The Look of Knowing: How Professors Navigate Personal Style
By Jude Kuykendall ‘28
Tortoiseshell glasses, a gray tweed jacket, and shiny derbies that rang out undeniable levels of knowledge with each clacking step. This was the first professor I met. A real, fully formed mythic figure, as if lifted from the set of Dead Poets Society. His jacket's threads and the soles of his shoes were well-scuffed and well-loved, but above these external markers, ripe with credibility, it was his eyes—weightless in sureity—that revealed his style through an indisputable rhythm, long-lived and deeply his.
Since arriving at Middlebury this fall and becoming immersed in a new sartorial landscape, everything felt vaguely idiosyncratic. Sooner or later, however, I was swept up by the styles that uniquely situated themselves into my bag of liberal arts professor clichés. Here, professors wear Chaco sandals in lecture halls, finance-bro vests in 75-degree weather, bangles that echo down stairwells, polka-dot skirts that lecture to rooms of sweatpants, and the occasional tweed jacket, just for good measure. Witnessing the sheer range of one professor’s stylistic expression sparked more than just admiration—it sparked a question: how do Middlebury professors navigate style to make it their own? I set out to explore the silhouettes, color palettes, and quiet statements that speak to who they are. Selected with the help of a few style-savvy classmates, I sat down with three professors whose visual identities are uniquely their own: Molly Anderson (Food Studies), Edward Vazquez (History of Art), and Carolyn Finney (Environmental Affairs).
First up, we have the self-proclaimed “anti-fashion” Professor Molly Anderson.
“There’s just no other blouse like this,” Professor Anderson said, holding up a striking blue top adorned with indigenous-inspired designs—tassels shaped like ears of corn. Made by a women’s cooperative in San Cristóbal de las Casas, the blouse represents more than style. Anderson, who spent years living in Latin America, gravitates toward handmade indigenous garments, but not only because of how they look. “I want to honor the people who created these things,” she told me. “Just because it's handmade doesn't mean it's beautiful, but beauty, color, authenticity, uniqueness—I appreciate that.” Her fashion choices are driven by ethics as much as aesthetics. “Did the person who made the clothing receive a fair wage?” she asked. She avoids big-box stores like Walmart or Costco, where “T-shirts, two for seven dollars” raises uncomfortable questions. For Anderson, dressing is also an act of solidarity, supporting workers, small-scale farmers, and just transitions beyond renewable energy. “It’s about decent work conditions,” she said. “That’s why I shop at women’s cooperatives, or even places like Neat Repeats—people abandon really good stuff.”
On campus, Anderson dresses with intentionality. “If I didn’t need to come in, I’d probably wear sweatpants,” she admitted. However, she feels a responsibility to dress respectfully, especially as a professor. “If I showed up in shorts or sweatpants, students might feel disrespected—and I definitely don’t want to convey that.” Still, she doesn’t expect students to dress up, and finds it funny when someone shows up in a tie, usually for a job interview. When asked about a forever outfit, she chose “sweatpants and a T-shirt” without hesitation. Her daughter, she added with a laugh, “will be flabbergasted—I shared the interview invitation with her, and she said, ‘That’s wild.’ She doesn’t consider me particularly stylish.” Yet Anderson’s look, rooted in values, culture, and comfort, is powerfully chic. This is exemplified in the one-of-a-kind pieces she often wears, such as her pair of gray boots made by Indigenous artisans in Canada and lined with rabbit fur. Despite being “anti-fashion,” Professor Anderson’s pieces, steeped in color, cultural meaning, and personal effervescence, are bound together to create a one-of-a-kind style that transcends fashion.
Next is Professor Edward Vazquez: a minimalist art and fashion devotee.
Professor Vazquez’s office
Professor Vazquez wears a lot of muted tones. “It’s just easy,” he says. “I don’t have to think about it.” His wardrobe is a blend of practicality and understated style. “I live in a kind of gray to black space for a decent amount of my clothing,” he adds. Over time, he’s settled into a minimalist uniform: neutral colors paired with reliable footwear like Blundstones and Red Wings. “They’ve held up,” he says. “My dad always had Red Wings in the garage.”
