Without a doubt, every closet and style needs to have a collection of casual shoes to rely on. The best casual shoes can withhold maximum use and still be a timeless model that’ll always be on trend. Picking out the right pair depends on your style and routine, which decides the level of support and comfort you require. A proper rotation of casual shoes can be made up of various styles, from boots to loafers to sneakers. When made with premium materials and construction these designs can easily be worn with most of your wardrobe and maintain its structure. This selection of shoes has proven to be timeless and quality-made designs that can be used for many years.
Sperry Authentic Original Penny Loafer
Any casual shoe in your closet should stand the test of time and still look fashionable. One brand that has successfully created numerous icon designs that have transcended any trend is Sperry. With their Authentic Original Penny Loafer, users get the ultimate casual shoe that doubles as a dress shoe. Giving you a more sophisticated everyday look, the penny loafer is a smart choice for those looking for comfort and luxury. The dark beige hue allows wearers to mix and easily match the shoe with most of the colors in your wardrobe. Available via Sperry for $110; and is an easy option to have in your closet.
Cole Haan ØriginalGrand 2.0 Oxfords
Although Oxford shoes might not seem like the most comfortable option, they can be when made with the best footwear technology. Like most Cole Haan options, the ØriginalGrand Oxfords are equipped with the brand’s SkyWeave technology , giving the shoe a spring-like cushion. The extra traction and flex grooves allow for more stability in each step. The laser-perforated leather uppers give the foot more breathability, giving the wearer better comfort. This Oxford shoe is available in various colorways via Cole Haan’s web store and retailers for $230.
Veja Campo Sneakers
Over the past couple of years, Veja has become a staple brand in casual sneakers. Specifically, the Campo sneakers have become the go-to for white leather shoes that work with almost any outfit. Made with ChromeFree leather uppers and panels, the Campo shoe has a smooth feel that makes it shine even more. With the abundance of colorways available, there’s no reason why users can’t find a pair that suits their needs. Using the small pop of color on the logo, users will also find that this pair is easy when trying to add something extra to their outfit. The Campo sneaker retails for $160 and is available via Veja’s web store and select retailers.
Clarks Desert Boots
Even a good pair of boots can make for the ideal casual shoe. During the colder months, boots become a must to keep your feet warm and comfortable. However, even casual boots need the best support to withstand all your daily activities. Made from either leather or suede uppers, Clarks’ Desert Boots are an easy-to-wear option that gives you the right amount of casual and style to complete your looks. Although the desert boots have a more sophisticated style, the rubber outsoles ensure it’s an ideal pick for any event. A simple and understated option, desert boots are a timeless option that will never go out of style, proving why this design remains one of the brand’s most iconic shoes. Clarks’ Desert Boots collection is available via the brand’s web store and selected retailers for $150 to $230.
Beckett Simonon Morgan Trainers
Just because casual shoes are made to be worn every day, it doesn’t mean they need to lack attention to detail or sophistication. Beckett Simonon’s Morgan Trainers is a clear example of how a well-built sneaker can still be a luxury addition to any closet. Constructed out of full-grain leather uppers, the Morgan Trainers are made to be durable and develop a unique patina over time. The wide waist and tall in-step ensure all-day comfort that allows your foot to breathe. Most importantly, the Vachetta leather lining helps manage temperature, control odor, and absorb sweat. With everything you would expect from a Beckett Simonon design, the Morgan trainer is a one-stop sneaker that’ll always have a place in your rotation. Available via Beckett Simonon, the Morgan trainer currently retails for $169.
Astorflex Brownflex Chukka Boot
While not required, any shoe that can easily transition from casual to formal instantly is a great bonus. Astorflex’s Brownflex Chukka Boot allows wearers to wear their favorite pair of boots daily and the ability to wear them to any unexpected formal event afterward. With a full leather lining, users will have comfort all day and a structured shoe that won’t fall after use. On the inside, the Brownflex Chukka boot has a custom footbed that molds after your foot for maximum comfort. Perfect for on-the-go days, this pair of chukka boots is key for a put-together wardrobe. Available via Huckberry, the Brownflex Chukka Boot retails at $225 and is offered in various rich colorways.
Cole Haan GrandPro Tennis Sneaker
The ultimate simple tennis sneaker, Cole Haan’s GrandPro Tennis Sneaker, is one of the most basic additions to any wardrobe. A lightweight option, it uses burnished, hand-stained leather with minimalist tonal stitching. A textile footbed adds breathability and comfort to the sneake,r making it an easy footwear option for daily use. The sneaker’s design and engineering help mimic the foot’s motion to become less tired. The rubber pods on the heel allow for more traction when moving. Available in six colorways via Cole Haan, this sneaker retails for $150.
