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Back to school fashion that’s not for the kids

Back to school fashion

Remember how fun it was to go back to school shopping in the fall? Growing up in Toronto, in September summer was giving way to fall; the leaves were changing, there was a new chill in the air, and going back to school meant a fresh new wardrobe to start off the school year right.

I recently dug up some back to school photos, and found myself pining for a time when life was simpler, my hair was straight (?!) and in desperate need of product, and I wore many a pair of penny loafers and high-top Reeboks. Since so many of the 70s and 80s looks I used to sport in grade school are back in fashion, I thought it would be fun walk down memory lane and put together my own 2017 back to school capsule wardrobe (with a bit of a modern twist). I’d wear any of these items today— even without the braces, frizzy hair and blown-out bangs.


They used to be tomboy cool and utilitarian, but in skinnier styles and cooler denims they’re a contemporary go-to.

Back to school fashion: Overalls

Skinny Overalls in Cedarburg Wash by Madewell. Shop here.

Back to school fashion

Quincey Denim Overalls by Free People. Shop here.


You know I’m loving my argyle sweater in this picture day photo. I used to wear argyle a lot, and I still love it— it’s classic, and it feels a bit “east coast prep school” to me— a bit irreverent in Los Angeles.

back to school fashion: argyle sweaterStella Mccartney Oversize cardigan. Shop here.

back to school fashion: argyle sweater

Equipment Rei Crewneck Argyle Sweater. Shop here.

Polo Shirts

When I think of polo shirts, I think of preppy 80s movie villains like James Spader. But that didn’t stop me from rocking a polo then… and now. I swear they make you look better-educated than you already are. (Obsessed with Kule, BTW).

Back to school fashion: Polo Shirt

The Piper by Kule. Shop here.

Alexa Chung Knit Polo. Shop here.


My Sony Walkman Sport was a permanent fixture on me through junior high and high school (it looked just like Julia’s below), and we’ve come a long way from having to carry around those ghastly bricks of plastic to listen to our favorite music. What was once revolutionary is now quaint and nostalgic— I’m happy we’ve evolved to fit-in-your-pocket MP3 players. And if you thought Apple had the market cornered on them, think again— Sony has some beautiful options.

back to school fashion: Walkman

Sony Walkman MP3 Player. Shop here.

iPod Touch by Apple. Shop here. 

Denim Dress

Oh, don’t you always look smart in a denim dress? (Book smart and fashion smart, that is). Add a crisp shirt underneath or a plain white tee, and you’re dressed for success. If the dress thing isn’t your thing, pair a jean skirt like the one below with a turtleneck and you’re ready for picture day. (The skirt below is like everything AYR does— fab.)

Back to school fashion: Denim Dress

The Sydney Dress by AG Jeans. Shop here.

The Smokeshow Skirt by AYR. Shop here.

Socks with Loafers

Though I feel this trend might be the riskiest of the bunch to pull off in 2017, I’m seeing so much of it that I’m starting to feel a bit more confident. If you can brave the initial Michael Jackson Thriller-ness of it, you’ll be happy to have cushion instead of blisters when sporting your old penny loafers. Take it up a notch with this season’s trendy sheer or fishnet socks if you dare.

Back to school fashion: Loafers with Socks

The Elinor Loafer in Dark Chestnut by Madewell. Shop here. 

The SARTO Jolette Penny Loafter at Nordstrom. Shop here.

Bryant Heather Ankle sock by Free People. Shop here.

Ankle Stripe Socks by Shop here.

Track Pants

Ready for gym class, and waaaay more fashionable than my track pants of days gone by. Perfect for the athleisure moment we’re having— you won’t want to change when you get home from school, because you’ll already be so comfy.

Back to school tsashion: Track pansMid-Rise Osaka Track Pants by Adidas. Shop here.

05Color Block Track Pants by Tory Burch Sport. Shop here.

High tops

Lived in them then, live in them now. I started wearing high top sneakers in high school, and they haven’t left my wardrobe since. I wish I still had my neon orange high-top Reeboks with the velcro straps… they really turned heads.

back to school fashion: High Tops

Chuck Taylor High Tops in White by Converse. Shop here. 

Vintage Sk-8 High Tops by Vans. Shop here. 

What’s your favorite back to school look? Even if you’re just heading to the office… let me know in the comments. 

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