Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on your calendar.
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Casual Dresses Made for Everyday Fall Plans
Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.
Easy Prints, Textures & Layers for the Season
Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.
What Makes a Dress Casual?
A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.
How Do You Transition a Casual Dress From Summer to Fall?
Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.
Which Fabrics Work Best for Everyday Dresses?
Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.
How Can You Style One Casual Dress for Different Plans?
Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.
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Bare It Boldly Open Back Mini Dress
Who knew soft could look this hot? This mini dress brings the drama with a low back cutout, halter neckline, and curve-hugging silhouette. Whether you're headed to dinner or turning heads at a party, this fit's got the bold factor locked.
Fit & Features
- Soft knit fabric with stretchy lining
- Scoop halter neckline with attached long sleeves
- Underwire bust design
- Open back cutout with adjustable halter tie
- Asymmetrical shark bite hem
- Runs true to size
Style Number/Barcode: 05102-000403
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Details Ponte Mini Dress
Structured, sleek, and a little daring. This ponte mini dress showcases chic details with its asymmetric mock neckline, knotted closures, and side slit detailing.
Fit & Features
- Smooth ponte knit fabric, minimal stretch
- Asymmetric mock neckline, short cap sleeves
- Knotted closures along the front
- Back zipper closure
- Form-hugging fit
- Side slit detail, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000406
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy And Captivating Bodycon Mini Dress
All eyes on you. This off-the-shoulder ribbed mini dress hugs every curve in soft, stretchy knit with a foldover neckline that adds just the right amount of flirt. The long sleeves balance the bodycon fit for a look that’s equal parts cozy and captivating.
Fit & Features
- Soft rib knit stretch fabric
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000405
Category Name: Casual Dresses
Price: $18.97 $42.90
On Sale: Yes
Availability: Out of Stock
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So Alluring Off-The-Shoulder Cutout Midi Dress
Dinner plans, last call, encore moment—this dress says yes to all of it. The off-the-shoulder neckline and front cutout keep things confident, elevated, and unforgettable.
Fit & Features
- Textured ribbed knit fabric, high stretch
- Off-the-shoulder neckline
- Long fitted sleeves
- Front cutout with hardware button details
- Bodycon silhouette
- Midi-length hem, high-cut side slit
- Runs true to size
Style Number/Barcode: 06005-000279
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
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- Textured ribbed knit fabric, high stretch
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Esmerelda Denim Rhinestone Bodycon Mini Dress
Special Occasion
Built for that slow-motion entrance, this denim bodycon mini dress catches the light with every step thanks to its rhinestone-studded corset design. Luxe structure meets after-dark sparkle, giving you a look that feels polished, powerful, and impossible to forget.
Fit & Features
- Denim fabric with allover rhinestone embellishment
- Strapless neckline with structured corset bodice, flexible boning
- Back zipper and hook-eye closure
- Front pockets for convenience
- Bodycon mini silhouette
- Runs true to size
Where to Wear:
GNO, bachelorettes, date nights, birthdays, holiday parties
Style Number/Barcode: 05001-000634
Category Name: Casual Dresses
Price: $19.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep Them Curious Tie Back Mini Dress
This dress keeps it minimal from the front and magnetic from the back—the open cut and tie detail gives just enough drama while the rib knit smooths everything into place. It’s an easy yes for plans when simple feels the sexiest.
Fit & Features
- Rib knit fabric with subtle texture
- Boat neckline with long fitted sleeves and flared cuffs
- Bodycon silhouette through the bodice and skirt
- Open back design with wide band and tie-back closure
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000402
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Bloom Cowl Halter Maxi Dress
Bold print, barely-there feel perfect for vacations. This maxi dress blends leopard and tropical florals with a plunging cowl halter and open back, finished with a statement floral hardware that stands out.
