If you’re still adjusting to getting dressed up again, the task of selecting a suitable assortment of vacation outfits can be unnerving. After being grounded for over a year, even seasoned travelers admit to struggling with what was once a reflexive habit. “I forgot how to pack!” said Dallas-based U Beauty founder Tina Chen Craig who, pre-Covid, would typically travel every two weeks. “I had to keep reminding myself, ‘Ok, what do I normally do?’”

Complicating matters is the fact that many women’s dressing habits have changed since most of the world locked down in 2020. “I’ve always been fashion-forward, but since the pandemic, now I want to be seen,” said Jessica Nabongo, a Detroit-based travel writer who set out to be the first Black woman to visit every country in the world. For Ms. Nabongo that means making her usual jet-setter wardrobe of cultish Nike FF720 trainers and jumpsuits more exuberant with colorful caftans, distinctive printed dresses, and no outfit repeats. “I never wear the same thing twice,” she said.

Whether you’re headed to the uneventful countryside or planning an intense tropical holiday, your packing process needn’t be an occasion to over-think. Below, four fashionable globe-trotters recall the most useful items they brought on recent trips to very different destinations. Plus, the regrettable pieces they should have left behind.

An expanded version of this article appears on WSJ.com.

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