Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and 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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Sweetest Style Eyelet Knit Mini Dress
Show off the sweetest style in this adorable eyelet knit mini dress. It features a sleeveless sweetheart neckline with a knot-front design at the bust, spaghetti straps, a mini-length hem, a form-hugging fit, and a dainty floral eyelet pattern. The lined knit fabric offers plenty of stretch. Complete your look with espadrille sandals for a weekend date.
Fit & Features
- Sleeveless sweetheart neckline, knot-front design
- Spaghetti straps
- Mini-length hem
- Form-hugging fit
- Floral eyelet pattern
- Lined knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4969
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keep It Cool Crew Neck Mini Dress
Keep it cool and casual in this effortless knit mini dress for hangs with friends! It features short sleeves, a crew neck, a bodycon silhouette, and a ruched drawstring that lets you customize the style. The dress is composed of a stretchy brushed knit fabric. Complete the look in cute flat sandals.
Fit & Features
- Short sleeve, crew neck
- Bodycon silhouette
- Ruched, adjustable drawstring
- Bodycon silhouette
- Mini-length hem
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4856
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Allure Polka Dot Mesh Mini Dress
Show off a flirty allure in this adorable polka dot mesh mini dress. It features a square neckline, short puff sleeves with ruffled trims, an open back with a chic bow tie-back design, ruching down the side seams, a mini-length hem, and a curve-hugging silhouette. The sheer mesh polka dot patterned fabric includes a partial knit lining. Style with platform heels for a fresh date look!
Fit & Features
- Square neckline
- Short puff sleeves, ruffled trims, elasticized hems
- Open back, bow tie-back design
- Ruched side seams, lower back zipper, hook and eye closure
- Mini-length hem, bodycon fit
- Sheer mesh fabric, polka dot pattern, partial knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5133
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Everyday Slay Ribbed Knit Midi Dress
Showcase an everyday slay in this curve-hugging midi dress! It features a sleeveless square neckline, spaghetti straps, an open back with a double strap design, a midi-length hem with a bodycon silhouette, and a thigh-high side slit for a sultry accent. The ribbed knit fabric offers plenty of stretch. Style with clear mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open back, double strap design, tie closure
- Midi-length hem, bodycon silhouette
- High side slit
- Ribbed knit fabric, lining at the bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4770
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute View Ditsy Floral Chiffon Skater Dress
You'll be a cute view in this ditsy floral chiffon dress at casual family parties or weekend getaways! It features puff short sleeves, a sweetheart neck, a front bust ruched drawstring, a stretchy smocked back, and a skater silhouette with a short-length hem. The dress is composed of a chiffon fabric with a ditsy floral print and a stretchy knit lining. Complete the look in trendy sandals.
Fit & Features
- Puff short sleeves, elastic ruffled hems
- Sweetheart neckline
- Front bust ruched drawstring
- Stretchy smocked back
- Skater silhouette, short-length hem
- Ditsy floral print, chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5022
Category Name: Casual Dresses
Price: $5.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Endless Sunshine Linen Tie-Back Midi Dress
For the sun-soaked days ahead, this linen midi dress will make a cute companion! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back closure, and a flowy ruffled hem. Style with trendy sandals and sunglasses.
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Tie-back closure
- Flowy ruffled midi hem
- Airy linen fabric, slight stretch
- Runs true to size
Style Number/Barcode: 05102-5012
Category Name: Casual Dresses
Price: $5.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Garden Walks Ditsy Floral Chiffon Dress
For your walks through garden parties or outdoor weddings, this ditsy floral chiffon dress brings the charm! It features a sleeveless sweetheart neck, adjustable spaghetti straps with ruffle trim, a skater silhouette, and a flirty lace-up back with tie closure and a ruffled short-length hem. Complete the look in statement heeled mules.
Fit & Features
- Sleeveless sweetheart neck
- Adjustable spaghetti straps, ruffle trim
- Skater silhouette
- Lace-up back, tie closure
- Ruffled short-length hem
- Ditsy floral print, chiffon fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05101-2347
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pleated Princess Bow Back Skater Dress
Look and feel like a princess in this skater dress for cocktail wedding showers or graduation parties! It features a sleeveless square neck, adjustable spaghetti straps, a pleated bodice with a pretty bow on the back, and a fit-and-flare short silhouette. Complete the look in stiletto mules and a clutch.
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Pleated bodice, back bow, zipper closure
- Skater, fit and flare silhouette
- Short-length hem
- Cotton-blend fabric, smooth woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2333
Category Name: Casual Dresses
Price: $5.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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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Soak Up The Sun Tropical Print Maxi Dress
You'll be ready for those relaxing beachside strolls in this gorgeous tropical print maxi dress. It features a sleeveless V-neckline, spaghetti straps, an alluring backless design, a flowy, floor-length hem, and a thigh-high front slit. The smooth knit fabric showcases a tropical palm leaf print. Style with slip-on sandals.
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Backless design, single lattice strap
- Flowy floor-length hem, high front slit
- Tropical palm leaf print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4997
Category Name: Casual Dresses
Price: $5.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Color Me Cute Linen V-Neck Skater Dress
Color you cute in this linen skater dress perfect for layering over your swimsuit on a beach day or pool party! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty ruffled underbust trim, and a tiered color block ruffled short-length silhouette. Style with trendy espadrille wedges.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Ruffled underbust trim
- Tiered ruffle layered skater silhouette
- Short-length hem
- Color block pattern
- Airy woven linen fabric, partial lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4994
Category Name: Casual Dresses
Price: $5.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Here To Twirl Ruffled Skater Dress
With this skater dress on, you're just here to twirl at the graduation party or birthday! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back design, and a flattering fit and flare short-length silhouette with a layered ruffled hem. Complete the look in rhinestone fringe earrings.
Fit & Features
- Sleeveless square neck, adjustable spaghetti straps
- Tie-back design
- Fit and flare, skater silhouette
- Layered ruffled short-length hem
- Woven fabric, sewn-in knit lining
- Runs true to size
Style Number/Barcode: 05101-2119
Category Name: Casual Dresses
Price: $5.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Charm Swiss Dot Chiffon Midi Dress
Unlock your sweet charm in this chiffon midi dress perfect for bridal showers, graduation parties, and more! It features a sleeveless V-neck with a twisted bust, adjustable spaghetti straps, a flirty tie-back design, and a flowy silhouette and ruffled hem. The dress is composed of an airy chiffon fabric with a swiss dot pattern and a smooth woven lining. Complete the look in faux pearl heels.
Fit & Features
- Sleeveless V-neck, twisted bust
- Adjustable spaghetti straps
- Tie-back design
- Flowy silhouette, ruffled midi-length hem
- Airy chiffon fabric, swiss dot pattern, smooth woven lining
- No stretch
- Runs true to size
Style Number/Barcode: 05102-5047
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Golden Hour Glow Abstract Print Cutout Midi Dress
Giving goddess vibes only—this midi dress is here to steal the spotlight. With a curve-hugging fit, waist cutout, and ruffled slit, it’s made for rooftop cocktails, date nights, and every content-worthy moment.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch, abstract print
- Sleeveless plunging cowl neckline
- Tie-back halter spaghetti straps, partially open back
- Waist cutout, rectangular metal accent
- High-cut front slit, ruffled trim
- Midi-length fitted silhouette
- Runs true to size
Style Number/Barcode: 05103-000428
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Charming Floral Eyelet Lace Dress
Always charming and cute, this floral eyelet lace dress boasts adorable allure! It features puff short sleeves, a square neck, a tie-back design, and a flattering skater silhouette and short-length hem. Complete the look in strappy sandals for a baby shower or family party.