Fit & Features
- Tropical floral and leopard print
- Sheer mesh fabric, soft knit short lining
- Plunge cowl halter neckline
- Open back, lower ruched seam
- Front tropical floral hardware piece
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000401
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love At First Glance Long Sleeve Bodycon Mini Dress
This one knows exactly what it’s doing. A long sleeve bodycon mini dress with a scoop neckline and button cutout that hugs close, highlights just enough, and feels made for date nights and Valentine’s plans.
Fit & Features
- Textured stretch knit fabric
- Scoop neckline
- Fitted long sleeves
- Front cutout detail
- Decorative button accents
- Mini length hem
- Runs true to size
Style Number/Barcode: 06005-000276
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Focus Moment Ribbed Knit Midi Dress
Soft curves, no effort. This ribbed knit midi dress hugs just right with a bodycon fit that moves from dinner plans to late-night photos without missing a beat.
Fit & Features
- Soft rib knit fabric, sewn-in stretch lining
- Sweetheart neckline with twisted bust detail
- Spaghetti straps
- Fitted bodice through the waist
- Bodycon silhouette through the hips
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000397
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Snug Cable Knit Mini Dress
Cozy meets curve-hugging. This cable knit mini brings that soft, flirty energy with a foldover off-the-shoulder neckline and bell sleeves for extra charm. Perfect for date nights in or dressing up your coffee run fit.
Fit & Features
- Soft cable knit fabric, stretch knit lining
- Foldover off-the-shoulder neckline
- Long bell sleeves
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000395
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Can’t Resist Off-The-Shoulder Mini Dress
A little cozy, a little flirty—this rib knit mini dress does both. Designed with a foldover off-the-shoulder neckline, ruched sides, and a soft front drape that flatters every curve, it’s your go-to for coffee dates, casual dinners, or weekend chic plans.
Fit & Features
- Soft rib knit fabric lined with stretch knit
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Side ruched seams
- Front drape accent, bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000396
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Glow Floral Mesh Bodycon Mini Dress
Sun-kissed and ready to steal the scene, this floral mesh mini dress brings that radiant, vacation-glow confidence. The soft bodycon fit hugs just right, with a halter plunge neckline and a draped sash that make your arrival feel effortlessly iconic.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch, large floral print
- Sleeveless plunging V-neckline
- Tie-back halter straps, partially open back
- Ruched waist, asymmetric metal hardware accent
- Ruffled side sash
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000392
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Untamed Glam Mesh Maxi Dress
For nights when subtle just isn’t in your vocabulary, this mesh maxi dress delivers full-throttle confidence. The abstract animal print, plunging neckline, and hardware detail hit that perfect mix of daring and glam, while the bodycon fit keeps the silhouette sleek and unforgettable.
Fit & Features
- Abstract animal print, mesh fabric, short knit lining
- Plunging neckline with hardware detail
- Fitted long sleeves
- Bodycon maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000391
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Attraction Cowl Neck Maxi Dress
Serving curves with a side of attitude. This leopard print mesh cowl neck maxi dress drapes just right with an open back and hardware detail that makes every step feel a little extra.
Fit & Features
- Leopard print, mesh fabric, knit lining
- Plunge cowl neck halter neckline, hardware insert
- Open back
- Curve-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000393
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bare It Bold Halter Mini Dress
This one doesn’t wait for an invite. A barely-there halter with bold cutouts and an O ring detail that knows exactly what it’s doing—made for warm destinations and sunset dinners.
Fit & Features
- Soft ribbed fabric with a slinky feel
- Triangle halter neckline with tie straps
- O ring center with waist cutout detail
- Mini-length skirt with ruffle hem
- Runs true to size
Style Number/Barcode: 05102-000389
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: OLIVE
Available Size: XS
Product Badge:- Sale
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Flirty Escape Paisley Floral Dress
Light, flowy, and a little flirty, the open tie-back moment on this floral paisley dress keeps things interesting from every angle. It’s giving easy confidence with just enough detail to make them look twice.
