Two women in We’ll Be Living In These Trending Off-Duty Dresses For Cool Weather pose elegantly in a stylish living room; one seated on a white sofa, the other leaning on a decorative side table. Both wear knee-high boots.

@CARACARA_NYC / INSTAGRAM

The Dress Edit

We’ll Be Living In These Trending Off-Duty Dresses For Cool Weather

With fall almost upon us, we’re turning all out attention to the season’s most coveted off-duty dresses for cool weather! From long-sleeved mini dresses that we’ll style up with boots to must-have midi designs in irresistible fall-colored prints. No matter your style, we guarantee you’ll find the autumn dresses of your dreams in our edit below. Not to mention, we’ve only selected pieces from the world’s most beloved womenswear designers. Scroll on and discover your new favorites from Altuzarra, Staud, Cara Cara, Veronica Beard, and so many more!

A woman in a We’ll Be Living In These Trending Off-Duty Dresses For Cool Weather stands against a rugged rock background. She appears contemplative, leaning slightly with one hand on the rocky surface.

@altuzarra / Instagram

A woman in the "We’ll Be Living In These Trending Off-Duty Dresses For Cool Weather" dress stands against a floral-patterned wall. She has long brown hair, a neutral expression, and is adorned with subtle jewelry. Dark foliage decorates the scene.

Paige

Add Your Fave Boots To These Dresses For Cool Weather

When it comes to must-have dresses for cool weather, we’re all about seasonal styles we can wear with boots. After all, if you pick the right ones, you can still rock mini and midi-length dresses throughout fall and even winter too! For example, we definitely didn’t hesitate to add the Vittoria Pimpernel georgette mini dress by Paige to our carts. Firstly, this gorgeous green dress has the most stunning floral print that’s simply made for this time of year. Secondly, the long sleeves, belted waist, and chic collared neckline mean you can dress it up or down depending on your off-duty plans! Us? We’ll be rocking it with knee boots for maximum impact!

 

Meanwhile, who could resist the Peirene Shibori-dyed silk mini dress by Altuzarra? The answer is nobody! This beautiful black, white, and red printed dress is a fall/winter dream come true and has you covered for everything from brunch dates to dinner plans. Firstly, its elegant high neckline, long sleeves, and belted waist work perfectly together to elevate your silhouette. Secondly, the mid-length hem makes this the perfect dress to style with high black boots for your Saturday/Sunday plans.

Shop more dresses selected and reviewed by our expert fashion buyers and stylists

  • ALESSANDRA RICH Printed Draped Silk Long Dress

    $2,110
  • ANTHROPOLOGIE Lace Twofer Blazer Midi Dress

    $268
  • CEFINN Loretta Printed Recycled-blend Crepe Midi Dress

    $500
  • RONNY KOBO Quinne Dress

    $578
  • MAC DUGGAL Pleated Deep V Long Sleeve Dress

    $398
  • ANDREW GN Crystal-embellished Feather-trim Gown

    $4,114
  • DVF Joshua Dress

    $498
  • 16ARLINGTON Solare Sequined Lace-up Midi Dress

    $1,490
  • ISABEL MARANT Albini Gathered Pink Printed Silk-blend Midi Dress

    $1,390

Dresses For Cool Weather We'll Be Wearing On Repeat

From early fall to the depths of winter, we want our dresses for cool weather to last! Therefore, we’re always on the lookout for expertly crafted dresses in versatile styles that we can happily wear again and again. So, it’ll come as no surprise we’re adding the Agan mixed-media Vegan leather midi dress by Altuzarra to our fall/winter line-up! This eternally chic dress will see you through countless events on your cold-weather calendar. Additionally, its all-black construction with asymmetric gold-button detailing is undeniably elegant. Simply add black heeled boots for an unforgettable entrance this weekend!

 

Can’t resist a print? Us neither. That’s why we’re head over heels for the Bliss striped maxi dress by Frances Valentine! This striking black and white dress offers a classic print with a modern, painterly edge. Additionally, it’ll look incredible with your winter boots no matter where you’re headed. It’s dresses like this that make saying goodbye to summer totally worth it!

Shop All Dresses For Cool Weather

A woman in a (We’ll Be Living In These Trending Off-Duty Dresses For Cool Weather) suitable for cool weather stands in front of a wall featuring a flamingo pattern. She holds a small wicker handbag and wears green sandals.

@fvalentineny / Instagram

A woman stands on a staircase, wearing a "We’ll Be Living In These Trending Off-Duty Dresses For Cool Weather" dress with floral patterns and long sleeves, adorned with gold buttons. She accessorizes with simple flat shoes and poses with the sea and sky in

Alessandra Rich

Fall Mini Dresses We Can’t Wait To Slip In To