Footwear holds a lot of weight in the overall look of an ensemble. And for guys, the confidence you get from rocking a fresh pair of kicks can’t be understated. Whether you’re traveling, out with friends, or at work, you always feel good when your footwear looks good. For the latter, finding the right shoes sometimes takes a little more thought than what you wear on your days off.
If your office calls for business casual apparel, you probably have a decent idea of what clothes to wear. Sometimes called “smart casual,” slacks, khakis, button-downs, polo shirts, and blazers are all key pieces that can be mixed and matched to create outfits for this dress code. But what about your feet? Keep reading to find the most comfortable shoes for men.
At Vionic, we recommend having at least a couple of go-to pairs of shoes in your arsenal that can be worn to work. That way, you’ll be able to put together a dapper (but not-over-the-top) outfit every time. Consider this your guide to the best men’s business casual shoes.

What Are the Best Men’s Business Casual Shoes?

With smart casual footwear, you don’t want to go too fancy, as it might throw off the rest of your look. On the other hand, you also want to be careful about being too informal. Sure, you can’t spell “business casual” without the word “casual,” but it’s really all about balancing the two styles. So, what shoes walk the line between professional and laidback with finesse?
The footwear pros at Vionic are well-versed in shoes for men’s wardrobes, including dress shoes, semi-dressy styles, and polished casual designs that work for a variety of occasions.
The best business casual shoes for men include:

• Loafers
• Derby shoes
• Oxfords
• Driving Moccasins
• Chukkas
• Chelsea boots
• Leather slip-ons
• Casual sneakers

Yep, you read that last one right. Sneakers can pass for work attire, but there are a few things to consider before heading out the door in a pair of trainers. Here’s what you should know about each of these shoe styles and how to curate professional outfits with them.

Loafers

The loafer has almost always been in style for men, and it very well may always be in style. This versatile, timeless shoe dates back to the 1800s, boasting a slip-on design that’s equal parts polished and approachable. Loafers are easy to get on and off, and they can be dressed up or down.
When you check out the types of dress shoes for men that we carry at Vionic, you’ll find tailored designs with full-grain leather uppers, fine stitching, removable footbeds, ultra-comfy orthotic support, and sturdy rubber outsoles.
Possibly the most comfortable men’s business casual shoe, loafers are a go-to for year-round office apparel. You can wear them with slacks, dress shirts, polos, or a casual suit.

Derby Shoes

Undoubtedly dapper, the derby shoe is one of the more laidback dress shoes for men. The style features signature open lacing, meaning the quarters are stitched on top of the vamp. Additionally, there’s no seam between the toe and the tongue.
Derby shoes are often made of suede, but you can also find them in full-grain leather. The men’s derbies from Vionic have soft yet sturdy uppers in neutral colors, exposed stitching, leather-wrapped molded footbeds, built-in arch support, and partial wooden soles.
If you’re trying to find the best business casual shoes for comfort, you really can’t go wrong with this put-together, wear-anywhere style. Derby shoes go with suit separates, chinos, and sometimes even jeans.

Oxfords

Oxfords are a little on the dressier side—at least compared to loafers and derbies. However, this brogue-style shoe is still an excellent choice for the boardroom, networking events, or an average day at the office. Featuring a classic wingtip or cap toe and closed lacing, the oxford’s eyelets are attached underneath the vamp.
Vionic’s oxford shoes have protective weather-treated leather uppers, handsome stitching, perforated (pin-prick) detailing, orthotic footbeds, and durable rubber soles. This timeless silhouette can lean fancy or veer toward a casual look, depending on what you wear with it. Try khakis or chinos and a polo or pressed button-down to look put-together but not too formal.

