You’re Finally Going on Vacation. Do You Remember How to Pack?

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.

Keep Up in the Country

Planning a bucolic escape? Then practical footwear and bug spray are musts, said celebrity stylist Micaela Erlanger. Based between New York and Miami, Ms. Erlanger, 36, keeps her casual wardrobe reliably chic when visiting her fiancé’s family’s upstate New York farmhouse. Among her sensible staples: a vintage Gap jean jacket, breezy Zimmermann sundresses and Madewell jeans. She admits the bejeweled sandals she brought on a recent jaunt were impractical, and currently favors comfy flats like Birkenstocks. Other mainstays include her fragrant Coqui Coqui insect repellent and Ziploc accessory bags, ideal for costume jewelry.

Do It Better in Texas

If heading to a desert art mecca, follow Harsha L’Acqua’s lead and pack classic, slightly eccentric go-tos. As the founder of Saira Hospitality, the constantly traveling Ms. L’Acqua has earned pro-packer status. For a recent trip to Marfa, Texas, Ms. L’Acqua, 38, relied on timeless accessories like a sun-shielding cowboy hat and cream Converse high-tops, which she elevated with long dresses and bright caftans. Too frivolous for the desert town? The multiple bikinis Ms. L’Acqua impulsively brought. Meanwhile, a printed kimono, which “might seem luxurious,” proved practical, doubling as an elegant morning dressing gown and a chic evening layering piece.

Conquer a Roman Holiday

For Mediterranean getaways, Tina Chen Craig finds easy dresses, buoyant skirts and versatile bathing suits most useful. On a recent trip to Rome and the island of Ischia, the Dallas-based U Beauty founder, who is in her 50s, adopted a carefree fashion approach. “I didn’t stress about looking cute, I was just so psyched to be leaving the country.” Ms. Craig toured landmarks in a fuss-free uniform of mid-length sundresses and Hermès’s Oasis sandals. A denim jacket proved too bulky for the hot Mediterranean, but Ms. Craig saved suitcase space by packing one-piece swimsuits by Tropic of C that pulled double-duty as bodysuits with skirts and linen trousers.

Turn Out in the Tropics

According to Jessica Nabongo, the Caribbean calls for statement swimsuits, lurid prints and wrinkle-resistant wares. A tireless Detroit travel writer who bills herself as the first Black woman to visit every country, she’s an admitted over-packer—a habit she manages with Flight 001’s packing cubes. For a recent trip to Anguilla, Ms. Nabongo, 37, filled them with vibrant, low-maintenance options, like an airy jumpsuit by Diarrablu. Her one regret: a tiered maxi dress, entirely too heavy for the steamy weather. More reliable fare included a Andrea Iyamah bikini, Havaianas flip-flops and white Miu Miu sandals.