Grey Fall Dresses
Get ready to embrace the cozy vibes and crisp air with a collection of grey fall dresses that are as versatile as your autumn plans. Whether you're sipping on pumpkin spice lattes or taking in the vibrant foliage, these dresses are your go-to for effortlessly chic style. From brunch with the besties to a spontaneous road trip, our selection is here to make sure you slay every moment of the season. With shades that complement the moody skies and textures that wrap you in comfort, these grey fall dresses are all about turning heads and making memories. So go ahead, strut your stuff—because fall never looked so fabulous!
$48.90
A grey floral mesh midi dress featuring a V-notch neckline, ruched bust, and bodycon silhouette.
$21 $29.90 30% off
A charcoal plaid mini dress with sheer lace trims and a chic bow detail for date night.
$36.90
A cozy heather grey ribbed knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$25 $34.90 28% off
A grey plaid strapless mini dress with a pleated hem and form-hugging knit fabric.
$9.97 $42.90 77% off
A slate A-line mini dress with a V-neckline and ruffled hem in soft knit fabric.
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This adorable strapless A-line mini dress is so your vibe! Designed with a stretchy lined knit fabric, it features a strapless straight-across neckline, chic pleated detailing at the bust, and a flirty flowy A-line silhouette on the mini-length hem. Style for a girl's night with statement earrings and strappy mules. Fit & FeaturesStretchy knit fabric with knit lining, Strapless straight neckline, no-slip strip, Pleated bust, A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Your Vibe Strapless A-line Mini Dress in Light Blue | Size: L | Knit Fabric
Bring on the cute attitude in this ponte mini skort brings featuring a flattering high-rise waist, and a skirt overlay designed with dual front slits along the form-hugging fit. Fit & FeaturesSmooth ponte knit fabric, minimal stretch, High-rise waist, Skirt overlay, dual front slits, Form-hugging silhouette, Mini-length hem, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Attitude Ponte Slit Mini Skort in Black | Size: L | Knit Fabric
A fashionista like you will adore this basic mini skirt for creating your day and night looks! Featuring an elasticized high-rise waistband, bodycon silhouette, and a flirty front hem slit on stretchy and smooth knit fabric. Style with a corset top and heels. Fit & FeaturesHigh-rise elasticized waistband, Bodycon silhouette, Front hem slit, Mini-length hem, Stretchy and smooth knit fabric, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: XS | Knit Fabric
This satin mini dress will be your favorite for celebrations, events, and date nights! Sleek and smooth satin shapes this off-the-shoulder dress, which features a flattering A-line silhouette perfect for styling with heels. Fit & FeaturesSmooth and sleek satin fabric, stretchy knit lining, Off-the-shoulder neckline, Short sleeve cuffs, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Pink | Size: S | Knit Fabric/Satin Fabric
A true showstopper of a mini dress perfect for adding a touch of sparkle to any occasion. The short-length rhinestone dress features a square neckline and adjustable spaghetti straps, while the A-line silhouette flatters your figure down to the uneven-cut hem. Complete the look in platform sandals for a dressy night out! Fit & FeaturesSleeveless square neckline, Adjustable spaghetti straps, Back zipper and hook-eye closure, A-line silhouette, Mini-length hem, uneven cut design, Rhinestone-embellished, mesh fabric, stretchy knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sparkling Perfection Rhinestone A-Line Mini Dress in Pink | Size: XS | Knit Fabric/Rhinestone/Mesh Fabric
Capture all the attention with your sultry allure in the Paige rhinestone formal bodycon mini dress! She features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, all-over rhinestone embellishments for that total glam girl vibe, a mini-length hem, and a bodycon silhouette to hug your gorgeous curves. The slinky knit fabric offers plenty of stretch. Style this mini dress with metallic heels for your next dressy night out! Fit & FeaturesSleeveless cowl neckline, Adjustable spaghetti straps, All-over rhinestone embellishments, Mini-length hem, bodycon silhouette, Slinky knit fabric, full-length knit lining, plenty of stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Paige Rhinestone Formal Bodycon Mini Dress in Light Blue | Size: M | Knit Fabric/Rhinestone
