The 19 Best Fall Dresses to Wear Throughout the Transitional Season

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The best time to shop for cold-weather clothing is before the leaves start to turn yellow. I’ve already started a running list of the best fall dresses, despite the first day of the season being weeks away.

As you navigate the transition to pumpkin spice season and fall foliage, my advice is to start by styling your fall dresses with heeled sandals and a straw bag while you still have the chance. As things start to cool off, swap in leather boots, a corduroy blazer, or even a rugby shirt layered on top if you’re feeling inspired by the recent looks at Copenhagen Fashion Week. Personally, I’m most looking forward to test-driving a minidress styled with coordinated tights, as seen on the FW 2024 runway at Miu Miu, or embracing the return of bohemian flair courtesy of labels like Chloé and Etro. Pay close attention to paisley prints in particular, they are on my radar this fall and about to have a resurgence.

Now if summer is all about showing off skin and embracing lightweight fabrics, fall is about a rich palette of chocolate browns and burgundies, creative layering with coats, and textures that feel warm and blanket-like against the skin. Ahead, you’ll find a range of fall dress styles—from office-appropriate silhouettes to elegant options well suited for the next batch of weddings or other special evening soirées. Each was selected based on reviews, editor opinions, and overall wearability to help you hone in on the best of the best. No matter what month you’re shopping for the perfect fall dress, you’ll find one that suits your needs and style.

Rosenda Dress

Embrace the colors of fall with a transitional long-sleeved cotton dress that is warm enough to wear while the weather is still nice, but can be paired with a sweater on cooler days.

Sizes: XXS–XXL

Colors: Multi

Dayla Crinkled Satin Slipdress

As you transition from warm nights to evenings for date nights or celebratory occasions, this dress will weather the shift with you. Make sure to bring along a sweater to wrap around your shoulders or you can layer a thin turtleneck underneath as temps get cooler.

Sizes: 2–10

Colors: Lilac, green

Paisley Crêpe Jersey Maxi Dress

Boho is back, and a pattern like an oversize paisley is an easy way to embrace the trend in a modern way that doesn’t feel costumey or kitschy.

Sizes: 2–14

Colors: Blue and brown

The Maude Dress

As a semiprofessional Hill House dress collector, I think this may be the label’s best sweater dress to date. The sweeping scoop neckline and blouson sleeves are pretty and polished, while the wool-blend fabrication guarantees a cozy and comfortable day wearing it. I’m envisioning myself wearing it with a long black hair ribbon and Miu Miu flats for a balletic moment, but the minimal design could go in all sorts of aesthetic directions.

Sizes: XXS–XXL

Colors: Gray, black

Meg Dress

This Rixo dress is at the top of my personal wish list. I love how the designers inventively combined two quintessential fall prints—the basic black-white polka dot and an exaggerated leopard print—into a single dress with a layered effect.

What reviewers say: “Absolutely adore this dress and know I’m going to get so much wear out of it, a forever dress. I sized down - I’m a 12 but was a bit big so kept the size 10.”

Sizes: 2–22

Colors: Leopard/polka dot

Genna Ribbed Knit Midi Dress

A knit dress gets an elegant spin via a fluted skirt and bell sleeves. You can comfortably wear this dress to the office or for date night.

Sizes: XS–XL

Colors: Army green

Fitted Knit Mock-Neck Dress

I always look to J.Crew for affordable workwear options, and this dress instantly caught my eye as a must-have for fall. The sleeveless turtleneck design is great for layering under a sweater.

What reviewers say: “I love this dress! It feels casual and comfy but has a classy look. I wore this with a blazer to a Board meeting, and it looked so fabulous. I’ve worn it with just by itself with flats--and it just gives off a Audrey Hepburn vibe.”

Sizes: XS–3XL

Colors: White, black, brown

Tie-Waist Long-Sleeved Denim Maxi Dress

After a hot summer of avoiding denim at all costs, I’m looking forward to breaking out jeans and other sturdy staples once again. I’d style this midi dress with tall boots and a fringe shawl to lean into the western vibe.

What reviewers say: “This dress is better than I imagined. It is true to size. I ordered my size XL and it fit perfect. I am 5'2" and it is a maxi dress that hits at the ankle. The material is sturdy and of good quality. This was a great buy and something that will never go out of style.”

Sizes: XS–XL

Colors: Blue

Famke Print Puffed-Sleeve Dress

For fall weddings, the ideal look is something light and dressy you can twirl in on the dance floor. The floral print and ruffle details set this style from Sea apart.

Sizes: 0–16

Colors: Red

Pintucked Crinkled Cotton and Linen-Blend Maxi Dress

Lauren Manoogian uses only the lushest, best-quality fabrics. So, though this dress is simple in silhouette and color, it will feel so delish when you’re wearing it. Pair it with a simple ballet flat for a breezy, laidback look that's perfect for warm August evenings then swap the flats for a heeled boot and layer a chunky knit on top when the fall chill starts to roll in.

Sizes: 1–2

Colors: Taupe

Timea Dress

Cozy flannel is a must-have fabric for cooler weather. This midi-dress alternative to your usual button-up tops features a fitted waist detail that adds a dressy touch.

Sizes: 34–55

Colors: Brown

Jules Dress in Wide Stripe

Darting and a defined waistline add a sleek shape to this shirtdress made of 100 percent cotton. I’d suggest styling it with a belt and a bold necklace to take the look to the next level.

What reviewers say: “Seriously the most flattering shirt dress I’ve encountered in a very long time. Great length, lightweight, and is slightly fitted through the chest. Definitely size up if you’re a larger cup size.”

Sizes: XS–XL

Colors: Blue stripe, white stripe

Gabrielle Dress

hot, streamlined, and so classic: This modal maxi dress is the sort that you never stop wearing once it arrives.

Sizes: 12–26

Colors: Black

Draped Knit Maxi Dress

Toteme’s drape-detail sweaterdress is a way to embrace heavier knit fabrics without them feeling too bulky or loose and losing the shape of your body underneath. Pair with pumps for a killer business look.

Sizes: XS–L

Colors: Gray

Ellicot Dress

This collared silhouette is inspired by the look of a classic rugby or polo shirt with stripes and a V-neck shape. A twist knot at the waist accentuates the body.

Sizes: XS–3XL

Colors: Black stripe, green stripe

Lydia Dress

As a longtime fan of Reformation’s dress silhouettes, I was most taken by the little details that set this style apart. Embroidery across the chest and color adds a daintiness that is a little cottagecore without feeling overdone.

Sizes: 0–12

Colors: Cafe, serenade

Check Ribbed Knit Midi Dress

It wouldn’t be a fall roundup without a plaid option. Burberry’s classic print has a colorful update for the season, with a cherry and chocolate combo.

Sizes: XS–XL

Colors: Red and brown

Aurelia Satin Trapeze Minidress

The swingy silhouette of this minidress makes it a fun option for styling with a pair of printed or sequined tights and heels.

Sizes: XXS–XXL

Colors: Black, blue, navy

Multicolor Boulle Midi Dress

Embrace a bit of playfulness via this printed dress, which features a graphic reminiscent of the inside of an Italian castle. It’s a bold way to show your love of art history—without saying a word.

Sizes: XXS–XL

Colors: Multi

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