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.” 

Born in 1954, raised in the small town of Redbank, New Jersey (“Off exit 109!” she jokes), Hales graduated from the University of Vermont with a degree in economics and applied to the Peace Corps. She was scheduled to go to Sierra Leone, but just as she was preparing to leave, civil unrest caused the Corps to pull its volunteers, and Hales was left without a job. Instead, she joined VISTA, a domestic version of the Peace Corps spearheaded by Lyndon Johnson to fight poverty in the US, and was sent to Yakima, Washington.

“I became a grassroots organizer,” she says. “I absolutely loved it. It begins with small battles, and you work to build up indigenous leaders, and then they take on bigger battles. Two months after I started, we had a situation. It was the late ’70s, and the city of Yakima had received an economic development grant which they were going to use to displace a very strong African American community. It wasn’t right. I remember, we had mimeographs. I can still smell them. I drew a picture of a bulldozer with a house in its bucket and stuck the mimeos up all over the neighborhood, encouraging folks to come to a neighborhood meeting. It was awesome and easy to mobilize the community around this very clear issue. I grew to understand civic action in a very real way and got a good handle on the way communities become competent. That’s where I come from, and that’s where I’ve been ever since.”

When the VISTA job ended, her parents wanted her to come home, but instead she took the apple-packing job and adopted a husky mutt who became her companion for the next 18 years. She was hired by the Forest Service to create a youth employment program, and it was there she met Bob Sourek, her former husband and the father of her two grown children. Together, they bought a farm in Carson, Washington, where they raised goats, pigs, and sheep, and also had a few horses. “We didn’t do too well with the sheep,” Hales confesses, “but the pigs were a hit. We raised them and then we ate them.”

She eventually landed at the Community Foundation in Vancouver, where she worked for 17 years. In the mid-’90s, while working toward a master of public administration at Lewis & Clark, she met Charlie Hales. Several years later their paths crossed at an art event. A city commissioner by then, he invited her to pull ivy with him at Forest Park, hoping to prove that Portland could be as verdant as her home in Skamania. They began dating in earnest in 2000, and married in 2004. Five years later, she became program director of First Stop Portland, an organization created by a Portland State University dean and a developer to manage the constant parade of delegations visiting Portland to study the city’s innovations in transportation and sustainability. Hales has shaped the job into a role akin to a civic ambassador.  

I stopped by Hales’s office at PSU. She was holding a meeting with her assistant director, Sarah Iannarone (“Deputy Kick Ass,” Hales jokes), and a student intern amid towers of bank boxes and potted plants. Self-contained and self-funded (at one time it received some money from the city, but the mayor deleted the program in his first budget review), First Stop hosts groups from places as far flung as Australia, China, Brazil, and Uzbekistan. Hales and her team set them up with local innovators and businesspeople focused on the city’s livability.

This is all well and good for the rest of the world, but what does Portland get out of it? “Sarah and I regularly scratch our heads on that very question,” says Hales, and then tells a story about a visit from the vice mayor of Amsterdam.

“We kept trying to show them our bicycle infrastructure and they were like, ‘Nah, we don’t want to see that.’ But they were very interested in how Portland got things done. They were amazed by the [public-private] partnerships. They were interested in the glue. At the end of the tour, the vice mayor was put this question, ‘Why are you here?’ He pulled out that day’s Oregonian, and there was a front-page story about our angst over whether people should use leaf blowers, and he said, ‘We think this is laughable in our country. We don’t understand your anguish, and yet you people do this. That’s why we’re here. We have a medieval city. You call us sustainable and green and we don’t even use these words. We were built around function and efficiency and commerce. But you are a city built around ideas, goals, and aspirations. We need more of your stuff, but you also need more of ours.’”

During separate conversations, I suggest to both Nancy and Charlie that there’s a Bill-and-Hill quality to them: that like the Clintons she doesn’t stand in his shadow, but by his side, with her own career and history of achievements. Both were quick to point out that the difference between Hillary Clinton and Nancy Hales is that Nancy isn’t political.

“She’s civic-minded. She goes to City Club meetings, she goes to neighborhood meetings and has an abiding interest in Portland, but she doesn’t like the gamesmanship of politics, nor is it her forte,” Charlie Hales said. “Her advice to me and her reaction to things that are going on is that of Everywoman, or Everywoman who’s paying attention.” 

When asked whether she would ever consider running for her husband’s job, she looked at me with mock horror.