Fashion has cycled over time. “I’ve been seeing a lot of Red Wings around these days......A lot of the way kids dress now feels very similar to how people dressed in high school for me—baggy pants, that more ‘Ravery’ look, Chloe Sevigny, etcetera.” In high school, Vazquez wore band tees from Pavement and Sonic Youth, along with the iconic striped Hang Ten shirts which he “wore to shreds.” With his undergrad years spent down south, his go-to was flip-flops, shorts, and t-shirts. “Used clothes in Florida were great, given the age of the general population,” he explains. During graduate school in the Bay Area, he gravitated toward jeans and t-shirts, often choosing shoes with suede toes, like Onitsuka Tigers or Sambas, because of their durability.
While Vazquez has eased into his more minimal niche, art-related bootlegs from Boot Boys Biz and artist collaborations from Supreme—featuring names like Christopher Wool and Mike Kelley—have piqued his interest over the years. “But you can only have so many,” he says. “Nowadays, I’d rather get my kid a nicer bike.”
When Vazquez first started teaching, he felt pressure to dress more formally. “I was 29 and looked younger than I do now,” he says. “It felt important to differentiate myself from the student body.” At first, that meant blazers and, occasionally, a tie. But over time, he realized he didn’t need to follow that template. “I wasn’t comfortable, and no one really cared.”
For Vazquez, style is about finding what works for you. “Someone I once knew told me that everybody has a superhero outfit. You’ve got to figure out what yours is, and once you do, stick with it, because that's where you're comfortable.” For him, that means a consistent rotation of black jeans, sweaters, and durable shoes, a minimalist theme that still manages to express his essence.
Last but never least is Professor Carolyn Finney—vibrant, grounded, yet always in motion.
“Clothing for me is a form of creative expression—and I’ve always loved it,” she said. “I feel like a painter who likes having all the colored pencils.” Her pieces come from everywhere: pop-up markets in Morocco, consignment shops in Santa Fe, small designers in Tokyo and London. “I always do damage in Santa Fe,” she laughed. One favorite, Funky Faja from Marrakesh, reworks old suit jackets with hand-painted flourishes. “I love finding up-and-coming artists—people doing their thing.”
She gravitates toward clothing with presence and purpose—Issey Miyake’s samurai-style pants made from recycled PET bottles, Marine Serre’s experimental silhouettes, Rundholz’s layered forms. “I love Rick Owens. I watched a pair of pants for eight months until they went on sale,” she said. Yohji Yamamoto, too: “I love his philosophy about originality and uniqueness. Just feeling like you’re not asking anybody for permission.” For Finney, design is art. “I like to know the designer’s philosophy—does it resonate with me?”
Style, for her, is intuitive. “I don’t wake up thinking I want people to see what I’m wearing. I just love the discovery.” She still remembers the pieces she fell in love with in college in the late 70s—zoot-suit trousers, drop-crotch pants, oversized tweed coats. “It was never about the money,” she said. “You’d go to the Salvation Army with $10 and come out with a few great pieces. It was about how you put it together.”
Once, in New Orleans, she bought a handmade ring from an artist named Dr. Foots. “It was my birthday. At the time, it felt expensive—$300—but I loved it.” He gave her a silver bead for her hair that she’s never taken off. Later, she found out he made jewelry for Erykah Badu. “If I have a chance to meet the person who made something, that’s what gives it juice for me.”
She told me about the time she wore a nondescript Rick Owens jacket during a conservation event in Seattle, then walked into a casual Mexican restaurant. Out of the blue, a teenage boy in line tapped her shoulder and asked, “Is that Rick Owens?” “His parents were laughing,” she said. “And I thought, I’m never making assumptions again. I felt seen. And it gave me such joy.”
Finney’s superhero outfit? “Something that moves. Platform shoes—I always wanted to be taller. Maybe an oversized linen jacket. Something that feels like: I’ve got this.”
In revisiting my first encounter with a professor—tweed and tortoiseshell—I came to see his style as more than an assured affirmation of knowledge. It was a quiet declaration of self. And though his garb was a tad cliché, there was something mythic about a person who could clothe themselves in distinct certainty—especially to a student like me, in the throes of identity construction, slowly learning both the immense gravity and futility of visual character.
Each of these three professors offers distinct approaches to navigating style. Yet they share a defining trait: a quiet self-assurance that their style is theirs, shaped by experience, honed over time. It’s something entirely of their own making.
That kind of authenticity doesn’t arrive all at once. It unfolds through experimenting with fashion, opening yourself to others, engaging with art, and simply moving through the world. It’s a process of trying things on—literally and figuratively—until something clicks. Eventually, you will recognize what fits not just your body, but the deeper part of your identity that longs to be reflected in the world.
Polaroids by Willa Sullivan. Digital photos by Jude Kuykendall.