The exhilarating return to the classroom is upon us, which means it’s back-to-school shopping season — and not just for grade schoolers. Whether you’re a teacher, student, aide, teaching assistant or volunteer, the start of the school year marks an opportunity to reset your style.
It’s a time when to have fun and play with the season’s trends (have you thought about?) or double down on the pieces you love by styling them in a new way. Ahead of the new school year, we asked six cool Canadians to share their back-to-school style strategy. Their number 1 lesson? Have fun.
Kate Bauer
Photo: Kate Bauer
“I think about clothing almost as much as I think about Canadian history,” said PhD student Kate Bauer.“I have always resisted the idea that academics have to dress a certain way. So even though I do follow some conventions, I’m always willing to bring a sense of playfulness to my professional outfits.”
What are your back-to-school wardrobe priorities?
“I teach one day a week on campus, and the rest of the time I am working on the final draft of my PhD thesis. I’m not the type to even if I’m just working from my desk at home, so I plan outfits that prioritize ease without sacrificing style: patterned maxi dresses, wide-leg trousers with an adjustable waist, high quality knits, comfortable but bold shoes.
I do a lot of hunting on Poshmark for natural fibres like cotton, wool, and linen, and I also like to prioritize Canadian boutiques and brands like and if I’m buying something new. If I need to shop from a fast-fashion retailer for something I absolutely cannot find elsewhere (like for under dresses and skirts), I do so mindfully and with a very clear list in mind — no browsing!”
What are your go-to brands and stores?
“I always do a back-to-school thrift trip. I love hunting through the racks at Value Village (the amazing oversized shirt I’m wearing in my photo was one of my best thrift finds ever). I also love checking out all three locations in ɫɫ. I cannot live without my from Veri because they’re bold, comfortable, polished, and ethically made. A black leather backpack is at the top of my wish list. I’m usually a tote gal, but I am planning to commute by bike a few days a week and I need a more secure bag. I’ve been eyeing some cool ones from small businesses on Etsy. I also always love getting a few new pairs of glasses — fresh frames can change an entire outfit. I’ve had the Kits saved for a while!”
Zahra Hassan
Photo: Zahra Hassan
Grade 6 and 7 teacher is still deciding what to wear for the first day of school, but it’ll likely be an all-black ‘fit with gold accessories. “It’s a look that feels both professional and stylish, and it helps me step into the new school year feeling empowered and ready,” she said.
How do you approach back-to-school shopping?
“As a teacher, I’m not just shopping for myself, but also thinking about my classroom and the little touches that will make it feel welcoming. Whether it’s finding the perfect planner, adding cosy decor to my desk or picking up pieces for my teacher wardrobe, it’s a time that makes me feel both prepared and inspired for the year ahead.
It’s also an icebreaker when students are meeting me for the first time. My outfits often spark curiosity or compliments, and it becomes an easy way for them to connect with me. ”
What do you prioritize in your back-to-school wardrobe?
“ I like to mix timeless basics with a few statement pieces to keep things fun, like or . I also make sure to include items that transition well from the classroom to after-school activities or coaching.
Sustainability is a big priority. Thrifting often inspires more creativity in how I put outfits together, since I’m working with one-of-a-kind finds rather than buying straight off the rack.
This year, I’m hunting for a few key statement pieces. These include the perfect oversized blazer — something structured but roomy, to mix that sharp tailoring with streetwear ease. those roomy, relaxed-fit jeans that give me that throwback ’90s and early 2000s street style. They’re comfortable, versatile, and pair perfectly with chunky sneakers or boots.”
Erin Weinberg
Photo: Erin Weinberg
For University of Manitoba English professor Erin Weinberg, back-to-school shopping can be a tough sell. “Trying on autumnal clothes in the August heat is a sweaty, uncomfortable affair!”On her first day, she’ll likely be wearing a dress. “I’ve been burned before, sweating through my cutest autumnal sweaters and giant leather clogs.”
She has a somewhat unconventional favourite shopping spot: “My go-to stores are garden centres. You’d be shocked at how many of them have little boutiques that cater to bodies of middle-aged women over size 10! This is where you find ponchos, scarves and cute sweaters: ideal academic looks.”
What role does fashion play in your work life?
“Now that I have my dream job, my work outfits have changed a lot. For one, they’re much more casual. They usually include some sort of literary merch, like a , or my brand-new Agatha Christie scarf (a gift from my partner in anticipation of my upcoming Christie’s Novels and Adaptation course!). I also have a lot more academic freedom; this means I can take sartorial risks, like wearing a keffiyeh to support my Palestinian students and colleagues, or wearing union merch when my faculty union is bargaining towards a new collective agreement.”
