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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Such A Charmer Ditsy Floral Skater Dress
Create a charming look for weekend dates with this adorable floral skater dress! It features a square neckline with a ruffled hem, short puff sleeves, dual high waist seams, and a short skater skirt with a flattering fit and flare silhouette. The lightweight chiffon fabric features a ditsy floral print pattern for the cutest spring or summer vibe. Style with espadrille sandals.
Fit & Features
- Square neckline, ruffled hem
- Short puff sleeves, elastic cinched hems
- Dual high waist seams, smocked back design
- Short skater skirt, fit and flare silhouette
- Ditsy floral print
- Chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4885
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Favorite Darling Eyelet Lace V-Neck Dress
You'll be everyone's favorite sight looking so darling in this eyelet lace dress at dinner parties! It features a sleeveless V-neckline, wide shoulder straps, a stretchy smocked back, and a flattering tiered skater short-length silhouette. Complete the look with a charming rhinestone barrette for a chic hairstyle!
Fit & Features
- Sleeveless V-neckline
- Wide shoulder straps
- Stretchy smocked back
- Tiered, skater short-length silhouette
- Eyelet lace fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2030
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love Letters Floral Chiffon Skater Dress
Don't be surprised if your mailbox is full of love letters after wearing this floral chiffon skater dress to the party! It features a sleeveless V-neckline, adjustable spaghetti straps, and a flattering fit and flare short silhouette. Complete the look in faux leather block heels for a graduation or dressy birthday party!
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Skater silhouette
- Short-length hem
- Floral embroidered chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2035
Category Name: Casual Dresses
Price: $5.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Forward Chiffon Puff Sleeve Skater Dress
Spring forward and add this adorable skater dress to your wardrobe! The short dress features a square neckline with ruching at the bust, short puff sleeves, an empire waist seam, an open back with a tie-back accent, and a short skater skirt with a flirty fit and flare silhouette. The airy chiffon fabric provides a lightweight feel. Style with strappy mules.
Fit & Features
- Square neckline, ruched bust
- Short puff sleeves, elastic cinched hems
- Empire waist seam
- Open back, tie-back accent
- Short skater skirt, fit and flare silhouette
- Sheer chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2024
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Life Floral Chiffon Skater Dress
Live the sweet life twirling in this floral chiffon dress at birthday parties or baby showers! Featuring an adorable off-the-shoulder neckline with ruffle trim, short-sleeve cuffs, a bust keyhole cutout with a tie accent, and a short skater silhouette. The dress is composed of a dainty floral print chiffon fabric with a knit lining. Complete the look in simple platform heels.
Fit & Features
- Off-the-shoulder neckline, ruffle trim
- Short-sleeve cuffs, elasticized hems
- Keyhole bust with tie, back zipper, hook and eye closure
- Short skater silhouette
- Dainty floral print
- Sheer chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2038
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spring The Fun Sweater Midi Dress
Spring into this sweater midi dress for daytime outings! It features a sleeveless square neck, adjustable spaghetti straps, contrast trim along the bodice, and a bodycon silhouette. Style with trendy mules to complete the look!
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Contrast trim bodice
- Bodycon silhouette
- Midi-length hem
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1640
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweet As Can Be Lace Midi Dress
Look and feel sweet as can be in this lace midi dress for a chance at romance! Features adorable short puff sleeves, a sweetheart neckline, a form-hugging silhouette, a flirty front slit, and a slight flare hem. Style with heeled sandals for a cute look for day dates and brunch!
Fit & Features
- Short puff sleeves
- Sweetheart neckline
- Back zipper and hook-eye closure
- Form-hugging silhouette
- Front slit, slight flare midi-length hem
- Lace fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2020
Category Name: Casual Dresses
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Only The Best Cutout Sweater Dress
Treat yourself to the best sweater midi dress to have this season! It features fitted long sleeves, an asymmetrical neckline with contrast trim, a form-hugging silhouette, and a flirty side waist cutout with contrast trim. Style with block heels to complete the look!
Fit & Features
- Fitted long sleeves
- Asymmetrical neckline, contrast trim
- Form-hugging silhouette
- Side waist cutout, contrast trim
- Midi-length hem
- Rib-knit sweater fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1639
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rock Babe Lace-Up Graphic Dress
If you're a rock babe this graphic short dress is the one for you! It features short sleeves, a crew neck, a front lace-up placket, and graphic detail with a script that reads, "Rock N Roll World Tour" along the fitted hem. Complete the look in over-the-knee boots.
