Women's Fall Midi Dresses

Women's Fall Midi Dresses are here to turn every sidewalk into your personal runway. It’s all about those effortlessly chic vibes that have you feeling like the main character, whether you’re headed to brunch, date night, or just showing up and showing out. Get ready to serve looks with midi dresses that are equal parts flirty and fearless—because you deserve a wardrobe that keeps up with your boldest moves. Let’s make every day a little extra and every moment unforgettable.

Show Filters

Sort: Recommended

Size

Color

Price

All Filters

27 results

Sort

Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in White

$38.90

A white sleeveless ribbed knit midi dress with a V-neckline and chic high front slit.

Windsor Laina High Slit Satin Midi Dress in Green

$59.90

A green satin midi dress featuring a cowl neckline, pleated bodice, high slit, and twist-back detail.

Sale

Windsor Romance In Bloom Floral Ruffle Slit Midi Dress in Green

$37 $52.90 30% off

A green floral strapless midi dress featuring ruffle trim, a high front slit, and airy woven fabric.

Sale

Windsor RSVP Ready Halter Midi Dress in Black

$9.97 $38.90 74% off

A sleek black knit bodycon midi dress featuring a halter sweetheart neckline and tie closure.

Windsor Margaret Formal Satin Wrap Midi Dress in Navy Blue

$59.90

A navy blue satin wrap midi dress with a cowl neckline and adjustable spaghetti straps.

Now Trending

Garden Party Goals Floral Corset A-Line Midi Dress in Ivory

$64.90

(12)

Giving cottagecore but make it glam. With a structured corset bodice and floaty A-line skirt, this floral midi dress is ready for twirls, tea dates, and compliments. Fit & FeaturesWatercolor floral print, Cotton woven fabric, multiple woven and tulle linings, Sweetheart neckline, adjustable spaghetti straps, Corset bodice, flexible boning, side zipper and hook-eye closure, Lace-up, stretchy smocked back design, Voluminous A-line silhouette, midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Garden Party Goals Floral Corset A-Line Midi Dress in Ivory | Size: M | Cotton/Woven Fabric

Flirty Agenda Floral Mesh Off-The-Shoulder Midi Dress in Mauve

$52.90

(4)

If the group chat says “dress up,” this is the one you’re sending a mirror pic in. This floral mesh midi dress smooths and sculpts with ruched detailing, while the off-the-shoulder sweetheart neckline keeps it flirty enough for weddings, cocktail plans, and every “dress cute” invite on your calendar. Fit & FeaturesSheer mesh fabric with full-length knit lining, high stretch, Floral print, Sweetheart neckline, off-the-shoulder straps, Ruched detailing, Back zipper closure, Midi-length flared hem, form-hugging silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirty Agenda Floral Mesh Off-The-Shoulder Midi Dress in Mauve | Size: XS | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric

Sale

Love Me Wild Leopard Floral Midi Dress

$19.97 $42.90
53% off

(4)

Romantic meets rebellious in this strapless mesh midi dress. The mix of leopard print and rose florals brings the drama, while the ruched fit and cascading sash keep it flirty and femme. It’s giving soft power with a wild twist. Fit & FeaturesLeopard and floral print, mesh-lined fabric, Strapless neckline, padded bra cups, Side ruffle sash, draped waist accent, Form-hugging fit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Love Me Wild Leopard Floral Midi Dress | Size: XS | Mesh Fabric

Romance Rewritten Off Shoulder Floral Midi Dress in Taupe

$49.90

(4)

This off-shoulder floral dress hugs your curves with ruched seams and a bodycon fit made for garden parties or shower celebrations! Fit & FeaturesFloral print, mesh-lined fabric, moderate stretch, Off-the-shoulder sweetheart neckline, Padded bra cups, Short-sleeve cuffs, back zipper and hook-eye closure, Ruched bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Romance Rewritten Off Shoulder Floral Midi Dress in Taupe | Size: XL

My Cute Side Tie-Back Floral Eyelet Midi Dress in White

$59.90

(4)

Take a ride on the cute side in this floral eyelet midi dress perfect for shower celebrations, brunch, or graduations! The whimsical tie-back design perfectly complements the ruffled A-line silhouette, making you feel feminine and enchanting. Fit & FeaturesFloral print, eyelet fabric, stretchy knit lining, Square neckline, Adjustable spaghetti straps, Tie-back design, A-line silhouette, ruffled, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor My Cute Side Tie-Back Floral Eyelet Midi Dress in White | Size: XXS | Knit Fabric

Sale

Romance In Bloom Floral Ruffle Slit Midi Dress in Green

$37 $52.90
30% off

(2)

She’s giving romance with a side of sass. This strapless midi stuns with flirty ruffle trim and a high front slit—aka your new fave for shower celebrations and dressy brunches! Fit & FeaturesFloral print, airy woven fabric, stretchy knit lining, Strapless sweetheart neckline, twist bust accent, Hidden side zipper and hook-eye closure, Curve-hugging silhouette, High front ruffled trim slit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Romance In Bloom Floral Ruffle Slit Midi Dress in Green | Size: S | Knit Fabric/Woven Fabric