“No way. I’m not a risk taker,” she said. “You have to be willing to take the arrows, and I’m just not. During the campaign we would hold focus groups, and some awful things would be said about Charlie. I’d be a puddle, and he’d be like, ‘That’s interesting. What’s for dinner?’”

Yet Nancy Hales has no shortage of political acumen, if less of the arrow-shooting (and -absorbing) variety than the kind that requires the forgotten ability to walk a mile in the other guy’s shoes. In October 1991, for instance, she represented Skamania County on the Columbia River Gorge Commission, as it forged the contentious first management plan for future development in the Columbia River Gorge National Scenic Area. Five years earlier, in 1986, when President Reagan signed the declaration that would make the Gorge an official Scenic Area, Skamania offices flew their flags at half-mast. It was a typical rural western gesture: here they were out in the middle of nowhere, minding their own business and taking care of themselves, thank you very much, and suddenly they were going to be compelled to obey rules set down by Washington, DC. The 400-page plan placed no small burden on Oregon’s Hood River County, and Washington’s Klickitat and Skamania Counties. 

Gayle Rothrock, who sat on the commission with Hales (then Nancy Sourek), remembers how devastatingly complicated it was to assemble a workable plan. “It was upriver vs. downriver orientations, Oregon vs. Washington planning expectations, urbane city dwellers vs. less sophisticated. There were Native American tribal members, the timber industry, orchardists, and new economy players investing heavily in something called windsurfing.”

In the end, the commission easily approved the plan, 9–3, but with Hales taking a side that would furrow the brow of most green-blooded Portlanders: she voted no. Her main concern was not the plan per se (she even pivoted with a suggestion that the counties be allowed to go beyond the proposed regulations) but that local governments needed latitude to do what was best for their own communities.

“My lifestyle was similar to that of my neighbors—we were raising livestock, gardening, chopping firewood to take us through winter,” she recalls. “My perspective on environmentalism, while informed by a New England college education, was also grounded by living close to the land.”

Hales wound up drafting the minority report, something of which she is still proud. “The record needed to reflect serious deliberation and disagreement,” she says. “We were not rubber-stampers; and each of us cared deeply about the end result.”

“In the end, despite our disagreement,” says Rothrock, “we still were able to have regard for one another.” 

One of Hales’s missions during her first year as First Lady has been to get acquainted with the spouses of the mayors of neighboring cities. She hopes to lessen the Big, Bad Portland image the rest of the region often harbors, in favor of more convivial, collaborative relationships. That would be most useful to her husband, who, if he is to tackle problems that can be fixed only with regional solutions (homelessness, drought management, traffic congestion, and transit issues come to mind), could benefit from the dividends of his wife’s effortless diplomacy.

An apolitical Hill to Charlie’s Bill notwithstanding, a First Team could still be unnerving for a citizenry that, as historian Lansing puts it, doesn’t like “too much power in one person”—or one pair. 

“If the Haleses, as a couple, got too big for their pants,” Lansing warns, “there might be a backlash.”

It’s unlikely. Even in the realm of fashion, Hales’s passion is less about the glamour than the little guy or girl. “Locally made clothes is a sort of shorthand for all local products,” she says. “Fashion is easy and visible, and helps highlight the larger issue of economic development in our city. But in my heart, my main concern is about fairness and equity. These people work very hard, and they should see some real compensation for their efforts.”

Portlanders have repeatedly voted to keep the city’s weak-mayor system, which affords the mayor little more power than any other city council member. But it’s still a city in which one person can change the game. Antoinette Hatfield says that Hales’s gift for connecting people makes her invaluable. “Times have changed. The thinking of the constituency has changed. Reaching out to other people is now the name of the game. If you know how to socialize with people, you get to know them better. If you know them better, they turn into friends, or at least people with whom you’re friendly. Friends work better together than adversaries. Politics is human relations.”

At the benefit for the Mounted Patrol at the Heathman, most of the crowd has poured their individual pots of tea and dug into the pâté maison and John’s Famous Lanai Banana Bread. Dressed in a pink tweed peplum top by local designer Lena Medoyoff and a black Tiffany Bean pencil skirt, Hales is still circulating, kneeling beside each table and introducing herself. The ubiquitous raffle closes the event, and the first number called is the First Lady’s. “Oh, absolutely not!” she laughs. Without missing a beat, she gives the prize, a silver bracelet, to the little girl in the black velvet dress who called her number.