The Best Women’s Footwear for Day-to-Night Urban Travel

If you’re planning a trip to a region that’s known for regular rain or unpredictability, add a pair of Bogs to your packing list. All the brand’s shoes and boots (leather collection included) are waterproofed with a lifetime guarantee and—best of all—they don’t even look like rain boots. The Carrie chukkas come in three different colors (black, brandy, and taupe) and the streamlined design and slight heel make this comfy ankle boot a winner, whether you’re biking across Copenhagen or bar hopping through New Orleans.

To buy: amazon.com, $140

At first glance, the Børn Sebra ($95) looks like a pretty standard moccasin: until you step into one and feel the difference. The flat is discreetly built on an athletic-inspired comfort foot bed, which means you will feel like you’re shuffling around at home in your slippers, no matter where in the world you are. The black suede option is perfect for fall and winter, and transitions from museum to dinner table in zero seconds.

To buy: amazon.com, $95

Believe it or not, a wooden shoe can be comfortable. Swedish Hasbeens are modeled after the wooden clogs popular in Sweden in the 1970s. They’re handcrafted using naturally tanned leather and high quality wood, which hugs the foot over time. Wide heels (in three different heights) also make these easy to walk in. And though they make boots in a similar style, we love the close-toed Lacy sandal year round because they look awesome on their own or with colorful tights.

To buy: amazon.com, $229

Forget what you know about Tevas, because they’re no longer just for water sports. Now, the brand has a variety of covetable boots, shoes, and sneakers, but the super stylish Foxy boots really won our hearts. The sturdy, heeled ankle boots—made unbelievably comfortable by a discreet rubber bottom—can withstand long days sightseeing and look equally amazing with a dress for a night out. Consider buying a pair of Foxy boots in all four colors.

To buy: amazon.com, $130

If you’re traveling to warmer climates this holiday season, don’t leave home without a pair of Avarcas. Available in a rainbow of colors and patterns, these traditional Spanish-made sandals (similar to espadrilles) are handmade using all natural leather and recycled tires. They slip off and on easily—ideal for either airport security or the beach—and the metallic finishes, such as bronze and pewter, transition particularly well from day to night.

To buy: amazon.com, $80

Another company doing their part to prove that comfort need not be unfashionable, Hush Puppies’ newest line of footwear features a variety of stylish shoes and boots, including sherpa-lined styles for colder climates. The secret behind the Mazin Cayto low zip-up ankle boot is a cushioned foot bed that conforms to each step, providing support while aiding circulation. Scuff, stain, and water-resistant suede makes the shoe a total workhorse. Opt for an autumnal color like wine or dark olive.

To buy: amazon.com, $119

There’s a reason chefs and nurses swear by Dansko clogs: They’re engineered to make you forget how long you’ve been on your feet. But the company also produces plenty of more modern and feminine styles, each just as comfortable as the last. The close-toed Marta sandal is crafted from water-resistant leather, and features a cushioned foot bed. It’s the epitome of fashion-meets-function. Either the black or the camel style will translate year round, especially when paired with patterned or colored tights too.

To buy: amazon.com, $135