Stylish, Versatile, and Comfortable: The Only 3 Travel Shoes You’ll Ever Need
One of my rules for packing carry-on only? Only bring two pairs of shoes—three, max, if you have a special occasion you need something more specialized for, like a cycling trip or a wedding—including the pair you wear in transit. Although the exact pair(s) I choose to pack will vary based on weather and what sort of activities I have lined up on my trip, I always reach for one of the shoes listed below. After years of researching, testing, and searching again, these 3 pairs of shoes stand out because they are versatile, stylish, comfortable, and even include some additional practical features, like water-resistance. Below: the best and only three pairs of travel shoes I ever pack.
Chelsea Boot by Sorel
These chunky Chelsea-style boots by Sorel are the perfect combination of fashion and function and my go-to for any fall or winter trip. For regular street and urban wear, I love how easy the classic design is to style with a variety of outfits—from skirts and tights for a nicer evening look to jeans and t-shirts for a more casual daytime ensemble.
But they’re also solid shoes for the odd outdoor adventure or hike. They’re comfortable, waterproof, and have decent tread, and though they’re not as supportive as a traditional hiking boot, I’ve stomped confidently in them on many trails. I even hiked the tallest peak in Portugal (Mount Pico) in them—though I wouldn’t recommend doing that intentionally (it was a last minute decision to do the hike), since the volcanic rock along the trail really scratched and destroyed them.
With a good pair of warm, thick socks (I like Smartwool), they will keep my feet warm and dry in cold and a little bit of snow. Unfortunately, the low, loose ankle means that snow can get in. That means they’re OK if I’m walking around the snowy streets of Boston, but less so for trekking through the snowy mountains of Alaska or Tahoe. On a trip to Alaska last spring, I did also end up packing a pair of waterproof, winter hiking boots.
Overall, Sorel’s Chelsea boots are a super versatile shoe that can easily be worn on active adventures in the woods and to nicer dinners out on an urban trip. From late fall to early spring, they’re often the only shoe I pack.
Water-friendly sneakers by Tropicfeel
Trip type: Hot, warm, and cool-weather travel where you plan on doing outdoor activities like hiking, kayaking, or rafting. They also double as water shoes.
Buy now: tropicfeel.com
As I got older and more into hiking, I discovered that most traditional hiking boots are overkill for the majority of day hikes—especially the less intense ones we tend to choose while traveling. The other problem I found with hiking shoes and travel is that many of them tend to be designed with a highly specific, single-activity purpose—and no one wants to bring a pair of hiking shoes and water shoes and casual about-town sneakers. I’ve literally been on the hunt for a good do-it-all sneaker for travel for years and was so excited to try Tropicfeel’s water friendly sneaker.
I initially ordered and tried on a few different options by Tropicfeel but ultimately bought the Jungle shoe because (vainly) they were the least dorky looking. As for durability, they’ve held up well over the past ~2 years of travel adventures except for one thing: the pull tab on one shoe began to fray after only a couple of wears.
For performance, I’d rate them pretty good but not perfect. The arch support and traction could be better, but overall I found them pretty comfortable for hours of hiking and walking. But the main reason why I recommend them is that this is a single pair of shoes that works for a wide variety of outdoor adventures. They’re quick-dry, lightweight, and pack down compactly (the heels collapse so they can be flattened in your luggage). As a slip on sneaker, I also found them especially handy in Asia, where I was taking my shoes on/off more frequently than in other regions, and on airplanes, where I want to be able to easily slip my shoes off/on as well.
Yes, there are other sneakers that will have better tread, or arch support, or other performance features that cater to outdoor situations, but for a versatile and lightweight, easy-to-pack sneaker, Tropicfeel is so far the best option I’ve come across in my years of testing gear. I will absolutely order these again after this pair falls apart.
Crescent Quilt Sandals by Roam
Trip type: Hot and warm destinations, beach vacations, and casual summertime trips
Buy now: Roam
For warm weather travel and beach vacations, the Crescent Quilt slides by Roam are my go-to. Even at home, I wear them all the time because they’re incredibly comfortable, easy to slip on/off, and look cute as part of a modern, fashion-forward ensemble. Similar to Birkenstocks, the footbed of the Roam’s shoes will mold to your feet after a few wears, which I love.
And while yes, you could find many other sandal options that are cheaper and pack down smaller, I’ve struggled to find a pair like that that doesn’t also give me horrible cuts and blisters. I’d much rather pay a little extra money and give up a little extra space in my bag for a pair of quality sandals that I know I can wear for days on end—and will last me a long time.
Overall, these are a comfortable, good quality sandal that looks modern and fashion-forward, while also not being overly bulky to pack.
Bonus: flip flops by Volcom
Trip type: Summer backpacking or bikepacking trips, or trips where I’ll be doing a lot of sauna-ing
I generally don’t like wearing flip-flops in my day-to-day and in urban areas where I prefer to feel a bit more put together with my outfits. However, there’s no denying that flip-flops are about the most compact and packable shoe type out there. I tend to only bring these if I know there will be some situations where a pair of flip flops will come in handy (like going to a sauna, hotels or campsites with shared showers, etc.), or if I’m on a backpacking or bikepacking trip and space really matters. While hiking on the Kumano Kodo in Japan for four days, I brought a pair of flip flops by Volcom in addition to my sneakers so that I would have something to wear to onsens and after a full day of hiking.
