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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All About Floral Sweetheart Crepe Skater Dress
Sweet and sassy, this floral skater dress is a must-have for your wardrobe! Featuring a trendy sweetheart neckline and adjustable spaghetti straps, this dress is perfect for any spring or summer occasion. Its skater silhouette and short-length hem will have you twirling all day, while the playful floral print will make you stand out in style! Complete the look with hoop earrings.
Fit & Features
- Floral print
- Stretchy crepe fabric, knit lining at the bust
- Sweetheart neckline
- Adjustable spaghetti straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3196
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Day Dream Lace Up Eyelet Skater Dress
Make your garden party daydream come true in this floral eyelet skater dress! This playful skater dress features a sweetheart neckline, spaghetti straps, and a lace-up back for a flirty touch. Its skater silhouette and short-length hem make it perfect for twirling! Complete the look with teardrop earrings and a bracelet.
Fit & Features
- Floral print, eyelet woven lined fabric, no stretch
- Sweetheart neckline
- Spaghetti straps
- Lace-up back
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3197
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Graceful Presence Sweetheart Floral Skater Dress
Have a graceful presence in this floral skater dress at showers or graduations! A charming dress with a sweetheart neckline and tie spaghetti straps, the skater silhouette flatters your figure, while the short-length hem adds a playful touch. Complete the look in wedge sandals.
Fit & Features
- Floral print, woven fabric lined with stretchy knit
- Tie spaghetti straps
- Sweetheart neckline
- Back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3194
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Adorable Factor Chiffon Sweetheart Midi Dress
Raise the bar looking adorable in this chiffon midi dress perfect for upcoming dressy occasions! The midi-length dress features short puff sleeves, a sweetheart neckline, a ruched bust, and a flirty cutout waist to show some skin. The flattering A-line silhouette boasts a playful front slit and a flowy midi hem. Complete the look with cute sandals and jewelry!
Fit & Features
- Short puff sleeves
- Sweetheart neckline, stretchy smocked back
- Ruched bust, cutout waist
- A-line silhouette, front slit
- Midi-length hem
- Chiffon woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-3189
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Chic Lace-Trim Knit Midi Dress
So sweet and chic, this lace-trim knit midi dress is perfect for elevating your date night look! Designed with a stretchy ribbed knit fabric, this mid-length dress includes an airy mesh lining. The sleeveless V-neckline has spaghetti straps and is accented with a dainty sheer lace trim for a stylish touch, and includes an angled underbust seam to accentuate your figure. The bodycon silhouette will show off your gorgeous curves. Pair this adorable midi dress with hoop earrings and strappy mules!
Fit & Features
- Stretchy ribbed knit fabric, full-length mesh lining
- Sheer lace trim
- Sleeveless V-neckline, underbust seam
- Spaghetti straps
- Mid-length hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5497
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Divine Cutie Tie-Back Ruffled Skater Dress
You'll look positively cute and divine in this short skater dress at brunch or graduations! Designed with a flattering square neckline, adjustable spaghetti straps for the perfect fit, and a tie-back design, this dress is perfect for every girlie. The skater silhouette and ruffled layer add a playful touch, while the short-length hem offers comfort and versatility. Complete the look in strappy mules.
Fit & Features
- Airy woven fabric, sewn-in knit lining
- Adjustable spaghetti straps
- Ruffled
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5733
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Radiant Vacay V-Neck Floral Chiffon Skater Dress
Twirl your problems away on vacay in this radiant floral chiffon skater dress! The sheer peasant long sleeves, V-neckline, and corset-inspired bodice add a touch of romance, while the skater silhouette and ruffled hem bring a playful charm. Perfect for any occasion, from vacation to brunch! Complete the look in cute wedge sandals and sunnies.
Fit & Features
- Floral print, chiffon fabric lined with woven fabric
- Keyhole back with button closure
- Skater silhouette
- Ruffled short-length hem
- Sticky bra or pasties recommended
- Runs true to size
Style Number/Barcode: 05101-3186
Category Name: Casual Dresses
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Has Sprung Floral Woven Skater Dress
Let your beauty bloom in this adorable floral woven skater dress! The lightweight lined woven fabric is accented with a dainty floral print for the sweetest allure. The short dress features a sleeveless sweetheart neckline with a padded bust and structured underwire for support. The corset-style bodice will snatch your waist and highlight your bust with a tie-front detail. The thin smocked shoulder straps lead to a smocked back design for added stretch with a zipper closure. The high waist flows out to a short skater skirt with a trendy bubble hem and a fit and flare silhouette. Pair with platform heels for the cutest party look!
