Getting Dressed for Wanderlust
Fashion Inspired by Destinations and Daydreams
Last week, my company announced a take what you need vacation policy. Saying goodbye to accrued hours feels exhilarating. I’ve fantasized about this kind of PTO for years. But the truth is, I’m deeply unequipped for this level of freedom. I’m the kind of person who plans a vacation with surgical precision. My husband, meanwhile, has already cooked up at least five trips for us to take.
Multiple trips feel ambitious. One feels realistic. Two, if the budget cooperates. But I like where his energy is at. And with The New York Times’ annual 52 Places to Go in 2026 list freshly out, the daydreams feel harder to ignore.
We haven’t nailed down a destination yet. Right now, it’s just the thinking that feels indulgent. Flipping through the article, four destinations caught my eye. Each calling for its own inspirational outfit, whether for a picturesque sunrise, a day of adventure, or an idyllic sunset overlooking the city. You might spot a local ingredient woven in for a little extra flair.
Getting dressed for wanderlust felt like the right place to start.
Winnie-the-Pooh’s England
Yours truly once played Piglet in a musical adaptation of Winnie-the-Pooh at age eleven. Therefore, I feel especially qualified to say my next sunrise belongs in Winnie-the-Pooh’s England, in East Sussex. This is where A. A. Milne lived and wrote, in a 16th-century farmhouse that now allows visitors into his study and Christopher Robin’s bedroom, before the land opens up into Ashdown Forest. Imagine sipping a cup of tea while overlooking the real-life Hundred Acre Wood, exactly as it’s always been.
Osa Peninsula, Costa Rica
My husband’s been traveling to Costa Rica for years and is desperate for me to tag along. I’ve never been one to fry on the beach for hours on end. Think SPF 60, a sun hat so large it swallows me whole, and an umbrella strictly for shade.
But add those three things plus a national park hiking trail for prime sloth and monkey spotting, and suddenly I’m very interested. It’s lush, it’s active, and it’s far less congested than your typical beach destination. Honestly, what more could you ask for?
Nagasaki, Japan
I’ve been wanting to get back to Japan, and this image of Nagasaki makes me want to grab my passport for the koi fish alone. A city that narrowly escaped the fate of Hiroshima, now anchored by an 800-year-old camphor tree, a jazz bar, and a revived train station, feels well worth the journey. With direct flights from LAX, what’s really stopping us?
Traena Islands, Norway
I’ve never been to a music festival, and after a dinner last Friday where a friend confirmed that the Stagecoach dust-in-your-eyes experience does not age gracefully past 40, I felt validated in my avoidance. But then there’s Traena Islands, and suddenly there are exceptions. Each summer, an offbeat music festival takes over this tiny Norwegian archipelago just below the Arctic Circle, staging concerts in caves, boathouses, and along the water. If I were going to commit, it would involve Norway, where the light never fully disappears, and the bar is appropriately high.
My husband’s been packed since this post went live. I’m still considering our options. Our passports are on standby. Wanderlust suggestions welcome.
I was waiting for the picture of you as Piglet.
You had me at wanderlust because I’ve always (always!) been afflicted by this particular disease 😂