A two-week vacation that covers a cosmopolitan city, some adventures in the jungles of Northern Thailand and a few days on the beach sounds great—until it's time to pack.

This was the challenge that hit me a few weeks ago when I started prepping for my belated honeymoon to Thailand. Luckily the weather wasn't much of a packing issue (hot, and also more hot) but taking the local culture into consideration—having appropriate clothing for the temples, and making sure to bring shoes that could be quickly removed to enter buildings as necessary—added an additional complication. And since our trip involved so much travel, we told ourselves we'd fit everything into two carry-on sized suitcases. Needless to say toting an array of shoe options was out of the question.

Instead, I pared it down to the basics: flip-flops for the beach, comfortable walking shoes for exploring Bangkok and a nice pair of sandals for going out at night. And one pair of Keen Venice H2 sandals, the ne plus ultra of ugly sports sandals, a category that also includes Tevas, Chacos, Merrills and some truly terrifying knockoffs of the same by Sketchers.

Ugly as they may be, the pure functionality makes up for it. What other shoe could go from a mountain hike into a river? Could offer stability when climbing onto a longboat without feeling like an anchor in the water? Could basically do the work of three shoes while taking up the space of one?

It started as a practical concession, sure, but the Keens soon earned my love. One evening in Bangkok we took a bicycle ride through the alleys of Chinatown, and the Keens felt like wearing any other sneaker, but the cool air from the open areas felt like putting my feet in a convertible with the top down—a major plus on a hot, sticky night—while the closed toe saved me from several potentially painful scrapes along the ride. (Bangkok's alleyways are really not built for biking, FYI.)

Slowly, over the course of 14 days, the Keens became a bigger and bigger part of my vacation wardrobe. After days of mostly wearing them for athletic/outdoorsy activities, I paired them with Thailand's famous elephant pants for a walk through Chiang Mai's crowded Sunday Walking Street. Once you have succumbed to the allure of elephant pants, it's way too late to worry about cool shoes.

Call me crazy, but I'm even starting to think they're pretty cute. I thought I was just buying a pair of ugly sandals, but apparently I was buying a whole new personality.