Upgrade Your Everyday Footwear With These Casual Shoes (2024)

The RS01 may look like a simple canvas sneaker, but it wears like a top-flight running sneaker mixed with a memory foam pillow. These editors-approved kicks are also a favorite of Pedro Pascal. They have a dynamic, retro-inspired knit upper to elevate any of your basic workwear trousers, while their durable gum sole guarantees these sleek kicks will provide the foot support you need for months or years of long wear.

These are perfect business casual work sneakers, especially if your business keeps you on your feet all day. And unlike other sneakers, these don’t require breaking in and are fully machine washable.

What Do Buyers Say? "Comfy, they look nice. My only (minor) complaint is that the design of the back of the shoe tends to push short socks down if you walk a lot, so sometimes my sock will bunch up under my heel," says one customer.

Pro-Keds has a rich history that spans way back to the 1950s when they first made shoes for basketball players (George Miken wore the brand at one point). The Royal Lo is the brand's timeless retro sneaker that looks better as it wears with age. Just make sure to upgrade to the all-leather model.

What Do Buyers Say? "I was pleasantly surprised by these shoes. They felt a little large, and a little hard in the insoles initially, but they proved themselves both supportive and comfortable after a little break-in period," says one customer.

Cole Haan's Shortwing Oxford has been a go-to shoe for business casual wardrobes for some time now. It's the perfect mix of cushioned comfort and timeless sneaker style.

I’ve been wearing these classic, best-selling Cole Hann dress sneakers since 2021, to the office or any office-adjacent events—happy hour, client meetings, etc. I love that they’ve got the uppers of dress shoes but the footbed of sneakers—it’s the best of both worlds, really. And on more than a few occasions, I had to wear these for hours on end, and their added comfort from the EVA midsole and patented cushioning has never failed me once. And they look incredibly on-point with jeans for a true business casual vibe.

What Do Buyers Say? "They are the perfect blend of a dress shoe silhouette and the comfort of a sneaker. It's one of my favorite pairs of business casual shoes that can take you from a client meeting, to out on the town, and lounging around," says lifestyle influencer Steven Fingar.

The OCA Low not only is one of the best everyday fashion sneakers we've tested out there, but it's also Ashton Kutcher's go-to kicks. The footbed feels incredibly comfortable with arch support—spring and cushioned. Right from the first wear, the fit felt perfect to us so we didn't need to break it in. The classic style just works as a versatile fashion sneaker; coupled with a canvas upper that breathes and a lightweight build, the OCA Low might just be your go-to kick.

What Do Buyers Say? "I took a chance and ordered these shoes right before our Italy trip. On heavy walking days, these were a lifesaver! So incredibly comfortable, great arch support, and no blisters even on the first wear," says one customer.

Read More: Cariuma's OCA Low Review

Cutting to the chase is the OG boat shoe design that has never looked out of style and definitely never will. As you slip your feet into them, you'll also find yourself reveling in the secure, customized fit provided by the signature 360° lacing system. What we love most about these OGs is that they now come with an OrthoLite insole to envelop your underfoot in comfort and provide shock absorption to each step. Coupled with the inclusion of an EVA heel cup that adds an extra layer of cushioning, we were even able to travel in these shoes for hours.

What Do Buyers Say? "The leather is nice and looks like full grain; it molds to your feed in a few weeks for a perfect, roomy fit. I have wide toes, and these shoes are the most comfortable ones I have. No extra foam or padding or that crap," says one customer.

These dad shoes, born in 1982, are now upgraded with a streamlined outlook and better performance to make a case for dad shoes that are pretty damn cool. Whether it’s the propulsive foam that helps you get back on your feet fast or the midsole cushioning that provides all-day comfort, you’ll feel like the patriarch of your household in them—even if you’re not a father. With a midsole that absorbs impact and provides underfoot cushioning and a footbed that delivers support, this is also one of our best-tested walking shoes.

What Do Buyers Say? "Overall it's a great shoe. It's stable and cushioned with moderate arch support, and looks darn good, too. The shoe is super comfortable," says one customer.

You can't go wrong with any On shoe model, but if you're looking for a stylish design built for more casual wear (as opposed to fitness) then The Roger is your pick.

