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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Casual Perfection Striped Tank Mini Dress
This adorable striped tank mini dress is the perfect casual style for a subtly elevated look! It features a sleeveless crew neckline, tank shoulder straps, a mini-length subtle curved hem, and a bodycon silhouette that offers a form-hugging fit. The striped ribbed knit fabric has plenty of stretch. Pair with strappy sandals.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Mini-length subtle curved hem
- Bodycon silhouette
- Striped print
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5102
Category Name: Casual Dresses
Price: $19.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mesh Well Square Neck Mini Dress
You and this mini dress will mesh well together! It features adorable sheer puff short sleeves with ruffle trim, a square neckline, a ruched bust and side seams, and a flattering bodycon silhouette. Complete the look with a statement choker for a family party!
Fit & Features
- Sheer puff short sleeves, ruffle trim
- Square neckline
- Ruched bust and side seams
- Bodycon silhouette
- Mini-length hem
- Mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5098
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Thing Off-The-Shoulder Mini Dress
Show your sweet side in this must-have mini dress for a stylish look at every event! It features an off-the-shoulder neckline, short sleeve cuffs, all-over ruching with an adjustable front drawstring, and a bodycon silhouette. The lined mesh fabric offers plenty of stretch. Complete the look in platform sandals.
Fit & Features
- Off-the-shoulder neckline
- Sheer short sleeve cuffs
- All-over ruching, adjustable front drawstring
- Bodycon silhouette
- Mini-length hem
- Sheer mesh fabric, knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-2399
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Girl Style Turtleneck Midi Dress
Elevate your fall wardrobe and show off a chic girl style with this bodycon midi dress! It features a sleeveless bodice, a turtleneck, a midi-length hem with a thigh-high side slit, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a layered chain necklace and ankle booties!
Fit & Features
- Sleeveless bodice
- Turtleneck
- Midi-length hem
- High side slit
- Bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5096
Category Name: Casual Dresses
Price: $17.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Easy Decision V-Neck Cutout Maxi Dress
A maxi dress you can style up or down? That's an easy decision! It features a sleeveless V-neckline, spaghetti straps, a knotted bust with cutout sides and back, and a hip-hugging slim silhouette with a sultry high-side slit on stretchy rib knit fabric. Complete the look in trendy sandals for a beach club or vacation!
Fit & Features
- Sleeveless V-neckline, knotted bust, spaghetti straps
- Side and back cutouts
- Hip-hugging, slim silhouette
- High side slit
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5094
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Showstopper Lace-Up Midi Dress
This midi dress is a casual showstopper! Make heads turn in this alluring dress featuring a sleeveless square neck, spaghetti straps that lace up in the back, a bodycon silhouette, and a fitted hem with a back-slit accent. Complete the look in dainty stiletto heels for a daytime celebration.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Lace-up back, lower zipper and hook-eye closure
- Bodycon silhouette
- Fitted midi-length hem, back slit
- Texture knit fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5095
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Revamp Zip-Front Mini Dress
This trendy zip-front mini dress will revamp your basic looks! It features a sleeveless mock neckline with a front zipper to style into a V-neckline, tank shoulder straps, a mini-length hem, and a bodycon silhouette that will hug your curves. The soft brushed knit fabric offers plenty of stretch. Style this mini dress with sneakers to keep it casual or mules for an elevated vibe!
Fit & Features
- Sleeveless mock neckline
- Zip-front design
- Tank shoulder straps
- Mini-length hem
- Bodycon fit
- Brushed knit fabric, full lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5092
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunkissed Beauty Tropical Print Cutout Maxi Dress
You'll be a stunning sunkissed beauty in this tropical print maxi dress that will give off alluring energy. It features a sleeveless asymmetric one-shoulder neckline with a single bungee spaghetti strap, a bold asymmetric side cutout at the waist with a chic O-ring accent, a hip-hugging fit, a sultry thigh-high side slit, and a floor-length hem. The smooth and stretchy knit fabric features an all-over tropical palm leaf print. Style with strappy sandals.
