Amid the collared shirts and cardigans, certain teachers catch the attention of many through their unique clothes and hairstyles, redefining the idea of “business casual.”

Jenna Ray

English teacher Jenna Ray’s style prioritizes practicality while incorporating touches of excitement through her hair color and humorous T-shirts.

Dyeing hair has been a part of Ray’s life for many years.

Said Ray, “I had spent most of my college years dyeing my hair fun colors, but since I was doing it all by myself, I ended up overbleaching and damaging my hair enough that I ended up shaving my head when I was 21.”

During the start of her teaching career, Ray was often mistaken for a student, which led her to opt for more formal clothing and return to her natural hair color.

Said Ray, “I let it grow back in my natural brown with the hope that it would be easier to land a job out of college if I looked more ‘professional.’”

Additionally, as a young teacher, she had to work through challenges of distinguishing herself from her students.

“I have always had a bit of a baby face — it’s the dimples! So when I started teaching in my 20s I would frequently be mistaken for a student,” Ray said. “To combat this, I tried to dress more formally — I would wear slacks, blouses and ballet flats.”

Over time, she felt that she matured not only as a person but also in her career, which further boosted her confidence in her style.

“Now that I’m in my 15th year as a teacher and a mom of two kiddos, I not only look distinctly older than the teens I’m working with, but I’m also well established as a staff member that I feel confident wearing the clothes I’m actually comfortable in,” Ray said.

While her style evolved, her hair remained natural throughout her career as a teacher. In 2016, a fundraiser organized by the Associated Student Body allowed teachers to provide different incentives in order to raise money for different charity organizations.

Said Ray, “I saw this as the perfect opportunity to dye my hair again while also supporting some great charities.”

The incentive that reinspired her to color her hair led to a decision to maintain it. Starting the school year with pink, her hair colors move around a color wheel, transitioning from red to purple, and now blue.

“I continue to dye my hair simply because it’s fun and I like it, which honestly I think are the only reasons you need to do anything related to your personal style,” Ray said. “I’ve still got some blue dye left, but by the end of the year I should be starting to go more teal or green.”

Teresa Filice

English teacher Teresa Filice enjoys styling herself and thinking of new outfit combinations with her collection of thrifted sweaters and shoes.

Said Filice, “I love pulling looks together, thinking about how different colors, textures and patterns might work together, and feeling good in what I wear to teach each day!”

Filice’s love for styling new outfits extends to her daily life in the classroom, with various students acknowledging her vintage style. While many teachers prefer buying from retail stores, she enjoys browsing secondhand stores, finding nostalgia through clothing items from years ago.

Said Filice, “I like finding thrifted or vintage pieces that connect to something from my younger years, or come from a part of the country I like to visit.”

Throughout her time at Cupertino, Filice has consistently incorporated her thrifted clothing into her outfits, even contributing to a sustainable lifestyle.

“The biggest style evolution I’ve had since I started teaching here in 2008 is including way more vintage or thrifted pieces in my wardrobe,” Filice said. “It’s good for our planet and it’s really fun to hunt and find cool pieces!”

Her view on fashion emphasizes expression and highlights her love for experimentation, as she tries out combinations that may seem “wrong” and finds delight in each outfit.

Jeremiah Rebustes

Jeremiah Rebustes, a math teacher, draws inspiration from a multitude of aesthetics, frequently updating his wardrobe to express his current mood.

“You can tell a lot about a person just based on their fashion sense,” Rebustes said. “I like showing my personality and my interests through fashion, whether that be through the clothing I wear or the accessories that go along with it.”

He frequently includes graphic T-shirts in his wardrobe, which allow him to showcase his interests to others and serve as a unique conversation starter.

Said Rebustes, “I think my students know that I am a big fan of anime just from the shirts I wear.”

At the start of his career, he felt no pressure to change his style. As Rebustes grew older, his preferences changed and his style slowly favored more comfortable clothing.

Said Rebustes, “I already had a good sense of what I liked and what I felt confident in, so I didn’t feel the need to change much.”

Rebustes frequently adapts his style to certain occasions, adding small bits of flair in each outfit to further express himself.

“Outside of work is where I really let my personality shine through my outfits. […] If it had to be somewhere formal, of course I would be wearing something appropriate. […] I’d say just something sleek and put together with simple jewelry and a nice pair of shoes to go along with it,” Rebustes said. “But if it was just a night out, I do tend to be more expressive with the clothes I wear and maybe even do my makeup a bit.”