On’s grand slam collaboration with Tennis champ Roger Ferrer wins by creating a sneaker that offers both technical benefits with tasteful style. The vegan leather Roger Clubhouse shoe in black especially elevates your look. And the best part is, the trademark On CloudTec® and Speedboard technology are both there—assuring both comfort and durability as you travel and commute.

What Do Buyers Say? "More of a casual fashion shoe, rather than a usable tennis shoe. That being said, they are very comfortable... I was very skeptical at first, but once I broke them in I couldn't be happier with the comfortability. These look great with a lot of different styles, very versatile," says one customer.

Style-wise, it’s a smart blend of chukka boots plus sneakers, which I’ve styled with a trucker jacket plus jeans or sweater over pants, and I’m never not satisfied by how these business casual shoes can transition from formal to casual and back and forth, just like that.

But the comfort of walking and being on your feet for hours on end is not to be underestimated, even at this price point: the outsole is light but tough, and absorbs impact to reduce underfoot fatigue; the leather upper is easily broken in; and the sponge insole is as comfortable as it comes.

What Do Buyers Say? "Unbelievable how comfortable these shoes are. They look like business and feel like my Converse. Very well made," says one customer.

The Daily Wool is a more sporty option for those who like the feel and performance of a wool shoe. The shoe is breathable, and soft, and looks great with any fit—whether you want to dress up or down, with chinos and polos, tees and shorts, shirts and jeans. The cushioning will hit your underfoot sweet spot and keep your feet going all day long with the right amount of support.

What Do Buyers Say? "These shoes are very comfortable and look great with jeans, pants or even shorts. Great versatility too, I wear these shoes to the golf course or out to dinner," says one customer.

Allbirds makes, hands down, the most comfortable slip-on shoes out there. In our testing, we were first and foremost impressed by the upper which is lightweight, breathable, and thermoregulating. Our favorite part about these shoes is how great they are for walking and everyday wear because of the midsole, which is made of foam to contour our feet and feel bouncy to absorb impact at each soft. Thus, we absolutely love how soft each of our landings feels as well. The insole is also odor-resistant and moisture-wicking so our feet will stay cool and dry.

What Do Buyers Say? "Enjoying these loungers as house slippers! Comfortable and breathable. You barely feel like you're wearing any shoes at all," says one customer.

If you're looking for a more elevated sneaker as your casual shoes, P448 makes its footwear in Italy with fine leather. The Jack sneaker styles have a luxe feel and come in a ton of fun variations and colors, making them a solid casual shoe pick if you're looking for expression. Plus, with memory foam insoles, each style feels damn comfy too.

What Do Buyers Say? "True to size, comfortable for walking long distances and stylish for any occasion. I love them," says one customer.

Amberjack The Chelsea

These business casual Chelsea boots are nothing but supportive and stylish. Having owned these for several months, I can say with confidence that these are perhaps the most comfortable boots I’ve ever tested—all thanks to Amberjack’s athletic performance build. The memory foam arch support plus the flexible outsole with extra support in the heel are both designed to let your feet move in comfort, and the upper is made with flexible materials. The construction won’t tire my feet out since it's soft and easy to break in yet very sturdy, but the overall versatile look for dressing up and down is also a highlight.

What Do Buyers Say? "I have to say these may be the most comfortable boots I've ever owned and they aren't even broken in yet! These are in a different league comfort-wise. The insole feels like you already have a cushy insert put in, something I often do with boots. They look great too, sleek stylish and look as if they will get a nice patina over time," says one customer.

There's hardly any retro sneaker more timeless and versatile than the Chuck 70. Todd Snyder gave the classic basketball shoe style that debuted over a decade ago a modern twist with a new thick textured canvas upper, a heavier recycled rubber gum sole, a comfortable cork liner, arch support, and durable stitching for everyday wear, even if you’re not double-dribbling.

What Do Buyers Say? "Bought these to workout in. They look great and are quite comfortable. They feel durable and seem like they will last a while," says one customer.

Known for their durability and versatility, owning a pair of suede Clark Desert Boots should be a no-brainer. With an origin that dates back to surviving the deserts in WWII, these boots are built for walking the long walk and carrying you through. As for the OG style, Clarks’ desert boots are also versatile enough for dressing for summer and for the rest of the year, and you’ll have fun mixing-and-matching with your casual office looks.

