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Best Men’s Travel Shoes Ready for an Adventure

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; multiple factors play a vital role in the decision-making process, with the most important being the destination of your travels.

Here are a few travel shoes that will allow you to soak in the beautiful sites while your feet remain comfortable.

1. Best Overall: Allbirds Men’s Tree Runners

allbirds tree

When it comes to spending a full day walking around town or checking out the sights, the Allbird Men’s Tree Runners are an optimal choice. The Tree Runners feature a sporty style and come in 3 classic colors and 10 limited edition colors (at the time of initial publication). 

But what really sets Tree Runners apart from many other shoes out there is the materials that they are made from. 

Here’s what makes these shoes so unique:

  • Uppers: Made from sustainably sourced silky soft eucalyptus tree fiber, they have a versatile look that can be dressed up moderately while also serving as an everyday sneaker.  
  • Insole: Derived from castor bean oil rather than petroleum oil, they provide adequate support for both your feet and back – extremely important if you plan on walking extensively while traveling.
  • Midsole: Rather than relying on rubber or other non-sustainable materials, Allbirds developed the world’s first carbon-negative midsole that is sourced from sugarcane.
  • Laces: Holding everything together will be the laces.  Instead of opting for virgin polyester fiber like other shoe brands, the laces used in the Tree Runners are made from 100% recycled polyester. 

When resorting to such materials, it inevitably begs the question – sure it sounds great, but how will they perform?  Our research found that men were extremely happy with the performance.

Now if this doesn’t seal the deal – perhaps the fact that these shoes are machine washable will.  Yes, you read that right.  If after you get back from your vacation and the shoes are starting to show some signs of wear and dirt buildup, you can toss these into the washer to get them looking like new again.

If there was ever a time that you wanted to vote with your wallet and support a company that not only makes shoes in a sustainable fashion but also give back to the community through the Soles4Souls program (read more here), then the Allbirds Tree Runners are a solid pick you will not regret.

Related: In-Depth Review of Allbirds


  • Excellently cushioned midsole for long days of walking
  • Laces won’t fall apart
  • Sporty style


  • Might be a bit too casual if you have a nice dinner planned

What You Need To Know

The Allbirds Tree Runners are an optimal choice for anyone planning on doing a great deal of walking while on their travels. They’re a sporty style, have excellent midsole cushioning, and are durable.  These are one of the most versatile travel shoes – not just from a performance standpoint, but also in the environmentally friendly way that these were made.

2. Most Stylish: Helm Declan Chukka


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.

Related: Types of Men’s Boots

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.


  • Offers classy look without sacrificing too much comfort
  • Excellent for a variety of different clothing combinations
  • Fast break-in period
  • Reputable brand


  • A bit on the high-end for pricing

What You Need To Know

The Helm Declan Chukka is the most stylish travel shoe around. They’re versatile, classy, and durable with a fast break-in period.

3. Best for Leisure: Brooks Brothers Leather Driving Moccasins

brooks brothers loafer

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.


  • Minimalist, yet still stylish design
  • Comfortable cushioned insole
  • Perfect for warm-climate vacations


  • Higher-end pricing
  • Only comes in dark brown

What You Need To Know

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.

4. Rancourt & Co. Court Classic Travel Shoe


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 one of the best travel shoes available.


  • 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


  • Though the company praises its versatility, we don’t believe they would fit with most formal dresswear options

What You Need To Know

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.

5. Timberland Kendrick Waterproof Chukka Boot


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.

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.


  • Exceptionally sturdy, will last for years
  • Excellent for standing for extended periods, all day long comfort
  • Great quality


  • Higher-end pricing
  • Only available in standard width

What You Need To Know

The Timberland Kendrick is the finest travel boot for all-day wear. It’s sturdy, high-quality, and won’t let you down.

6. Merrell Travel Suede Hiking Shoe


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.


  • Gripping outsoles offer added traction
  • Base offers flexible support


  • Not fashionable
  • Likely not water-resistant

What You Need To Know

These are function over form, but still one of our favorite pairs of travel hiking shoes thanks to the added traction and comfort.

John Wellman

John Wellman is one of the most experienced and respected fashion experts specializing in men's clothing. He has worked in the fashion industry for over fifteen years, during which time he has provided an expert eye and advice to numerous fashion clients.

John has developed a keen understanding of the nuances of men's style and the importance of selecting the right pieces for a particular look. He has been praised by peers and clients alike for his ability to create classy yet edgy looks that stay true to the personality of the client.

John has a passion for men's style and believes in the importance of dressing with confidence and flair. He looks forward to continuing to make an impact in the fashion world and to helping men look and feel their best.

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