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Oregon in the winter: It gets wet. It gets cold. It gets dark. Quite often, all at the same time.
Of course, the weather is not going to stop, so you shouldn’t let it stop you either. It’s a question of style—storming style.
So, how best to cope sartorially with months of gloom-drizzle? A lot of it comes down to sensible advice people from inhospitable climes have followed for centuries:
Be an onion—wear functional layers you can peel off as necessary.
Keep your feet warm and dry with proper footwear.
Protect your head—much of your body warmth is lost up top.
Fresh air and physical activity are good for you—stick to breathable fabrics.
Pacific Northwest weather is flaky—be ready to get outside as soon as the sun comes out!
To get you started on your new winter-positive path, we’ve rounded up a selection of gear from our region made to withstand everything the Pacific Northwest might throw your way.
Just remember: If you dress for success, you’ll never be miserable outdoors again. And even if you still are, at least you’ll look fabulous.
BOOTS
Let’s start at the bottom, shall we? Hailing from our own fair city, Bogs makes footwear fit for all sorts of Oregon activities, from hunting and fishing to simply mucking about in your own rain-soaked backyard. In many respects, they have has designed next-level wellies—rubber boots that are more comfortable, warm and—dare we say it—stylish even. They have full-on insulated winter options, but for most of us here in Portland, their waterproof Chelsea rain boots will more than suffice.
Kicker Rain Chelsea Neo boots ($110), bogsfootwear.com
SOCKS
What better to put on your feet before you slip into your new rain boots than some classy merino wool socks from a women-focused brand based in Beaverton? LadySquatch aims to make ecologically responsible, locally sourced apparel. It also donates a portion of profits to charities dedicated to empowering women and children. For manly men’s socks, head to Portland heritage brand Danner for a pair with a lumberjack-approved Doug fir pattern.
Sunrise merino wool socks ($30), besquatch.com
Doug fir merino socks ($19), danner.com
HEADWEAR
If you like merino on your feet, you might just love it on your face, too, with this wonderfully quirky spiky wool balaclava. Forget being bothered by the wind or rain while you’re sporting this. Even better, the feds won’t be able to use AI to identify you as you strut confidently down the street. You can find it at Altar, a Portland clothing company operating a digital marketplace and a retail shop inside Cargo Emporium located in the Central Eastside.
Spiky wool balaclava ($42), altarpdx.com
There is also less comprehensive head protection available. The Portland company Rustek is focused on making more sustainable caps, beanies and other hats. One chonky “Sherpa” beanie, in particular, caught our eye for its winter-busting potential. But there are plenty of great options to choose from here. Besides making plastic-free and renewable products, Rustek also donates to have two trees planted for every hat it sells.
Sherpa beanie ($74.95), rustek.co
GLOVES
If your hands are frozen stiff, you can always stuff them in your pockets, but a better solution would probably be some nifty Storm Liner gloves from Hood River’s Dakine. Made from midweight fleece, you can wear them by themselves or use them to upgrade your winter gloves or mittens. They have a grippy silicone pattern on the palms and are touchscreen compatible—so you don’t have to do that annoying strip-off-one-glove thing to tap on your phone.
Storm Liner gloves ($33), dakine.com
OUTERWEAR
Sure, we could point you to the Mackinaw and Tin Cloth jackets from legendary Pacific Northwest brand Filson—but why would we do that when there’s Portland’s very own Poler making The Napsack? This ingenious invention is essentially a mobile sleeping bag, allowing you to walk around wherever the winter spirit may take you. Simply slip it over your head, pop your arms and legs out, cinch it up to your waist and you’ve got hooded coziness to go. Poler says it’s the greatest thing to happen to camping since s’mores, and who are we to disagree? If that’s not enough, Poler also has a reversible insulated poncho allowing you to cosplay you’re a flying squirrel.
The Napsack ($130), reversible poncho ($100); poler.com
A good waterproof jacket is going to shape your attitude toward the wet season in myriad ways, so consider this sleek and functional women’s trench from Outdoor Research. Hands raised—how many of you thought OR was an Oregon company? They’re actually from neighboring Washington, but we won’t hold that against them if they can make a rain jacket that looks this good. Speaking of which…the Seattle brand Freeman makes a classy, waxed cotton raincoat for men—yes, it’s spendy, but at least you won’t feel like you’re donning a glorified garbage bag every time it starts to drizzle.
Women’s Aspire 3L Trench ($269), outdoorresearch.com
The Freeman Dry Wax Raincoat ($400), freemanseattle.com
DOGWEAR
Just because your pooch is furry doesn’t mean they don’t get cold, too. Fortunately, Ruffwear from Bend has designed a waterproof insulated vest to shield your dog from the elements while you frolic together all winter long. It even has a storm collar that folds up for extra protection. Put this on your dog and you can pretend you’re both living in your own personal Jack London novel. The well-designed vest also conveniently comes in six different sizes, so your canine friend’s comfort is assured no matter their breed.
Vert Waterproof Insulated Vest ($99.95), ruffwear.com
Oregon Winter is Willamette Week’s annual winter activity magazine. It is free and can be found all over Portland beginning Friday, November 21, 2025. Find your free copy at one of the locations noted here, before they all get picked up.
