The Weirdly Chic Nature of Portland Style

Ashley Sophia Clark for Frances May

American style is as regional as accents or craft beer. To help define these nuances, we’re connecting with influencers in the country’s most stylish cities. First up: Portland, Oregon.

I actually don’t even own a pair of pumps.”

It’s astonishing how freely Tonya Smith admits this, considering she’s built quite a social-media following as the style blogger behind The Moptop.

Or it would be, anyway, if it weren’t for the fact that Smith lives in Portland, Oregon. Indeed, the thought of her tiptoeing through the perpetually waterlogged city in silk Manolos seems almost criminal.

“A lot of the locals don’t really dress up much,” she says. “Portland is so close to so many mountains and places to go hiking and get outside, that it really influences the style here. We can get away with wearing more outdoorsy pieces.”

Smith’s affinity for sensible shoes aside, it’s not as if everyone in town is constantly traipsing around in ponchos and Hunter Wellies. The local style contingent is pulling the weight of a fully loaded cargo ship sailing beneath Burnside Bridge. Dig through the Instagram feeds of Portland influencers, and you’ll unearth plenty of gems — photos that capture masterful minimalism, romantic elegance, effortless cool.

The Moptop’s go-to bag? “A cute backpack. I walk everywhere and it’s easier to carry.” Click to see her full Instagram.

Whereas people in other cities seem to struggle with dressing stylishly for the weather, Portlanders have it down pat. Their ability to integrate fashion and function is as prevalent as the drizzle. Instead of wasting time with passing trends, they’ve mastered the art of sophisticated layering.

“Layering has become an essential style card,” says Lavenda Memory, namesake of the blog Lavenda’s Closet. It’s a card she plays well. An outfit she posted earlier this year balances both color and proportion, chicly combining a plaid button-down, distressed cable-knit sweater, and car coat with contrasting leather sleeves.

But by her own admission — and despite being a former fashion photographer — Memory hasn’t always possessed sartorial intuition. “I struggled with how to dress my body in my early twenties, and Portland allowed me to experiment without feeling phony or judged. I finally arrived to this boho, modern-classic style that feels just right.”

In a town too casual for the LBD to be the wardrobe staple, the must-have instead is a free spirit. “I think there’s an eccentricity here that has become inherent, almost ingrained in even the most modest dresser,” Memory says. “[Portlanders] feel entitled to experiment and evolve our own fashion sense because anything goes here. It’s a very liberating place to discover and grow into your personal style.”

“The Fremont Bridge is my greatest style inspiration,” says Memory. “It has this romantic, clean design… It also connects the West and East sides of the city, which represent two different styles—one more posh, the other more urban.” See her Instagram.

Jade Sheldon, an illustrator and photographer who’s lived in Portland all her life, echoes Memory’s sentiments. “Portland encapsulates individuality. It celebrates it in every way. There is no one kind of Portlander,” she says. “You have people who are about hiking, biking, and blazing trails, or others who are technology types dressed up or down in the Silicon Forest.”

Despite these idiosyncrasies, Sheldon insists there’s a deep-rooted sense of community. “[The city’s] connection with nature helps individuals have a better connection with each other, too. It results in a tighter-knit community overall, and I can’t say I know any other cities that feel the same way.”

In Sheldon’s case, her personal style reflects her work as a fine artist. “It has shaped the way I look at both fashion and beauty by making me aware of the simple details. One small change to an outfit can make the whole look come together, or throw it off,” she says. “Whether that is an eye-catching pair of heels, a simple and beautiful watch, or even a bold lip color.”

Sheldon describes Portland style in three words: “Indie. Free. Boots.” See more from her Instagram.

It’s all in the details as well for Pamela Baker-Miller, founder of independent clothing boutique Frances May in downtown Portland. A Brooklyn native, she’s found that Portlanders are sticklers for craftsmanship over trends. “Portlanders buy now, wear now,” she says. “We are practical and care about wears per buy. We prefer quality to quantity and classic to trendy. We care how things are made and who is making them.”

She’s taken this to heart, favoring international cult favorites (APC, Acne, Rachel Comey) and revered local designers when stocking her shop. “When we opened eight years ago, there were only, maybe, two other stores that did anything remotely similar to Frances May. Since that time Portland has changed immensely,” says Baker-Miller. “Retail, restaurants, and bars have exploded. With these changes, Frances May has also evolved… [it has] encouraged us to dig deeper to establish our own identity and decided look.”

In Baker-Miller’s eyes, it’s not just the folks at Frances May who are coming into their own, though. It’s the entire city of Portland. “Our cool factor used to be non-existent, and now we are a tourist destination.”

Baker-Miller’s three wardrobe staples are Stutterheim raincoats, perfectly broken-in jeans, and (surprisingly) sunglasses. “One must always hope.” See Frances May’s Instagram.

Of course, there’s a difference between Portlanders refining their image and revamping it entirely. It doesn’t seem as though anyone is interested in cleaning house just because a lot of guests come to town. “Portland is still managing to keep it weird,” Baker-Miller assures. “There’s still the kilt-wearing unicyclist and the man walking his cat on his shoulder every morning. [That’s] what makes Portland special.”

What we’re loving about Portland style:

Clean color palettes | Oversized coats | Slim-fit turtlenecks | Boho accessories | Luxe backpacks | Statement boots | Simple jewelry | Quirky textiles | Denim

Feeling inspired by Portland style? Ask your stylist to include similar looks in your next trunk or fitting.

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