A great pair of boots earns its place in your wardrobe long after the first cool day of fall. The right pair can carry you through a full day in the city, a weekend outdoors, a dinner party, or an occasion that calls for something more polished. As temperatures drop, boots also bring texture, coverage, and character to outfits built around denim, tailored trousers, and winter layers.
TO BOOT New York’s selection of premium men's boots spans casual suede boots, refined calfskin styles, and versatile designs that move easily between the casual and dressy. If you’re looking for your next pair, these seven boot styles are a good place to start.
Chelsea Boots: The Effortless Essential
Chelsea Boots are defined by their clean ankle-high shape and elastic side panels, often called gores. Those panels and a rear pull tab let you slip the boot on without laces, while its uninterrupted silhouette works especially well under slim or straight-leg trousers.
For dressier days, the Icharus Black Calf Leather Chelsea Boot pairs full-grain Italian calfskin with a sleek profile and a Blake-stitched rubber sole. Wear it with dark tailoring for an evening event, or with black denim and a wool coat for dinner. The Icharus Dark Brown Suede Chelsea Boot brings a softer, more relaxed texture to the same streamlined shape. Try it with blue denim, chinos, or a textured jacket for an easy fall look.
Chukka Boots: Relaxed Style With Desert Boot Heritage
Chukka Boots (also known as desert boots) typically rise to the ankle and fasten with two or three pairs of eyelets. Their short lacing and simple profile make them easy to style with chinos, denim, and casual trousers.
The style has long been associated with polo, while its close relative, the desert boot, has a distinct military story. During World War II, Nathan Clark noticed British officers wearing lightweight suede boots sourced from Cairo. Those practical boots inspired the original Desert Boot introduced in 1950, helping make the relaxed chukka silhouette a lasting menswear favorite.
TO BOOT's Caine Brown Waxed Suede Chukka Boot takes the style in a rugged direction. Its two-eyelet upper is made from waxed calf suede, whose finish helps repel moisture and gives the brown leather subtle variations in color. A hand-hammered leather sole and stacked heel keep the construction rooted in traditional shoemaking. Wear Caine with dark jeans and a sweater, or with chinos and a casual blazer.
Classic Plain Toe Boots: Understated and Versatile
A plain toe boot leaves the front of the shoe free of decorative seams or panels. That simplicity puts the focus on the leather, the shape of the last, and the finishing details. It also makes a plain toe one of the easiest boots to dress up or down.
The Jarreau Dark Brown Calf Plain Toe Boot has a comfortable round last, tonal stitching, and matching sole edging. Its artisanal vintage character looks natural with denim or cords, while the restrained design works just as well with tailored trousers. For days when you want one pair to take you from the office to an evening out, a dark brown plain toe is a dependable choice.
Apron Toe Boots: Heritage Detail for Everyday Wear
An apron toe is marked by stitching that outlines the front of the boot. It adds texture and a touch of workwear heritage without overwhelming the silhouette. The details around that seam can change the mood of the boot: a sleek shape reads more refined, while substantial lacing and a lug sole give it a more rugged feel.
The Kearney Burnished Brown Apron Toe Boot combines a hand-stitched apron with full-grain calfskin, burnished by hand for tonal depth. Metal speed hooks make the upper faster to lace, and a rubber lug sole adds traction for busy days on your feet. Wear Kearney with jeans and a field jacket, or use it to give wool trousers and a heavy knit a more grounded look.
Deerskin Boots: Supple, Grained, and Oh-So Comfortable
For a softer take on the apron toe boot, the Keith Brown Deerskin Boot is made from supple Cervo deerskin with a naturally grained surface. Its broken-in feel from the first wear, speed-hook lacing, and lightweight rubber sole make it especially appealing for all-day wear.
Western Boots: A Subtle Statement that's Not Just for Cowboys
A modern Western boot borrows cues from traditional cowboy footwear—a taller ankle, elongated toe, and pronounced heel—then pares back the decoration. The result brings a distinctive shape to dress casual outfits without requiring a head-to-toe Western look.
The Deacon Dark Brown Calf Leather Western Boot is a refined example. Tonal stitching keeps the Western detail subtle, while the elongated toe and sculpted heel give it presence. Its burnished Italian calfskin and leather sole with a rubber inset balance polish with practicality. Let the shaft sit beneath straight-leg jeans for a relaxed outfit, or pair Deacon with tailored trousers and a jacket for an event where you want a little more personality.
Jodhpur Boots: Equestrian Detail, Modern Polish
Named for Jodhpur, India, and closely linked to riding and polo dress, the Jodhpur boot is an ankle boot recognized in fashion footwear by its strap and buckle. It shares the Chelsea’s sleek, close-fitting appeal, but the wraparound fastening adds a more decorative finish.
The Desmond Black Calf Dress Jodhpur Boot makes that detail the focal point. Its polished buckle and ankle strap add visual interest, while a discreet inner zipper makes the boot easy to put on without undoing the strap each time. Black calfskin, a sleek toe, and a flexible rubber sole make Desmond a strong choice with a suit, dress trousers, or dark denim.
Zip Boots: Clean Lines, Easy Wear
Zip Boots offer the convenience of a slip-on while allowing for a closer-fitting shaft. When the zipper sits on the inside, the outer profile stays clean and uninterrupted.
The Emerson Dark Brown Suede Zip Boot is an easy example to wear often. Its taller, above-the-ankle shape and unadorned vamp show off the depth of its Italian suede, which is lightly aerographed for texture. An inside zipper makes it quick to put on, while a rubber sole adds stability. Try Emerson with five-pocket pants and a cardigan during the workweek, then wear it with denim and a casual coat on the weekend.
Choosing the Right Leather for Fall and Winter Boots
Material can change both the look and the feel of a boot:
- Smooth calfskin has a cleaner, dressier appearance that suits tailored clothing, parties, and evening events.
- Suede adds a soft, rustic texture that feels at home with denim, corduroy, flannel, and knitwear.
- Waxed Suede, while moisture resistant, is not completely waterproof. The wax acts as deterrent against moisture, but still allows some moisture to seep in.
- Idro Suede is a water-resistant suede material that's been specially treated to repel moisture.
- Deerskin is prized for its supple hand and natural grain; boots like the Keith feel exceptionally soft from the first wear.
The sole construction and material choice matter, too. A rubber or lug sole provides traction for everyday walking. A leather sole gives a different, more traditional finish, as seen on the Caine chukka. Combination soles where the main body of the sole is made from oak bark-tanned leather with a rubber insert offers the best of both worlds, offering the comfort of leather soles with the much needed traction of rubber.
Choose your sole according to where you’ll wear the boots most often, and remember that treated suede is not as waterproof as rubber or crepe soles found on more contemporary styles.
What Is Idro Suede?
Idro comes from the Italian word element for water. In the TO BOOT lineup, Idro suede is premium suede specially treated to repel water while retaining the soft feel and deep, velvety appearance that make suede appealing in the first place. It gives workwear-inspired boots a practical finish without taking away their rich texture.
The Ellington Dark Brown Idro Suede Boot shows why that combination works. Handcrafted in Italy, it has four pairs of eyelets for an adjustable fit, two speed hooks that make lacing quicker, and a padded collar for comfort. A rubber lug sole adds traction, making Ellington a useful choice for travel, long days out, and fall weather that may change along the way.
Find the Boot That Fits Your Fall
Shop the complete collection of boots for men at TO BOOT New York. For a polished event, reach for a calfskin Chelsea or Jodhpur. For everyday wear, start with a plain toe, apron toe, or easy zip boot. A chukka brings relaxed texture to weekend outfits, while a minimalist Western boot makes a memorable finishing touch. Whatever your plans this fall and winter, explore TO BOOT men’s boots to find the shape, leather, and fit that feel right for you.