Fit & Features
- Paisley floral print fabric
- Halter V-neckline, tie straps
- Open tie-back design
- Flowy skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000384
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: OLIVE
Available Size: S, M, L
Product Badge:- Sale
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Daylight Darling Eyelet Dress
This dress feels like sunshine plans waiting to happen. A knit eyelet skater dress with a scoop neckline and tie-back detail that brings the flirty flair to every plan.
Fit & Features
- Eyelet knit fabric
- Scoop neckline
- Spaghetti straps
- Tie-back design
- Layered ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000383
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wander Off Tie Back Skater Dress
This paisley skater dress flows effortlessly with a halter V-neckline and an open tie back that feels easy, breezy, and effortlessly styles with sandals for sun-soaked days.
Fit & Features
- Paisley print, airy woven fabric
- Halter V-neckline with tie straps
- Open tie-back design
- Flowy skater silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000380
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Brunch Crush Eyelet Skater Dress
Caught feelings for this one instantly. This eyelet knit skater dress hugs through the bodice, then flares into the prettiest mini, made for brunch dates, grad pics, and those “just stepped out” kind of days.
Fit & Features
- Eyelet knit fabric with knit lining, moderate stretch
- Sleeveless square neckline
- Princess seams
- Adjustable spaghetti straps
- Mini-length hem
- Skater silhouette, godet detailing
- Runs true to size
Style Number/Barcode: 05102-000381
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Back To Bold Mock Neck Mini Dress
Minimal from the front, major from the back. This mini dress offers a bold cutout back with hoop accents and a bodycon fit that turns heads and gives your rotation a trendy upgrade.
Fit & Features
- Ribbed knit fabric with stretch
- Mock neckline with fitted long sleeves
- Sleek bodycon silhouette through the bodice
- Open-back cutout detail with a detachable hoop chain accent
- Mini-length skirt with a front side slit
- Runs true to size
Style Number/Barcode: 06005-000261
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Luxe Moments Removable Faux Fur Mini Dress
Giving retro glam with a cozy twist, this ribbed mini dress brings major soft-lux vibes. The faux fur collar and cuffs add effortless drama, making it the perfect piece for chilly nights when you still want to look very put together.
Fit & Features
- Rib knit fabric
- Deep V neckline with a removable faux fur collar
- Long sleeves with removable faux fur cuffs
- Front button-down design for adjustable coverage
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000378
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Vibes Geometric Knit Halter Mini Dress
Meet the mini dress that knows how to make an entrance without trying too hard. The geometric knit hugs just right, giving you that effortless, sculpted look for beach nights, rooftop drinks, and the best vacay vibes.
Fit & Features
- Sheer embroidered knit fabric, knit lining, high stretch
- Abstract geometric pattern, metallic woven threading
- Sleeveless V-neckline
- Tie-back halter straps, partially open back
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000377
Category Name: Casual Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fierce Instinct Lace-Up Romper
Unleash your wild side—this lace-up romper stuns with its bold animal print and flirty tiered skirt. The fitted bodice and strappy details keep the look daring, playful, and perfect for a night out.
Fit & Features
- Animal print, knit fabric
- Sweetheart neckline with lace-up front
- Adjustable spaghetti straps
- Tiered mini skirt with flared hem
- Shorts lining
- Runs true to size
Style Number/Barcode: 06503-000201
Category Name: Casual Dresses
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Babe Bow And Floral Print Skater Dress
Soft florals, sweet bows, and a neckline made to flatter—this one feels instantly charming. The V-shaped drop waist and flutter sleeves keep it light, feminine, and perfect for brunch plans, daytime dates, and photo ops.
Fit & Features
- Poplin woven fabric, delicate lace trim detailing
- Bow and floral print
- Flattering V-neckline
- Short flutter sleeves
- Button-down front, V-shaped drop waist
- Short skater silhouette, pleated detailing
- Runs true to size
Style Number/Barcode: 05101-000768
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free