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The Back to School Roundup, in Downtown Oakville.

The race to gather all those back-to-school supplies has begun. Fear not, parents, Downtown Oakville has plenty of choices to get your kids ready for their first day back.


While shopping this year, keep in mind that some learning might be at home. Sweats are a must, and it's also an excuse to hit up Roots. This iconic Canadian brand has a great selection of loungewear for everyone in the family, from parents and little kids to teens and everyone in between.

Core One - Apple Specialist Store

Core One is your go-to shop for new backpacks and all your electronic needs. An official Apple supplier, they have all the latest gear and gadgets from MacBooks to Herschel Backpacks. Worried about them losing their gear? We recommend checking out the Apple Air Tag, slip one in their school bag, and just like that, they're on your radar in the Find My app.

The Running Room

As their feet grow fast so you'll no doubt need to invest in a new pair of school shoes. Running Room focuses beyond just style; their gear is made to promote and sustain a daily active living. Whether they choose a new pair of Nikes or Asics, they'll look good and feel good, and you can feel good about that.

COBS Bread

It's that time of year when lunches need to be made 5 days a week. Never fear, COBS Bread to the rescue. COBS serves up daily baked loaves of bread and snacks to help parents pack the healthiest lunchbox possible and make that late-night lunch prep a cinch.

Write Impressions

You can't go back without a cool selection or original writing tools and supplies. Write Impressions offers a selection of stationary essentials, ranging from notebooks to writing tools and unexpected finds.

Must Boutique

Fashion is thriving in Downtown Oakville with big brands like Anthropologie and Lululemon, alongside exclusive boutiques. With so many options, don't forget to pamper yourself with some retail therapy and check off your back-to-school shopping list in style. We recommend Must Boutique for one-of-a-kind pieces, all designed in Italy.

The big back-to-school trends for 2021 take us right back to being a student in the '90s. We're talking everything from high-waisted mom jeans to bodysuits and sweater vests. Even if your teenager has to wear a uniform to school, you'll still need to outfit those teenage girls on the weekends. Enter Mendocino, a leading boutique for cutting-edge global fashion and the most-wanted brands.

HB Face

To teach your teen or tween about makeup application – head to the experts at HB Face for all your cosmetic supplies. Getting a new set of makeup brushes can feel like getting a new outfit, stationery, or art supplies. Introducing the HB Brush kit. This kit of 5 brushes is curated to include all the essentials to create a complete makeup look. As an added peace of mind, the HBFace line is distributed in Canada and 100% cruelty-free.


Jacardi's Preppy-Chic collection just hit the shelves and features a new school wardrobe filled with creative and colorful energy for the littles on the list. This collection of back-to-school outfits and uniforms are preppy, sporty, and chic, with a hint of French style.

Don't forget the shoes. Patent leather, with delicate finishing details, velcro fasteners, t-strap, or laces, the new fall shoe collection will guarantee style and comfort all day long.

And there you have it, a sample of just some of the back-to-school school finds waiting to be wrangled in #DTOakville.

Back to School Giveaway

Don't miss your chance to win a $500 Back to School Prize Pack. Simply sign-up for your chance to win.

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