Earlier this winter, I embarked on a three-week road trip with 30 sled dogs聽from Wisconsin to Alaska, all while living out of a single backpack. Every day, many times a day, I took the dogs out of the truck and walked them鈥攊n temperatures ranging聽from 50 to 0 degrees. The nights were freezing. The cold wind burned. And everything I wore had to fit by my feet in the truck. As such, I sought out the warmest yet most squishable clothes I could find鈥攖he clothes you鈥檇 pack for a carry-on-only winter vacation聽or聽a layover in Quebec on your way to the Bahamas. Here are the ones that impressed me the most.
Pakems Cortina Boots ($90)

Packing Size: A Nalgene
聽are basically little jackets for your feet that happen to have soles attached, which means they fold down completely flat.聽I usually keep mine in the exterior water-bottle pocket on my backpack. The boots are water-resistant with fuzzy liners, so it feels like you鈥檙e wearing slippers even as you shuffle through slush, and they鈥檙e plenty cozy for walking around town or doing chores outside. Don鈥檛 worry if you get 鈥檈m wet; they鈥檒l dry completely by a hotel-room heater overnight. Not to brag, but I鈥檝e had the same pair for three years, and I鈥檝e gotten a聽lot聽of compliments on them at聽gas stations at two in the morning.
Trew Super Down Shirtweight Jacket ($185)

Packing Size: A聽Kitten
聽has the best comfort-to-size ratio I鈥檝e encountered in a jacket鈥攚hich is relative, of course, because it packs聽very聽small. In fact, no matter how full your suitcase is, I pretty much guarantee that you can find a way to squeeze in this garment. As a shell, it鈥檒l keep you mostly dry in a rain shower and mostly warm on a snowy night; as a midlayer, it adds a nice burst of warmth with almost no weight. If you wear it as an outer layer, do keep in mind it鈥檚 best for activities that aren鈥檛 highly abrasive鈥攎ine got two small tears over the course of the road trip, but one of those was when a puppy chewed on it and the other was when I caught it on a shovel, so your mileage may vary. The nylon also has a nice matte texture that makes it unassuming and versatile; you can wear it over a flannel indoors without your outfit screaming 鈥淗ello, I鈥檓聽wearing a puffer in your living room!鈥澛燗nd then everyone asks you if you鈥檙e cold, but you鈥檙e not! You just like to feel snuggly, OK?聽
Seirus SolarSphere Ace Mitt ($35)

Packing Size: Two Eggs
The insulation in 聽is designed to capture the sun鈥檚 heat, but you can never count on good weather, so I tested them through several dark nights to see how they performed. The result? Even without sunlight, they鈥檙e surprisingly warm鈥攁nd small enough to stuff into the pockets of your jeans. Add thin wool liners and they鈥檒l keep your hands comfortable for an afternoon on the slopes.
Helly Hansen Odin Stretch Hooded Jacket ($240)

Packing Size: Half a Bread Loaf
聽achieves two things I didn鈥檛 know jackets could do: be super stretchy聽like a sweater, and be both very thin and very warm at the same time. Surreally warm. I鈥檝e been using it as outerwear while I do light work outside in temperatures down to minus 20 degrees, and it somehow keeps me the perfect temperature.聽I don鈥檛 overheat and get sweaty, but my core stays toasty the whole time. Its performance鈥攊n contrast to its lightness and size鈥攊mpressed me so much that I went out and bought two yards of the Odin鈥檚 insulation, ,聽so that I can hand-sew it into a bunch of my extreme-weather gear. Anyway, this truly perfect garment is also waterproof and breathable, all for less luggage space than a cotton hoodie.
Skida Alpine Headband ($20)

Packing Size: One Headband
Do you need a , strictly speaking? No. But do you like to wash your hair a lot when you鈥檙e traveling? Obviously not. So do you want something that will cover your greasy roots, keep your ears warm, and add color to your outfit, while taking up as much space聽as聽a tube of chapstick? Yes. Yes, you do.聽