Fit & Features
- Puff short sleeves
- Square neck
- Tie-back design
- Skater silhouette
- Short-length hem
- Ditsy floral print, eyelet lace, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5030
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready To Ruffle V-Neck Mini Dress
You'll bring the flirty flare with this mini dress for bridal showers or day dates! The dress features a sleeveless ruffle V-neckline, straps with ruffle trim, and a bodycon silhouette on stretchy and smooth knit fabric with lining. Complete the look in trendy flat sandals and a purse!
Fit & Features
- Sleeveless ruffle V-neckline
- Straps with ruffle trim
- Bodycon silhouette
- Mini-length hem
- Stretchy, smooth knit fabric with lining
- Runs true to size
Style Number/Barcode: 05102-5049
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Ticket To Flirty Ditsy Floral Mini Dress
Your ticket to looking fun and flirty is this ditsy floral mini dress perfect for a staycation or weekend getaway! It features a sleeveless sweetheart neckline, spaghetti straps, a front bust tie with a keyhole accent, and a bodycon silhouette. The soft brushed knit fabric offers plenty of stretch. Complete the look in heeled sandals.
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Front bust tie, keyhole accent
- Bodycon silhouette, mini-length hem
- Ditsy floral print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5115
Category Name: Casual Dresses
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casually Cute Floral Off-The-Shoulder Dress
Step out looking casually cute in this floral mesh mini dress for lunch with the girls or a bridal shower! It features an off-the-shoulder neckline, sheer short-sleeve cuffs, a ruched bust, and side, and back ruched seams that accentuate your curves along the bodycon silhouette. Complete the look with a dainty ring set and heels.
Fit & Features
- Off-the-shoulder neckline
- Sheer short-sleeve cuffs
- Back zipper and hook-eye closure
- Ruched bust, side and back seams
- Bodycon silhouette, mini-length hem
- Ditsy floral print, mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4914
Category Name: Casual Dresses
Price: $5.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Looking Sensational Smooth Knit Maxi Dress
Rise to the occasion looking sensational in this basic smooth knit maxi dress perfect for dressing up or down! It features a sleeveless scoop neck, sleek spaghetti straps, a bodycon silhouette, and a flirty back-slit accent composed of double-lined smooth knit fabric. Complete the look in lucite mules for a bridal shower or casual party!
Fit & Features
- Sleeveless scoop neck, spaghetti straps
- Bodycon silhouette
- Back slit accent
- Maxi-length hem
- Double-lined smooth knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5158
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pop On Over Bubble Hem Skater Dress
Pop on over to every party you're invited to in this poplin skater dress featuring adorable puff short sleeves, a wired V-neckline, a high waist seam, and a flattering fit and flare silhouette with a short bubble hem design. The poplin woven fabric includes a sewn-in knit lining. Style this skater dress with rhinestone strappy heels to complete the look!
Fit & Features
- Puff short sleeves, cinched hems
- Wired V-neckline, back zipper, hook and eye closure
- High waist seam
- Fit and flare skater silhouette
- Short bubble hem design
- Poplin woven fabric, sewn-in knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2299
Category Name: Casual Dresses
Price: $6.97 $56.90
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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Butterfly Kisses Rhinestone Mini Dress
Every heart will flutter with your winged beauty! This rib knit mini dress features a sleeveless scoop neck, spaghetti straps, a rhinestone butterfly design, and a bodycon silhouette. Complete the look in cute sandals for a casual party or lunch!
Fit & Features
- Sleeveless scoop neck
- Spaghetti straps
- Rhinestone butterfly design
- Bodycon silhouette
- Mini-length hem
- Soft rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4944
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Looking Like A Day Dream Eyelet Lace Dress
Look like a daydream come true in this eyelet lace mini dress for your next date! It features adorable puff sleeves with ruffle trim, a sweetheart neck, a ruched bust seam, and a bodycon silhouette with a flirty tiered ruffle hem. Complete the look in cute stiletto heels.
Fit & Features
- Puff short sleeves, ruffle trim
- Sweetheart neck
- Ruched bust seam
- Bodycon silhouette
- Tiered ruffle mini-length hem
- Eyelet lace fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2184
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale