensive than some others, but if you invest in a quality pair you will find they’re not only more comfortable but they’ll last longer. I’ve had the same pair of Thursday Captain Boots for seven years and they still look great.
The Bottom Line
To quote Alan Flusser again, “No single article of clothing is so articulate as a shoe.” Boots are no different. And with the wide variety of options and the ability to wear them in multiple settings, they should be a mainstay of your fall wardrobe.
Mark James Remillard
Mark Remillard is a journalist and podcaster based in New York. For much of the last decade, he’s worked for ABC News as a radio news reporter and anchor. In 2017, he wrote and hosted an investigative true-crime podcast called “A Killing on the Cape.” He followed it in 2020 with a 10-part investigative podcast on late sex-offender Jeffrey Epstein, called “Truth and Lies: Jeffrey Epstein” and won a national investigative journalism award. Mark’s been interested in men’s style ever since he was a kid and saw Jim Carrey don a zoot suit in the 1994 film, “The Mask.” While learning classic men’s fashion and developing his own style, Mark’s mother taught him basic sewing and he’s been altering his clothing by hand ever since. He’s currently studying law at Fordham University and got married to his wife, Catherine in their apartment over Zoom during the height of the pandemic in 2020.
Edited by Rachel Butler
Photography by Rob McIver
