7 Extra-Cute S.F. Teachers Share Their Back-To-School Style

Now that the second week of September is behind us, it means school is officially back in session. And while some of you class-bound folks might be lamenting the return of dress codes and homework, others are embracing the opportunity to go full-force with fall’s hottest trends. And what better way to celebrate back-to-school, extra-cool fashion than tapping seven mega-cute teachers around town, and having them show off their front-of-class garb, along with tips on how to skirt the line between fun and conservative dressing? Not to mention their inspiring and colorful ruminations on the joys of teaching—and learning! Check them out after the jump, and get inspired to put on your extra-chic thinking caps, stat.
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Erica Edwards
School: Martin Luther King Academy Head Start in Marin City
Subject: Preschool
What's your go-to teaching outfit? "A pair of jeans, a comfy T-shirt, a cozy sweater, funky earrings or a headband, and my trusty blue Converse high tops. Plus, a change of clothes in the trunk of my car in case of finger-painting emergencies!"
How do you balance dressing as fashion-forward and school-appropriate? "I add personality to my outfits with accessories and I try to adapt my fashion to the lessons that my students are learning. Whenever we learn about a new color, I usually incorporate that color into my outfit. And I'm starting to collect themed earrings of every kind—food, animals, etc.—to build student vocabulary and to strike up conversation with them on the playground."
What dress-code rule is hardest not to break? "It can be really hard not wearing my favorite dresses and outfits to school. Sometimes, on beautiful days, I want to wear sundresses or a pretty blouse, but I have to be realistic. Paint and Play-Doh will cover my clothes by the end of the day, so I save my favorite clothes for the weekend."

Photo: Michelle Drewes
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Where do you go back-to-school shopping? "I am definitely a teacher on a budget, and love to find awesome items at second-hand stores—it's always an adventure."
How do you transition from school clothes to after-work event clothes? "Step one: Shower to wash off the germs. Step two: Raid my closet and find an outfit that would be the opposite of what I would wear at school, like a blouse, skirt, boots, and long earrings. If I don't have time to change, I'll add a scarf, change my hairstyle, and swap my Converse for flats or boots."
What's the best part about being a teacher? "The hugs. And graduation! It is the best feeling in the world when I see my students standing in front of their parents, smiling, proud of all they've accomplished, and ready for the next step of their educational journey."

Erica's dress by Lipsy, available at Bloomingdales, 845 Market Street (between 4th and 5th streets); 415-856-5300. Cardigan, bag, and shoes her own.

Photo: Michelle Drewes
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Valerie Caveney
School: Menlo-Atherton High School
Grades: 9th and 12th Grade
What's your go-to teaching outfit? "I'm from the East Coast, so I dress like a ninja quite often. On a sleepy Monday, I'm in a black pencil skirt with a black Vince turtleneck, a chunky necklace, and Delman flats. I tell the kids I'm mourning the weekend."
How do you balance dressing as fashion-forward and school-appropriate? "Throw a blazer over it or a cami under it. Accessories are easy, too. My little sister has a jewelry line called Kula Kai, so she gives me those final touches."

Photo: Michelle Drewes
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What dress-code rule is hardest not to break? "Honestly, I think my personal dress code is stricter than most—to the point where I change the station if Katy Perry's 'Teenage Dream' comes on. Seriously, so gross."
Where do you go back-to-school shopping? "My other sister has a boutique in Charlotte called The Pink Hanger that I like to raid, but in S.F., I always find something at Jeremy's or Nordstrom Rack."

Photo: Michelle Drewes
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How do you transition from school clothes to after-work event clothes? "Just remove the blazer, apply Chanel Mademoiselle to pulse points, and step into some higher heels."
What's the best part about being a teacher? "The stories. You can't make this stuff up."

Valerie's Aqua Fitted Girlfriend Blazer, $88, and Theory tank available at available at Bloomingdales, 845 Market Street (between 4th and 5th streets); 415-856-5300. LF jeans, Kelsi Dagger shoes, Hype bag, and Kula Kai earrings her own.

Photo: Michelle Drewes
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Ashley Scatena
School: Tam Valley Elementary School Subject: Kindergarten
What's your go-to teaching outfit? "Skinny jeans, a tank, a long sweater, and boots."
How do you balance dressing as fashion-forward and school-appropriate? "You can find cute clothes that are comfortable, including heels. I think it is so important to dress in your own particular style. Wear clothes that make you feel good."
What dress-code rule is hardest not to break? "I probably break all the rules of teacher dress code!"
Where do you go back-to-school shopping? "I shop in Union Square, at the Chestnut Street boutiques, and online. Shopbop is my favorite for online shopping."
How do you transition from school clothes to after-work event clothes? "Throw on heels and a leather jacket. Take off the shrinky-dink earrings and macaroni necklaces I was given that morning, and throw on real jewelery."
What's the best part about being a teacher? "It is an honor to teach kids how to read and write. I feel so grateful to have a job that I absolutely love!"

