Wouldn't it be awesome to have a good pair of travel-friendly boots? Boots which are flexible, easy to put on or take off, and can withstand bad weather conditions? That's the beauty of the Chelsea. No other laceless boot has same kind of appeal and lasting power.
Why did these unconventional boots become such a massive hit? Well…they were simply embraced by prominent figures over the past century. From royalties like Queen Victoria to rock ‘n' roll bands like the Rolling Stones and Beatles, the world would learn about Chelsea boots – and see how versatile and attractive they were.
Instead of eyelets and those (at times) pesky laces…you don't need to do anything to tighten the boots once you've worn them. The elastic panels on either side (plus a zipper on the inside) keep your feet secure but still very comfortable. To slide the boots on and off, just tug on a small fabric loop attached at the back. It's that efficient.
Buying Men's Chelsea Boots For Travel
I suggest choosing a dark color for Chelsea boots. Narrow it down to black, oxblood or a darker shade of brown. As for the overall design – a cut or rounded-off toe definitely works better than a heavy square toe. You want the heels between 1 and 1.5 inches in height. That's the formula for the most elegant Chelsea boots you can ever wear.
Men's Travel Dress Shoe #2 – Double Monk Strap
Legend has it that as far back as the 15th century, monk straps had already existed in the form of sandals – worn by real monks living in the Alps. An English man was said to have traveled there and taken home a pair. And those sandals would evolve into the shoes we know of today.
It's really no surprise that men like the double monk strap. Right off the bat, it looks interesting and stands out from a sea of oxfords and other shoes with laces. The straps and buckles aren't just there for tightening the shoe…but also as accessories.
Double monks might've started out as too casual for people. But more and more guys are using them whether they're dressed up or down. They now wear them with a casual suit or something simpler (like a t-shirt and jeans). The extra details of these shoes can level-up a more laid-back wardrobe. It's all the more reason to travel with them – even if you're on vacation.
Buying Men's Double Monk Straps For Travel
The only version to watch out for is suede double monk straps. Suede isn't as versatile of a color compared to black or dark brown. There's also a chance of the shoes getting blemished as suede material absorbs liquid more easily (so it'll be tough when it's raining or snowing).
Men's Travel Dress Shoe #3 – Penny Loafer
Did you know the penny loafer was historically quite practical? The hole along the horizontal band was meant to store change (hence the name “penny”) so schoolchildren could ride the bus every day.
You probably won't find that version of penny loafers anymore…but those available right now look pretty awesome…and feel great to walk around in.
Among the three, they're probably the most convenient to wear when you're navigating through airports. You can slip them on and off without any effort necessary.
The downside to penny loafers is due to their slipper-like appearance, they're not viewed as dressy shoes. That means you won't get away with wearing them to weddings or business conferences (stick to oxfords for those). So do place dress code above convenience when you travel for certain events.
Buying Men's Penny Loafers For Travel
Here you can select most colors for the penny loafers. Darker browns go perfectly with the casual stuff men usually wear: dark shorts or jeans. A lighter brown may be better if you've got khaki trousers or blue jeans. If your loafers are similar to the color of the sports jacket you're traveling with…that's better. The only color I wouldn't suggest is black (since it'll look too formal) unless you believe it's really your color.
Men's Travel Dress Shoes: Additional Tips
1. In general, shoes with the best leather quality are manufactured in the U.S. or European countries like Italy, France or the U.K. You can count on the leather to age well.
2. Check if the shoes you're interested in are Goodyear-welted and Blake-stitched. It's this shoe construction that allows the shoes to be re-soled after some time.
3. Avoid going sockless when traveling in dress shoes. This to help keep the leather dry (as leather tends to expand after absorbing moisture but never returns to its original shape).
4. For wet dress shoes – always store them in a cool, dry place. Don't leave them next to a heater or fire because high-level heat can end up destroying the leather.
5. Leather soles: I prefer shoes with leather soles over rubber ones. Leather is more formal and reflects a higher-quality product. The problem is leather soles take a while to get traction (and you wouldn't enjoy slipping or sliding along airport floors). Some types may become rigid over time which can make your feet uncomfortable. The solution? Overlay each leather sole with a strip of rubber. A good cobbler should be able to do this correctly.
With your shoes taken care of, click here to discover 25 tips on how to travel in style.
I'm Antonio Centeno, the founder of RMRS. I'm a former Marine Corps Officer with a BA in Evolutionary Biology and Philosophy (Cornell College 98') and an MBA from The University Of Texas at Austin (07'). I studied the Science of Style in London, Hong Kong, and Bangkok and have created over 5000 videos/ articles to help men dress better. Click here to discover more about our mission here at RMRS.
Ready to earn more money and command respect with the right clothing? Want to start dressing sharp today? Click here to discover The Style System , the BEST Professional Style Course on the planet!
Men's Travel Dress Shoe #3 – Penny Loafer
Men's Travel Dress Shoe #3 – Penny Loafer
