Updated On April 05,2020

Best Men's Travel Shoes That Your Feet Will LOVE

When planning a trip, what shoes you should bring with you is a commonly under-planned step. With all of the possible complications that often come with travel, having a comfortable pair of travel shoes can make a world of difference. However, finding the right pair isn’t merely a matter of style or price; there are multiple factors that play a vital role in the decision-making process.Furthermore, we will also answer popular questions men have when choosing and wearing travel shoes, along with taking a look at other alternative footwear you may want to think about before making your purchase.Let’s get started:

No.1 Rancourt & Co. Court Classic Travel Shoe Best For: Best Overall Reason for listing: The Court Classic has a stylish, minimalist design, it’s durable and comfortable, and comes in a variety of different colors. It’s great for guys in search of the ultimate travel footwear. It’s difficult to accurately nail down the “best” travel shoe overall, but the Rancourt & Co. Court Classic Travel Shoe is worthy of mention. Paired with a color-choice of black, natural chromexcel (brown leather color), or white, the minimalist design allows outfit versatility—meaning they work well for many occasions, from casual to semi-formal.The upper section of the Court Classic is made from full-grain leather (cowhide) which provides the absolute best durability of any leather type. The inside of the shoe has a soft suede lining, which makes going sockless an option, and keeps your feet from getting sweaty.While the Court Classic isn\'t always the best choice for every situation, its foam footbed and custom-made rubber sole provide a comfortable and well-rounded travel shoe experience—effectively earning its place on our list as the overall best travel shoe around.
Pros
- Minimalist style with three neutral colors
- complimenting a variety of different outfit choices
- Combination of leather upper and suede lining provides both durability and comfort
- Best quality leather available
Cros
- Though the company praises its versatility
- we don’t believe they would fit with most formal dresswear options
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No.2 ARKK Copenhagen Raven Mesh HL Best For: Best for Walking Reason for listing: The ARKK Copenhagen Raven Mesh HL travel shoes are an optimal choice for anyone planning on doing a great deal of walking. They’re a sporty style, have excellent midsole cushioning, and are durable, but they do take a while to break-in. When it comes to spending a full day walking around town or checking out the sights, the ARKK Copenhagen Raven Mesh HL travel shoes are an optimal choice. They are a sporty style choice and come in black or white with nylon laces that are quite durable.The upper consists of a complementary combination of neoprene and mesh materials, with a custom-made midsole specifically designed to provide additional support and comfort. The shoe does use a standard rubber outsole, but it only adds a negligible amount of extra weight. They do require some use to break in, so make sure to take them for a spin before heading on your trip, or you’ll have to deal with some unnecessary discomfort.Overall, with fantastic support and comfort, the Raven Mesh HL is the perfect travel shoe if you intend to do a lot of walking on your next trip.
Pros
- Excellently cushioned midsole for long days of walking
- Laces won’t fall apart
- Sporty style
Cros
- Works the best with casual wear
- Has an initial (though short) break-in period; wear before leaving
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No.3 Helm Declan Chukka Best For: Most Stylish Reason for listing: The Helm Declan Chukka are the most stylish travel shoe around. They’re versatile, classy, and durable with a fast break-in period, but they aren’t the most comfortable travel shoe choice. The Helm Declan Chukka is a stylish travel shoe for those who want to look their absolute best during their travels. With a black leather lining, Blake stitch construction, and a Fineline sole (learn more about this type of sole here), the Chukka provides a pleasant combination of style and outfit versatility without sacrificing too much in comfort.They come with a durable rubber midsole, brass finish eyelets, and cotton laces (which are not the most durable, but suitable for their purpose). The shoes are handcrafted, designed to be form-fitting, and true to size, with a reportedly quick break-in period as well. They are available in tan, brown, and black.While the Helm Declan Chukkas aren’t the most comfortable, they are definitely the most stylish travel shoe under $300, and you’ll look great in them too.
