20 Cute Fall Dresses to Carry You Into the New Season
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 might just be the best fashion of the year! After all, it’s the season when you can really make the most of your wardrobe by piling on all those cozy layers. But before you race to your closet to unpack your best cardigans and fall coats, you’ll want a few pieces that can help ease you into the new season. Enter: these cute fall dresses!
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 boots. Then just toss a 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:
A flowy midi makes for an easy autumn ensemble—especially this one from Ree’s line. It has long sleeves, a flattering smocked waistband, and a tiered A-line skirt, while the patterned crinkle fabric gives it plenty of easygoing charm.
Equal parts chic and cozy, this prairie-inspired pick is calling your name! With its smocked bodice, puff sleeves, and perfectly seasonal plaid print, you'll definitely want to answer.
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 loose and swingy fit that’s accented with a sleek tie neck. The allover paisley print makes it even better!
Just imagine Ree’s lovely dress layered with a jacket or cozy cardi! The style features voluminous puff sleeves and a flowy tiered skirt, creating an easy silhouette that looks especially cute with boots.
Yes, the polka dot trend is continuing into fall! This option puts a playful spin on the classic pattern with a rich brown hue. The tie waist creates a complimentary look, making it a go-to pick for fall days and nights.
If you love the look of denim but want something a little more polished than jeans, this Pioneer Woman dress is for you. The defined waist and flowy skirt give it a flattering shape, while ruffle details add a sweet finishing touch.
That delicate floral lace fabric is reason enough to love this dress. Add in a ruffled tie neck and blouson sleeves, and you’ve got a mini that feels both romantic and easy to wear. Style it with boots and a denim jacket.
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 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.
Yes, sweater dresses can be so chic! This one has a stretchy ribbed texture and midi length that ties at the waist to hug all the right places—all while keeping you warm, too.
The perfect blend of femininity and fall sophistication, this one is crafted from delicate chiffon with a 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.
This dress is perfectly fall! The Swiss dot fabric and tie at the waist add feminine, flirty flair. Add a pair of cowboy boots or don some heels for whatever your day has in store.
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.
A paisley print is always the perfect choice for any fall ensemble! That pattern plus a loose, stretchy tunic fit will have you feeling comfortable throughout the season.
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.
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!
You absolutely need this timeless number! The soft cashmere and eye-catching turtleneck style will keep you cozy as the leaves start to change.
Macie Reynolds is the assistant editor of E-Commerce and SEO for The Pioneer Woman.
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