Q & Answer: What Shoes Should I Bring On Vacation?

Ben writes: This May, my wife and I are honeymooning in Europe for two weeks. I know that I will be doing a heavy amount of walking. Do you have any suggestions for footwear that will allow me to keep pace with my wife without looking like the ugly American?

Packing shoes for a trip - especially one that requires more than one level of formality - is always tough. When I travel, I fight not to bring more than two pairs of shoes, with one of those pairs on my feet. I don’t always win the fight.

I’ve got plenty of dress shoes that are perfectly comfortable, but none that I’d want to walk miles in. So if I’m bringing a pair of dress shoes to make a big presentation or what-have-you, I’m usually looking to compliment them with a “walking shoe.”

Depending on the season and context, that usually boils down to one of two things: a simple sneaker, or a comfortable boot.

I actually own the Grenson chukka boots pictured above, in a slightly darker brown. I find they work great with jeans or khakis, though I obviously wouldn’t wear them with shorts were I headed somewhere hot. In fact, they’re sort of a three-season shoe - fine anytime but summer. Sometimes I’ll substitute the chunkier, hardier Alden Indy Boot for these. Most importantly, I can put in a few miles on these, and be happy to see them the next day.

I also frequently bring sneakers on trips that will involve walking. As usual, I’d say the simpler the better. Above are a classic, the Adidas Samba. I usually wear Common Projects, which are great but expensive. I’m hoping Kent Wang gets in a full size run of his plain white sneaks soon. And of course if it’s summer, there’s stuff like Jack Purcells and Supergas, among others.

Traveling’s really an exercise in building a capsule wardrobe. You want to carry as few pieces as possible, and have as much interchangability as possible. So: keep it simple, and you’ll be fine.

Q and Answer: What’s the Difference Between Chukka Boots and Desert Boots?

Derek writes to ask: What’s the difference between Chukkas and Desert Boots?  They seem to be all the rage right now.

This is a sort of square/rectangle situation. All desert boots are chukkas, not all chukkas are desert boots.

Chukka boots get their name from polo - a chukka is a period in that sport. They’re a two- or three-eyehole ankle-high boot like the dark brown ones pictured above. They can be made in anything from canvas to shell cordovan, it’s their form that makes them chukkas.

Desert boots are a specific subset of chukka boots. Like chinos, their popularity stems from WWII soldiers (and surplus-sellers) bringing them home from the war, and the emergence of casual style in the 1950s. They’re based on the boots worn in desert campaigns by British soldiers. They always have crepe rubber soles. The classic style is the light suede seen above, though crepe-soled chukkas come in all kinds of leathers.