Fit & Features
- Short sleeves
- Crew neck
- Front lace-up placket
- Graphic detail/ front reads, "Rock N Roll World Tour"
- Short and fitted hem
- Jersey knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1459
Category Name: Casual Dresses
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casually Cool Slit Maxi Dress
Stroll outside looking casually cool and cute in this basic maxi dress design with a sleeveless scoop neck with bungee spaghetti straps, a form-hugging silhouette, and a high-cut side slit. Complete the look in a crop denim jacket and sneakers.
Fit & Features
- Sleeveless scoop neck
- Bungee spaghetti straps
- Form-hugging
- High-cut side slit
- Maxi-length hem
- Rib-knit fabric, lined, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4883
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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True Staple Short Skater Dress
A true staple for daytime soirees and celebrations! This short skater dress features a classic sleeveless square neck, adjustable spaghetti straps, a tie-front bust, flexible boning inserts along the bodice, and is composed of smooth woven fabric with a stretchy knit lining. Complete the look with a bracelet and heels.
Fit & Features
- Sleeveless square neck, adjustable spaghetti straps
- Back zipper and hook-eye closure
- Tie-front bust, flexible boning inserts
- Skater silhouette
- Short-length hem
- Woven fabric stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2016
Category Name: Casual Dresses
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Babe Cutout Sweater Dress
You'll be such a trendy babe in this adorable cutout sweater dress! Featuring a sleeveless high neckline with a racerback design, a front keyhole cutout at the bust, alluring side cutouts at the waist, a midi-length hem, and a curve-hugging silhouette, this dress is a perfect pick for a night out with the girls. Style with platform heels and a chic handbag.
Fit & Features
- Sleeveless high neckline, racerback design
- Front keyhole cutout at the bust
- Dual side cutouts at the waist
- Midi-length hem, curve-hugging fit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1633
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chain Effect Midi Dress With Belt
You'll make a chain reaction by stepping out in this rib knit tank midi dress featuring a sleeveless square neck, tank shoulder straps, a detachable chain belt with lobster clasp closure, and a form-hugging silhouette. Complete the look in a chic blazer for happy hour!
Fit & Features
- Sleeveless square neck
- Tank shoulder straps
- Detachable chain belt with lobster clasp closure
- Form-hugging silhouette
- Midi-length hem
- Double-lined rib knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4882
Category Name: Casual Dresses
Price: $19.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Moves Eyelet Lace Mini Dress
The perfect sundress for bridal showers or outdoor parties! It features adorable puff short sleeves, a square neck, side ruched seams along the bodice, and a bodycon silhouette with a mini-length hem. Complete the look in trendy espadrille wedges.
Fit & Features
- Puff short sleeves
- Square neck
- Side ruched seams on bodice
- Bodycon silhouette
- Mini-length hem
- Eyelet lace, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4874
Category Name: Casual Dresses
Price: $5.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bae Breeze Cotton A-Line Short Dress
Enter looking like bae just breezed in! Capture cuteness in this cotton short dress featuring short puff sleeves, a square neck, an open lace-up back, and an A-line silhouette. Style with a trendy crossbody bag and heels.
Fit & Features
- Short puff sleeves
- Square neck
- Open lace-up back, zipper and hook-eye closure
- A-line silhouette
- Short-length hem
- Cotton fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4876
Category Name: Casual Dresses
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Play The Game Checker Mini Dress
Play the game of style with this checkered mini dress and you'll definitely get a checkmate! The sleeveless dress features a square neck, tank-style straps, flexible boning inserts, a bodycon silhouette, and a mini-length hem. Complete the look in a crop denim jacket for a casual daytime outing.
Fit & Features
- Sleeveless, square neck, tank-style straps
- Flexible boning inserts
- Back zipper and hook-eye closure
- Bodycon fit, short-length hem
- Checkered pattern
- Rib-knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4877
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Loving Is Easy Eyelet Lace Tie Mini Dress
Loving this eyelet lace mini dress is easy! Perfect for lunch with friends or bridal showers. The dress features a sleeveless square neck, spaghetti straps, a ruched bust tie, and a bodycon silhouette. Complete the look in trendy sandals.