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Single bungee spaghetti strap
- Asymmetric side cutout at the waist, O-ring accent
- Hip-hugging fit, high side slit, floor-length hem
- Tropical palm leaf print
- Knit fabric, mini-length lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5091
Category Name: Casual Dresses
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Miami Mood Tropical Print Cutout Maxi Dress
This alluring tropical print maxi dress is an iconic pick for a summer vacay to Miami! It features a sleeveless halter neckline with cross-front straps, a sultry center bust cutout followed by a chic O-ring accent, dual waist cutouts on each side, a backless design with dual tie-back straps, a floor-length hem with dual thigh-high front slits, and a flowy A-line silhouette. The lightweight woven fabric showcases an all-over tropical palm leaf pattern. Style with hoop earrings and clear mules.
Fit & Features
- Sleeveless halter neckline, cross-front straps, tie-back design
- Center bust cutout, O-ring accent, dual waist cutouts
- Backless design, dual tie-back straps, elasticized back waistband
- Floor-length hem, dual high front slits, A-line silhouette
- Tropical palm leaf print
- Woven fabric, lined bust, no stretch
- Runs true to size
Style Number/Barcode: 05102-5087
Category Name: Casual Dresses
Price: $5.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Way With Lace V-Neck Mini Dress
Let this lace mini dress speak your favorite language, romance! The short dress features a sleeveless V-neckline, spaghetti straps, a bodycon silhouette, and a sheer lace overlay with a sewn-knit lining. Complete the look in rhinestone mules for a wedding shower or birthday brunch!
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Sheer lace overlay, sewn-in knit lining
- Minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5088
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Fave Ribbed Knit Mini Dress
This basic casual ribbed knit mini dress will be a new fave for the season! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a mini-length hem, and a form-hugging silhouette. The lightweight ribbed knit fabric offers plenty of stretch. Style with a denim jacket and sandals for a cute everyday vibe.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Mini-length hem
- Form-hugging bodycon fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5086
Category Name: Casual Dresses
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Slice Of Summer V-Neck Tank Maxi Dress
Break yourself off a slice of this summer-ready rib knit maxi dress you'll love taking on vacation or around town! It features a sleeveless plunge V-neckline, tank shoulder straps, a form-hugging slim silhouette, and a sexy high-side slit. Complete the look with statement earrings and sandals.
Fit & Features
- Sleeveless plunge V-neckline
- Tank shoulder straps
- Form-hugging, slim silhouette
- High side slit
- Maxi-length hem
- Soft and stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5080
Category Name: Casual Dresses
Price: $5.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Basic Crew Neck Tank Mini Dress
A sweet basic mini dress for all your styling needs this season! It features a sleeveless crew neckline, a bodycon silhouette, and a mini-length fitted hem on smooth and stretchy knit fabric. Complete the look with trendy sunglasses and sandals for a trip to the farmer's market!
Fit & Features
- Sleeveless crew neckline
- Bodycon silhouette
- Mini-length fitted hem
- Smooth and stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5079
Category Name: Casual Dresses
Price: $5.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Stylish Ribbed Knit Midi Dress
This simple yet chic ribbed knit midi dress is the casually stylish staple you need. It features a sleeveless scoop neckline, thin tank shoulder straps, a midi-length hem, and a curve-hugging silhouette. The lined knit fabric offers plenty of stretch. Complete the look with a denim jacket and clear mules.
Fit & Features
- Sleeveless scoop neckline
- Thin tank shoulder straps
- Midi-length hem
- Form-hugging fit
- Lined ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5077
Category Name: Casual Dresses
Price: $5.97 $23.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Chic Cutout Midi Sweater Dress
Create the perfect casual chic look with this of-the-moment sweater dress. It features a sleeveless scoop neckline with contrast piping, thin tank shoulder straps, a front waist cutout with matching contrast piping, a midi-length hem with a front slit, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Style with clear mules.
Fit & Features
- Sleeveless scoop neckline, contrast piping
- Thin tank shoulder straps
- Front waist cutout, contrast piping
- Midi-length hem, front slit
- Curve-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1700
Category Name: Casual Dresses
Price: $44.90
Availability: Out of Stock
Product Badge:- Clearance
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Wild And Chic Zebra Print Mini Sweater Dress
Add a wild flair to your everyday look with this chic zebra print sweater dress. It features a sleeveless V-neckline, halter straps with a tie-back design, an open back, a mini-length hem, and a curve-hugging fit. The sweater knit fabric offers a moderate stretch. Style with a mini handbag and clear mules for a fashion-forward look.
