Advertisement
  • Newsletter
  • Subscribe
Style

20 Gorgeous Dresses To Wear Now And Into Fall

Say yes to a stylish frock that will easily adapt to cooler temps.
By Ingrie Williams
20 Gorgeous Dresses To Wear Now And Into Fall

The calendar has officially flipped to September, but summer’s balmy temps will linger for at least another few weeks. To satisfy the desire for a fall style update that you won’t have to wait weeks to enjoy, turn to the versatility of a transitional dress. These finds are ideal candidates: lightweight enough to be worn ASAP with sandals, devoid of any high-summer details (catch you next year, eyelets!) and primed for layering later with tights and a chunky knit or loose cardigan over top. A few of these hardworking frocks will even work worn with a thin turtleneck underneath for added warmth that also looks chic. From short flouncy styles to bold colours and fresh takes on classics (like the shirt dress), here are twenty dresses that are ready to go the distance through the final quarter of 2021.

Reformation

Mochi Es dress, $288, thereformation.com

A model wearing reformation's brown with white polka dots, long sleeves and a sweetheart neckline dress with black flats

Frank and Oak

Printed babydoll dress, $119, frankandoak.com

Frank and Oak  Printed babydoll dress

Addition Elle

Long raglan sleeve A-line dress, $80, penningtons.com

Advertisement
A model in an Addition Elle Long blue printed raglan sleeve A-line dress

MICHAEL Michael Kors

Cotton chambray smocked dress, $250, michaelkors.ca

MICHAEL Michael Kors Cotton chambray smocked dress

Gap

Ruched dress, $85, gapcanada.ca

A plum coloured short-sleeved gap Ruched Dress on a white background

Uniqlo

Drawstring 3/4 sleeve dress, $50, uniqlo.com/ca

Uniqlo  Drawstring ¾ sleeve dress

WINNERS

Long sleeve tiered smock dress, $50, winners.ca

Advertisement
WINNERS mint green Long sleeve tiered midi smock dress

Eloquii

Rib collar sweater dress, $126, eloquii.com

Eloquii  Rib collar sweater dress

Banana Republic

Deep V-neck maxi dress, $209, bananarepublic.gapcanada.ca

Banana Republic  Deep V-neck maxi dress, $209

Zara

Printed midi dress, $80, zara.com

A model in a Zara black and white Printed midi dress

Contemporaine

Opulent medallion smocked dress, $150, simons.ca

Advertisement
A model sitting on a bar wearing Contemporaine  Opulent medallion smocked dress

Joe Fresh

Long sleeve tiered dress, $39, joefresh.com

20 Gorgeous Dresses To Wear Now And Into Fall

H&M

Calf-length dress, $50, hm.com/ca

Model in sunglasses in H&M  Calf-length dress

Levi’s

Mira dress, $98 (avail early Sept.), levi.com

Levi’s Mira dress, a black-and-white check long-sleeved dress with a ruffled collar

J.Crew

Puff-sleeve cotton poplin mini shirtdress, $174, jcrew.com

Advertisement
A model in a beige J.Crew  Puff-sleeve cotton poplin mini shirtdress with white socks and white clogs

Vero Moda

Rillo flounced wrap dress, $65, veromoda.ca

Vero Moda Rillo flounced wrap dress

Babaton

Shoulder pad dress, $60, aritzia.com

A model in a black Babaton  Shoulder pad dress

Marshalls

High-neck floral mini dress, $50, marshalls.ca

Marshalls High-neck floral mini dress

Old Navy

Long-sleeve midi sweatshirt shift dress, $50, oldnavy.gapcanada.ca

Advertisement
Old Navy Long-sleeve midi sweatshirt shift dressOn-Figure

Madewell

Lucie smocked midi dress, $219, madewell.com

20 Gorgeous Dresses To Wear Now And Into Fall

The very best of Chatelaine straight to your inbox.

By signing up, you agree to our terms of use and privacy policy. You may unsubscribe at any time.

Advertisement
Advertisement
Copy link
The cover of Chatelaine magazine's spring 2025 issue, reading "weekend prep made easy"; "five delicious weeknight meals", "plus, why you'll never regret buying an air fryer"; "save money, stay stylish how to build a capsule wardrobe" and "home organization special" along with photos of burritos, chicken and rice and white bean soup, quick paella in a dutch oven, almost-instant Thai chicken curry and chicken broccoli casserole in an enamelled cast-iron skillet

Subscribe to Chatelaine!

Want to streamline your life? In our Spring 2025 issue, we’ll show you how—whether it’s paring down your wardrobe, decluttering your messiest spaces or spending way less time cooking thanks to an easy, mostly make-ahead meal plan for busy weeknights. Plus, our first annual Pantry Awards.