Fit & Features
- Floral woven fabric with knit lining, minimal stretch
- Sleeveless sweetheart neckline, padded bust with underwire
- Thin tank shoulder straps
- Smocked back design, zipper and hook and eye closure
- Corset bodice, tie-front detail, high waist seam
- Short skater skirt with bubble hem, fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3187
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romance Era Floral Brocade Corset Mini Dress
You'll be in your romance era in this chic floral brocade corset mini dress! Designed with a detailed floral brocade woven fabric with a knit lining, this dress will bring the allure to your date night look. The top is shaped with a sleeveless sweetheart neckline with a padded bust and structured underwire to provide support and eliminate the need for a bra. The corset-style bodice has flexible boning to create that sultry snatched silhouette. Find your perfect fit with the adjustable spaghetti straps that lead to a back zipper closure. The form-hugging silhouette on the mini-length dress will flaunt your stunning curves. Complete your 'fit with stilettos.
Fit & Features
- Floral brocade woven fabric with knit lining, minimal stretch
- Sleeveless sweetheart neckline with structured and padded bust
- Corset bodice with flexible boning, high waist seam
- Adjustable spaghetti straps, back zipper with hook and eye closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05101-3177
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Feelings Sleeveless Ditsy Floral Mini Dress
Give yourself a sweet feeling in this ditsy floral mesh mini dress perfect for spring and summer soirees! With a sweetheart neckline, padded bra cups, and adjustable spaghetti straps you;ll feel confident and comfortable. The side ruched seams accentuate your curves along the bodycon fit for a playful touch. Complete the look with a choker necklace.
Fit & Features
- Ditsy floral print, mesh fabric, sewn-in knit lining, stretchy
- Adjustable spaghetti straps
- Sweetheart neckline, padded bra cups
- Back zipper and hook-eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5550
Category Name: Casual Dresses
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Delightful Charm Halter A-Line Midi Dress
Step out looking delightful in this charming sleeveless midi dress for parties or showers! The halter pleated neckline and open back add a flirty touch, while the beaded tie waist cinches your waist for a flattering A-line silhouette. Complete the look with sunglasses and sandals!
Fit & Features
- Woven fabric, no stretch
- Halter pleated neckline
- Open back, zipper and hook-eye closure
- Beaded tie waist
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5648
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Awaken Beauty A-Line Lace Short Dress
Transform into a vision of beauty in this lace short dress at every party! This stunning dress boasts a sleeveless square neckline with a tie, enhancing your feminine charm. The A-line silhouette and short-length hem flatter your figure, while the intricate lace fabric adds a touch of elegance. Complete the look in stiletto mules and a purse!
Fit & Features
- Lace fabric lined with stretchy knit
- Square neckline with tie
- Wide shoulder straps
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5552
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Intentions Sleeveless Knit Mini Dress
Take your wardrobe to the next level in this little black dress perfect for day or night plans! This mini dress boasts a sleeveless high square neckline and spaghetti straps for a chic and modern look. The bodycon silhouette hugs your curves, while the mini-length hem adds a touch of flirtatiousness. The lightweight knit fabric offers a moderate stretch. Complete the look in a trendy crop jacket, mules, and a purse!
Fit & Features
- Knit fabric with moderate stretch
- High square neckline
- Spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1881
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Think About Me Lace-Up Floral Skater Dress
Captivate everyone's thoughts in this floral skater dress sure to be the prettiest pick anyone has ever seen! With a square neckline and spaghetti straps, it's perfect for warmer days. The lace-up back and bow tie adds a playful touch, while the skater silhouette and mini-length hem flatter any figure. Complete the look with an adorable hair bow and sunglasses!
Fit & Features
- Floral print, woven fabric lined, no stretch
- Spaghetti straps
- Square neckline, bow tie
- Lace-up back
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5490
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetest Allure Strapless Floral Eyelet Knit Midi Dress
Give off the sweetest allure this summer season in this floral eyelet knit midi dress! The stretchy sheer eyelet knit fabric is detailed with an adorable ditsy floral print and includes a full knit lining for coverage. The mid-length dress features a strapless straight-across elasticized neckline and a bodycon silhouette to highlight your gorgeous figure. Style with espadrille wedges for weekend brunch!
Fit & Features
- Stretchy sheer eyelet knit fabric, full knit lining
- Ditsy floral print
- Strapless straight elasticized neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5488
Category Name: Casual Dresses
Price: $5.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Whimsical Beauty Strappy Back Textured Knit Skater Dress
Radiate whimsical beauty in this gorgeous textured knit skater dress perfect for graduations or parties! The sheer textured knit fabric includes a full-length knit lining and offers plenty of stretch. The dress is shaped with a sleeveless square neckline and dual spaghetti straps leading to a bold open back with a cross-back strappy design. The high waist flows out to a short skater skirt with an adorable fit and flare silhouette. Style with hoop earrings and espadrille sandals.
Fit & Features
- Sheer textured knit fabric, full-length knit lining
- Plenty of stretch
- Square neckline, dual spaghetti straps
- Open back, cross-back strappy design
- High waist, short skater skirt
- Fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3142
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Mindset Lace Up Mini Dress
Discover your new mindset in this floral mini dress perfect for wedding showers or brunch! This bodycon dress features a square neckline, spaghetti straps, and a lace-up back for a flirtatious appeal. The side ruched seams accentuate your curves even more on the soft brushed knit fabric that offers a stretchy knit lining for coverage. Complete the look with a trendy purse.