Fit & Features
- Sleeveless V-neckline
- Halter straps, tie-back design
- Open back
- Mini-length hem
- Curve-hugging silhouette
- Zebra print, sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1699
Category Name: Casual Dresses
Price: $3.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rendezvous In Satin Slip Midi Dress
Have a chic rendezvous in this satin slip midi dress featuring a sleeveless V-neck, bungee spaghetti straps, a fitted a-line silhouette, and a sultry front slit along the hem. The dress is composed of smooth, non-stretch satin fabric. Complete the look in lace-up stiletto heels.
Fit & Features
- Sleeveless V-neck
- Bungee spaghetti straps
- Fitted a-line silhouette
- Front slit
- Midi-length hem
- Non-stretch woven satin fabric
- Runs true to size
Style Number/Barcode: 05101-2383
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Subtle Love Ditsy Floral Mini Dress
Effortlessly cute with subtle detail, what's not to love about this ditsy floral mini dress? It features a sleeveless V-neckline with a ruched bust seam, spaghetti straps, and a bodycon silhouette. Complete the look in trendy flat sandals for a brunch.
Fit & Features
- Sleeveless V-neckline, ruched bust seam
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Ditsy floral print
- Ribbed stretchy knit fabric, knit lining
- Runs true to size
Style Number/Barcode: 05102-5073
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smooth Essential Square Neck Mini Dress
A sleek and smooth mini dress a fashionista such as yourself will adore styling up or down! It features a sleeveless square neckline, spaghetti straps, and a bodycon silhouette. The dress is composed of a smooth, double-lined knit fabric with a moderate stretch. Complete the look in statement heels and jewelry.
Fit & Features
- Sleeveless square neckline, spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Smooth, double-lined knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5071
Category Name: Casual Dresses
Price: $5.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Fun Chain Strap Midi Dress
Perfect for your next getaway, this tropical midi dress is a must to pack in your carry-on! It features a sleeveless square neck, half chain and adjustable spaghetti straps, a bodycon silhouette, and a flirty side slit. the dress is composed of a tropical print slinky-knit fabric with a sewn-in knit lining. Complete the look in heeled sandals.
Fit & Features
- Sleeveless square neck
- Half chain, adjustable spaghetti straps
- Bodycon silhouette
- Side slit, midi-length hem
- Tropical print
- Slinky knit fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5070
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Paradise Lost Halter Cutout Midi Dress
Escape to paradise in this halter midi dress that'll make everyone lose their train of thought! It features a sleeveless halter neckline with tie-back straps, a center O-ring insert and cutout bodice, and a flattering bodycon silhouette with a side slit hem. The brushed knit fabric offers plenty of stretch. Complete the look in bold hoop earrings.
Fit & Features
- Sleeveless halter neckline, tie-back straps
- Center O-ring insert, cutout bodice
- Bodycon silhouette
- Side slit, midi-length hem
- Partially lined brushed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5068
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Iconic Moment A-Line Mini Dress
Step out in this iconic little black dress for many chic moments of the night! The dress features a sleeveless V-neckline, spaghetti straps, a flattering A-line silhouette, and a mini-length hem on slinky knit fabric. Complete the look in lace-up heels for a date night!
Fit & Features
- Sleeveless V-neckline, spaghetti straps
- A-line silhouette
- Mini-length hem
- Slinky knit fabric, knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5066
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Nautical Vibes Striped Mini Dress
Elevate your summer style and give off chic nautical vibes in this striped mini dress! It features a sleeveless scoop neckline, spaghetti straps, a faux wrap waist design with a tie-front detail, a mini-length hem, and a form-hugging fit. The stretchy brushed knit fabric features an all-over horizontal striped pattern. Complete the look with espadrille sandals for a beachside brunch!
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Faux wrap waist design, tie-front detail
- Mini-length hem, form-hugging fit
- Horizontal striped print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5067
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darling Twirl Crepe Ruffle Skater Dress
Delight with your darling twirls in this crepe skater dress perfect for family parties or brunch! It features adorable puff short sleeves, a V-neckline, and a ruffled layered short-length hem with a fit-and-flare silhouette. Complete the look in this skater dress with sleek hoop earrings.
Fit & Features
- Puff short sleeves
- V-neckline
- Back zipper and hook-eye closure
- Skater silhouette
- Ruffled layered short-length hem
- Crepe fabric, partial stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5064
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale