I Swapped NYC for a Tropical Destination—3 Easy Free People Looks I Brought With Me

Welcome to Word on the Street, a quarterly series in which one editor takes to the streets of New York City to snap her favorite fashion moments and shop them out just for you.

I'll never be the editor who tells you to buy an entire new wardrobe for one trip. However, shopping for an upcoming vacation is the ultimate form of retail therapy. Opening a package full of linen pieces and shell jewelry signals that an escape is imminent. As the snow fell outside my window, I scrolled through Free People's latest free-est collection and dreamed of a warmer destination. Adding straw hats and sandals to my cart helped me feel like I was inching toward summer, even as we braced for our second blizzard of the season. That's when it clicked: Why not take Word on the Street somewhere warm and showcase the free-est collection the way it's meant to be worn? So into my suitcase went three easy, comfortable, and effortlessly stylish outfits—each one shopped out for you below.

This first outfit made me feel like I was getting away with wearing pajamas (win!). The Don't Call Me Pant Set ($128) checks all the vacationwear boxes: comfortable, cute, and mix-and-matchable with the other pieces in my suitcase. In terms of accessories, this pillbox-style straw hat felt fresh and different from the other sun hats in my collection. I also love a drop necklace to dress up what would otherwise be a very casual look.

Vacation dressing is an opportunity to be more playful with my personal style. In NYC, I wear my Lowen Midi Skirt ($70) in navy and white constantly, so when I saw this colorful style drop, I knew it would be perfect for my trip. I styled the skirt with a turquoise necklace for an additional pop of color and my current favorite basic, a We the Free Lucy Layering Top ($48).

This last ensemble represents the free-est ethos to a T: It's made for free-spirited days in the sun. The flowing linen set, braided sandals, and hair scarf capture the bohemian vibe. The materials are perfect for the hot Florida weather, but I could also see myself wearing this in Copenhagen, California, and every other free-spirited summer destination.