How to Dress for a Portland Rainy Day

The Doc is forever in.

Fit for a Rainy Day — Oregon Winter 2024 Dressing for Winter piece (Jake Nelson)

Ah yes, winter—perhaps the most “Pacific Northwest-coded” season. Don’t get us wrong, springtime in Portland is lovely, but completely confusing fashionwise—one minute it’s raining, the next it’s warm...not dependable, and God knows we wouldn’t be caught dead wielding an umbrella. And Portland summer, we love you, but the hotter you get, the less clothing we can comfortably wear and, thus, the fewer diva moments we can achieve. Fall? OK, fine, perhaps fall fashion lends itself equally as well to all the layering, statement pieces, and crochet slays that winter fashion does—but this is the winter guide, after all.

So, whether you’re new to the Pacific Northwest and in need of inspiration or simply looking to branch out from your everyday hiking apparel (no shade, let’s just try some jeans, babes)—here are our tips for a cute-’n’-cozy Portland winter look.

Properly Coated

As previously insinuated, Oregonians have been known to be vehemently anti-umbrella. Thus, the combination of a solid rain jacket and a chunky beanie is crucial. Beaniewise, we’re currently obsessed with this hand-knit, scrap-yarn beanie from PDX small business LobosMade.

Fit for a Rainy Day — Oregon Winter 2024 Dressing for Winter piece (Jake Nelson)

And as for a nice rain jacket—whether you’re looking for Patagonia, Columbia, The North Face, Arc’teryx...hit up thrift shops first. You might just get lucky and save yourself upwards of $200. Oh, and if you’re feeling crazy, maybe branch out from black or navy blue...could be fun.

In-Vest

Another winter item we’re loving right now is a Sherpa vest. You can get them anywhere—we got a Madewell brand one from the Grand Avenue Goodwill for $10—they’re so cute and cozy, and the perfect in-between for any of my hiker/fashionistas out there.

Fit for a Rainy Day — Oregon Winter 2024 Dressing for Winter piece (Jake Nelson)

The Doc Is Forever In

In terms of winter footwear, whether you’re in need of a classic rain boot, a functional hiking shoe, or a fuzzy slipper—a pair of Doc Martens can do it all. They’re sturdy, they last forever, they’re cozy, they’re cute yet edgy, trendy yet timeless—and, most importantly, they’re so much cooler than Blundstones...I said what I said.

If all else fails, we’ll leave you with this—Portland winter fashion is: Doc Martens, striped sweaters, big cozy hoodies, wool socks, chunky scarves with outrageous patterns, crochet beanies, baggy jeans, oversized leather jackets, fuzzy earmuffs, red rain boots, fingerless gloves (sometimes being fashionable requires sacrifice), bows, silver jewelry, layered knits, dark makeup, blush, sparkly eye shadow...

In other words, Pacific Northwest fashion is literally whatever you want it to be. Even if that means remaining in your hiking clothes year-round...but jeans are also awesome.


This story is a part of Oregon Winter, Willamette Week’s annual winter activity magazine. It is free and can be found all over Portland beginning Friday, December 13, 2024. Find your free copy at one of the locations noted here or at our online store, before they all get picked up!

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