What’s involved in planning your back-to-school wardrobe this year?
“I want the clothes to fit me in this moment. There’s no point in buying new or relying on old clothes that I hope will fit at some point. They also have to be easy to wash and not easy to wrinkle. I don’t have time for dry-cleaning or ironing; I sometimes even begrudge air-drying! I totally respect those who take more time and energy to dress, but I don’t have it in me when I’m keeping track of what I’m teaching today, Friday, next week, and next month.
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Sandeep Gill
Photo: Sandeep Gill
“Ever since I was a little girl, back to school shopping was everything,” said Brampton, On-based elementary school teacher and . “What am I gonna wear on the first day? What are the new items I need to add to my closet? How do I want to show up?” Decades later, that mentality remains — with a twist. “[Fashion] is how the students get to know me. It’s how I identify and represent myself to them; so when they walk into the classroom they have an idea of who they’re going to be dealing with.”
What are you looking to add to your closet this season?
“I was just in Rome and I picked up a bunch ofvintage piecesthat I’m so excited to wear.
I’ve been eyeing Japanese-style sneakers like the ones from. They have such a great colour range; you can buy bright yellow or leopard print.
I recently wore a belt over a sari and that got me thinking [that] I can incorporate belts in unique ways in the classroom as well.”
What are your tips for back-to-school shoppers?
“Back-to-school doesn’t have to mean brand new head to toe. I’d say to remind yourself of the pieces you already have, grab some vintage pieces that excite you and then replenish some ride-or-die pieces (I get my basics from Uniqlo!) so that you have a fresh piece to style for the new school year.
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Eternity Martis
Photo: Eternity Martis
Author and journalism professor at ɫɫ Metropolitan Universitystarts shopping for back-to-school as soon as August arrives. “It always feels like a new beginning,” Martis said.“I’m standing in front of very fashion-forward students, and I think that what you wear as a professor, especially a young woman of colour, can really dictate your own confidence but also how students view and engage with you.
What’s your biggest consideration when shopping for back to school?
“I don’t want to feel uncomfortable when I’m teaching. I’m definitely not a fan of business casual — I feel restricted. So I aim for elevated casual: dresses, linen pants, denim (jackets, dresses, tops — not jeans!), leather pants (straight-leg or joggers) and oversized shirts.
I’m a huge sucker for matching sets . I’m still looking for the perfect dark blue denim top and jean set. I’m usually not a fan of dark denim, but together it just looks so classy and polished. I also want a pair ofthough I’ve heard the break-in period is painful.
I’ll be wearing my satin midi skirts from H & M and Marshalls too. I’m going to be brave and try pairing them with basic T-shirts, chunky knit sweaters, silk tops and combat boots.”
What’s your first-day outfit?
“I’m wearing a denim dress from the Gap, carrying my and Toms black platform sandals. This outfit feels approachable, smart and youthful. ”
Gladys Palacios
Photo: Gladys Palacios
For early childhood educator Gladys Palacios, . “I need to be able to move freely throughout the day, whether I’m sitting on the floor with my students, doing activities or moving around the classroom.” She looks for clothes with a little something special, whether it’s the stitching, a unique cut, or an unexpected design element. “Dressing well boosts my confidence and genuinely makes me happy,” Palacios said.
What are you shopping for this back-to-school season?
“
I’m looking for a few key pieces to refresh my fall wardrobe starting with rich-coloured long-sleeve tops and some big, cosy sweaters. Even when I’m wearing darker tones, I always add a pop of colour because it lifts my mood. And once I get to the classroom, I always change into my casual or Keds. They’re comfy, supportive, and perfect for keeping up with a room full of kindergartners!”
What are your go-to brands for school outfits?
“Simons, Zara, Mango, American Eagle, Winners, and Old Navy all hit my price point, and I always manage to find something great no matter what I’m looking for. And the from Old Navy are everything. I own them in all the fall and winter colours — they’re comfy, stylish and perfect for work.
The first day is always a big one, especially for our littlest learners who are stepping into a school setting for the very first time. I’ll be wearing my favourite pair of American Eagle jeans and a playful top I found at Winners (both pictured); it’s fun and airy, perfect for the first day of school!”
These interviews have been edited and condensed for clarity.
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