The cutest ways to bundle up your little ones this fall

Whether you sent your children off to school for the first time (cue the tears as I recently sent my youngest off to nursery), or back for another great year of fun, you probably only shopped for the first day (or week or month) of new clothes for them. We have a feeling that as the temperatures drop you might be finding those sweaters from last year are fitting a little too snugly, so we're rounding up the coolest and coziest key wardrobe pieces to keep your kid looking tops, and toasty, on the playground this fall.

Sweet Sweats

We love the retro nod of these matching sweats from this cool LA brand. Wear together or separately, this look will impress more than just the King's horses and all his merry men!

Humpty Dumpty Fleece Hoodie Ice Blue & Terry Fleece Pant Ice Blue, AKID Brand, $68 each

Wooly Wear

This retro army-inspired wool sweater will work double duty for utility (super cozy for cool temps) and fashion (pair with denim for off-duty mini model vibes).

Finger in the Nose Rudy Buttoned Crew Neck Sweater Slate Blue, Advice from a Caterpillar, $126

Alpaca Amazingness

Straight outta Brooklyn, but made in Peru by a women's collective from the finest alpaca. You won't feel bad sending your wee ones out into the winter wild wearing these!

Oeuf Alpaca Leggings, Advice from a Caterpillar, $100

Refined Ruffles

Pretty but with an edge - pair with biker boots and own that playground!

Dress with Side Ruffles, Zara, $35.90

Cozy Canadiana

This Hopper Hunter flannel charcoal check shirt is just the thing for stylish kin. Gender neutral tones, Canadian-made label with options for father-child twinning. Cue collective "ahhhhhhh".

Hopper Shirt in Charcoal Check, Hopper Hunter, $80

Kozy Kitten

This little head topper is prrrrrrfect for the soon-to-come cool October days.

Oeuf Animal Hat Cat Black, Advice from a Caterpillar, $80

Jazzy Jumpsuit

Who doesn't love a one-piece? This one is simple, stylish & sassy.

Jumpsuit with Buttoned Sleeves, Zara, $45.90

Rain Runners  

A cornerstone of any children's fall wardrobe - we love the fleece lining for additional tootsie warmth.

Aigle Woodypop Rainboot, Sole Kids Shoe Company, $65

Cardigan Casual

A casually cool layering piece to accommodate the unpredictable temps of the autumn. Pair with a dusty rose turtleneck and specs for little librarian vibes.

Girls Rib Open Cardi, Joe Fresh, $21.75 (until Sept 28)

Bombastic Bomber

Camo, floral and quilting are the perfect trifecta of this seasons trends. Embrace it with a sweet edgy-yet-feminine topper.

Girls' Quilted Bomber Jacket, Joe Fresh, $29.25

Handsome Hoody

An easy wardrobe basic that works as well for gym class as it does for Friday night pizza parties.

Toddler Boys Kangaroo Hoodie, Joe Fresh, $16.50 (until Sept 28)

Beautiful Bows

Feminine but minimalist, this is gorgeous. We'd get it in our size too.  

Sporty Sweater with Bow Mid-ecru, Zara, $35.90

Trendy Trousers

The drop-crotch and neutral colour will appeal to hipster kids from Toronto to Tofino, and the vintage long-john fabric will surely keep their little legs insulated from the chill.

Waffle Trousers Dark Mauve, Zara, $25.90

Furry Friend

This sweet pom pom topped toque is guaranteed to keep heads turning and little heads warm.

Miles Baby Knit Navy Pom Pom Hat, Tiny Trendsetter, $29.99

Fine Fleece

Stylish but practical, this is a great additional layer for our littles as we navigate the changing seasons

Kids Pile Lined Sweat Long Sleeve Full-Zip Hoodie, Uniqlo , $29.90