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25 Cute Fall Dresses to Wear in Any Transitional Weather

You'll want to shop all of these cozy styles!

Headshot of Macie ReynoldsBy Macie Reynolds
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Walmart / Lulus

Fall fashion is the best of the year! It's the time for really showing off your wardrobe thanks to all those layers you're sure to style. But before you rush to your closet and unpack all of your best cardigans and fall coats, you'll need a few transition pieces fit for the season. That's where these cute fall dresses come into play!

Our Top Picks

  • 1
    Lulus Tiered Midi Dress

    Comes in Several Colors

    Lulus Tiered Midi Dress

    $69 at Lulu's
    Read more
  • 2
    Floral Print Long Sleeve Dress

    Under $30

    Floral Print Long Sleeve Dress

    Read more
  • 3
    The Pioneer Woman Dress with 3/4-Length Puff Raglan Sleeves

    Ree's Style

    The Pioneer Woman Dress with 3/4-Length Puff Raglan Sleeves

    Read more
  • 4
    Navy Blue Floral Print Dress

    900+ Reviews

    Navy Blue Floral Print Dress

    Read more
  • 5
    Baltic Born Sari Babydoll Dress

    Best Shirt Dress

    Baltic Born Sari Babydoll Dress

    Read more

While dresses for fall often come in shades of wine, mustard yellow, and brown, you don't have to wear the same old thing. Try something with a fun print, an oversized silhouette, or embellishments in Ree Drummond's style like embroidery and ruffles. Also, although we all love midi dresses and maxi dresses, don't count out short dresses or flowy numbers—they can double as cute fall dresses too, especially if you pair them with tights and a cute pair of ankle boots. Then just toss a suede jacket on top.

Of course like with any other season, fall dresses, ahem, fall on a spectrum of casual to fancy. Running around town? Try a sweatshirt dress or a long-sleeve dress with a casual tie-waist. Heading to a wedding? You can rock fall wedding guest dresses in knit maxi or a boho ruffled styles. Though if you ask us, you can never go wrong with sweater dresses. And don't forget to pick out your Thanksgiving dresses, too! It's all up to you—and you'll feel cozy no matter what!

1
Comes in Several Colors

Lulus Tiered Midi Dress

Lulus Tiered Midi Dress
1
Comes in Several Colors

Lulus Tiered Midi Dress

$69 at Lulu's
Credit: Lulus

This dress is perfectly fall! The Swiss dot fabric and crochet lace adds a feminine, flirty flair. Not to mention, the tiered style can be dressed up or down. Add a pair of cowboy boots or don some heels for whatever your day has in store.

2
Under $30

Floral Print Long Sleeve Dress

Floral Print Long Sleeve Dress
2
Under $30

Floral Print Long Sleeve Dress

Credit: Amazon

Florals aren't just for spring and summer. Fall florals are just as glorious—this wine-colored tiered maxi dress is proof.

3
Ree's Style

The Pioneer Woman Dress with 3/4-Length Puff Raglan Sleeves

The Pioneer Woman Dress with 3/4-Length Puff Raglan Sleeves
3
Ree's Style

The Pioneer Woman Dress with 3/4-Length Puff Raglan Sleeves

Credit: Walmart

Hello, transition piece! This fabulous dress from Ree's clothing collection is just what you need to move from summer to fall—especially with darker florals and a golden hue. It also features
a voluminous silhouette with puff sleeves in a soft challis fabric.

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4
900+ Reviews

Navy Blue Floral Print Dress

Navy Blue Floral Print Dress
4
900+ Reviews

Navy Blue Floral Print Dress

Credit: Lulus

This fabulous find belongs in your closet immediately. The dark blue hue and vibrant floral print adds a much needed pop of color to your fall wardrobe. And here's a style tip: pair it with a belt or brown suede jacket to really stand out.

5
Best Shirt Dress

Baltic Born Sari Babydoll Dress

Baltic Born Sari Babydoll Dress
5
Best Shirt Dress

Baltic Born Sari Babydoll Dress

Credit: Baltic Born

Pair this adorable babydoll dress with your favorite boots and it can easily take you from the office to dinner with friends thanks to a stylish yet sophisticated collar atop a button-down front.

6
Best Boho Style

Mitilly Boho Leopard Print V Neck Maxi Dress

Mitilly Boho Leopard Print V Neck Maxi Dress
6
Best Boho Style

Mitilly Boho Leopard Print V Neck Maxi Dress

Now 22% Off
Credit: Amazon

Fall doesn't have to be all about earth tones and neutrals. Take a walk on the wild side with this blue leopard print maxi dress.

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7
Available in Sizes: XS-XXL

African Peacock Maxi Wrap Dress

African Peacock Maxi Wrap Dress
7
Available in Sizes: XS-XXL

African Peacock Maxi Wrap Dress

Now 33% Off
Credit: Silk & Salt

Animal print is a neutral year round. We all know and love leopard and zebra, but what about peacock? You heard that right! The deep blues and greens on this boho-chic dress are perfect for the cooler time of year. It's versatile too! Tie it as you like, forming different necklines according to the occasion.

8
Extended Sizes Available

Gap Puff Sleeve Smocked Maxi Dress

Gap Puff Sleeve Smocked Maxi Dress
8
Extended Sizes Available

Gap Puff Sleeve Smocked Maxi Dress

Credit: Gap

Here's one with a lightweight and breathable fabric that's perfect for those days when it’s not-too-hot and not-too-cold. We also have to point out the oh-so-pretty ruffled and smocked accents.