Blundstone 500 Chelsea Boot
One of their most iconic designs, the Blundstone 500 Chelsea Boot is the ultimate casual boot. It is crafted with stout brown premium water-resistant leather that molds to your foot over time. Using a durable TPU outsole and cushioned midsole for comfort, this durable design is the perfect piece to complete any wardrobe. The SPS Max Comfort system in the boot helps with shock absorption in each step. Complete with a removable footbed and steel shank for stability, this is one of the only boots you need year-round. The Blundstone 500 Chelsea Boot is available in four colorways via the brand’s web store and retails for $190.
On Cloud 5
Considered one of On’s first breakout designs, the Cloud 5 is the ultimate casual sneaker that doubles as an athletic shoe. With a lightweight design and clean silhouette, the Cloud 5 is the perfect balance between a performance shoe and a casual sneaker. For the days filled with a few extra miles, the On Cloud 5’s CloudTec in Zero-Gravity foam leaves users with extra cushion in every step. Other features like the breathable antimicrobial mesh and molded heel design ensure you stay comfortable all day. Available in various neutral hues, the On Cloud 5 allows wearers to easily incorporate the shoe into their existing wardrobe. The Cloud 5 is available via On and selected retailers for $140.
Allbirds Tree Runners
It’s no secret that Allbirds’ commitment to sustainable practices and lightweight designs has made it a leader in athletic sneakers. Besides Allbirds’ unique construction, it also dons a comfortable and airy design that makes it practical for everyday usage. Made directly from sugarcane, the brand’s SweetFoam midsole gives the shoe a cushioned boast. 100% machine washable, the Allbirds Tree Runners are a practical option for those looking to get plenty of use out of their shoes. This wool knit sneaker is available in 12 colorways, giving you plenty to choose from. Fans can grab their Allbirds sneakers via the Allbirds website or selected retailers for $98.
Thursday Boot Company Captain Cap Toe Leather Boots
Made with some of the finest leather around, Thursday Boot Company’s Captain Cap Toe Leather Boot is all about bringing premium materials to your casual footwear. Featuring Goodyear Welt construction and studded rubber outsoles, these boots are made to last. The perfect lace-up boots for the colder months, these sleek leather boots are sophisticated and casual to mix up your wardrobe. The lined, supple glove leather interior and cork-bed midsoles ensure the inside of your boot is as comfortable and cushioned as the inside. Available in classic, rugged & resilient, and storming lug sole collections, these boots have several variations for every type of dresser. These boots are available via Thursday Boot Company and retail for $199.
Ralph Lauren Merton Leather Boat Shoe
A staple brand in Americana fashion, Ralph Lauren knows how to build quality products that last generations and the Merton Leather Boat Shoes are no exception. Although the name states otherwise, boat shoes don’t require boat access. These casual and sophisticated footwear options are perfect for those laidback days when you want to slip on your shoes and go. Crafted from smooth, heavyweight leather that gets softer over time, the Merton Boat Shoe is a classic example of understated luxury. With a padded insole and treaded rubber outsole, these boat shoes are ideal for days you don’t know what to know. Available via Ralph Lauren’s web store and retailers, these boat shoes are obtainable for $138.
Tod’s Gommino Driving Shoes in Leather
Just as with boat shoes, driving shoes are excellent casual shoes that don’t sacrifice style. The Tod’s Gommino Shoes are crafted using calfskin leather upper and exposed handmade stitching. Complete with leather lining and insoles, the Gommino shoe uses the calfskin texture to create the illusion of a much more casual style. On the bottom, the maxi rubber pebble outsole adds a relaxed layer to your footwear. An easy shoe to wear with casual bottoms or formal pants, this versatile shoe can easily transform with your everyday wear and dressier outfits. Purchase the Gommino Driving Shoes in Leather via Tod’s web store and selected retailers for $795. These classic and timeless designs are available in various styles and materials to find the one that best matches your fashion.
Allen Edmonds Park Avenue Cap Toe Oxford
Although most casual shoes are depicted as sneakers or slip-ons, there are dressier options that can double as a laidback option. First introduced in 1982, the Allen Edmonds Park Avenue Cap Toe Oxford offers a luxurious feel whether dressed up or down. Created with a 360-degree bench-welt construction and leather-lined interior, this Oxford shoe is made for comfort and longevity. A classic and timeless design, an Oxford shoe won’t go out of style. Available via Allen Edmonds for $425, the Park Avenue Cap Toe Oxford can also be found in nine colorways for a wide range.
Johnston & Murphy Bolivar Calfskin Oxfords
The ultimate hybrid between a dress shoe and a sneaker, the Johnston & Murphy Bolivar Calfskin Plain Toe is the perfect blend for a sophisticated casual shoe. Mixing Italian, hand-stained calfskin uppers with a rubber outsole, this shoe blends the best of formalwear and everyday style. While it’s not often that a casual sneaker can be adopted into dressier situations, this Bolivar Plain Toe can be easily worn in multiple situations. Completed with a molded, polyurethane footbed that molds to the foot, this design is equally comfortable as it is chic. Available via Johnston & Murphy, this hybrid retails for $275 and can be found in three colorways.