Fit & Features
- Brushed knit soft fabric lined with stretchy knit
- Ditsy floral print
- Spaghetti straps, lace-up
- Side ruched seams
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5489
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy Vibes Long Sleeve Chiffon Skater Dress
This dreamy long sleeve chiffon skater dress has a flowy silhouette to give you that effortlessly ethereal look! The short dress is crafted with an airy sheer chiffon fabric for a lightweight feel, and includes a partial knit lining for coverage. The bodice is shaped with a V-neckline with a chic pleated surplice design, and the sheer long balloon sleeves have cinched hems. The back features a partially smocked design for added stretch. The high waist seam flows out to a short skater skirt with a fit and flare silhouette and a faux wrap-front design. Complete your outfit with block heels for a bridal shower or birthday party!
Fit & Features
- Sheer non-stretch chiffon fabric, partial knit lining
- V-neckline with pleated surplice design
- Long unlined balloon sleeves, elastic cinched hems
- Smocked back, zipper with hook and eye closure
- High waist seam
- Short skater silhouette, faux wrap-front design
- Runs true to size
Style Number/Barcode: 05101-3139
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Favorite Fleur V-Neck Floral Chiffon Skater Dress
Give them a twirl in this adorable floral chiffon skater dress at birthdays or graduation parties! Featuring puff short sleeves, a tie front bust, and a stretch smocked empire waist, this dress will hug your curves in all the right places. The skater silhouette and ruffled hem add a playful touch to this flowy chiffon dress. Complete the look with teardrop earrings.
Fit & Features
- Floral print, chiffon fabric lined with stretchy knit
- V-Neckline, tie front
- Skater silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05101-3135
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Jet Set For Sun Strapless Tropical Midi Dress
Jet set for fun under the sun in this tropical midi dress for endless compliments while on vacation! The midi-length dress features a strapless neckline, a form-hugging silhouette, a flirty side slit and asymmetrical hem, and an adjustable side drawstring so you customize the style. Complete the look in sandals for a sunset dinner!
Fit & Features
- Strapless neckline
- Form-hugging silhouette
- Adjustable side drawstring, side slit
- Asymmetrical midi-length hem
- Tropical print, mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5486
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Arrival Rose Floral Chiffon Maxi Dress
Make a gorgeous arrival in this rose floral chiffon maxi dress for showers, birthdays, or family parties! The sweetheart neckline and adjustable spaghetti straps provide a flattering and comfortable fit, while the padded bra cups offer support and shape. The maxi-length hem and high front slit add a touch of sultry, making you feel so beautiful! Complete the look in chic wedge sandals and sunnies.
Fit & Features
- Rose floral print
- Chiffon fabric lined with stretchy knit
- Padded bra cups, adjustable spaghetti straps
- Back zipper and hook-eye closure
- High front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3128
Category Name: Casual Dresses
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swing Into The Season Tie-Back Eyelet Skater Dress
Swing into the season in this charming eyelet skater dress perfect for birthday brunch to day dates! The cap sleeves and sweetheart neckline add a touch of romance, while the padded bra cups provide support. The tie-back design and fitted bodice add a playful twist to the skater silhouette and flirty ruffled short-length hem. Complete the look in strappy platform sandals and a purse!
Fit & Features
- Eyelet lace fabric with woven lining
- Padded bra cups
- Tie-back closure
- Skater silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-3121
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Flair Ruffled Wrap Chiffon Mini Dress
This adorable floral chiffon mini dress will bring the flirty flair to your spring parties! Designed with a dainty floral print on lightweight lined chiffon fabric. This mini-length dress features a sleeveless sweetheart neckline with a built-in padded bust, spaghetti straps that lead to an open back with a cross-back strappy design, and a corset-style bodice with a fitted high waist. The A-line silhouette has a faux wrap-front creating the cutest asymmetric ruffled hem. Complete your look with strappy sandals.
Fit & Features
- Sheer chiffon fabric with knit lining, minimal stretch, dainty floral print
- Sleeveless sweetheart neckline, padded bust
- Spaghetti straps
- Open back, cross-back straps with tie closure, lower zipper, hook and eye closure
- Corset bodice, high waist seam
- Faux wrap-front, asymmetric ruffled hem, A-line fit
- Runs true to size
Style Number/Barcode: 05101-3113
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Flair High Slit Ditsy Floral Knit Midi Dress
Bring the sweet flair to date night in this high slit ditsy floral midi dress! The all-over ditsy floral print on the stretchy knit fabric is the perfect amount of sweetness with the sultry details of the mid-length dress. The sleeveless scoop neckline features a tie-front at the bust for a cute touch, spaghetti straps, an alluring thigh-high side slit to showcase some leg, and a slim-fit silhouette to showcase your figure. Style this midi dress with a faux leather jacket and heels!
Fit & Features
- Ditsy floral print, stretchy knit fabric
- Sleeveless scoop neckline with bust tie
- Spaghetti straps
- Thigh-high side slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5485
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free