Pros
- Offers classy look without sacrificing too much comfort
- Excellent for a variety of different clothing combinations
- Fast break-in period
- Reputable brand
Cros
- A bit on the high-end for pricing
Buy At Helmboots
No.4 Brooks Brothers Leather Driving Moccasins Best For: Best for Leisure Reason for listing: The Brooks Brothers Leather Driving Moccasins are minimalistic yet stylish, comfortable, and perfect for most leisure activities, but are a bit higher-priced and only come in one color. Brooks Brothers Leather Driving Moccasins are perfect for any leisure trip, whether you intend to spend your time lounging on the beach, or strolling through a gorgeous national park.Available exclusively in dark brown, these driving moccasins come with a comfortable leather insole and a rubber outsole that provides improved flexibility and traction. The upper is a simple, yet stylish design, with the lip embossed with the Brooks Brothers signature fleece logo.While these shoes aren’t optimal for long days of walking or hiking, the Brooks Brothers Driving Moccasins are an excellent choice for most leisure activities, and can be kept as an additional pair for comfortable night-drives.
Pros
- Minimalist
- yet still stylish design
- Comfortable cushioned insole
- Perfect for warm-climate vacations
Cros
- Higher-end pricing
- Only comes in dark brown
Buy At Brooksbrothers
No.5 Sperry x Vineyard Vines Boat Shoe Best For: Best Slip-Ons Reason for listing: The Sperry x Vineyard Vines Boat Shoes are the perfect slip-on for summer or warm destinations. They’re well-made, form-fitting, but are only available in one color and medium width sizing. Most slip-on shoes are fairly similar in design and included features, but the Sperry x Vineyard Vines Boat Shoe stands out from the rest. These shoes are an easy and excellent choice for a leisurely trip to a warmer climate.The upper is genuine leather, which is the least durable of any leather type, but the stitching and two-eye design are remarkably well-crafted. The hand-sewn design does require some break-in, but after that initial period, it fits quite nicely to the shape of your feet. The outsole is a durable rubber design that further adds to the comfort of the shoe.On the downside, these shoes do only come in a single color, Gray Harbor. This which has a noticeably blue outsole, limiting your outfit color-scheme choices. Overall, the Sperry x Vineyard Vines Boat Shoes are a comfortable choice, perfect for those who appreciate the ease and grab-and-go functionality of a slip-on.
Pros
- Stylish for summer occasions
- Well-made rubber outsole provides extended durability and comfort
- The hand-sewn design fits comfortably to the shape of your foot (but does require some break-in first)
Cros
- Only one color available
- limited outfit combinations
- The width size is available in Medium only
Buy At Vineyardvines
No.6 Birkenstock Boston Clogs Best For: Most Comfortable Reason for listing: The Birkenstock Boston Clogs are the most comfortable travel shoe on the market. They’re durable, flexible, cushioned, and listed for a reasonable price, but they aren’t that outstanding in the looks department. If you’re not too concerned about being overly-stylish or having a shoe that doesn’t exactly match all of your outfits, the Birkenstock Boston Clogs are the pick. Although the word “clog” sort of implies an uncomfortable shoe, the Birkenstock Boston Clogs are hands-down the most comfortable travel shoe available.The upper consists of a thick suede shell with a buckle strap accent and the outsole is made from Ethylene Vinyl Acetate (EVA)—the most flexible, durable, and shock-absorbing material in the world.The insole is an exceptionally soft foam material, which when combined with the EVA outsole, provides a fantastic amount of cushioning and support. They’re available in black, tan, and brown, and are a reasonable price.The Birkenstock Boston Clog certainly isn’t the most attractive looking shoe (style is subjective), but they are the best choice for the comfort-minded man who would prefer to spend his trip walking on a cloud.
Pros
- Supremely comfortable and cozy
- Durable materials
- Flexible and supportive outsole
- Reasonable price
Cros
- Not the most stylish choice (again
- style is subjective!)
Buy At Urbanoutfitters
No.7 Brooks Brothers Leather Flip Flops Best For: Best for Hot Weather/Caribbean Reason for listing: The Brooks Brothers Leather Flip Flops have a rubber outsole that provides extra comfort, they’re of excellent quality, they’ll keep your feet nice and cool in hot climates, and are reasonably priced. If your next trip is to any hot or Caribbean-esq climate, you can’t go wrong with the Brooks Brothers Leather Flip Flops. Available in dark brown and tan, these flip-flops are made from genuine leather and have a rubber outsole which provides extra support and durability.They’re decently priced, and make an excellent extra pair of shoes to throw on when you’re in the mood for walking along the beach or heading to a festival. Surprisingly, however, these flip-flops do require some breaking-in before they reach their full comfort potential.