Driving Moccasins

As one of the most comfortable office shoes, men appreciate the practical and contemporary business casual appeal of driving moccasins. They’re a versatile fallback for busy guys who want to be professional without looking too dressed up.
We also like that driving moccasins can be worn in the summer or winter. They go with chinos, linen suits, dark-wash jeans, and even pressed shorts. The driving mocs from Vionic have supple leather uppers, horse-bit detailing over the vamp, removable leather-skinned insoles, rubber outsoles with excellent traction, and supportive contouring to help realign your stride.

Chukkas

Then there’s the chukka (sometimes called the desert boot), which is similar to the derby, except it rises up over the ankles.¹ Often made of calfskin, or velvety suede with an open lacing system, this men’s boot style is the ideal balance of polished and casual.
At Vionic, we’re big fans of the chukka boot’s laidback masculine appeal. When you browse our styles, you’ll find supple suede silhouettes and weather-treated designs made for versatility and year-round use. You can rock this shoe style with pressed slacks, black or dark-wash denim, or chinos.

Chelsea Boots

Featuring elastic side panels with pull tabs behind the heels, the Chelsea boot is a versatile slip-on shoe you can wear to work through the fall and winter since some are considered waterproof boots.² Vionic’s Chelsea-style boots for men can be worn with professional outfits or dressed down on your days off. They’re impressively lightweight and come with smooth leather uppers, co-molded footbeds, and active rubber soles.

Leather Slip-Ons

Leather slip-ons are arguably the most comfortable business casual shoes you can find. This footwear style has some sneaker-like features, as well as some dressier characteristics.
Featuring active outsoles and smooth leather uppers with gore side panels, Vionic’s slip-on men’s shoes are the best of both worlds. Many of our designs are treated for weather resistance, plus you’ll get podiatrist-designed orthotic support and reliable rubber outsoles.

Casual Sneakers (Maybe)

As we mentioned, sneakers can sometimes work as business casual footwear, but it really depends on the specific rules of your dress code. Some employers that have a business casual dress code allow sandals, others require closed-toe styles, and some offer leeway to wear tennis shoes. Check out our selection of the best mens sandals!
If you’re allowed to wear athletic shoes, there are a few things to keep in mind before incorporating them into your 9-to-5 wardrobe. We recommend wearing casual sneakers (AKA streetwear sneakers or fashion sneakers) to work because active styles don’t typically pair as well with khakis, chinos, and other professional attire.
Lace-up sneakers are great for the office, as long as they’re clean.³ You might consider a pair of laced leather or suede tennis shoes or a retro-inspired style. As for color, your safest bet is white, black, navy, tan, gray, brown, or another neutral hue.

Where to Buy Comfortable Work Shoes for Men

What you wear on your feet is a big part of how you present yourself at work, so the right business casual shoes are essential. You want stylish footwear, and yet you’re also not willing to sacrifice comfort. So, what’s a guy to do? If you’re in the market for new work shoes, you’ve come to the right place.
Supportive footwear has come a long way from the outdated styles you may associate with orthotics. Men’s shoes from Vionic align with the latest fashions. Our designs include stylishly relaxed loafers, chukka boots, oxfords, derbies, leather slip-ons, and Chelsea boots, plus lots of cool sneakers. They’re expertly engineered with unbeatable arch support, contouring, and stability—all hidden within the soles. Depending on the occasion, these shoes could also be a perfect for groom wedding shoes.
Browse men’s business casual shoes from Vionic today.

External sources:

1. “Everyone Needs a Solid Shoe Rotation. Here’s How to Start Building Yours”. Esquire. Jan 12, 2021, https://www.esquire.com/style/mens-accessories/advice/g1436/12-best-shoes-for-men/
2. Trent Bartlett. “7 stylish men’s shoes that every man should own”. The Trend Spotter. https://www.thetrendspotter.net/7-dress-shoes-every-man/
3. Jake Woolf. “These Business-Casual Shoes Are the Wear-with-Everything Footwear You’ve Been Dreaming Of”. GQ. Mar 24, 2017, https://www.gq.com/story/business-casual-shoes-lug-sole-lace-up