25 Cute Fall Dresses for an On-Trend Transitional Look
You'll want to shop so many of these cozy styles.
Every item on this page was chosen by an editor from The Pioneer Woman. 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!
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. And though the go-to fall look might be 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 shirt 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 boho tiered styles. But truthfully, you can never go wrong with sweater dresses. It's all up to you—and you'll feel cozy no matter what!
Check out even more fall fashion inspo:
- Best Fall Hats for Women to Complete Your Look
- Fabulous Fall Nail Ideas to Try
- Cute Fall Sweaters to Snuggle Up In
Equal parts chic and cozy, this prairie-inspired pick is calling your name! With its easy-wearing, button-front dress design, blouson sleeves, and paisley print, you'll definitely want to answer.
Thanks to those seasonal blossoms, this number can be pulled on for so many autumn events. It has a cascading silhouette along with the cutest puff sleeves. And don't forget your fall hat!
With its quintessential fall texture and swingy babydoll silhouette, this corduroy button-up dress is the definition of effortless autumn style. The structured collar adds a touch of polish, while the flowy fit keeps it comfy.
The warm blooms on a deep green background 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.
Just imagine this lovely dress layered with a cropped jacket or cozy cardi! The romantic trim adds a hint of vintage charm, while the lightweight crepe silhouette decorated in florals is soft, graceful, and fall-ready.
Talk about trendy! Perfectly blending structure and softness, this adorable dress has a lightweight chambray fabrication and features a flattering mini silhouette, feminine bow detail at the neckline, and pretty puff sleeves. It also has functional pockets!
Bold patterns are great for jazzing up your fall wardrobe. The fun bandana-inspired print on this dress does just that! Plus, it has a flirty flounce hem and a button placket that enhances the energy.
Blu Pepper Plaid Tiered Midi Dress
The kind of dress that feels just as right at the pumpkin patch as it does at weekend brunch. Designed with a flowing tiered skirt and framed in a soft, heritage-inspired plaid, it captures the season’s cozy spirit with a feminine twist.
Yes, sweater dresses can be so chic! This one has a stretchy ribbed texture and midi length that hugs in all the right places, while keeping you warm, too. See? Effortless va-va-voom!
Vince Camuto Printed Border Shirt Dress
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. It has a sophisticated shape and self-tie belt to accentuate your figure. The allover paisley print that's finished with a border design just makes it even better!
Don this dress and you'll be garnering all the compliments all season long. It's crafted from airy georgette with a fluid drape and refined boat neckline for understated glamour. Add the self-tie belt to cinch the waist just right.
Thanks to its sleek knit fabric, subtle structure, and body-skimming silhouette, this sweater dress brings the ultimate cozy sophistication to cooler days.
The perfect blend of femininity and fall sophistication, this one is crafted from delicate chiffon with a painterly floral print. The flowy A-line silhouette flatters with ease and movement whether paired with tall boots or wedges.
Plaid is quite possibly one of the most popular (and most comfy) fall/winter patterns. Dress it up with a tiered silhouette and balloon sleeves like this one.
Florals aren't just for spring and summer. Fall florals are just as glorious—this wine-colored tiered maxi dress is proof.
This dress is perfectly fall! The Swiss dot fabric and tie at the waist add 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.
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.
Baltic Born Sari Babydoll Dress
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.
This fabulous find belongs in your closet immediately. The dark blue hue and vibrant floral print add 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.
Puff sleeves and a flattering tie 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!
Macie Reynolds is the assistant editor of E-Commerce and SEO for The Pioneer Woman.
22 Best Cowboy Boots to Wear With Fall Outfits
Where to Get Ree’s Fall 2025 Magazine Cover Look
How to Dress Fisherman Core for Fall 2025
25 Cute Cardigans to Layer Over Your Outfits