Ashley wears her own Theory dress.

Photo: Michelle Drewes
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Sara Caldwell
School: University High School
Subject: 9th and 12th Grade Science
What's your go-to teaching outfit? "J.Crew minnies, a sweater, and flats. Definitely no heels!"
How do you balance dressing as fashion-forward and school-appropriate?
"Layers!"
What dress-code rule is hardest not to break? "We require closed-toed shoes in the lab, and I have to be really careful to not forget! It's not a good example when the teacher has to run back to her car to change!"
Where do you go back-to-school shopping? "Crossroads on Fillmore, Cris, and the new Madewell store."

Photo: Michelle Drewes
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How do you transition from school clothes to after-work event clothes?
"Jewelry! What I wear to work is usually pretty basic, so I keep a pair of statement earrings in my desk in case I go out. This sometimes means I end up at Mezzanine in my Danskos..."
What's the best part about being a teacher? "Every day is different. As a teacher, you can plan, but you never know what your students will need or be thinking on a given day, and I love engaging in the challenging work of growing and becoming learners together. There's always something new!"

All clothes, Sara's own.

Photo: Michelle Drewes
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Bailey Thomson
School: Rocketship Mateo Sheedy Elementary School in San Jose
Subject: 3rd Grade Math
What's your go-to teaching outfit? "An Ann Taylor Loft sleeveless dress and TOMS wedges, plus a cardigan or blazer."
How do you balance dressing as fashion-forward and school-appropriate? "For me, dresses are the name of the game. They are easily layered with sweaters and tights for chilly weather, and they are comfortable for long, long work days. Plus, dresses can easily be casual or more formal based on accessories."
What dress-code rule is hardest not to break? "I'm not allowed to wear open-toed shoes at work, which is a real challenge in the warm San Jose weather."

Photo: Michelle Drewes
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Where do you go back-to-school shopping? "Ann Taylor Loft, Urban Outfitters, and J.Crew."
How do you transition from school clothes to after-work event clothes? "Change flats to heels, freshen my makeup, and add bolder accessories."
What's the best part about being a teacher? "I teach 89 intelligent and thoughtful kiddos who think I look beautiful no matter what I wear! Working with them and serving their families is enough to keep me going."

Bailey wears a Marc by Marc Jacobs Sweater, $198, Equipment Blouse, and Current/Elliott cords, available at Bloomingdales, 845 Market Street (between 4th and 5th streets); 415-856-5300.

Photo: Michelle Drewes
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Laurin Rubin
School: Menlo-Atherton High School
Grades: 9th through 12th Grade
What's your go-to teaching outfit? "My Free People skirt, Rugby sweater, and gold flip-flops."
How do you balance dressing as fashion-forward and school-appropriate? "I try to shop at stores that are stylish, fashionable, and affordable. I want to dress my age, yet keep it professional."

Photo: Michelle Drewes
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What dress-code rule is hardest not to break? "I love Fridays because they tend to be a bit more casual around campus and I can wear my jeans and Vans. Sometimes I wish everyday was a Friday. But who doesn't?"
Where do you go back-to-school shopping? "I will admit that I like to shop the sale rack at some of my favorite shops like Lucky Brand, Free People, J.Crew, Banana Republic, Anthropologie, Nordstrom, and Macy's. And some thrift shops never seem to fail me!"

Photo: Michelle Drewes
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How do you transition from school clothes to after-work event clothes? "Well, I ride my beach cruiser to school nearly every day, so I pack my basket with my going-out clothes and change in the women's restroom after school!"
What's the best part about being a teacher? "I must say the best part of my job is when I see my students succeed in areas they didn't believe they were capable of succeeding in. I love creating opportunities in my classroom for students to set short- and long-term goals, and I am always ecstatic when they achieve them."

All clothes, Laurin's own.

All clothes, Sara's own. Photo: Michelle Drewes
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Stephanie Young
Position: Elementary School Principal What's your go-to teaching outfit? "I aim to wear something practical for working with students and being in the cafeteria, that is also professional and put-together. Usually, this is slacks and a sweater. Dressing in layers for foggy S.F. is key!"
How do you balance dressing as fashion-forward and school-appropriate? "Hopefully, at least one of my pieces has its own little flair. For me, it's often red shoes."
How do you transition from school clothes to after-work event clothes?
"If I am going to an event after work, I will often put a top to change into in my bag."
What's the best part about being a principal? "The best part about being in education is working with students to reach their potential and having fun while doing it."

Stephanie's floral tank by Joie, available at Bloomingdales, 845 Market Street (between 4th and 5th streets); 415-856-5300. Pants her own.

Additional styling by Klassy Goldberg and Jessica Velez.

Photo: Michelle Drewes
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