What Do Buyers Say? "Clark’s are comfortable, durable, sturdy and has styles that make a great fashion statement for every and any occasions," says one customer.

Having been around since 1936, the Weejuns is the OG penny loafer style that still looks great today. In fact, our Gear & Commerce Editor has had them since 2020 and affirms that their craftsman-like construction can hold up even after years of wear. When it comes to business casual, we also love that these fit within the trend of wearing jeans with loafers, but also are foolproof when it comes to chinos and dress pants.

What Do Buyers Say? "As the OG, Weejuns are an excellent choice for beginners venturing into this style. With their timeless silhouette, a wide array of styles, and true-to-size fit, Weejuns provide great value for your money," says personal menswear stylist Turner Allen.

Every man must own a pair of Arizona sandals in their lifetime. It's an unwritten footwear rule. The combination of comfort, versatility in styling, and incredibly long lifespan is why these bad boys take the crown. According to board-certified foot surgeon Brad Schaeffer, D.P.M., their design plus support structure work together to offer everyday comfort in a city-friendly design. "They have a solid cork footbed and contouring for our arch and toe box. I love the overall feel and wearability of these sandals and have been wearer since my teen years," says Dr. Schaeffer.

What Do Buyers Say? "I’m particularly partial to Birkenstock’s Arizona sandal—it’s the all-purpose shoe that works well in practically every situation. I love to pack them for vacation because I wear them everywhere—to the beach, to dinner, around the hotel. They pair as easily with a bathing suit as they do with a camp shirt and pleated cotton trousers," says Justin Berkowitz, men’s fashion director at Bloomingdale’s.

They say that fine wine gets better with age. The same can be said for a great leather boot, such as the Captain lace-up dress boot that you’ll want to keep within arms reach for years to come. Made with Goodyear welt construction, it’ll last you a lifetime. With footbeds that form to your feet and provide all-day comfort, you’ll want to sport them 24/7. Dress them up or down, your choices are endless.

What Do Buyers Say? "I wear these almost every day and the quality is superb. These really hold up as you'd expect. I get a lot of compliments on these," says one customer.

Driving loafer? Penny loafer? The answer is yes. M. Gemi’s ingenious design combines the summer laidback panache of moccasin driving shoes with the classic design of the penny loafer to take the guesswork out of your “What type of loafers look best on me?” concern. We love that it’s incredibly lightweight and barefoot-friendly, even for walking. Our favorite part however is the oval toe which offers a comfortable fit and no-break-in-needed wear right out of the box.

What Do Buyers Say? "M. Gemi’s Pastoso Uomo loafer is a classic Italian leather penny loafer style. The leather is soft and easy to wear. They also have a few colors that come with a contrasting sole which makes them interesting," says stylist Alyssa Dineen.

Hey Dude has taken men's footwear by storm over the past couple of years. (The Wall Street Journal even wrote a trend piece on these interesting kicks.) Whether you're for it or not, it's impossible to ignore Hey Dude’s provides a high level of comfort at a generous price point. The shoes are also super easy to throw on, making them a pair of great summer shoes. Best of all is the fact they are insanely affordable too. Simply put, don't knock 'em until you try 'em.

What Do Buyers Say? "These shoes are so comfortable and do not make your feet feel hot at all. I have no arches on my feet and have had difficulty finding comfy shoes for my feet without having to buy separate insoles and these ones are not that case! I stand on my feet all day teaching and my feet do not hurt at the end of the day," says one customer.

Bordering on sneaker territory, though the welt stitch and derby-style leather upper is enough to pass for dress shoes under the right circ*mstances. If you have a relaxed work dress code or are looking to elevate above sneakers without losing the comfort, these are the shoes for you. The perforated upper, padded ankle and tongue, and pretty much the entire sole provide the feel of a top-end running shoes.

What Do Buyers Say? "I ordered the shoes on line and was skeptical of their potential fit and looks. Surprisingly they fit perfectly, even on my imperfect feet, and they look great. Very comfortable to wear all day," says one customer.