Shop Wolf & Shepherd dress shoes starting at $325 here
For men, Wolf & Shepherd makes beautiful Italian leather dress shoes that you can actually run in — the founder confirmed this claim by wearing them during the 2018 Running of the Bulls in Spain. They feature sheepskin lining, plush memory foam insoles, and an "HDeva" heel that absorbs the shock of heel strikes. They're pricey but worth the comfort and you'll find yourself wearing them for any work occasion, travel-related or not.
Day Glove, $115, available at Everlane
For women, the Everlane Day Glove is the flat that truly fits like a glove. These simple, rounded leather flats come in a variety of versatile colors and can transition seamlessly from office to dinner. With a back pull tab, small side vents, and a cushioned insole, they're just as functional as they are stylish.