How to Travel with 1 Pair of Shoes and Still Look Put Together & Comfy

First things first, this is not a trick that works for any and all vacations. If you have any specialized plans that require specific footwear—hiking, a wedding reception, afternoons at the beach—odds are the shoes you’ll need for that event won’t be able to see you through the entire rest of the trip. However, if you’ve got a long weekend jaunt to visit friends with plans that mostly revolve around exploring the town, going out for fun meals or hanging out in museums, you can absolutely stick with just one pair of shoes.

Actually, my first piece of advice is to take a look at your itinerary (or make one yourself) to see exactly what your needs might be. Think about what shoes you’d wear for each activity if suitcase space was unlimited. Then, like a March Madness bracket, start whittling that list down to only the most versatile pair.

For example, I have a college reunion weekend trip to Bend, OR, coming up and while there is no set in stone plan for what we’ll all do each day I know there will be at least some light hiking, lots of exploring in Bend and at least one dinner out on the town. At home, I’d likely opt for three different pairs of shoes here—sneakers with ample traction, a comfortable walking shoe and a cute pair of ballet flats or kitten heels for dinner. But there can be only one winner, and so let the games begin!

The kitten heels are obviously the first to go. While cute, they are not something I would want to wear for a full day out and about walking all over town. And I know whatever restaurant we choose won’t be too fancy, so a more practical shoe won’t feel totally out of place there. On the flip side, I know the hike will be something fairly easy and low-key, meaning I can swap out my rugged hiking boots for something much sleeker, like a regular pair of running sneakers. This means I’ve settled on bringing just the one comfortable walking shoe for my entire trip. But which pair, exactly?

Now it’s time to start planning all the other elements of your outfits. Laying out the exact combination of sweaters and jeans and skirts and T-shirts and dresses and jackets you hope to wear for each day of your trip can narrow down exactly which shoe works well with all of them. If I’m going someplace cold and plan to wear lots of pants and chunky knits, a chunkier sneaker will work well with all those pieces. But if the weather is hot and I’ll be decked out in shorts and minidresses all weekend, sandals with ample support (like Chacos or Tevas) or a low-profile sneaker will likely look cuter.

Lastly, remember the key to a good and memorable vacation is not in having compliment-worthy shoes for each and every day. Who cares that your comfy-yet-dorky brown loafers are not the shoe you would have chosen for dinner out with friends if you were at home? Your friends only care that you’re there with them, and no one else in the restaurant is likely to notice or care either. And if they do, that’s really on them—judging the strangers around you on their footwear choices is a weird pastime. Let’s not, ok?

At the end of the day, traveling with only one pair of shoes comes down to planning ahead and accepting that the middle ground shoe option, while not perfect for anything, is 100 percent acceptable for anything.