Travel Season is Upon Us—Here's Where Every Fashion Insider is Heading This Year
Now that summer is coming into focus, so are our travel plans. Our browser tabs have been open to Google flight searches, our recent saved social media posts feature cool destinations, and our shopping carts are quickly being filled with vacation-worthy items. In fact, in about two months, our social media feeds will be filled with stylish getaways of all sorts—from the manicured beaches of the Hamptons to the charming cobblestone streets in Europe. Naturally, we'll be keeping you up-to-date on where the style is set is jetting off to, but what's even better than making predictions as to where insiders will be heading is to go ahead and ask them directly, which is exactly what we did.
Whether it's the under-the-radar Croatian island where Katie Holmes' stylist Brie Welch is heading, the Sardinian coast where the Milan-based founder of Le Sundial is booking, or the small, much-less-talked-about Greek island where stylist and consultant Shay June is retreating, we have the intel on the coolest getaways the style set will be taking this year. Ahead, discover the seven destinations they're jetting off to—and, of course, what they're packing.
Brie Welch, eBay Resident Stylist
"My main plans this summer involve costuming a film in New York! Thus my confirmed travel plans will be in late September to attend a friend's wedding on the unspoiled island of Lopud in Croatia. May stay a night near Dubrovnik at Hotel Osmolis - a beautiful modernist concrete hotel designed by architect Damir Vitkovićl. I'm really looking forward to being on a car-free island, which means a lot of walking! I will pack plenty of ballet flats and transformable clothing, like scarves that can function as both a halter top and a skirt—trends we saw in the recently launched eBay Watchlist Trend report. Travel/vacation dressing is driving searches on eBay—specifically for scarf halter tops, which are up 97%—likely because they are effortless and very packable! My free time will hopefully consist of rotations of beach time, napping, and eating—and of course celebrating love at a Franciscan Monastery where the wedding will be held."
Silvia Dusci, founder and creative director, Le Sundial
"This year, I’m looking forward to returning to Sardinia, a place I visit every summer. After a busy year, I always try to spend at least ten days there—it has become something of a personal reset ritual. The slower pace, long days by the sea, and the simplicity of island life help me disconnect completely and come back feeling refreshed, inspired, and ready for what’s next. I'm packing The Dune Necklace by Le Sundial. I love pairing substantial jewelry with the simplest summer uniform. I'll also bring The Row Gemma Flats, my most worn summer shoes for the second year running, and the Alice Dress from Skall Studio, a light, effortless piece that's perfect for warm Mediterranean days. Together, they form the kind of wardrobe I love most on holiday (never without a big straw bag and a shawl): undone, comfortable, and quietly refined."
Shay June, stylist and content creator
"I’m planning to head to Greece specifically Tinos, laidback small island that’s not overrun (yet). Here’s what I’m bringing with me: a Ferragamo mini dress from the spring 2026 runway, a great minimalist skirt-and-top set from In House Studio, a Janessa Leone textured raffia hat, and a stunning fringe embroidered halter top from Aflalo."
Julia Rabinowitsch, founder, The Millennial Decorator
"This summer, I am headed back to one of my all-time favorite Italian cities, Florence. Something about the artistry in every single corner of the city, inspires me endlessly. I love the actual Florentine culture, at restaurants like Trattoria Cammillo, or shopping at real Italians local spots like Loretta Caponi or Quercioli & Lucherini for undergarments. As Florence is a city I do a ton of walking in, I'll be packing pieces that are comfortable yet make a statement, and can take me from day to night after a full day of exploring."
Gabriella Gofis, Substack writer and Marketing Director, Starling Jewelry
"My family is originally from Sicily and we are visiting our family there for my cousin’s wedding. We planned a trip to Malta before Sicily and can’t wait. For what I'm planning to pack, definitely the Tank Air halter, it's the most flattering halter tank ever, my classic Havaianas always, but specifically the Top flip-flops, and the Donni poplin pants for, well, everything."
Mimi Nguyen, content creator
"Packing for vacation is easy for me, because it really doesn’t change much from what I wear day-to-day in the city. Obviously if the weather is different it will slightly change, but I just pack what I’m wearing on repeat with a few fun accessories and swimsuits if the weather permits. A few things I will be bringing on my trip to the Dominican Republic: These Ulla Johnson sandals that I wear these all over the city and will absolutely be bringing them to the beach. They’re a minimal but elevated flip-flop that are so flattering on the foot. Then my Liffner basket bag—it's flat so it packs well for travel. And a Sea New York bucket hat to protect my face from the sun. I’ve been getting a ton of micro-needling, lasers, and facials lately to maintain my skin so I must keep my face out of the sun as much as I can. This is a chic, packable, and washable hat."
Aemilia Madden, writer, editor, and consultant
"This summer I’m going to Copenhagen fashion week for the first time and I’m so excited to experience the city in the summer. People always assume I’ve gone before, I guess because my style reads slightly scandi? I’m not sure, but I’m looking forward to making it official, and hopefully getting to explore a little outside of the official events. I’d love to go hiking or take a swim while I’m there. I’ll be packing dressy pieces for the shows, but knowing that people get around fashion week there by walking or bicycle (right up my alley) everything will still be comfy."
