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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Forever Chic Satin Midi Dress
Sleek and chic, this satin midi dress will be your new go-to! It features a sleeveless cowl neckline, dual spaghetti straps that lead to a cross-back design, and a mid-length fitted silhouette with a subtle flared hem. Style this dress with clear heels and a trendy shoulder bag.
Fit & Features
- Sleeveless cowl neckline
- Dual spaghetti straps
- Cross-back design
- Mid-length fitted silhouette
- Satin fabric
- Runs true to size
Style Number/Barcode: 05101-0942
Category Name: Casual Dresses
Price: $20.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Glam Tie Dye Ruched Mini Dress
Keep it glam with a retro mini dress! The dress features a sleeveless square neckline, adjustable spaghetti straps, a tie-dye print, a ruched body, and a mini-length silhouette. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Tie-dye print
- Ruched body
- Mini length silhouette
- Form hugging fit
- Runs true to size
Style Number/Barcode: 05102-1377
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Twist Ribbed Knit Midi Dress
Give your midi dress a stylish twist with chic details! The dress features a sleeveless crew neckline, a twist knot accent at the back with a lower back keyhole, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless crew neckline
- Twist knot accent at back
- Lower back keyhole
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0942
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Moves Eyelet Mini Dress
Make some seriously stylish moves with this mini dress! The dress features a square neckline, short puff sleeves, an eyelet design, an open back with tie-back straps, and a mini-length silhouette. Complete look with wedges.
Fit & Features
- Square neckline
- Short puff sleeves
- Eyelet design
- Open back with tie back straps
- Mini length silhouette
- Form hugging fit
- Runs true to size
Style Number/Barcode: 05101-1003
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Affair Long Sleeve Ruched Midi Dress
Make a casual-chic impression in this long sleeve ruched midi dress showcasing a folded off-the-shoulder neckline and a bodycon silhouette. Pair with heels.
Fit & Features
- Smooth knit-lined fabrication, moderate stretch
- Off-the-shoulder neckline, foldover accent
- Fitted long sleeves
- Ruching
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3723
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Frenzy Off The Shoulder Skater Dress
Start a frenzy with a floral dress that brings the romance! The dress features an off-the-shoulder neckline with a sweetheart bust, quarter-length short sleeves, a floral print, and a skater-length silhouette. Complete look with wedges and a floppy hat.
Fit & Features
- Off the shoulder neckline
- Sweetheart bust
- Quarter-length short sleeves
- Floral print
- Skater length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4179
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish And Lovely Eyelet Mini Dress
Keep it stylish and lovely with a mini dress that brings sweet details! The dress features a sleeveless square neckline with a mini tie front, adjustable spaghetti straps, an eyelet pattern, and a mini-length silhouette. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Mini tie-front
- Adjustable spaghetti straps
- Eyelet pattern
- Mini length silhouette
- Form hugging fit runs true to size
Style Number/Barcode: 05102-1276
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Sweet Puff Sleeve Mini Dress
Rock a look that's so sweet this season! The mini dress features an off-the-shoulder neckline with a sweetheart bust, short puff sleeveless, ruching at the bodice, and a mini-length silhouette. Complete your look with statement earrings and wedges.
Fit & Features
- Off the shoulder neckline, sweetheart bust
- Short puff sleeves
- Ruching
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1551
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Chic Cutout Midi Dress
Keep it chic with a midi dress that brings all the appeal. The dress features a sleeveless scoop neckline, a midriff cutout, spaghetti straps, a mini-length silhouette with a midi length overlay. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with wedges.
Fit & Features
- Sleeveless scoop neckline
- Midriff cutout
- Spaghetti straps
- Mini length silhouette with overlay
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0995
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Drawn In With Glam Ruched Mini Dress
Get drawn in with glam in a cute mini dress! The dress features a sleeveless V-neckline, spaghetti straps, a ruched drawstring at the center, and a mini-length silhouette. The dress is composed of a textured knit fabric that offers a form-hugging fit. Complete the look with hoops and mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Ruched drawstring at center
- Mini length silhouette
- Textured knit fabric
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-1496
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Florals Ribbed Knit Mini Dress
Bring the charm with a floral mini dress that is perf for your next brunch date! The dress features a sleeveless sweetheart neckline, tie-front, spaghetti straps, ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with wedges.
Fit & Features
- Sleeveless sweetheart neckline
- Tie-front
- Spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4062
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Passion Sleeveless Mini Dress
Channel the romance with a floral mini dress that brings charm to your look. The dress features a sleeveless V-neckline, tie-front, spaghetti straps, ditsy floral print, and mini-length silhouette. Complete look with mules and a charm necklace.
