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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Blissful Cutie Halter Cutout Skater Dress
Get swept off your feet in this cute skater dress for any casual occasion! With its halter neckline and cutout bodice, this dress is designed to show off your figure, while the ruffled mini-length hem adds a flirty touch.
Fit & Features
- Gauze woven fabric, woven lining
- Halter neckline with spaghetti strap ties
- Stretchy smocked bust
- Cutout bodice
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6017
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
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Playful And Pretty Corset Lace-Up Midi Dress
Playful and pretty, this corset midi dress has a timeless silhouette. It has a unique lace-up back, a flattering A-line fit, and convenient side pockets that warm your hands.
Fit & Features
- Woven poplin lined fabric lined with stretchy knit
- Sweetheart neckline with bust tie
- Adjustable shoulder straps
- Lace-up back, side zipper and hook-eye closure
- A-line silhouette, front slit, side pockets
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3968
Category Name: Casual Dresses
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
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Steal The Show Strapless Lace Maxi Dress
Steal the show in this strapless lace maxi dress designed in a semi-sheer style and a flattering form-hugging fit with a flared hem. Pair with earrings and heels.
Fit & Features
- Semi-sheer lace fabric with knit lining
- Strapless neckline
- Form-hugging fit
- Flared maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3965
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
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Here To Be Loved V-Neck Eyelet Skater Mini Dress
Layered or worn solo, this stunning skater dress features a forever flattering mini-length silhouette and an adorable eyelet pattern for the perfect femme finish.
Fit & Features
- Eyelet woven fabric, stretchy knit lining
- V-neckline, bust tie
- Adjustable spaghetti straps
- Stretchy smocked bodice
- Skater silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3950
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
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Game Set Slay Sweater Dress
She’s giving preppy with a playful twist. This sleeveless sweater dress hugs in all the right places with contrast trim and a flared mini-length hem that makes it a serve for every season!
Fit & Features
- Rib knit stretchy fabric
- Square neckline and tank shoulder straps, contrast trim
- Skater silhouette
- Pleated, flare mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2219
Category Name: Casual Dresses
Price: $21.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Vibes Long Sleeve Ruched Midi Dress
Channel sleek vibes in a midi dress that features a boat neckline, fitted long sleeves with thumb holes, and ruching that enhances curves. Complete look with strappy heels to take you from the office to happy hour!
Fit & Features
- Smooth knit fabrication, double-lined
- Boat neckline
- Long sleeves with thumb holes
- Ruching
- Midi length hem
- Runs true to size
Style Number/Barcode: 05101-3954
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fun In Floral Lace Mini Dress
So fun in floral print, this lace dress is featured in a form-hugging A-line silhouette and playful mini-length hem. Pair with cute wedge sandals for a cute summer look!
Fit & Features
- Floral print, lace fabric, stretchy knit lining
- Square neck with bust tie
- Adjustable spaghetti straps
- Form-hugging A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6015
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Glam Ribbed Knit Long Sleeve Mini Dress
The ribbed knit dress features a mock neck, long sleeves accented with thumb holes, and a mini-length hem. For a casually glam vibe, complete the look with ankle booties.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Mock neckline
- Long fitted sleeves with thumb hole accents
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-6014
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Looking Sweet Eyelet Knit Tiered Skater Dress
You'll look extra sweet for your next weekend brunch in this adorable eyelet knit skater dress. The strapless neckline, ruched side seams, drop waist, and short tiered design are all flirty details you'll adore.
Fit & Features
- Sheer eyelet knit fabric with full-length knit lining, moderate stretch
- Strapless straight neckline
- Ruched side seams
- Drop waist
- Short tiered design, skater silhouette
- Runs true to size
Style Number/Barcode: 05102-6012
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
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Adorable Looks Tie Front Bodycon Midi Dress
All of your adorable looks this season will include this eyelet midi dress with a flirty tie front and bodycon silhouette. This dress is perfect for shower celebrations or graduations!
Fit & Features
- Eyelet fabric
- Tie front sweetheart neckline
- Spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6008
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Life Is Sweet Eyelet Bodycon Ruffle Mini Dress
The sweetest eyelet mini dress for shower celebrations, graduations, or brunch! It boasts flirty tie shoulder straps, a flattering bodycon silhouette, and a ruffled hem for cute flair.
Fit & Features
- Eyelet fabric
- Square neckline, tie shoulder straps
- Bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6006
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Sweet Ruffled Eyelet Lace Mini Dress
Make your sweet impression in this eyelet lace mini dress detailed with ruffled straps and an adorable ruched neckline. The form-hugging fit will highlight your stunning curves.
Fit & Features
- Eyelet lace fabric lined with stretchy knit
- Sweetheart neckline, ruching
- Ruffled straps
- Mini-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-6002
Category Name: Casual Dresses
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Twist Off-The-Shoulder Soft Knit Mini Dress
The cashmere-like soft knit mini dress features an off-the-shoulder neckline, a popover accent with twist detail, long bell sleeves, faux wrap ties at the waist, and a fitted short-length hem. Complete a cozy stylish outfit with clear heels or ankle booties.
Fit & Features
- Soft cashmere-like knit fabrication
- Off-the-shoulder neckline
- Popover accent with twist detail
- Long bell sleeves
- Faux wrap ties at the waist
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-6003
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Flair Ditsy Floral Mini Dress
Show off a charming flair in this adorable ditsy floral mini dress designed with eyelet knit fabric. The sweet vibes of the print are the perfect pairing with the sassy short bodycon silhouette.
Fit & Features
- Sheer eyelet knit fabric with knit lining, high stretch
- Ditsy floral print
- Sleeveless square neckline, dainty rosette detail, eyelet trim
- Adjustable spaghetti straps
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5999
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Sunny Eyelet Knit Mini Skater Dress
This adorable mini skater dress is perfect for sunny weekend plans. Made with a breezy eyelet knit fabric, you'll love the flirty tie-back detail and fit-and-flare ruffled silhouette.
Fit & Features
- Eyelet knit fabric, sewn-in knit lining
- Scoop neckline
- Adjustable spaghetti straps
- Tie-back detail, lower open back
- Short skater silhouette, tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-6000
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Look Eyelet Knit Skater Dress
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette.
Fit & Features
- Eyelet knit fabric with knit lining
- Sleeveless square neckline, underbust seam
- Adjustable spaghetti straps
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6001
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tea Time Corset Lace-Up Floral Skater Dress
It's time to spill the tea at the garden party in this chic floral skater dress with a pretty corset bodice that snatches your waist and a lace-up back that turns heads!
Fit & Features
- Floral print, poplin woven lined lace trim fabric
- Square neckline, lace trim, underwire bust, wide shoulder straps
- Corset bodice, flexible boning, lace trim, lace-up back
- Drop waist seam
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3923
Category Name: Casual Dresses
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lovely In Eyelet A-Line Mini Dress
Make a lovely impression in this eyelet A-line mini dress at bridal showers or brunch with the girls!
Fit & Features
- Eyelet lace fabric, stretchy knit lining
- Strapless neckline
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5997
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Fling V-Neck Paisley Skater Dress
Swing into spring in this paisley skater dress for an adorable look all season! With a flirty halter V-neck and a flowy mini-length hem, this dress is ready for brunch or day dates.
Fit & Features
- Paisley print, chiffon fabric, woven lining
- Halter V-neck
- Spaghetti strap ties with tassels
- Stretchy smocked bodice
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5994
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Preppy Edit Pinstripe Mini Dress
The perfect dress for fall—this strapless pinstripe mini dress blends polished structure with playful pleats. Toss on a blazer or knee-high boots for seasonal chic.
Fit & Features
- Pinstripe pattern, woven fabric
- Strapless collared neckline
- Button front
- Fitted bodice
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5993
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Flirt Lace Trim Scoop Neck Knit Mini Dress
Fit & Features
- Soft rib knit fabric, moderate stretch
- Lace trim scoop neckline with bow tie
- Fitted long sleeves
- Bodycon silhouette
- Mini-length hem, dual slit accents
- Runs true to size
Style Number/Barcode: 06005-2199
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Destination Paradise V-Neck Floral Maxi Dress
The perfect floral maxi dress for your next getaway! Designed in a sleeveless silhouette, this dress features a flattering V-neckline, sleek spaghetti straps, and a form-hugging fit with a flowy floor-length hem. Complete the look with earrings.
Fit & Features
- Floral print, mesh lined fabric
- V-neckline
- Spaghetti straps
- Form-hugging fit
- Flowy floor-length hem
- Runs true to size
Style Number/Barcode: 05101-3915
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Buckled Beauty Off-The-Shoulder Knit Mini Dress
An off-the-shoulder mini dress perfect for everyday slays. It features long sleeves and a foldover neckline with trendy buckled accents and a bodycon silhouette. Complete the look with boots.
Fit & Features
- Stretchy rib knit fabric
- Off-the-shoulder neckline, folded with buckled accents
- Long sleeves
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5992
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Vibe Ditsy Floral A-Line Midi Dress
Look oh-so-darling at weekend brunch in this ditsy floral A-line midi dress! The sleeveless sweetheart neckline is detailed with a dainty lace trim and tie-front design.
Fit & Features
- Woven fabric
- Ditsy floral print
- Sleeveless sweetheart neckline, dainty lace trim, lace trim spaghetti straps
- Tie-front detail, underbust seam
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5989
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free