Nancy Hales, first lady of Portland, has invited me to attend Alley 33, a fashion show of local Portland designers. Before the show we plan to meet at Union Rose, a boutique on SE Stark Street featuring only Portland-made garments and where, coincidentally, we both like to shop. Hales is such a champion of the store that on election night 2012, when a campaign staffer for her husband, Charlie, suggested it would be fun to dress everyone in locally made clothes, she arranged for a rack of dresses from Union Rose to be wheeled into campaign headquarters; each female staffer chose one to wear for the evening. (The men chose shirts from Bridge & Burn, a local clothing line specializing in menswear.) 

I’d figured we’d each leave the shop in our own cars, but when Hales arrives she asks if we might ride over together to SE Hawthorne Boulevard, where the show will be held. It’s August, and she is dressed fittingly in an oatmeal linen skirt and sheer rayon blouse, white with green polka dots, and open-toed sandals. My 1995 Pathfinder, with its cracked windshield and odors of dog, horse, and traces of patchouli (from when the hippie stepdaughter borrowed it), is shameful. It’s certainly no place for any lady, much less the First Lady.

But there’s no way out. Charlie Hales, her husband, the mayor since January 2013, has dropped her off. As we head to the Pathfinder I apologize in advance, the way people do, and she says, “Oh, I’m sure it’s fine,” also the way people do. But then we reach the car, and she settles in and says, “Wow, this is nice.”

“I hope you’re enjoying the crack in the windshield.” 

“Mine has three cracks. And it looks like you might actually have power steering.” It turns out Hales has a history of beater-truck ownership. The Honda she drove when she was raising her kids in Stevenson, Washington, and making the 110-mile-round-trip commute each day to Vancouver to her job running the Community Foundation for Southwest Washington, perished with 425,000 miles on it. Her “new” old truck, a 1987 Toyota, is a “mere adolescent,” she says, with 118,000 miles, no radio, no power brakes, and only occasional heat. Later, I’ll lay eyes on it and see the wooden roof rack that Charlie and his brother built, and the potpourri of bumper stickers: Health Care is a Human Right; Outdoor School, No Child Left Inside; Keep Portland Meshugenah!; Friends of Trees; International Brotherhood of Teamsters.

It’s one of the complexities of Nancy Hales, a badass side that isn’t readily apparent. Despite her whiff of chic—the short Marilyn Monroe–platinum hair, the slim waist, and the ability to show off the creations of the local designers she loves—she is, at bottom, a small-town girl whose résumé includes a stint packing apples in Yakima.

The third annual Alley 33 event is held in an actual alley, on the east side of Mag-Big, another “makers” store that Hales frequents. The show is packed with young, stylish Portlandians (ink, fedoras, heavy black-framed glasses). As the music booms and models hit the catwalk, Hales takes pictures with her phone of the outfits that appeal to her. She has relationships with several of the designers featured at the show. She favors silk cowl-neck dresses designed by Alyson Clair, whose new line from Clair Vintage Inspired is on the runway tonight. “I love seeing her in my dresses,” says Clair. “I want her to wear the hell out of them.”

Meanwhile, Mayor Charlie Hales is courtly; he stands to one side and holds his wife’s lemonade as she poses for more pictures. I ask whether he’s enjoying himself: “This doesn’t really seem up your alley.” 

He laughs, then says, “Being married to Nancy, my alley has gotten a whole lot wider.” The mayor’s style, in that he has one, tends toward Wonk Classic—tassled loafers, khakis, blue dress shirts. “If I walk into the room, there might be a ripple because ‘that’s the mayor,’” he adds. “If Nancy walks into the room, people pay attention because she simply lights the place up. I don’t want to say that I’m gray and she’s multicolored, but that does just about sum it up.”

That natural sparkle is now shining in a new sky: Hales is the first spouse or partner of a Portland mayor in living memory (maybe ever) to embrace the concept of “First Lady.” The role is admittedly weird and anachronistic, a branch of Downton Abbey grafted onto the trunk of 21st-century American elected leadership. But in her own spirited way, Nancy Hales is shaping the label into a job, confident that a local First Lady can contribute something, even if no one is quite sure what. 

