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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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
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Social Butterfly Crochet Knit Mini Dress
Style up this adorable crochet knit mini dress for a casual party vibe! It features a sleeveless V-neckline with the cutest butterfly crochet embroidered design, spaghetti straps, a mini-length hem, and a form-hugging silhouette. The smooth knit fabric includes a full-length lining and offers plenty of stretch. Complete the look with hoop earrings and espadrille sandals.
Fit & Features
- Sleeveless V-neckline
- Butterfly crochet embroidered design
- Spaghetti straps
- Mini-length hem
- Form-hugging fit
- Knit fabric, full-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5065
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swept Off Your Feet Button Ruffle Maxi Dress
Oh-so-breezy! Sweep the room off their feet when you enter in this maxi dress featuring a sleeveless V-neckline, adjustable spaghetti straps, button-down front closures, and a flowy ruffled hem with a skin-flaunting front slit. The dress is composed of a smooth woven fabric with a sewn-in knit stretchy lining. Complete the look in espadrille wedges for a trip to the coast!
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Button-down front closures
- Front slit design
- Flowy ruffled maxi-length hem
- Smooth woven fabric, sewn-in knit stretchy lining
- Runs true to size
Style Number/Barcode: 05102-5061
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Date Night Allure Side Slit Midi Dress
Give off an enticing allure on your next date night in this sleek knit midi dress! It features a sleeveless square neckline, thin tank shoulder straps, an asymmetric midi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Complete the look with strappy stilettos.
Fit & Features
- Sleeveless square neckline
- Thin tank shoulder straps
- Asymmetric midi-length hem, high side slit
- Curve-hugging fit
- Knit fabric, full lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5057
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Encore Crepe Slit Maxi Dress
Prepare for a standing ovation whenever you're seen in this crepe maxi dress perfect for casual wine nights by the fire pit or a spring getaway! Featuring a sleeveless square neck, spaghetti straps, a curve-hugging silhouette, and a sultry high slit along the flowy long hem. Complete the look in cute flat sandals.
Fit & Features
- Sleeveless square neck, spaghetti straps
- Curve-hugging silhouette
- Front high slit
- Flowy maxi-length hem
- Crepe knit fabric, mini-length knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5058
Category Name: Casual Dresses
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Beauty Chiffon A-Line Midi Dress
Create a truly beautiful look for spring and summer weddings in this floral chiffon midi dress! The airy chiffon fabric showcases a blooming floral print and includes a stretchy knit lining for coverage. The tea-length dress is shaped with a sleeveless square neckline and adjustable spaghetti straps for a perfect customized fit. Smocking at the back provides added stretch and features a secure zipper closure. The fitted high waist seam flows out to a classic A-line silhouette with a front slit for extra movement. Style this pretty midi dress with sleek hoops and block heels.
Fit & Features
- Sheer chiffon fabric with stretchy knit lining, floral print
- Sleeveless square neckline, no-slip strip, adjustable spaghetti straps
- Stretchy smocked back, zipper with hook and eye closure
- High waist seam, front slit
- A-line silhouette
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05101-2356
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Mode Tropical V-Neck Midi Dress
Enter vacay mode with the perfect tropical midi dress that'll have you looking fabulous! It features a sleeveless V-neckline, adjustable spaghetti straps, a form-hugging silhouette, and a sultry side slit cutout. Complete the look in chic mules for a dinner by the beach!
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Form-hugging silhouette
- Side slit cutout, slit
- Midi-length hem
- Tropical palm leaf print, stretchy knit fabric, bust lining
- Runs true to size
Style Number/Barcode: 05102-5056
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirt With Confidence Strappy Back Midi Dress
Blow kisses to all of your admirors as you pass by in this chic one-shoulder midi dress! It features a wide shoulder strap and an asymmetrical strappy back design, a bodycon silhouette, and a center back slit accent on stretchy ribbed knit fabric. Complete the look with a sleek bracelet and clutch.
Fit & Features
- Sleeveless one-shoulder neckline
- Wide shoulder strap, asymmetrical strappy back design
- Bodycon silhouette
- Center back slit accent
- Midi-length hem
- Stretchy ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-5054
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Room To Grow Floral Cutout Midi Dress
You'll flourish this season in this fresh floral midi dress perfect for outdoor parties, family gatherings, and baby showers! The dress features adorable puff short sleeves, a sweetheart neck, a ruched bust seam with a cutout accent, a stretchy smocked back, and a flowy midi-length hem with a flirty side slit. Complete the look in platform wedges.
Fit & Features
- Puff short sleeves
- Sweetheart neck
- Ruched bust seam, stretchy smocked back
- Cutout accent
- Flowy midi-length hem, side slit
- Floral print, airy woven fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2358
Category Name: Casual Dresses
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacation Mode Tropical Print Maxi Dress
Activate vacation mode with this sultry tropical print maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, ruching down the side seam leading to an alluring thigh-high slit, an asymmetric maxi-length hem, and a bodycon silhouette that will hug your curves. The stretchy knit fabric features an all-over bold tropical palm leaf pattern. Style with strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross-back design
- Ruched side seam, high side slit
- Asymmetric maxi-length hem, bodycon silhouette
- Tropical palm leaf print
- Smooth knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5055
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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70s Groove Floral Tie-Back Skater Dress
Get into the groove of this 70s-inspired printed floral dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a flattering skater short-length silhouette. Complete the look in rhinestone mules for a dressy date!
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Tie-back design
- Skater silhouette
- Short-length hem
- 70s-inspired floral print
- Woven fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5053
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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The Perfect Basic Knit Mini Dress
This casual knit mini dress is the perfect basic for creating cute everyday 'fits! It features a V-neckline, short fitted sleeves, a mini-length hem, and a form-hugging fit. The cotton-blend fabric offers a moderate stretch. Style with hoop earrings and strappy mules.
Fit & Features
- V-neckline
- Short fitted sleeves
- Mini-length hem
- Form-hugging fit
- Cotton-blend smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5050
Category Name: Casual Dresses
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale