Travel Season Is Upon Us—Here's Where Fashion Insiders Are 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 inundated 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 set is jetting off to, but what's even better than making predictions about where insiders will be heading is asking them directly, which is exactly what we did.
Whether it's the under-the-radar Croatian island where Katie Holmes's stylist Brie Welch is heading, the Sardinian coast where the Milan-based founder of Le Sundial is booking, or the 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. [I] 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 of 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 10 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
"Tinos is known for its locally sourced, ingredient-driven culinary scene. I'm really excited to try Marathia and O Ntinos. I'll be spending a lot of time at the beach, so I'm planning out easy beach-to-dinner looks. I love sets like the In House Studio set for this. The Ferragamo number is a little dressier, but I'm already envisioning this color against an olive tan and beach waves. And of course, it's not an island vacation without a fun hat to pair with simple poplin sets. [I] love this Janessa Leone option—fun without feeling contrived or impractical."
Julia Rabinowitsch, Founder of 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, Tastemaker and Creative Advisor
"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 heading to Catania and Taormina. I'm not the best at planning every single outfit for a trip because I love basing my outfit on how I'm feeling in the moment. I'll usually feel pulled to a piece of clothing and work around it. So when packing, I love to include a variety of things that I know will go well together for day to night and then some fun statement items and accessories to jazz up a simple look. I bring a lot of cotton pants and skirts because they're so easy to style. Obviously, I have to bring a variety of sunglasses because those bring a ton of interest, especially if the outfit is a little more low-key. [I'm] always bringing a few special vintage pieces; give me all the lace."
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: [I wear] these Ulla Johnson sandals … all over the city and will absolutely be bringing them to the beach. They're minimal but elevated flip-flops 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 microneedling, 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."

Anna is an NYC-based senior fashion editor who has been a member of the Who What Wear team for over eight years, having begun her career in L.A. at brands like Michael Kors and A.L.C. As an editor, she has earned a reputation for her coverage of breaking trends, emerging brands, luxury shopping curations, fashion features, and more. Anna has penned a number Who What Wear cover interviews, including Megan Fox, Julia Garner, and Lilly Collins. She also leads the site’s emerging travel vertical that highlights all things travel and lifestyle through a fashion-person lens.