In late September Hales hosted a mother-daughter tea at the Heathman to raise money for the police bureau’s Mounted Patrol. She opened her remarks with a story about how after Charlie was elected, her kid brother began calling her the FLOP. “I reported this to Antoinette Hatfield [the widow of Sen. Mark Hatfield], who said, “No, you’re the FLOPIT, First Lady of Portland–In Training.”

The line got a laugh, which was Hales’s intention—she generally has a dry sense of humor—but she was also serious. Aside from the fact that being the first lady of a city doesn’t carry with it the same sense of hallowed tradition that accompanies the role of FLOTUS, Portland is, well, Portland. Flipping back through the pages of recent history: Sam Adams’s domestic partner, Peter Zuckerman, an award-winning writer, kept a low profile as First Guy; Tom Potter’s wife, Karin Hansen, a former high school teacher, may be best known for a number of contentious blog entries, in which she excoriated the city council and people who opposed her husband; Vera Katz was unmarried during the 12 years she held office; Sigrid, wife of John Elwood “Bud” Clark, the legendary tavern owner who took office in 1985, had no use for the spotlight, aside from the one that shone on the Oregon Symphony, where she was a violinist. 

Jewel Lansing is a former city and county auditor, a historian, and the author of Portland: People, Politics, and Power, 1851–2001. She knows her Portland mayors, all the way back to the first one, Hugh D. O’Bryant, who took office in 1851. She contends that Nancy Hales stands apart. “The most famous First Lady, if you could call her that, was the wife of George Williams (1902–1905),” Lansing says. “She had a reputation as a spendthrift, and started a religious cult centered around long-term fasting. But Portland has never had any mayoral spouses who have embraced the role in the way that Nancy Hales has. There’s simply been no real precedent for her.”

On the surface of it, being a First Lady or Gentleman on the city level seems mostly a matter of desire; if your spouse gets elected, you can dive in or hang back as your personality and urge for limelight dictate. But Hales’s background, experience, and skill set make her an uncanny match for the role. 

“I am a community wonk,” she says a few minutes into our first meeting. Hales has invited me to join her and the mayor at Sunday Parkways in North Portland. In its fifth year, the event is meant to encourage Portlanders to explore the city using “active transportation,” and on this late-July day the First Couple and I plan to ride the full 9.5-mile loop.

Charlie is dressed to cycle in last year’s blue Sunday Parkways T-shirt and Lycra bike shorts, but Nancy wears a khaki golf skirt and polo. Her earrings match her helmet. As we ride through the neighborhood, the mayor stops to thank every police officer posted at the roadblocks. On a rough patch of asphalt, he says, “This road needs to be fixed.”

“Too bad you don’t have a bucket of whatever it is you fix a road with hanging off your handlebars,” I say.

“Pavement slurry,” Nancy calls out. “Six months ago who knew I would ever know the name for that?”

The delight Hales takes in her role is obvious. She and the mayor, both of whom have been married before, have five children between them, all in their twenties and thirties and out of the house; this leaves the couple free to spend most weekends attending community events. The night before, they’d partied at the Human Rights Campaign Gala. Several days later she participated in the Voyage of the Visionaries, an annual ride of trails and parks wonks that this year coursed 26 miles from Corbett along the Historic Columbia River Highway, ending in Cascade Locks. She invited me along, assuring me not to worry if I wasn’t a hard-core cyclist, claiming that the day was about “policy, not Lycra” and that “it was all downhill.” (It wasn’t, but Hales’s reassurance bespeaks of a glass-half-full worldview.) 

This generosity of spirit comes naturally to Hales. Echoing the sentiments of many who know the First Lady, Portland writer (and former neighbor) Natalie Serber says, “She has a giant heart. When you are sick, she brings over Chinese food, plants flowers in your garden, and then when you begin to feel better, she takes you for a makeover.” 

 The only luck I had soliciting a disparaging remark was from an acquaintance in city government who wished to remain anonymous. She told me that some women in her office sniff that Hales is too pretty, too thin, too blond, and too put together to represent Portland, a sentiment that may simply reflect Stumptown culture, more impressed with eccentricity than glamour. When I report this to Hales, she is flabbergasted. “Seriously? That blows me away. That’s awesome. I mean, is it awesome? I’m a middle child. The person who was put together was my older sister.”