How to Fit Your Entire Vacation Wardrobe in a Carry-On Bag

We tapped four well-traveled creatives to help you avoid a lost baggage fiasco.

How to Fit Your Entire Vacation Wardrobe in a Carry-On Bag
Photo: Courtesy of Kalani Miller

If you spend any amount of time on social media, you know that checking a bag these days puts you at high risk for entering a collective personal hell. Bags are piling up, airport officials are overwhelmed, and London Heathrow cancelled over 150 flights just to curb the amount of lost baggage on their hands. There’s never been more reason to pack a carry-on, especially with all of those trips you put on the COVID back-burner. However, packing a carry-on bag for a long-awaited vacation can be hard. Everyone is guilty of a little pre-vacation shopping, and a carry-on may not fit all of your travel knick-knacks or your 10-step skincare routine. Luckily, we checked in with a few well-seasoned travel experts for their tips and tricks on how to make it through an entire trip with just a carry-on bag.

Olivia Lopez, Creative Strategist

Photo: Courtesy of Olivia Lopez

What summer trip are you packing for?

"This summer, I’m traveling to Saint Tropez, Istanbul, Venice, Ibiza, Minorca, and Antiparos in Greece."

What must-have items do you always have in your carry-on bag?

"A silk or cashmere pashmina, a swimsuit, a pair of sneakers, some sandals, travel-sized skincare, and transitional day-to-night dresses. Because the physical act of travel takes such a toll on your skin, bringing mini-sized vessels of my favorite skincare brands allows me to maintain a self-care ritual while I'm away. Pashminas are versatile travel essentials that you can style as a cover-up from a mid-day blast of sun or wear as a blanket on a chilly night. I especially like to pack minimal swimsuits that can be styled as a chic bodysuit under skirts or denim. And you never know where the day will take you, so it's always good to bring a pair of sneakers in case you end up on a trail."

How do you maximize space in your carry-on when packing light? Do you have any packing tips?

"When I’m on a multi-city tour, I use packing cubes to compartmentalize the different uses of my wardrobe: whether it’s using different cubes from destination, or for function. For example, day time separates go into one cube while workout wear and swim go into another. They also help maximize space and keep your suitcase clutter-free."

Photo: Courtesy of Monical Mendal

What summer trip are you packing for?

"I'll be based in Milan this summer and traveling all over Italy."

What must-have items do you always have in your carry-on bag?

"1. My Porto pouch. I use it for literally everything (and own it in every color). It's perfect to keep your essentials (keys, wallet, phone) in one place while you're in transit, but it's also my go-to bag that I take from day-to-night.

2. A Smythson Panama Agenda. I'm old school. I like writing things down; it helps me stay more organized when I'm on the go. Every year, I buy the Smythson Panama Agenda, which is the perfect pocket size. (It even fits in my little Porto pouch!)

3. A portable charger. I have no idea how I would function without one. I rely on my phone so much when traveling—from using GPS to taking photos to staying in touch with friends and family abroad via Whatsapp—my phone's battery is always drained by mid-day. A portable charger is a true game changer.

4. A duster cardigan. In the summer, I usually only travel with two knits for cooler nights, days in transit, etc. I love the Makena sweater from Naked Cashmere. It looks so pretty and put together over a dress and is super cozy for a plane ride."

How do you maximize space in your carry-on when packing light? Do you have any packing tips?

"Take it from someone who can go two months in a single carry-on: roll your clothes, don't fold!"

Makena Cardigan

Naked Cashmere

Panama Agenda


The Pouch


Jen Olson, Brand Marketing Consultant

Photo: Courtesy of Jen Olson

Is there any summer trip in particular that you're packing for?

"I've been going back and forth between Los Angeles and New York City for work, so it's been important to pack light and easy for the hot summer days."

What must-have items do you always have in your carry-on bag?

"During the summer, I always travel with a crisp white tank, cut-off shorts, and an easy summer dress. I love Away's 'Bigger Carry On.' It allows me that little bit of extra space that I need for last-minute packing. I also don't travel without Dôen's pouches—I use it as a toiletry bag as well as the sweetest summer purse!"

How do you maximize space in your carry-on when packing light? Do you have any packing tips?

"Ideally, I try to plan out every outfit so that I don't overpack. Otherwise, I'm throwing in items last minute that I never end up wearing!"

Kalani Miller, Co-Founder of MIKOH Swim

Courtesy of Kalani Miller

Is there any particular trip you're packing for this season?

"I always make sure that my carry-on is packed and ready to go—I have spent the majority of this year living out of suitcases and traveling around! We left the U.S. at the beginning of April and have since been to Australia and Indonesia, with plans to travel to South Africa, Europe, and Tahiti. I am currently in a small island chain called the Mentawai in Indonesia off North Sumatra on a boat trip chasing surf."

What must-have items do you always have in your carry-on bag?

"I think it’s really important for all of your items to have a home in your suitcase in the exact same spot, so trip after trip you always know where to find them. I keep my passport in the same location each time I travel—that is number one! Then having the correct converters and chargers is essential for work and communication. A MIKOH bikini, cover up, and sarong are always in there. I also love the Sayama Jumpsuit because it can be dressed up or down—it’s best to have a change of clothes in case your bags don’t show up!

I am a big reader, so I always make sure my Kindle is charged and loaded up with books along with my journal and film camera. I’m a bit of a vitamin junkie so I have to travel with many vitamins. My toiletry kit also always travels with me. A couple of my favorite clean beauty brands for travel are Symbiome, Osea, DermaE, Sunday Riley, Caudalie, Tata Harper, and Goop!"

How do you maximize space in your carry-on when packing light? Do you have any packing tips?

"I have refillable travel-size toiletry holders that I put my favorite products in. Honing in on the essentials is really important. Imagine what you would need if your bag was missing for three days—you'd be surprised at what are truly essentials. Normally, three to five days before a trip, I lay everything out and then slowly add or remove stuff. I think that's the best method because then you rarely forget anything. And don’t forget to make lists!

I am still up in the air on packing cubes, to be honest—sometimes they can really help with organization, but I think if you can stay streamlined, you don’t really need them. When packing my clothes ahead of traveling for the next few months, I focus on really good basic pieces and then mix in fun pops of color or a cute top. Basics for me would be a good pair of vintage Levi’s, a great white tee and tank, a cashmere sweater, and a good sweatsuit. I am loving the MIKOH Opihi Top currently and it’s ability to be dressed up or down. Also, I will never forget a hat!"

Belize Top

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