Fit & Features
- Sleeveless square neck, spaghetti straps
- Ruched bust tie
- Bodycon silhouette
- Mini-length hem
- Eyelet lace fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4873
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Silhouette High Slit Maxi Dress
Show off your stunning silhouette in this curve-hugging high-slit maxi dress! It features a sleeveless square neckline, tank shoulder straps, a partially open back with a twist-back design and a lower back cutout, a maxi-length hem with a trendy thigh-high side slit, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch and has a sewn-in knit lining. Style with clear mules.
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Partially open back, twist-back design, lower back cutout
- Maxi-length hem, thigh-high side slit
- Bodycon silhouette
- Ribbed knit fabric, sewn-in knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4875
Category Name: Casual Dresses
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On The Go Crew Neck Slit Midi Dress
The perfect casual midi dress to look stylish while on the go! It features cap short sleeves, a crew neck, a bodycon silhouette, a side ruched drawstring, and a flirty slit along the hem. The dress is composed of a super soft brushed knit fabric with plenty of stretch. Style with cute slide sandals and a tote bag!
Fit & Features
- Cap short sleeves
- Crew neck
- Bodycon silhouette
- Side ruched drawstring, slit accent
- Midi-length hem
- Soft brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4872
Category Name: Casual Dresses
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Stunner Chain Strap Midi Dress
Embrace the warmer months and showcase a stunning summertime style in this ribbed knit midi dress. It features a sleeveless square neckline, adjustable spaghetti straps with multi-colored front beaded and chain accents, a hip-hugging fit that will show off your natural curves, and a midi-length hem with a thigh-high front slit for a sassy detail. The ribbed knit fabric offers plenty of stretch. Complete the look with espadrille wedges for a playful summer vibe.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps, multi-colored front beaded and chain accents
- Hip-hugging fit
- Midi-length hem, high front slit
- Ribbed knit fabric, lined bust
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4871
Category Name: Casual Dresses
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swirls Of Style Satin Midi Dress
Stylish marble swirls capture all the attention on this satin midi dress featuring a sleeveless v-neck, adjustable spaghetti straps, flexible boning inserts along the bodice, and a curve-hugging silhouette with a front slit accent. Complete the look in a casual crop jacket.
Fit & Features
- Sleeveless v-neck, adjustable spaghetti straps
- Flexible boning inserts
- Back zipper and hook-eye closure
- Front slit, curve-hugging, midi-length hem
- Marble print
- Satin fabric, knit lining, no stretch
- Fits true to size
Style Number/Barcode: 05102-4867
Category Name: Casual Dresses
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Charm Tie-Front Midi Dress
Make them all fall for your stylish charm in this adorable midi dress! It features a sleeveless V-neckline with a cute tie-front detail, spaghetti straps, a midi-length hem with a high front slit for a subtle sultry vibe, and a slim-fit silhouette. The lightweight knit fabric has plenty of stretch. Pair with hoop earrings and block heels for a date night.
Fit & Features
- Sleeveless V-neckline, tie-front detail
- Spaghetti straps
- Midi-length hem, high front slit
- Slim-fit silhouette
- Lightweight knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4864
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual-Chic Style Muse High Slit Maxi Dress
Show off your elevated casual-chic style in this high slit maxi dress. Featuring a sleeveless crew neckline with tank shoulder straps, trendy side cutouts at the waist, a maxi-length hem, and a thigh-high side slit, this dress will get you major compliments. The ribbed knit fabric offers plenty of stretch. Complete the look with sleek hoops and strappy heels.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Dual side cutouts at the waist
- Maxi-length hem
- High side slit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4866
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Frolic In Floral Tie Midi Dress
Frolic all over town in this floral midi dress perfect for an afternoon tea with the girls! It features a sleeveless V-neck, spaghetti straps, a knot tie bust, a curve-hugging silhouette, and a flirty front slit. The dress is designed with a ditsy floral bud print on stretchy knit fabric. Complete the look in trendy wedge sandals.
Fit & Features
- Sleeveless V-neck
- Spaghetti straps
- Knot tie bust
- Curve-hugging silhouette
- Front slit, midi-length hem
- Ditsy floral bud print, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4865
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale