Every January I take about 50 students to Washington, D.C., and almost every January, the weather serves up sub-freezing daytime temperatures and icy air. Cold weather packing can be challenging because of the sheer bulk of winter clothes; you can't just grab a bunch of flimsy, tiny summer tanks and swimsuits and sail away with one light backpack. However, in about 25 cold-weather trips, I have learned by trial and error to master one of the trickiest packing situations.
Now, let's get you packed for your cold-weather trip to somewhere wintery and wonderful!
My standard packing notes
Travel packing, cold-weather trips included, is about simplicity and style, not fashion at its most creative or expressive. Simplicity frees you—literally, of unnecessary stuff, but also of the internal clutter of having to manage stuff. Style frees you, too; the better you feel, the more able you will be to stop thinking about how you look and wholly immerse yourself in the present.
I make packing sketches for our trips instead of packing lists. Draw your potential packing list and then draw all the outfits you can make with those pieces (it doesn't matter how well you draw; this is just for you!). I always end up taking several things out of my bags when I realize how little I need to make lots of great combinations. Bonus: your packing sketch will be a sweet souvenir.
An outfit formula
For cold-weather packing and its inherent bulk, I find it helpful to use this outfit formula. It works for practically any number of days because the layers allow you to keep rewearing and remixing, and in cold weather, your clothes require less laundering anyway.
Two pairs of jeans, or pants that you love (I like to vary the cut and wash to lend some variety)
Three sweaters (wear the heaviest one as your travel outfit)
One pair of snow-friendly, low-heel boots; most versatile is something like a weatherproof leather Chelsea boot without not strong "hiking" vibes
One pair of snow-friendly alternate shoes (like a waterproof, grippy-sole white sneaker)
Thin layers for each day of your trip (see below for my favorites)
Two or three fleece-lined leggings or tights
If you need to dress up during your cold-weather trip, add a slip skirt that packs down to nothing, looks great with boots and sweaters, and hides your fleece leggings underneath.
Alternate the sweaters, bottoms, and shoes to create a surprising number of outfits with just a few pieces.
And remember: most of your outfits will be covered by your coat, anyway, so pick one that's chic, sleek, and very warm. Choose cold-weather accessories (hat, scarf, and gloves) that you really like for the same reason.
Fleece-lined leggings: These waterproof, fleece-lined leggings have been so helpful on many cold-weather trips layered under dresses or skirts. I've appreciated how comfortable and well-made they are without costing a gazillion dollars (what is it with leggings??).
Fleece-lined tights: There's a German maxim, "There's no such thing as bad weather, only bad clothes." Layer fleece tights under your jeans or pants and enjoy the cold weather!
Down coat: Yes, flattering puffer exist! This coat has been viral since it first emerged years ago—warm, stylish, and a million pockets for your gloves, phone, and everything else.  I have happily worn my J.Crew down coat for years; try their excellent seasonal sales or search secondhand on Poshmark.
Tissue turtlenecks: These are excellent for layering and mixing to add a little style punch without bulk.
Belt bag: I strongly prefer a belt bag to a crossbody or shoulder bag for cold-weather trips because there's nothing worse than getting trapped and tangled in all your layers. A belt bag is ideal for wearing under your coat (I turn mine toward the back to avoid weird bulges) and you won't need to constantly untangle yourself from straps. This one looks good, comes in dozens of colors, and is far more affordable than those uber-trendy athletic wear brands.
Tech gloves: Use your touchscreens without exposing your fingers to frostbite.
Cashmere beanie: This beanie has a beautiful, perfectly flattering shape and comes in 26 gorgeous, subtle colors. I also love this affordable, iconic knit cap that looks good on everyone.
Slip skirt: For cold-weather trips to sacred places, going to Mass, dressing for dinner, or just looking nice in your photos, a slip skirt is ideal—it hides fleece leggings, pairs beautifully with sweaters and boots, and you can roll it up and stuff it into whatever random corner of your suitcase is available. I like that this one feels silky but is super low-maintenance.
Merino wool boot socks: Merino is warm, feels pleasantly nubby on your feet, holds up to tons of use, never smells funky, and wicks moisture. For cold-weather trips, I prefer these to super-heavy, super-thick wool socks—they're warm without stuffing your boots to bursting. (Some merino enthusiasts even say they wear these socks multiple times before a wash, and I can understand why they say that, but y'all. Wash your socks.)
Thin cotton base layers: Add zero-bulk warmth and protect your sweaters so you can rewear them throughout your trip. I pack these base layers on every single trip I take.
Long sleeve base layers: I layer these silky long sleeve base layers over the short sleeve base layers for warmth without bulk under sweaters.Â
Weatherproof boots: I have used and loved these every January; they are comfortable for my problem feet and lined with sherpa to be extra toasty. For cold-weather trips when I need a boot that dresses up more, I pack something like these.
Toups and Company organic skincare products: I can’t survive winter without this frankincense tallow balm or tinted lip balm. They're the single organic, nontoxic moisturizers in the entire world that has worked for my face and lips...I could go on and on. A teeny bit goes a long way. My jar lasts about two months with twice daily use. From this small-batch, small business, I also love, use daily, and subscribe to the the mineral makeup (a jar lasts me a few months).
High waist jeans: I have loved these two very different cuts from Levis—a high waist keeps all your layers securely tucked and actually adds some extra warmth to your core. The Ribcage Bells are extremely and universally flattering, plus have lots of room for your boots. The Ribcage Straight are an always-stylish straight, slightly-cropped cut that looks great with everything and won't drag in the slush and salt.
Other cold-weather packing essentials:
Handwarmers: I slip these into my gloves, shoes, and pockets when it's truly freezing. I haven't tried the rechargeable kind, but they're also a thing.Â
I'm a huge fan of bone broth for many health benefits; these bone broth packets are a decent substitute when I can't pack my usual cartons of liquid broth.
Over ear headphones are warmer than earbuds.
Cold weather is a sneaky dehydration trap; I love my glass water bottle for easy refills.
The best travel umbrella for sleet and snow.
I could sing on and on the praises of my favorite travel backpack. It offers tons of pockets and compartments to keep you organized and has some smart features like security pockets, water-resistant exterior, and comfortable straps. The zippers are beautiful and function smoothly. Details!
If you're not using packing cubes yet, you'll love how instantly organized they make your luggage and how easily you'll be able to keep track of where everything is while you're living out of a suitcase.
This little flat-pack gadget bends and folds to hook onto anything (I use mine to hold my phone on seat backs or tray tables). Slip it in your bag and enjoy not using your phone at angles that destroy your neck.
Please tell me you wouldn't dream of drinking Starbucks or some other random coffee just because you're traveling. I have used this coffee press on a moving bus, in airports, and in more hotel rooms than I can count. It makes incredible coffee every time. All you need is a hot water source (and coffee or tea, of course).
I bring this plastic-free travel kettle to pair with my travel Aeropress.
A good pair of noise-reducing earplugs is always helpful.
A note about Amazon
These links connect mostly to products sold on Amazon. This is not the only place you can buy most of these items, but I set it up this way because of Amazon's ubiquity (everyone I know already has a Prime account). You can also try finding the items you like at other retailers, local shops, or secondhand markets.
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