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We thoroughly research all the products we feature, and we honestly think they’re great. But just so you know, things you buy from links on this page may earn us a commission. All prices were accurate at publish time.

It’s almost time for kids to head back to school, which makes this the best and worst time of year for parents. Best? No longer having to hear your kids proclaim, “I’m bored!” every five minutes. Worst? Back to school shopping—specifically, trying to strike the balance between buying quality (and dare we say, cute?) products and not spending so much that you can’t afford to get your kid braces this year. Back to school shopping can be stressful for parents and students alike. But it doesn’t have to be.

We’ve compiled a list of quality “then” and “now” back to school essentials that will work for your kid, whether they want a classic, retro-inspired option that we all know and remember, or the updated version. Reading and writing may not have changed since you were in school, but backpacks have gotten much, much more high tech.

CALCULATORS VS. TABLETS

Amazon

Checking your math homework previously meant using a standard desk calculator. You can still get one of those, or you can use a handy dandy new tablet. With an Amazon Fire tablet, there is still a calculator. Plus, the entire Internet. All of it. All the internet.

Casio Colourful Calculator, $28 at Amazon; Amazon Fire 7” Tablet, $70 at Amazon

HIGHLIGHTER VS. ERASABLE HIGHLIGHTER

Amazon

Highlighting your notes has been a great study aid for years, but it did make it more difficult to sell used textbooks. Now there are erasable highlighters. So simple, yet so brilliant.

BIC Brite Liner Grip Highlighter, $4 at Amazon; Crayola Take Note Erasable Highlighters, $10 at Amazon

LUNCH PAIL VS. LUNCH BAG

Amazon, Staples

 

Give your kids the ultimate throwback with a retro lunch tin or bring things into 2019 with a jersey-style lunch bag that shows off their favourite soccer team.

Dr. Seuss Tin Tote, $22 at Amazon; Manchester City Lunch Bag, $34 at Staples

BACKPACK VS. CHARGER BACKPACK

Amazon

Holding books, gym shorts and a sandwich used to be enough to make a backpack useful, but now that built-in chargers are a thing, the school satchel must also charge iPhones, laptops and tablets. And look cool. That part hasn’t changed.

JanSport Super Break Backpack, from $27 at Amazon;  ECEEN 7 Watts Solar Backpack, $120 at Amazon

VINTAGE STYLE TYPEWRITER VS. VOICE CONTROL PRINTER

 

Amazon, Epson

If you’ve got yourself an angsty teen on hand, who fancies themselves the next J.D. Salinger, they might feel more “authentic” writing the next Great Canadian Novel on a vintage-style typewriter. For the kid with a lot to print, this Epson ET-3710 will certainly do the job because these supersized ink tanks come with TWO YEARS of ink. That’s a whole lot of essays. Plus, voice activated printing is straight from the future.

Amazon Classic Manual Typewriter, $165 at Amazon; Epson EcoTank ET-3710 Wireless Color All-in-One Cartridge-Free Supertank Printer, $480 at Amazon

PENCIL CASE VS. CHIC CASE

Indigo

Store your school supplies in a retro case or go for a more mature look with a wide selection of pencil cases that can double as your first mini-makeup bag. Those Lipsmackers don’t hold themselves.

Yoobi Binder Zip Case, $10 at Indigo; Large  Pencil Pouch City Vibes, $18 at Indigo

 

GLASS BOTTLE VS. SELF-CLEANING BOTTLE

Indigo, LARQ

Bring a 1950s feel to your lunch box with a bottle inspired by the home milk deliveries of past generations, or spring into the future with a self-cleaning water bottle form Larq.

Juice Bottle, $8 at Indigo; Larq Self-Cleaning Water Bottle, $94 at Indigo

 

THERMOS VS. BENTO

The Bay, Amazon

Keep your food and beverages warm with a classic style thermos or update your lunch game with a Lidahaotin bento-style insulated thermos, which can store hot or cold items with a stainless-steel divider between the different food items.

HBC x Thermos Briefcase Bottle, $45 at The Bay; Lidahaotin Insulated Thermos, $19 at Amazon

REUSABLE PAPER VS. RESUABLE LUNCH BAGS

Okay, so this reusable brown paper bag is a step up from the brown paper bags of childhood lunch’s past. We also love the move away from disposable plastic bags and towards snack bags that can be frozen, microwaved or even boiled. Unfortunately, we still can’t guarantee that your kids will remember to rinse out their lunch containers.

Reusable Snack Bag, $12 from Amazon; Stasher Reusable Bag, $12 from Indigo

RECORD PLAYER VS. ECHO DOT

Indigo, Amazon

When kids get home from school and feel like dancing away the rest of the day, they can either use the Fisher Price record player for a fun and classic playlist, or play music, hear stories, and even call mom or dad with the Amazon Echo Dot. The one built for kids is unfortunately still unavailable in Canada, but add some parental controls to the Echo Dot and you’re golden.

Fisher-Price Classic Music Box, $40 at Indigo; Amazon Echo Dot  $35 at Amazon

CLASSIC WATCH VS. SMART WATCH

The Bay, Amazon

If your little one learned to tell time during summer break, they may want to go back to school with a new watch. Send them with a traditional analog or upgrade to a fun smart watch that helps kids learn how to tell time and lets them take video selfies, naturally.

Timex Youth Analog Watch, $40 at The Bay; Vtech Smart Watch For Kids, $70 at Amazon