Those looking to create a complete wardrobe can’t miss having quality boots that last. A sturdy pair of boots can help elevate even the most casual outfit. Boots can also be the perfect comfortable footwear for a dressy event. Finding the right pair can be challenging and daunting, considering plenty of boot types. However, when it comes to a classic and timeless boot, there’s none better than a traditional ankle boot.
Ankle boots can come in various versions, from chukka to Chelsea. Although the ankle boot category comes with multiple subsections, the common denominator is the shorter height of the upper. This shorter height allows wearers to keep a casual touch to their look without sacrificing style. Depending on the ankle boot, you can easily wear them on all terrains and various occasions. The following ankle boots have proven to be some of the easiest to style and comfortable footwear in the category, making them a proper investment for any wardrobe.
Brunello Cucinelli Leather Ankle Boots
A sleek and smooth option, these Brunello Cucinelli Leather Ankle Boots are a luxurious option for those looking for a cozy option for formal looks. Made with polished calfskin, the polished leather on these boots gives them an extra shine that makes them pop. The boots’ leather and rubber bottom adds comfort and traction to the wearer, letting them wear them longer. The leather lining and internal side zipper finish the boot, making it a simple design without taking away quality. These boots are available in a dark brown hue and retail for $1,550.
Blundstone 550 Chelsea Boots
Considered one of Blundstone’s best-selling boots, the 550 Chelsea Boot is a classic example of what a quality ankle boot should look like. While not all Chelsea boots are considered ankle boots, they are a style of ankle boot perfect for everyday looks. In particular, the Blundstone 550 Chelsea boot combines premium materials with a luxury rugged design. Equipped with a cushioned midsole and durable TPU outsole, this boot is ready to keep you comfortable all day. Removable footbeds with XRD Technology in the heel strike zone are included for shock absorption. Fans can purchase these timeless boots in one of eight colorways via Blundstone’s web store for $199.95.
Sorel Carson Chelsea Boot
A recognizable name is comfort and durability, Sorel knows what it takes to construct a boot. Although many of their boots are made for active and physical wear, their Carson Chelsea boot is a durable take on a classic design. Although the waterproof suede uppers give the traditional Chelsea boot look, the molded rubber outsole with rubber welt detail gives it a more outdoorsy look. While still functional for daily looks, these ankle boots can also take you off-road. The removable die-cut TPU foam with textile topcover footbed gives wearers plenty of comfort and security. Complete with a seam-sealed construction, this durable boot is ready for anything you might have planned. Available for purchase via Sorel’s web store, this boot is available in two color combinations for $155.
Clarks Clarkdale Easy Boot
Although an understated pair, the Clarks Clarkdale Easy Boot is a sophisticated option that fulfills the role of a true ankle boot. With uppers made of premium beeswax, this classic design is the perfect shoe for any dressy-casual outfit. Inside, a molded leather-lined Contour Cushion footbed gives wearers the comfort they need throughout the day. A natural crepe outsole and hard-wearing rubber piece on the bottom of the boot deliver the ultimate timeless look. The premium leather storm welt adds a rugged touch, making it feel modern. Available via Clarks’ retailers and web store, this boot design comes in four distinct colorways and can be purchased for $160.
Todd Snyder, Nomad Chelsea Boot
A modern take on the Chelsea boot, Todd Snyder’s Nomad Boot is an example of how a luxury boot can upgrade your look. Made with suede uppers, crepe soles, and elastic side panels, these shoes have all the makings of a timeless design. Balancing the look of a formal and casual boot, this Todd Snyder choice is a versatile shoe you can wear almost anywhere. Available in tan and dark brown options, these boots have a branded pull tag on the back and contrast stitching. Without a heel, the flat sole allows users to walk around with ease comfortably. Priced at $398, these Chelsea boots are available via Todd Snyder’s web store.
Allen Edmonds Patton Weatherproof Cap-toe Boots
Molded after previous designs, Allen Edmonds’ Patton Weatherproof Cap-toe Boots has undergone a refresh with a shorter height and sleeker design. Featuring a traditional welt construction and weatherproof sealed seams, this boot design helps keep wearers comfortable and dry all day. A lace-up derby cap toe boot, this Allen Edmonds shoe also has a leather lining and CustomCork insoles for maximum fit and protection. While the overall look of the Patton Cap-toe Boot appears similar to a dress boot, this ankle boot is a perfect solution for an elevated daily look. Available in a brown tone for $495, the boot can be purchased via Allen Edmonds’ site.
Beckett Simonon Bolton Chelsea Boots
Made to order for a handcrafted finish, the Bolton Chelsea Boots from Beckett Simonon perfectly balance premium materials and quality craftsmanship. Using a full-grain leather upper, this boot will develop a unique patina over time, giving each owner a distinct design, unlike the rest. Inside, the Vachetta leather lining helps users regulate temperature, and sweat, and cancel odor. The SBR rubber heel helps give better stability and traction, giving even more support. Also included is a steel shank, which is riveted into the insole and outsole for more balance. However, unlike most, this boot is made by qualified artisans who ensure each seam and stitch is up to the highest standard. The Bolton Chelsea Boots are available in four distinct hues via Beckett Simonon’s website and retails for $259.
Red Wing Heritage Weekender Boot
A classic Chukka Boot, Red Wing Heritage’s Weekender Chukka Boot is a perfectly design shoe that can serve as a casual or formal boot. Crafted using lightweight, flexible stitchdown construction, this ankle boot is comfortable, even if you opt for a sock-less look. Using a Hill outsole gives the design a chunkier look, providing more traction and stability. The oil and waxed nubuck leather provides the sleek and sophisticated look that goes with anything in your wardrobe. Available in a stylish copper tone, the Weekender Boot can be found via Red Wing’s web store for $249.
Rothy’s Chukka Boot
While most sophisticated boots come with a premium suede or leather material, Rothy’s Chukka boot takes a different approach. Available in two classic colors: butternut and black, this boot is composed of waterproof merino wool. Using merino wool allows this boot to be flexible yet structured enough to provide wearers with the optimal balance of support and breathability. Cushioned insoles add more support on the inside, allowing users to don these boots all day. The sturdy lug outsoles add stability by adding significant traction to the boot’s bottom. This boot’s water-resistant characteristics are enough to keep your feet dry and protected despite being made of wool. Available via Rothy’s web store and retailers, this classic Chukka retails for $249.
Wolverine 1000 Mile Old Rip Van Winkle Batch IV Boot
Although unveiled by Wolverine as a limited edition option, the Batch IV Boot with Old Rip Van Winkle is much more classic than one would think. Inspired by Old Rip Van Winkle’s decadent flavors, the rich tones of the boot deliver a sophisticated and sleek ankle boot. Using premium leather in its uppers, this hue will continue to change over time with a unique patina. The rawhide laces and classic wedge outsoles add to the edge of the design, giving you the ideal casual and formal mix. Available via Wolverine for $424.95, this ankle boot is a quality investment for your wardrobe.
