If a wanderlust pro could only pack 4 outfits for a vacation, here’s what she would bring

February 18, 2020 at 10:30AM by CWC


You’ve been planning this year’s vacay for months, and now it’s two days away and all you’ve packed are your fave grab-and-go snacks, your hydrating skin-care products for the plane, and your passport (#priorities).

But before you start stressing about what you’re actually going to wear, try this packing-light formula from travel expert Michelle Halpern for what to pack in a carry-on that’s comfortable, can be worn multiple ways, and will look great in photos (because, again, #priorities).

“When packing for a trip, there are really three main factors that go into my overall strategy: how long the trip will last, what the average weather is at that time of year, and what specific activities I’ll be partaking in,” Halpern says.

“When packing for a trip, there are really three main factors that go into my overall strategy.”

Once you’ve answered these three questions, you can start raiding your closet. But make sure you save room in your suitcase for footwear, because according to Halpern, the right shoes can make or break a trip. “If you’re not comfortable in the shoes you’re wearing on your adventures, you won’t enjoy the trip,” she says. “So investing in comfort is so important.”

Kate Spade Autumn/Winter Sale

Her go-to shoes are classic, look great with many different outfits, and above all, keep her feet happy (i.e. leave your stilettos at home). That’s where kicks like Sperry’s new PLUSHWAVE shoes come in clutch, because they’re so lightweight you can pack a couple pairs(which is key for carry-on-only travel), and they have ample cushioning for hours of walking. “I love that they’re so easy to slip on quickly,” Halpern says, “and that the PLUSHWAVE technology provides extra comfort.”

Because you’d hate to cut your adventure short as a result of aching feet, Halpern is sharing how she packs her carry-on to prioritize style and travel light, while still managing to bring more than one pair of shoes.

Need some inspiration for what to pack in a carry-on? Scroll down for Halpern’s four go-to traveling outfits.

what to pack in a carry-on

On the plane

Just like the under-eye masks you’re wearing around the plane (never any shame in hydrating), your transit outfit should be centered around self care. But that doesn’t mean you have to sacrifice looking cute. “For the plane, I typically always go for comfort—so usually a pair of joggers or leggings with a comfortable tee and travel wrap since I’m always cold on planes,” says Halpern, founder at Live Like it’s the Weekend.

To make your sprint through the airport (or the hours walking laps during your layover) easy on your feet, you’ll want shoes that are made for moving and are easy to slip on and off at security. Sperry’s Authentic Original PLUSHWAVE Boat Shoes dress up any low-key look, and will be like hugs for your feet—no matter how long your journey is.


what to pack in a carry-on

Exploring the city

On a day of exploring, Halpern keeps it casual. “For walking around a new city, I’ll throw on a pair of jeans and a basic tank top or long sleeve shirt, depending on the weather,” she says.

Finish off your simple-chic look with a pair of Sperry’s Seaport Penny PLUSHWAVE Loafers, which have a light-as-air feel plus extra traction, so even if you end up getting lost, you won’t be tripping over your feet.

Dinner plans

If you know you won’t have time to change between exploring and dinner, opt instead for an outfit and shoes that can go from day to night.

“For dinner, I love a long, lightweight dress because it’s easy to dress up for evening with a few nicer accessories, but also repurpose during the day with more casual pairings,” Halpern says. Plus, re-wearing pieces will save you room when packing—and give you an excuse to go shopping while you’re there.

For shoes that will do the trick in both scenarios, pack Sperry’s Authentic Original PLUSHWAVE Boat Shoes, which are dressy enough for a nice dinner, but won’t leave you rummaging through your suitcase for bandaids to cover your blisters like heels would.

Night out

The only thing that can ruin a fun night of dancing faster than bad music is uncomfortable shoes. Avoid that sitch altogether by pairing Sperry’s Seaport Penny PLUSHWAVE Loafers with a flowy dress—also a dancing essential—so you can keep the party going as long as you’d like (you are on vacation after all).

Clip the strap back onto your clutch to turn it into a cross-body bag (“A cross-body bag is key too so you can let loose on the dance floor hands free,” Halpern says), and in case it gets cold, grab the wrap you wore on the plane. And just like that, now you’re the packing expert.

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Top photo: Stocksy/Kike Arnaiz

Author Well+Good Editors | Well and Good
Selected by CWC