Fit & Features
- Sleeveless V-neckline
- Tie-front
- Spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2692
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Headed To The Tropics Mini Dress
Get ready to head to the tropics with this mini dress! The dress features a sleeveless scoop neckline, adjustable spaghetti straps, tropical palm leaf print, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Tropical palm leaf print
- Mini length silhouette
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0480
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Vibes Smocked Mini Dress
Channel those floral vibes with a smocked mini dress that nails those lowkey vibes just right! The dress features a sleeveless square neckline, spaghetti straps, a floral print, a mini-length silhouette, and a smocked body throughout. The dress offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Floral print
- Mini length silhouette with ruffled hem
- Smocked fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0802
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Into Florals Maxi Dress
Spring into the season with a maxi dress that ushers in the romance. The dress features a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a floral print, and a flowy A-line silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross back
- Floral print
- A-line silhouette, mini skirt length lining
- Floral print
- Lined chiffon fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-0979
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Darling Gingham Print Mini Dress
Stay on trend with a pretty mini dress that is perf for brunch with the squad! The dress features a sleeveless square neckline, spaghetti straps, gingham print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Gingham print
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4074
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Sweetheart Smocked Mini Dress
You'll be a total summer sweetheart in this adorable mini dress! It features a sleeveless square neckline with a ruffle trim, a tie-front bust detail, tie-shoulder spaghetti straps, a smocked body, and a mini-length, curve-hugging silhouette. Style this dress with casual sandals.
Fit & Features
- Sleeveless square neckline, ruffle trim
- Tie-front bust detail
- Tie-shoulder spaghetti straps
- Smocked body
- Short, form-hugging fit
- Woven fabric
- Runs true to size
Style Number/Barcode: 05102-0496
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Day Crochet Knit Midi Dress
Keep it casual with a midi dress that will have you channeling your bohemian side. The dress features a sleeveless V-neckline, spaghetti straps, a tie waist belt, and a midi length silhouette, The dress is composed of a crochet knit fabric that offers a relaxed fit with a slight stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tie-waist belt
- Midi length silhouette
- Crochet knit fabric
- Relaxed fit, slight stretch
- Runs true to size
Style Number/Barcode: 06005-0921
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty And Chic Paisley Printed Mini Dress
Showcase a pretty and chic vibe in this on-trend paisley printed mini dress. It features a sleeveless V-neckline, a tie accent at the bust, ruffle detailed shoulder straps, and a mini-length, curve-hugging silhouette. Style this dress with wedges for weekend brunch with the girls.
Fit & Features
- Sleeveless V-neckline
- Tie-front at the bust
- Ruffled shoulder straps
- Smocked back
- Short, form-hugging fit
- Paisley printed chiffon fabric
- Runs true to size
Style Number/Barcode: 05102-0571
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glitzy Look Glitter Strapless Skater Dress
Channel all the glitz and glam in this adorable glitter knit skater dress featuring a strapless straight neckline, ruched side seams, and a subtle drop waist. The pleated skater silhouette flares out to a trendy uneven mini-length hem. Style with metallic heels for a school dance or party!
Fit & Features
- Stretchy glitter knit fabric
- Strapless straight neckline
- Ruched side seams
- Subtle drop waist
- Pleated skater silhouette
- Uneven mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5809
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feelin' Fab Tie-Dye Mini Dress
You'll be feelin' oh-so-fab in this trendy tie-dye mini dress. It features a sleeveless scoop neckline, spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. This dress would be perf for a casual date styled with a cute crossbody purse and clear heels.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Ruched detailing, drawstrings at the hem
- Short, form-hugging fit
- Ribbed knit fabric, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-1334
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ditsy Floral Daze Ribbed Knit Mini Dress
Get caught in a floral daze with this cute mini dress! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ditsy floral print
- Mini-length silhouette, ruching down the sides
- Ribbed knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-3119
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy Vacay Vibes Maxi Dress
Bring the dreamy vacay vibes to your next getaway in this gorgeous maxi dress. It features a sleeveless V-neckline, adjustable spaghetti straps, a high waist, and a flowy floor-length silhouette with a chic front slit. The mesh fabric has a tropical floral print, making the maxi dress a perf pick for summer. Complete the look with strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Back zipper closure
- High waist
- Flowy floor-length silhouette, front slit
- Mesh fabric, floral print
- Runs true to size
Style Number/Barcode: 05101-0523
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mesmerizing Beauty Lace-Up Wrap Dress
Mesmerize with a wrap dress that showcases your best angles! The dress features a sleeveless scoop neckline, spaghetti straps, a lace-up back, a high slit, and a wrap silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit, Complete look with mules.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Lace-up back
- High slit
- Wrap silhouette
- Knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05101-0586
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free