9
Best Details

Madewell Embroidered Ruffled Flannel Mini Dress

Madewell Embroidered Ruffled Flannel Mini Dress
9
Best Details

Madewell Embroidered Ruffled Flannel Mini Dress

Now 66% Off
Credit: Madewell

Not only will the felted flannel material of this dress keep you cozy through the cooler seasons, but darling details like a cutwork statement bib, eyelet embroidery, and scalloped edging will keep you looking so cute, too.

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10
Best Tiered Dress

Lucky Brand Bohemian Tiered Maxi Dress

Lucky Brand Bohemian Tiered Maxi Dress
10
Best Tiered Dress

Lucky Brand Bohemian Tiered Maxi Dress

Now 46% Off
Credit: Amazon

With this breezy boho dress, brunches and farmers markets are just calling your name! Can we get a little love for the tassel ties and contrast trim paired with fall florals? While we love the cascading skirt, you can also throw on a belt for a more fitted style.

11
Stylish Find

Jessica Simpson Amella Trumpet Sleeve Mini Dress

Jessica Simpson Amella Trumpet Sleeve Mini Dress
11
Stylish Find

Jessica Simpson Amella Trumpet Sleeve Mini Dress

Credit: Amazon

A paisley print is always the perfect choice for any fall ensemble! That pattern plus a pleated waist and eye-catching trumpet sleeves makes for a dress that will have you garnering all the compliments all season long.

12
Best Transitional Dress

BoHo Bliss! Embroirdered Bell Sleeve Dress

BoHo Bliss! Embroirdered Bell Sleeve Dress
12
Best Transitional Dress

BoHo Bliss! Embroirdered Bell Sleeve Dress

Credit: Amazon

Bright colors don't have to fade in the fall—this dress proves it! The embroidered details are stunning and it's made of 100% cotton, meaning a dress like this will be breathable on those transitional hot days.

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13
Best Maxi Dress

Anthropologie The Somerset Maxi Dress

Anthropologie The Somerset Maxi Dress
13
Best Maxi Dress

Anthropologie The Somerset Maxi Dress

Credit: Anthropologie

This pick is Anthropologie's bestselling and best-reviewed dress... ever! With a smocked waist, pintucked hem, and tiered silhouette, it's flattering on everyone. Plus, that pattern is just so transitional.

14
61,000+ Reviews

Amoretu Long Sleeve Tunic Dress

Amoretu Long Sleeve Tunic Dress
14
61,000+ Reviews

Amoretu Long Sleeve Tunic Dress

Now 40% Off
Credit: Amazon

If you really want to lean into a fall color palette, this tiered tunic dress is the perfect shade. It's great for early fall when the weather can't seem to figure itself out.

15
Best Casual Dress

Mud Pie Sweatshirt Dress

Mud Pie Sweatshirt Dress
15
Best Casual Dress

Mud Pie Sweatshirt Dress

Credit: Amazon

You can officially live in your sweats without judgement! Say hello to the more casual version of the sweater dress: the sweatshirt dress.

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16
14,000+ Reviews

Autumn Knit Dress

Autumn Knit Dress
16
14,000+ Reviews

Autumn Knit Dress

Credit: Amazon

Puff sleeves and a flattering tie feature in the front set this knit dress apart. This photo features Ree's favorite color, but it also comes in plenty of others. Pair it with dark tights and you're good to go!

17
Editor's Pick

Baltic Born Esma Mini Dress

Baltic Born Esma Mini Dress
17
Editor's Pick

Baltic Born Esma Mini Dress

Credit: Baltic Born

Bold patterns are great for jazzing up your fall wardrobe. This dress has rich, perfect-for-autumn colors that let the groovy print speak for itself. The flare skirt and braided tie just make it even better!

18
Best Midi Dress

Everlane The Ribbed Wrap Midi Dress

Everlane The Ribbed Wrap Midi Dress
18
Best Midi Dress

Everlane The Ribbed Wrap Midi Dress

Now 45% Off
Credit: Everlane

Equal parts chic and cozy, this number can be pulled on for so many autumn events. It has a wrap silhouette for adjustable styling along with a refined rib texture and just-right length.

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19
Best Mini Dress

Madewell Corduroy Tiered Mini Dress

Madewell Corduroy Tiered Mini Dress
19
Best Mini Dress

Madewell Corduroy Tiered Mini Dress

Now 38% Off
Credit: Madewell

Nothing feels more fall than corduroy! This dress has delightful details such as a tiered skirt and voluminous sleeves. Plus, its easy off-the-body fit means it's as comfortable as it is cute.

20
Little Black Dress

R.Vivimos Velvet Wrap Dress

R.Vivimos Velvet Wrap Dress
20
Little Black Dress

R.Vivimos Velvet Wrap Dress

Now 20% Off
Credit: Amazon

Take it from us, you need a little black dress for every season. And for fall, what better than this velvet number? We're loving the high-low hem and tie closure for a fun and flirty look.

Headshot of Macie Reynolds
Macie Reynolds
Assistant Editor

Macie Reynolds is the assistant editor of E-Commerce and SEO for The Pioneer Woman.

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