A woman sits perched gracefully, wearing a Simple Fall Dress For An Effortlessly Stylish New Season in olive green pleats. She gazes to the side with her dark hair pulled back, and large hoop earrings complement her outfit.


The Dress Edit

Simple Fall Dresses For An Effortlessly Stylish New Season

With cooler weather well on the way, these simple fall dresses are set to take over your closet for the season ahead. From the chicest all-black maxi’s to neutral-hued sweater silhouettes, we’ve sought out the most coveted designer looks you’ll want to live in this fall. The best news? We’re spoiled for choice and every one of the dresses in our edit is available for you to shop right now! Keep scrolling to discover the chicest dresses from Ulla Johnson, Veronica Beard, Anthropologie, Chloe, Doen, and more. You’ll be wishing for colder days to arrive the moment you set eyes on them…

A woman in a Simple Fall Dresses For An Effortlessly Stylish New Season sits on a wooden floor against a grey background, looking at the camera with her hair tossed slightly by the wind. She wears large hoop earrings.


A woman in a Simple Fall Dress with long sleeves and a tiered skirt, standing in a room with a pink and tan wavy patterned floor.

Ulla Johnson

Simple Fall Dresses That'll Go Perfectly With Your Fall Footwear

Since we’ll be living in designer boots for the season ahead, we’ve tracked down all of the chicest simple fall dresses to go with them. Spoiler alert: That’s pretty much every dress on our list! That said, dresses like the Dao brushed ribbed-knit maxi by Jacquemus will be a must in the coming months. Firstly, this dress boasts a beautiful scoop neckline, long sleeves, and a stylish, thigh-high split in the maxi-length skirt. Secondly, the caramel cream hue is the ultimate cooler weather shade that’ll take you seamlessly through from early fall to winter! Our advice? Pair yours with knee-high boots for an effortlessly elegant fall ensemble. It’ll work just as well for formal plans as it will for off-duty ones. Not to mention, a dress like this will stay in style for countless years to come.


Meanwhile, when the occasion calls for something a little dressier, you’ll likely be stepping out in heels. In this case, we highly recommend the faux leather seamed swing dress by Avec Les Filles. The perfect way to take your evening looks from summer to winter? Opt for leather effect silhouettes! They’ll be warmer than silk and cotton fabrics yet look just as chic and dressy for your evening plans. Additionally, when they boast a sleek square neckline, a fitted bodice, and a voluminous skirt like this dress does, you’re guaranteed best-dressed status.

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

  • RHODE Anton Midi Dress

  • ALEXANDRA MIRO Odetta Printed Maxi Dress

  • BHLDN Hayden Strapless Stretch Crepe Midi Dress

  • GUESS Emilie Rhinestone Long Sleeve Minidress

  • ULLA JOHNSON Cornelia Ruched-side Velvet Midi Dress

  • VICTORIA BECKHAM Ruffled Lamé Gown

  • ISABEL MARANT Atina Cable-knit Merino Wool-blend Mini Dress

  • EMILIA WICKSTEAD Miley Checked Crepe Midi Dress

  • DÔEN Amande Printed Cotton-voile Maxi Dress


Simple Fall Dresses That'll See You Through Winter Too

Making an investment in simple fall dresses from your favorite designers? You’ll want to make sure you can wear them for more than just one season! Luckily, all of the dresses on our list will work seamlessly from late summer to fall and fall to winter. So, when it comes to the latter, we’re all about dresses like the crocheted cotton-blend maxi dress by Chloe.


Firstly, this dress is flawless with its classic crochet construction, soft white colorway, long sleeves, and chic high neckline. Secondly, you can pair it with boots for fall and throw a coat over top for a stylish winter look. You’ll have all eyes on your outfit no matter how or when you wear it!

Shop All Simple Fall Dresses

Simple Fall Dresses For An Effortlessly Stylish New Season


A woman in a flowing white Simple Fall Dresses For An Effortlessly Stylish New Season and black boots stands confidently in a rustic room with white plastered walls and a bare concrete floor. Her curly hair cascades over her shoulders.


Nail Seasonless Dressing In Gorgeous Black Floral Print Dresses