Shoes are the bane of my existence when I travel. They’re big, heavy, and they smell if you wear them too long. For most people, shoes end up being the largest, most cumbersome item in their luggage.
My preference is to vacation in warm climates, so most of the time I’m able to get away with taking only a single pair of shoes with me. They’re usually my Chaco sandals, which are the my favorite footwear in the world. If I’m planning a trip where I need an actual pair of shoes instead of just sandals, then I’ll take one other pair depending on what activities I’ll need them for.
If I need something fancy, which to be honest is extremely rare – because who the hell wants to wear clothes like that when you’re on vacation – then I’ll pack my standard work shoes that I wear to the office every day, which are these Rockport Margin Oxford shoes in black (shown in the photo below). They’re nice enough to pass for real dress shoes yet are surprisingly comfortable like an athletic shoe. I’ve done a good bit of city walking in these and my feet are always nice and comfortable at the end. They’re also quite durable. I wear them daily to work and only have to replace them once about every 3 to 4 years.
A more common situation that arises instead of the above is that I will plan a trip that involves some serious hiking or other outdoor activity. Sometimes my Chacos are insufficient for these outings. If that’s the case, then I’ll take my Brooks Cascadias. These are lightweight, comfortable trail running shoes that I wear on the weekends at home when I’m out and about on the mountains around my area getting some exercise on the hills. They’re also great travel shoes, but if I didn’t do trail running as my leisure activity of choice, then any decent pair of running shoes would do.
Really though, if I’m not climbing up mountains, going someplace cold, or visiting a hoity toity destination that will judge me on my footwear, the Chacos on my feet are the only footwear I need.