30 It Buys That Will Define the Most Stylish Vacations of 2026

Anna LaPlaca's avatar
By
published
in Buying Guides
vacation It items 2026
(Image credit: @christietyler; @dualipa)

Let's be honest—one of the best parts of going on a vacation is planning the looks you're going to wear before you go. If you ask me, no vacation wardrobe is complete without one standout dress (or several), and each summer, there are always a handful of specific styles that end up achieving cult status. Whether it's the affordable Zara find everyone agreed was worth it or the dream designer bikini we all couldn't scroll on social media without seeing someone wearing, there are always a few vacation dresses that break through the rest to become, well, "it."

We're still technically a month out from the official start of summer, but I'm already well into my vacation shopping (and vacation planning) and starting to see the early signs of the dresses destined for greatness. While I was shopping for what to bring on my next trip, these 30 picks, ranging from airy cotton midis to fun printed minidresses, stood out to me. Whether you're traveling somewhere locally or packing up your passport for an adventure abroad, bringing along one of these vacation dresses is an absolute must. If you don't, another fashion person is destined to.

Explore More:
Anna LaPlaca
Anna LaPlaca
Senior Editor

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.