Ultimately, it is his love for self-expression that carries over to his daily outfits, whether it be in school or a special occasion.

Said Rebustes, “I just want to feel confident, comfortable, and [be] the best version of myself.”

Stella Demetriou

Math teacher Stella Demetriou favors a more contemporary style while also prioritizing pieces that are easy to move in — perfect for a busy school day.

Demetriou especially prioritizes professionalism and practicality for long days in the classroom. Her outfits may also include trending clothing items that she adapts to her own personal look, if she finds them suitable for herself.

“In the last few years, I’ve definitely incorporated some of the trends like wide-leg pants and blazers into my wardrobe,” Demetriou said. “[…] Wide-leg pants are easy to move around in during the day, and blazers are a simple way to make an outfit look a bit more polished without feeling too formal.”

Over the course of her career, Demetriou’s style shifted towards more comfortable items including shoes and other clothing.

“In my early teaching days, you’d often see me in higher heels, but these days I’m much more likely to reach for flats or sneakers,” Demetriou said. “I do try to stay current with denim trends, but I also have high-quality pieces from my first years of teaching that have stood the test of time and are still in my regular rotation.”

In addition to her practical style, Demetriou occasionally changes her hairstyle as a way of switching up her look.

“Most of the time I wear my curly hair down, but in the warmer months especially I tend to put it up more often. I’ll do ponytails, half-up styles or my go-to bun when my hair is long enough to pull it all back,” Demetriou said.

Her enthusiasm for adding new clothing to her wardrobe further adds to the enjoyment of crafting new outfits together through color and other elements.

“To me, fashion is a source of joy,” Demetriou said. “I love the process of mixing and matching different clothes and accessories. I’m a big fan of layering and finding fun ways to incorporate pops of color into my outfits.”

Carley Stavis

Art teacher Carley Stavis finds herself gravitating towards patterned and colorful clothing. She also owns a large collection of rings and hats. Like many teachers, Stavis mixes and matches different outfit combinations depending on her mood, favoring a more “maximalist” style.

“Honestly, the through-line in my style over the years has been less about a specific aesthetic and more about whatever energy I’m going for or wanting to try to cultivate that day,” Stavis said. “Some days that’s a crazy statement coat and a mixed-up stack of fun jewelry.”

Stavis also prioritizes sustainability above all. She finds that nowadays, it is much easier to consume secondhand items and avoid the fast fashion industry. She sources her clothes from reputable companies with higher-quality materials.

“I’m also just obsessed with the backstory of things in general […] I love objects that have already lived a life and enjoy the thrill of the hunt as a shopper,” Stavis said. “Knowing where something came from, who made it, how it got to me — all of that adds something I feel like I can actually tangibly sense in my body and soul when I wear it.”

At the start of her career, Stavis felt that expressing herself as a younger teacher in front of students was difficult due to the small age difference and she struggled with finding her own style.

“It’s also honestly a little challenging as a young teacher to figure out your true style in a role where you’re standing in front of very opinion-prone teenagers all the time who will light you up with commentary, who are also walking trend-displays themselves in a lot of ways,” Stavis said. “So differentiating yourself with how you are dressed can feel important as you’re getting started.”

As an art teacher who works with paint and other supplies, Stavis found it would be more practical to fill her closet with items that could protect her clothing.

Said Stavis, “I went on Etsy to track down an inexpensive vintage French chore coat to keep in the classroom so I could throw it on for our super messy class days.”

15 years into her teaching career, Stavis’s fashion has transformed through her growing confidence, opting for more comfortable pieces of clothing compared to when she first started.

Said Stavis, “I think when you’re newer somewhere and you’re a very young professional who doesn’t have much work experience yet, you’re a little more careful about how you show up and often end up imitating the style of the professionals you think you’re supposed to look like at work rather than just leaning into your own more authentic likes or dislikes.”

Stavis now enjoys looking back at the different style eras and exploring the shifts she had in her outfits across the years, and she eagerly awaits what the future has in store.

“I genuinely look forward to seeing how my style interests or patterns will keep morphing as I go through future chapters of life,” Stavis said. “I aspire to be an old retired lady one day who wears crazy stuff just to go walk around the block or get groceries.”