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!

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Cozy Knit Off-The-Shoulder A-Line Mini Dress in Heathergrey

$36.90

A heather grey knit mini dress with an off-the-shoulder neckline and A-line silhouette.

Windsor Sculpted Chic Ribbed Knit Midi Dress in Grey

$44.90

A grey ribbed knit midi dress featuring a sweetheart neckline with a twist accent and long sleeves.

Windsor Everyday Cute And Cool Denim Mini Dress in Grey

$52.90

A grey denim mini dress featuring a zip-up front, belted waist, and sleeveless collared neckline.

Windsor Preppy Edit Pinstripe Mini Dress in Grey

$49.90

A grey pinstripe mini dress in woven fabric featuring a strapless collared neckline and pleated hem.

Smoke And Mirrors Strappy Back Mid Dress in Grey

$49.90

A grey mesh midi dress featuring a draped cowl neckline, open strappy back, and bodycon fit.

Windsor Fierce Flirt Animal Print Mini Dress in Grey

$49.90

A grey animal print mini dress featuring a draped cowl neckline, halter straps, and layered ruffled hem.

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Senorita Mesh Strappy Mini Dress in Pink

$32.90

(92)

Look and feel like a sultry senorita in this mesh mini dress perfect for an chic night on the town! It features a sleeveless cowl neckline, dual adjustable spaghetti straps with a tie-neck closure, and side and back ruched seams designed to flaunt your curves along the bodycon silhouette. Complete the look with hoop earrings. Fit & FeaturesSleeveless cowl neckline, Dual adjustable spaghetti straps, tie-neck closure, Side and back ruched seams, Back zipper and hook-eye closure, Bodycon silhouette, mini-length hem, Mesh fabric, brushed soft knit stretchy lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Senorita Mesh Strappy Mini Dress in Pink | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric

Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Pink

$32.90

(86)

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: L | Knit Fabric/Satin Fabric

Windsor Lucy Taffeta Bow Mini Party Dress in White

$79.90

(72)

The Lucy mini party dress is sleek and simple from the front and stunning from the back. Turn heads as you stun from the back with a flirty big bow tie with a dramatic train that glides against the floor! Fit & FeaturesTaffeta structured woven-lined fabric, slight stretch, Strapless, square neckline, non-slip grip, Hidden side zipper, hook and eye closure, Front and back pleating and ruching, Form-hugging, mini-length hem, Detachable back bow with train, Runs true to size, Where to Wear:Homecoming, weddings, brides, bachelorettes, big birthday events, fancy date nights, gorgeous dinner parties, cocktail soirees, rehearsal dinners, engagement photoshoots and parties Free Shipping on All Orders Over $75. | Windsor Lucy Taffeta Bow Mini Party Dress in White | Size: XS

Windsor Cute Attitude Ponte Slit Mini Skort in Black

$27.90

(68)

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

Windsor Lena Strapless Bodycon Beaded Mesh Mini Dress in Black

$84.90

(61)

Express your devotion to romance in the Lena mesh mini dress perfect for modern brides, birthday girls, or graduates! The strapless cowl neckline adds a touch of elegance, while the bodycon fit accentuates your figure. Fit & FeaturesBeaded mesh fabric, stretchy knit lining, Strapless cowl neckline, Back zipper and hook-eye closure, Bodycon fit, mini-length hem, Runs true to size, Where to Wear:Prom, date nights, bachelorettes, girl's night out, birthdays Free Shipping on All Orders Over $75. | Windsor Lena Strapless Bodycon Beaded Mesh Mini Dress in Black | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric

Get Down With Basic Slit Mini Skirt in Black

$16.90

(54)

Minimal, but never boring. This sleek mini skirt brings the heat with a flirty slit and body-hugging fit made for going out or dressing up your everyday looks. Fit & FeaturesStretchy and smooth knit fabric, High-rise elasticized waistband, Mini-length hem, short front slit, Bodycon silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: M | Knit Fabric

Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Navy Blue

$35.90

(48)

Show off a flawless allure in this figure-flaunting mini dress! Designed with a sleek knit fabric with a fab sheen, this mini-length dress offers plenty of stretch so you can dance all night. The sleeveless bodice is shaped with a pleated cowl neckline for a chic draped effect and spaghetti straps. The pleating across the bodycon silhouette will accentuate your stunning curves. Style with metallic heels for a club night out.Fit & FeaturesStretchy sleek knit fabric, Sleeveless pleated cowl neckline, Spaghetti straps, Pleating, Bodycon fit, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Navy Blue | Size: L | Knit Fabric

Windsor Catalina Rhinestone And Pearl Formal Mini Dress in White

$69.90

(43)

Bling on the sultry glamour with the sparkling details of the stunning Catalina formal mini dress with a bodycon silhouette that will flaunt your gorgeous figure! Fit & FeaturesSheer mesh fabric, full-length knit lining, plenty of stretch, Mini iridescent rhinestones, faux pearl embellishments, Sleeveless cowl neckline, Adjustable spaghetti straps, Mini-length hem, bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, girl's night out, date nights Free Shipping on All Orders Over $75. | Windsor Catalina Rhinestone And Pearl Formal Mini Dress in White | Size: L | Knit Fabric/Rhinestone/Mesh Fabric

Stunning Sophistication Rhinestone Mini Dress in Wine

$42.90

(38)

Keep it sophisticated with a satin mini dress that radiates luxe. The dress features a sleeveless square neckline, detachable rhinestone embellished spaghetti straps, ruched side and back seams, and a form-hugging silhouette and mini-length hem. Complete look with rhinestone heels and a satin clutch. Fit & FeaturesSleeveless square neckline, Detachable rhinestone spaghetti straps, Ruched side and back seams, Form-hugging silhouette, Mini-length hem, Lined sleek satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Stunning Sophistication Rhinestone Mini Dress in Wine | Size: M | Rhinestone/Satin Fabric

Perfect Glow Strapless Pleat A-Line Satin Mini Dress in Gold

$39.90

(30)

You'll have that perfect glow in this satin mini dress at the party! This stunning mini-length dress features a strapless neckline for a classic style, and a side pleated seam adds a touch of sophistication and creates a flattering A-line silhouette. Complete the look with stiletto heels. Fit & FeaturesSatin fabric lined with stretchy knit, Strapless neckline, Side pleated seam, A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfect Glow Strapless Pleat A-Line Satin Mini Dress in Gold | Size: L | Satin 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.

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