Pros
- Long-lasting for a reasonable price
- Supportive and durable rubber outsole
- Excellent quality
Cros
- Need to be broken in first
Buy At Brooksbrothers
No.8 Helm Pablo Chelsea Boot Best For: Best for Europe Reason for listing: Want to look stylish and sophisticated during travels thorough Europe? Enter Helm's sleek profile Pablo boots. They're made from high-quality leather, easy to break-in, and work with a wide variety of outfit choices, but they do have a high price tag. European and American shoes have a lot of similarities in features and styles, but not everything stylish here is stylish there, and vice versa. A particularly attractive and stylish European shoe is the Helm Pablo Chelsea Boot.With brown, tan, chocolate, and black color options, the Pablo Chelsea Boot offers a versatile and elegant look fitting for both streetwear and formal occasions. The upper is full-grain leather (the most durable type of leather) with a zipper-enclosure, and the liner is natural leather.These Brazilian, handcrafted boots run true to size and, after a short break-in period, conform nicely with your feet.The Pablo Chelsea Boot by Helm combines the look of an Italian motorcycle boot and a European zipper boot, resulting in an elegant and sophisticated design perfect for travels across Europe.
Pros
- Stylish European design
- suitable for casual and formal occasions
- Easy to break-in
- Made from the highest quality leather available
- Reputable brand
Cros
- Higher-end pricing
Buy At Helmboots
No.9 Nike Air Force 1 Best For: Great Athletic Travel Shoes Reason for listing: Nike’s Air Force 1 are an excellent travel shoe for anyone who’s into athletics. They keep your feet cool, comfortable, and are reasonably priced, though, they’re not the best for most long-distance running. If you love to train, play sports, or simply enjoy being active where ever you are, the Nike Air Force 1 sneakers are the best athletic travel shoe option. Named after the Air Force One, the sneaker is designed specifically for high-performance athletics.The leather upper has a custom perforation at the front, which increases air-flow to your toes and keeps them from sweating. The insole is a flexible foam material that provides soft cushioning with extra rebound support. With a rubber outsole and padded ankle collars, the Nike Air Force one sneaker offers top of line comfort and support for most types of athletic activities.It also doubles as a causal-wear shoe, available in black or white.Overall, these sneakers are durable and will keep your feet comfortable, ensuring your shoes don’t come between you and your maximum athletic performance.
Pros
- Sporty and sleek style
- High-performance during even the most intense training sessions
- Designed for comfort and support
- Reasonable price
Cros
- Not the best athletic shoe for long-distance running
Buy At Urbanoutfitters
No.10 Kendrick Waterproof Chukka Boot Reason for listing: The Huckberry Rancourt & Co Brunswick Boot is the finest travel boot for all-day wear. It’s turdy, high-quality, and made exclusively in the USA, but, it is on the higher end for pricing and it’s only available in standard width. Having a waterproofed shoe is absolutely essential if you’re heading somewhere with torrential rains or snowstorms. The Kendrick Waterproof Chukka Boot is both affordable and has highly-effective waterproofing, making it the best waterproof travel shoe.The leather upper is treated with the company’s “Timber-Dry” tech, which keeps the leather from absorbing water, offering maximum waterproofing efficiency. The boot also includes an OrthoLite insole (removable), which, as we covered earlier, works brilliantly for both older and younger men who value extra comfort and support. The outsole uses synthetic materials which are excellent at keeping water out and your socks dry in even the wettest conditions.This boot is also relatively heavy (1.3 lbs), so it isn’t the best choice for those who wish to travel light.Overall, the Kendrick Waterproof Chukka Boot is a suitable and affordable choice if you’re going to be trekking through the wild outdoors, facing some intense rain or cold on your next trip.
Pros
- Exceptionally sturdy
- will last for years
- Excellent for standing for extended periods
- all day long comfort
- Great quality
- 100% made in the USA
Cros
- Higher-end pricing
- Only available in standard width
Buy At Nordstrom
No.11 Merrell Travel Suede Hiking Shoe Reason for listing: These are function over form, but still one of our favorite pairs of travel hiking shoes thanks to the added traction and comfort. Another of our favorite pairs is the Merrell Travel Suede Hiking Shoe. Built to keep your feet comfortable during hours of exploring the great outdoors, these will easily get you through your next amazing adventure.Available in two color options, both 100% suede, you\'ll enjoy outsoles with added grip to keep you upright on any terrain. Unfortunately, suede is not often water-resistant and the product description does not mention anything to the contrary.
Pros
- Gripping outsoles offer added traction
- Base offers flexible support
Cros
- Not fashionable
- Likely not water-resistant
Buy At Amazon