This chic side slit knit mini skirt will give you a fabulous fit and become a favorite in your closet! The ponte knit fabric offers a structured fit with moderate stretch. The high waist features an elasticized waistband for comfortable wear, while the mini-length hem and side slit accent will give that sultry flair. The bodycon silhouette will hug your gorgeous curves. Style this mini skirt with a basic bodysuit and ankle booties for happy hour. Fit & FeaturesPonte knit fabric, moderate stretch, High-rise elasticized waist, Mini-length hem, Asymmetric seam, side slit, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fabulous Fit Side Slit Knit Mini Skirt in Black | Size: L | Knit Fabric
Windsor Brenda Low Back Bow Taffeta Skater Dress in Black
$19.97 $64.90
69% off
Chat, dance, and twirl the night away in the Brenda taffeta skater dress! The short dress is ready to party with a voluminous silhouette and a stunning low-cut back with a statement bow. Fit & FeaturesTaffeta fabric lined with tulle, stretchy knit fabric, Tank shoulder straps, Low back with bow, Skater silhouette, Short-length hem, Runs true to size, Where to Wear:Prom, brides, weddings, bridesmaids, fancy date nights, dinner parties, cocktail events Free Shipping on All Orders Over $75. | Windsor Brenda Low Back Bow Taffeta Skater Dress in Black | Size: XS | Knit Fabric
A sassy mini dress to slip on when the sun goes down and the beat is calling you to the dancefloor! This dress is featured in a sultry bodycon silhouette with a halter neckline accented with hoop inserts. Fit & FeaturesAbstract print, stretchy knit fabric, Cowl halter neckline, hoop accents, Bodycon silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sun Goes Down Halter Abstract Bodycon Mini Dress in Brown | Size: S | Knit Fabric
Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The ruched sides and ruffled hem add a playful touch to the bodycon silhouette. Fit & FeaturesDouble-lined brushed knit fabric, moderate stretch, Strapless straight neckline, Ruched side seams, Bodycon silhouette, Mini-length tiered ruffled hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Here Comes The Sun Strapless Ruffled Mini Dress in Brown | Size: S | Knit Fabric
Grey Fall Dresses
When it comes to leveling up your closet with pieces that look effortlessly cool and feel like a total power move, nothing hits quite like a gray fall dress. There’s just something about that shade—soft dove, deep charcoal, or those in-between smoky hues—that’s pure magic for those in-between days and nights. Grey is the ultimate neutral, but she’s never boring; she’s the friend who blends in when you need her to, but always brings a little edge. Whether you’re running from a coffee date to a late-night study sesh or plotting your next big adventure, a gray fall dress is that versatile staple you’ll reach for again and again. It’s the perfect canvas for layering: think chunky boots, a moto jacket slung over your shoulders, or a pop of color with your favorite mini bag. And if you’re into gifting, a gray fall dress is a total win. It’s the kind of pick-me-up your bestie will love unwrapping, especially when she’s on the hunt for something that works for literally every plan on her calendar. From brunches and birthday dinners to surprise road trips, these dresses are made for making memories and serving looks, all at once.
Choosing the right dress is all about finding what makes you feel like the main character. With windsor fall dresses, you’ve got options for every vibe. Maybe you’re all about that bodycon silhouette that shows off your confidence, or you’re vibing with a flowy midi that lets you twirl through your day without a care. Look for details that make you smile—like ruched sides, playful cutouts, or a little shimmer woven in. If you’re shopping for yourself (and honestly, you deserve it), think about where you’ll wear your new gray fall dress. Is it going to be your go-to for those spontaneous nights out, or are you looking for something cozy you can dress up or down? Layering is key, so pick a style that plays nice with your favorite jackets, scarves, and statement boots. And hey, if you’re building out your bestie’s closet, a gray fall dress is the ultimate “I got you” gift. She’ll love how easy it is to style, and every time she wears it, she’ll think of you hyping her up.
If you’re feeling inspired to keep the neutral party going, don’t sleep on adding deeper tones to your lineup. A brown dress is the perfect way to bring a little warmth and richness to your wardrobe, especially for those chillier days ahead. For more inspo on how to style those cozy vibes, check out our Brown Winter Dresses and keep your closet ready for every invite. No matter how you wear it, a gray fall dress is your secret weapon for turning any moment into a main event—so go ahead and let your confidence take the lead.