12 Softside Luggage Pieces for Packing Winter Clothes

I’ve been traveling with hardside luggage ever since Away introduced its industry-changing collection almost a decade ago; I love its solid good looks and that it’s virtually indestructible. What I don’t love about hardside luggage, though, is that it’s less flexible when it comes to how much you can actually stuff inside, which is important when I need to pack bulky sweaters, scarves, and boots for cold-weather trips.

This winter, I switched to softside luggage. (It was an easy decision because two of my favorite brands, Away and Dagne Dover, recently launched stylish softside luggage collections.) Softside suitcases let me fit all the winter clothes I need — and even pack a few extra sweaters — because the fabric is so malleable. 

These flexible bags also make it easier to take items in and out of my bag at the airport, especially my big winter jacket, which I pack for cold-weather trips since I often fly from warm San Diego. I would have to awkwardly open my hardside suitcase on the floor in the middle of an airport to pull my coat, making sure nothing else fell out in the process. Last month, however, when I landed in New York with my new softside suitcase, I easily unzipped the top of my carry-on and pulled out my jacket en route to the shuttle. Then, on the way back, I simply tossed my jacket and new waterproof shoes (an unexpected but necessary purchase) into my amazingly forgiving checked bag without unzipping the entire thing — it was like a miracle.

If you’re traveling this winter, here are 12 softside pieces to consider. I’ve focused mainly on carry-ons because I think that’s where softside luggage really shines — you can access what’s inside, even during your flight — but every brand has checked bag options as well. You can pack your entire winter wardrobe — or have enough room to buy new pieces on your trip.

Away The Softside Carry-on

The gold standard, this carry-on will change the way you think of softside luggage. First of all, it’s gorgeous but strong. As I’ve traveled with it, its smooth spinner wheels have glided across European cobblestones as easily as the streets of San Francisco; plus, the bag can expand to hold a whopping 15 percent more when necessary. Although I’m obsessed with the clay pink (which you can grab on sale for $191), my husband was so jealous of how much easier it was for me to access my things that he decided to order the bag in jet black.

Away The Softside Large

I’m taking this beauty on an upcoming month-long trip that includes a Virgin Voyages cruise, a few days in Morocco, and a Capture Kenya Expeditions tour because it provides plenty of space to pack everything I need for these very different destinations. It’s durable enough to withstand all kinds of weather conditions and being frequently moved; plus, its patented compression pad system will help keep me organized and fit more items throughout my travels. I love that the clay pink hue (which is $50 off right now!) will stand out when coming around the baggage carousel so I can grab it and go. Did I mention it’s gorgeous?

Dagne Dover Seattle Carry-on Luggage

I’m a huge fan of women-founded Dagne Dover, so it was a no-brainer that I would fall in love with the brand’s luggage as well. There are two carry-on options, but I went for the smaller one (20.5 inches) rather than the larger style (23.5 inches) because I don’t want to take the chance that I’ll have to gate check it if it doesn’t fit into some regional plane’s overhead bin. The size is actually perfect for weekend getaways, and one of the best things about the bag, besides the fact that it’s made with recycled materials, is that it features two separate padded tech pockets for easy access to both my laptop and iPad.

Dagne Dover Sydney Checked Luggage

I love a matching luggage set so I added this Dagne Dover checked bag, again opting for the smaller 25-inch version (versus the 28.5-inch one) because it weighs two pounds less. It has the same 360-degree Smooth-glide Wheels for easy maneuvering and many organizing options, which include a roll-up divider, straps, and pockets so I can fit in everything I need for a week away — with room to spare.

Cotopaxi Allpa 38L Roller Bag

Cotopaxi is synonymous with adventure so you know this backpack-turned-roller bag is built to last. A hybrid of sorts, it features the strength of a molded EVA backbone and the flexibility of soft luggage. It’s made of 100 percent recycled fabrics and has a front pocket for easy access to essentials; plus, the flexible material makes it a breeze to store anywhere. Available in four eye-popping colors and guaranteed to last a lifetime, it’s no wonder one reviewer called it “the best of the best of the best.” 

Calpak Luka Soft-sided Carry-on

I’m a big fan of the puffer trend, especially for winter, and this Calpak Luka carry-on bag pulls it off beautifully in four classic and three limited hues. The puffy material is soft and cushiony, adding an extra layer of protection for my belongings, especially my laptop, which fits right into its own padded compartment. Compact and lightweight, it’s a great weekend choice that no one else will mistake as their own. 

TravelPro VersaPack+ Carry-on/Large Check-in Spinner Set

TravelPro is a favorite of pilots and flight attendants, and this two-piece set makes it easy to see why. Water- and stain-resistant, these bags feature smooth spinner wheels and built-in TSA-approved locks, and they expand up to two inches. They even come with their own laundry bags to separate dirty clothes. The carry-on also features shoe bags and internal compression systems, while the check-in includes packing cubes. Together, these suitcases are really all you need for your travels.

Delsey Paris Sky Max 2.0 Softside Expandable Luggage

It’s probably not surprising that this line of softside suitcases from the popular French luggage brand Delsey Paris is bursting with both style and substance. What may surprise you, though, is the fact that it’s ultra-lightweight despite a long list of thoughtful details like pockets, straps, and dividers. Heavy carry-ons can be difficult to lift to place in the overhead bins, so this under-six-pound bag is a welcome pick.

Victorinox Werks Traveler 6.0 Carry-on Frequent Flyer

Made of ballistic nylon (the material used for flak jackets during World War 2), this extremely durable Victorinox bag is as good-looking as it is practical. Measuring just under 23 inches, it comes with the well-designed Pack More system that helps get you organized and enables you to, well, pack more. The outside is water-resistant and abrasion-proof, and you’ll find useful features like a TSA-approved combination lock, USB port, and dual caster wheels for added security, comfort, and convenience. 

Kipling Darcey Softside Carry-on Rolling Luggage

Yes, that adorable monkey keychain hanging from the zipper means that this conversation piece comes from the popular brand Kipling. The immediately recognizable mascot represents the brand’s unique crinkle nylon fabric and its commitment to fun and fashion. It’s lightweight, sturdy, and waterproof, making it a trusted travel companion. 

SwissGear Sion Softside Expandable Carry-on

With more than 15,700 five-star reviews, this Amazon best-selling bag is a great choice for travelers who need a little more leeway in their packing options. Its durable fabric comes in eight vibrant colors and expands as necessary. One traveler with limited mobility said they needed a “rock solid” carry-on in terms of functionality and durability and found it in this bag. “I’m blown away by this item, especially given its affordable price point,” they wrote. 

Bagsmart Softside Expandable Carry-on

This value-priced carry-on boasts many of the features of a much more expensive bag, including lots of pockets, high-performance spinner wheels, and a surprising amount of room. One five-star reviewer and frequent traveler wrote, “Two years later and this bag is still an outstanding purchase,” calling it “a very sharp-looking bag.” It comes in a variety of colors and offers high-capacity expandability so you can pick up an extra souvenir or two.

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