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25 Cute Fall Dresses to Wear All Season Long

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

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Walmart / Lulus

Every item on this page was chosen by a The Pioneer Woman editor. We may earn commission on some of the items you choose to buy.

Fall fashion is the best of the year! Why? Well, it's the time for really showing off everything your wardrobe has to offer 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
    Perceptions Patchwork Fit + Flare Dress

    Best Pattern

    Perceptions Patchwork Fit + Flare Dress

    $10 at JCPenney
    Read more
  • 2
    The Pioneer Woman Mixed Print Ruffle Maxi Dress

    Editor's Pick

    The Pioneer Woman Mixed Print Ruffle Maxi Dress

    Read more
  • 3
    Anthropologie The Somerset Maxi Dress

    Best Maxi Dress

    Anthropologie The Somerset Maxi Dress

    Read more
  • 4
    Lulus Tiered Midi Dress

    Comes in Several Colors

    Lulus Tiered Midi Dress

    Read more
  • 5
    Loft Jacquard Flounce Swing Dress

    Best Mini Dress

    Loft Jacquard Flounce Swing 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
Best Pattern

Perceptions Patchwork Fit + Flare Dress

Perceptions Patchwork Fit + Flare Dress
1
Best Pattern

Perceptions Patchwork Fit + Flare Dress

$10 at JCPenney
Credit: JCPENNEY

A patchwork design of flowers in a variety of autumn hues makes this dress just delightful. You'll also enjoy the flattering fit and flare wrap style.

2
Editor's Pick

The Pioneer Woman Mixed Print Ruffle Maxi Dress

The Pioneer Woman Mixed Print Ruffle Maxi Dress
2
Editor's Pick

The Pioneer Woman Mixed Print Ruffle Maxi Dress

Credit: Walmart

Have you seen Ree's new fall clothing collection? We've got our eyes on this fun and flouncy floral piece. It has a tiered skirt and smocked waist to accentuate your figure while ruffles along the hems add some extra va-va-voom!

3
Best Maxi Dress

Anthropologie The Somerset Maxi Dress

Anthropologie The Somerset Maxi Dress
3
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.

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4
Comes in Several Colors

Lulus Tiered Midi Dress

Lulus Tiered Midi Dress
4
Comes in Several Colors

Lulus Tiered Midi Dress

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.

5
Best Mini Dress

Loft Jacquard Flounce Swing Dress

Loft Jacquard Flounce Swing Dress
5
Best Mini Dress

Loft Jacquard Flounce Swing Dress

Now 41% Off
Credit: Loft

If you look closely, you'll notice a subtle chevron pattern in shades of gray that makes this pick so chic. A tier of flounce at the hem adds a feminine touch, too.

6
Best Wrap Style Dress

Perceptions Floral Fit + Flare Dress

Perceptions Floral Fit + Flare Dress
6
Best Wrap Style Dress

Perceptions Floral Fit + Flare Dress

Credit: JCPenney

The golden blooms on this dress are the epitome of autumn. With a wrap style that works to show off your shape while staying sophisticated, you can wear it from the office straight to any evening events.

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7
Best Boho Style

Mitilly Boho Leopard Print V Neck Maxi Dress

On Sale
Mitilly Boho Leopard Print V Neck Maxi Dress
7
Best Boho Style

Mitilly Boho Leopard Print V Neck Maxi Dress

Now 12% 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.

8
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
8
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.

9
Best Sweater Dress

Mongolian Cashmere Turtleneck Sweater Dress

Mongolian Cashmere Turtleneck Sweater Dress
9
Best Sweater Dress

Mongolian Cashmere Turtleneck Sweater Dress

Credit: Quince

You absolutely need this timeless number! The soft cashmere and eye-catching turtleneck style will keep you cozy as the leaves start to change.

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10
Under $30

Floral Print Long Sleeve Dress

On Sale
Floral Print Long Sleeve Dress
10
Under $30

Floral Print Long Sleeve Dress

Now 24% Off
Credit: Amazon

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

11
60,000+ Reviews

Amoretu Long Sleeve Tunic Dress

On Sale
Amoretu Long Sleeve Tunic Dress
11
60,000+ Reviews

Amoretu Long Sleeve Tunic Dress

Now 30% 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.

12
900+ Reviews

Navy Blue Floral Print Dress

Navy Blue Floral Print Dress
12
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.

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13
14,000+ Reviews

Autumn Knit Dress

On Sale
Autumn Knit Dress
13
14,000+ Reviews

Autumn Knit Dress

Now 10% Off
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!

14
Best Shirt Dress

Baltic Born Sari Babydoll Dress

Baltic Born Sari Babydoll Dress
14
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.

15
Available in Sizes: XS-XXL

African Peacock Maxi Wrap Dress

African Peacock Maxi Wrap Dress
15
Available in Sizes: XS-XXL

African Peacock Maxi Wrap Dress

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.

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16
Best Tiered Dress

Lucky Brand Bohemian Tiered Maxi Dress

Lucky Brand Bohemian Tiered Maxi Dress
16
Best Tiered Dress

Lucky Brand Bohemian Tiered Maxi Dress

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.

17
Best Details

Madewell Embroidered Ruffled Flannel Mini Dress

Madewell Embroidered Ruffled Flannel Mini Dress
17
Best Details

Madewell Embroidered Ruffled Flannel Mini Dress

Now 59% 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.

18
Little Black Dress

R.Vivimos Velvet Wrap Dress

R.Vivimos Velvet Wrap Dress
18
Little Black Dress

R.Vivimos Velvet Wrap Dress

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.

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19
Extended Sizes Available

Gap Puff Sleeve Smocked Maxi Dress

Gap Puff Sleeve Smocked Maxi Dress
19
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.

20
Best Transitional Dress

BoHo Bliss! Embroirdered Bell Sleeve Dress

BoHo Bliss! Embroirdered Bell Sleeve Dress
20
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.

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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