Traveling in Heels: A Modern Dilemma

Finding heels that look graceful and feel wearable for a full day of travel is nearly impossible, isn’t it? Most of what lines the duty-free shops or the glossy boutiques is made for looking, not living. Blame fashion’s stubborn old ideas. For us, the question has always been: why can’t travel friendly heels handle cobblestones in Florence or a last-minute sprint through Charles de Gaulle? Women have stories of carrying backup sneakers, or worse, barely making it through the evening because of aching feet. We get it. There has to be a better way.

What Sets Joan Oloff Apart

Joan Oloff shoes don’t just feel different, they’re built different, from the inside out. Dr. Oloff spent years in her father’s Brooklyn shoe store, then even longer treating the real aftermath of bad shoes as a foot doctor. The result is shoes that look every bit as refined as their old-world Italian cousins but feel more like custom-fit ballet slippers. Patented comfort technology redistributes pressure, meaning your toes don’t go numb on airport walks and your arches feel cradled in all the right places. It’s the sort of clever reengineering only someone who’s seen (and felt) the problem could solve. You’ll feel it the second you step into them. Explore more at our full collection.

Golden Hours: The Deborah Heel for Glamorous Getaways

If you have dinner in Capri on your wish list, or a rooftop cocktail hour in Manhattan, you’ll want a heel that really delivers. The Deborah 2.0 heel in champagne gold metallic is everything a travel friendly heel dreams of being. It’s sleek and sophisticated, with just enough shimmer to feel festive without crossing into flashy. The best part is the support hidden inside, like the foam underfoot and arch support that quietly keep you steady. We’re not exaggerating when we say it works with jeans at a café or a dress at an opening night. Nothing fussy, just pure luxury in a form you don’t have to compromise on.

Nude Neutrals: Effortless Versatility with Callie

A nude heel that actually feels as good as it looks is rare, almost suspiciously so. The Callie in nude leather is surprisingly soft, almost like it’s already molded to your foot, which means long layovers or city sightseeing won’t punish you for dressing well. It works with everything from an easy slip dress to tailored trousers, and if you pack light, you’ll realize you only need this one pair. The clean lines and gentle toe box don’t just flatter, they care for your feet after hours of movement. No breaking-in period, just instant comfort the moment you slide them on.

Packing Tips to Keep Your Shoes Travel Ready

Protecting your shoes is almost as important as picking the right pair. We’ve learned to always nest shoes toe-to-heel for the best use of space, and slip them into travel pouches, usually the fabric ones that come with the shoes. Stuffing the toe with tissue helps keep their silhouette. For extra care on the move, a small shoe brush tucked in your bag is surprisingly handy, especially if you’re heading somewhere dusty or wet. And while it’s tempting to pack multiple heels, we find that the perfect pair or two—designed for all-day comfort like Joan Oloff’s—makes overpacking unnecessary.

Embracing the Freedom of Travel in Style

When travel friendly heels no longer slow you down or leave you limping by sunset, you start to rethink what’s possible. Joan Oloff’s philosophy is that comfort and elegance can absolutely coexist, so why settle for anything less? We hope your next adventure feels as effortless as slipping into your favorite pair of heels, without worrying about the journey ahead or missing a single moment. For more options that truly support you wherever you roam, browse our shoe collection.