Q & Answer: Bringing The Right Shoes For A Trip

August 20, 2015

Q & Answer: Bringing The Right Shoes for a Trip

Terry asks: Do you have any recommendations for travel shoes? I’d like to find something that’s dressy enough to wear at a nice restaurant, casual enough to go with jeans, and comfortable enough to wear for a week without having to go for a full leather sole. Any suggestions?

Few shoes will do everything for you, which is why we recommend bringing at least two pairs on any trip. One of those should probably be sneakers. You can wear them for long city walks or use them for exercise. Looking in my own closet, I’d probably go with my pair of Nike Flyknit Ones.

The other pair will depend on your exact trip and needs.

  • Urban, Formal Business: If you need to wear a business suit, pack a pair of appropriate shoes. Oxfords are a natural choice, although for a little more versatility, consider wingtip bluchers. If the styling is right, you can also wear them with jeans (consider the rounder toe options from Alden and vintage Florsheim).
  • Urban, Casual Business: If you don’t need to wear a suit, try wingtips, plain toe bluchers, or dressy chukkas. Any of those will straddle the line between formal and casual, which means you can pair them with everything from tailored sport coats to casual leather jackets. One of my favorites in this category is Crockett & Jones’ Brecon, which are easy to lace-up when you’re going through airport security.
  • Urban, Vacation: Same as what you’d bring for casual business, although you can also consider more informal styles. If it’s going to be raining or snowing at your destination, pack a pair of pebble grained or shell cordovan boots built with storm welts and/ or Dainite soles. I usually grab my Crockett & Jones or Brooks Brothers boots when I visit family in Canada.
  • Resorts and Beaches: Bring something you can wear to a nice restaurant (maybe leather loafers), but also something you can wear near water. Boat shoes, espadrilles, and sandals all make for good choices. I also like certain styles of woven slip-ons from Rivieras Leisure Shoes.
  • Woodsy Trips: For hiking, camping, and other outdoor activities, consider hiking boots, camp mocs, trail mocs, or rugged workboots (just make sure they’re not too heavy, as those will leave your feet tired). Tip: don’t pack boots, just wear them on the plane so they don’t take too much space in your luggage. You can leave ‘em loosely laced for comfort once you’re up in the air.
  • Backpacking Around: If you’re backpacking through a foreign country, skip the dressier stuff and get two pairs of really comfortable walking shoes. Crepe soled boots made with really soft leather uppers will be just as comfy as your favorite sneakers. You can consider Clarks’ Desert boots or their upscale alternatives. I also like Eastland’s Made-in-Maine Mohegans, which are easy to find on discount for about $150.
  • Optional: If you have the space for it, I really like La Portegna’s travel slippers. They’re easy to roll up and make unfamiliar hotels feel a little more comfortable.

(photo via Voxsartoria)

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