Windsor Modern Romance Floral Midi Dress in Ivory

$44.90

(2)

Floaty, flattering, and quietly stunning. This floral midi dress features a V-neckline, slim straps, and a front slit that adds just enough movement for dinners, weddings, and everything in between. Fit & FeaturesGarden floral print, knit-lined fabric, V-neckline, Spaghetti straps, Front slit accent, Form-hugging midi silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Modern Romance Floral Midi Dress in Ivory | Size: L

Windsor Easy Romance Strapless Floral Midi Dress in White

$44.90

(2)

Light, flowy, and quietly striking. This strapless floral mesh midi dress features a body-skimming fit with an asymmetrical ruffle hem that adds movement and charm to bridal celebrations, birthday brunches, or dates! Fit & FeaturesFloral print, mesh-lined fabric, Strapless neckline, Form-hugging silhouette, Asymmetrical ruffle trim midi hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Easy Romance Strapless Floral Midi Dress in White | Size: L | Mesh Fabric

Floral Whispers Off-The-Shoulder Midi Dress in Green

$46.90

(1)

A floral moment worth remembering. This off-shoulder midi dress flatters with a ruched body, draped sleeves, and a side slit that shows just enough—perfect for weddings, date nights, and every romantic plan in between. Fit & FeaturesFloral print, smooth knit stretch fabric, Off-the-shoulder neckline, Short-sleeve cuffs, Front slit design, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Floral Whispers Off-The-Shoulder Midi Dress in Green | Size: XS | Knit Fabric

Day Date Floral Print Puff Sleeve Midi Dress in White Print

$64.90

Effortless plans, elevated instantly. This floral print midi dress brings that easy, cinched-in fit with a pretty, flowy feel—perfect for brunch dates, garden parties, and everything in between. Fit & FeaturesCotton-blend fabric with lining, Floral print, Square neckline, ruched bust, Short puff sleeves with cinched hems, V-shaped waist seam, stretchy smocked back, Midi-length flowy A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Day Date Floral Print Puff Sleeve Midi Dress in White Print | Size: L | Cotton

Women's Fall Midi Dresses

There’s something about fall midi dresses that just gets it—the way they capture that in-between mood when the air is crisp but not quite cold, and your calendar is suddenly stacked with everything from coffee dates to late-night dinners. These are the dresses you reach for when you want to look effortless but pulled together, whether you’re heading to work, meeting friends for brunch, or just running errands with a little extra flair. Midi lengths hit that sweet spot: long enough for a bit of drama, short enough to keep things playful, and versatile enough to pair with ankle boots, sneakers, or whatever shoes you’re obsessed with this season. They’re the unsung heroes of transitional dressing, handling everything from those unpredictable early fall breezes to the inevitable “should I bring a jacket?” debate. And let’s be real—there’s a certain magic in finding a dress that works just as well layered under a chunky cardigan as it does solo with a statement belt. If you’re shopping for yourself, think about how these dresses can flex with your schedule: a midi with sleeves for chilly mornings, a sleeveless style for those random warm afternoons, or a wrap silhouette that flatters every curve and feels like a little confidence boost every time you slip it on.

Midi dresses aren’t just a smart choice for your own closet—they’re also a go-to gift for anyone who loves fashion but hates fuss. They’re the kind of present that says, “I know you, and I know you want to look good without overthinking it.” Think of your sister who’s always on the hunt for something new to wear to the office, your best friend planning a fall getaway, or your mom who appreciates a dress that can go from lunch to happy hour without missing a beat. With so many prints, textures, and necklines to choose from, you can easily find a style that fits their vibe—whether that’s classic and understated or bold and trend-forward. And if you’re feeling stuck, you can never go wrong with a timeless black midi. It’s the ultimate blank canvas: dress it up with gold jewelry and strappy heels for a night out, or keep it casual with a denim jacket and sneakers for daytime plans. If you’re ready to explore the endless ways to style this wardrobe MVP, check out our curated collection of Womens Black Midi Dresses for inspiration that goes beyond the basics.

When it comes to choosing the perfect fall midi dress, it’s all about balancing comfort, versatility, and those little details that make you feel like you’ve got your life together—even on the days you definitely don’t. Look for fabrics that move with you: think ribbed knits for cozy vibes, silky satins for a touch of luxe, or lightweight chiffon for a bit of romance. Don’t underestimate the power of a good print—florals, plaids, and abstract patterns can instantly elevate your look and make even the simplest outfit feel intentional. And if you live for those “where did you get that?” compliments, keep an eye out for unexpected touches like puff sleeves, cutouts, or a subtle slit that adds just enough edge. The best part? Midi dresses are made for layering, so you can keep wearing your favorites long after the leaves start to fall. Throw on a leather jacket when the temperature drops, swap sandals for boots, or add tights and a scarf for extra warmth without sacrificing style. Whether you’re refreshing your own wardrobe or picking out a gift that’s guaranteed to get worn on repeat, fall midi dresses are the answer to that “what do I even wear?” panic—season after season, occasion after occasion.

Reset Your Password

Email Sent

Order Status

Women's Fall Midi Dresses

Home Women's Fall Midi Dresses

Now Trending

Women's Fall Midi Dresses

Related Collections