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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Preppy And Trendy Plaid Ruched Mini Dress
Keep it preppy in a plaid mini dress that is perf for your next brunch with the squad! The dress features a plaid print, a sleeveless square neckline, spaghetti straps, dual ruched drawstrings, and a mini-length silhouette. Complete look with mules and a jelly purse.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Plaid print
- Dual ruched drawstrings
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-1679
Category Name: Casual Dresses
Price: $19.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Totally Fab Tie Dye Midi Dress
Keep it totally fab with a midi dress that channels those pretty vibes! The dress features a sleeveless V-neckline, spaghetti straps, a tie-dye print, and a midi silhouette with a high side slit. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tie-dye print
- Midi silhouette
- High side slit
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-1633
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Splash Of Style Tie Dye Midi Dress
Add a splash of style with a pretty midi dress! The dress features a sleeveless cowl neckline, spaghetti straps, a strappy back design, a tie-dye print, and a midi-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with clear mules.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Strappy back design
- Tie-dye print
- Midi length silhouette
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-1659
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Vibes Tie-Dye Knit Mini Dress
Bring the casual vibes this season with this trendy tie-dye knit mini dress. It features a crew neckline, short sleeves, side ruching, and a mini-length, curve-hugging silhouette with side ties at the hem. Complete the look with cute sneakers for the perf everyday outfit.
Fit & Features
- Crew neckline
- Short sleeves
- Side ruching
- Side ties at the hem
- Short, form-hugging fit
- Knit fabric, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-1588
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy Glam Tie Dye Ruched Mini Dress
Keep it dreamy in a tie-dye dress that channels a retro feel! The dress features a sleeveless square neckline, spaghetti straps, a ruched body, tie-dye print, and a mini-length silhouette. Complete look with wedges and a denim jacket for a cute date outfit.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ruched body
- Tie-dye print
- Mini length silhouette
- Brushed knit fabric
- Form hugging, moderate stretch, runs true to size
Style Number/Barcode: 05102-1520
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Preppy And Trendy Plaid Mini Dress
Keep it on a trend with a preppy plaid dress to channel those cool-girl vibes. The mini dress features a sleeveless square neckline, spaghetti straps, plaid 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
- Plaid print
- Mini-length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1508
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feelin' Flirty Floral Mini Dress
This flirty floral mini dress is a must-have for summer parties! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a back zipper closure, ruched detailing, and a short, form-hugging fit. Style this dress with a chic charm necklace and wedges.
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Back zipper closure
- Ruching
- Mini-length, curve-hugging silhouette
- Mesh fabric, floral print
- Runs true to size
Style Number/Barcode: 05102-1497
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Instincts Basic Tube Dress
Tap into your stylish instincts with a basic tube dress. The dress features a sleeveless square neckline and a midi-length silhouette. The dress is composed of a knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a jelly purse.
Fit & Features
- Sleeveless square neckline
- Midi length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0975
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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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Effortless Ruched Knit Mini Dress
Create an effortless everyday outfit with this on-trend knit mini dress. It features a mock neckline, short sleeves, a front ruched detail with a drawstring, and a mini-length, curve-hugging silhouette. Complete the look with classic sneakers and a cute crossbody purse.
Fit & Features
- Mock neckline
- Short sleeves
- Front ruched detail with a drawstring
- Short, form-hugging fit
- Double-lined brushed knit fabric
- Runs true to size
Style Number/Barcode: 05102-1478
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Vibes Sleeveless Mini Dress
Showcase a gorgeous glow in this sunset-hued tie-dye mini dress! It features a sleeveless scoop neckline, tank shoulder straps, and a short, curve-hugging silhouette. The brushed knit fabric offers plenty of stretch. Style this dress with a denim jacket and sneakers for a casual look.
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Mini-length, form-hugging fit
- Brushed knit fabric, plenty of stretch
- Tie-dye print
- Runs true to size
Style Number/Barcode: 05102-1483
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Staple Ribbed Knit Mini Dress
This comfy ribbed knit mini dress will be a new casual staple in your closet. It features a sleeveless scoop neckline, adjustable spaghetti straps, and a short, curve-hugging silhouette with a rounded hem. Style this dress with a denim jacket and sneakers for the perf everyday look.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Mini-length, form-hugging fit
- Rounded hem
- Ribbed sweater knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-0968
Category Name: Casual Dresses
Price: $4.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Chic Ribbed Knit Mini Dress
Elevate your everyday look with this casually chic mini dress. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette. Style this ribbed knit dress with the matching jacket and sleek hoop earrings.
Shop Matching Jacket: Casually Chic Ribbed Knit Cropped Jacket
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Short, form-hugging fit
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-1492
Category Name: Casual Dresses
Price: $19.97 $25.90
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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Basic Chic Ribbed Knit Dress
Style up your everyday outfit with this elevated basic dress. It features a crew neckline, short sleeves, side ruching that leads to a slit, and a curve-hugging silhouette. The ribbed knit fabric includes a lining and offers plenty of stretch. Complete your look with sneakers and cool shades for the day or a faux leather crossbody purse and mules for the night.
Fit & Features
- Crew neckline
- Short sleeves
- Side ruching
- Side slit
- Form-hugging fit
- Lined ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-1466
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Must-Have Everyday Ribbed Knit Dress
This must-have ribbed knit dress is perf for an everyday outfit! It features bungee spaghetti straps, a square neckline, ruching, and dual drawstrings at the hem. Style the dress as a mini and pair it with sneakers for a casual brunch with friends, or make the dress a midi length and style with clear heels for a date night.
Fit & Features
- Bungee spaghetti straps
- Square neckline
- High waist seam and side ruched detailing
- Dual drawstrings
- Style as a mini or midi dress
- Ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-1455
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Butterfly Charm Ruched Mini Dress
Bring the charm with a butterfly print dress that springs you into the season. The mini dress features a sleeveless square neckline, spaghetti straps, a butterfly print, a ruched body, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with butterfly earrings and wedges.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Butterfly print
- Ruched body
- Mini-length silhouette, form-hugging fit
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1454
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetest Style Floral Mini Dress
Showcase the sweetest style this summer season in this floral mini dress! It features a sleeveless bodice, spaghetti straps, a sweetheart neckline with a tie-front at the bust, and a mini-length, curve-hugging silhouette. The knit fabric has an all-over adorable ditsy floral print that will pair perfectly with a denim jacket and sandals.
Fit & Features
- Spaghetti straps
- Sweetheart neckline
- Tie-front at the bust
- Short, form-hugging fit
- Knit fabric, moderate stretch
- Ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-1431
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirtatious Vibes Floral Mini Dress
Bring the flirty vibes in this adorable floral mini dress perf for summer! It features an off-the-shoulder sweetheart neckline with a ruffle trim, a tie-front detail, short puff sleeves, an all-over ditsy floral print, and a mini-length, curve-hugging silhouette. Complete the look with cute wedges for a weekend brunch.
Fit & Features
- Off-the-shoulder sweetheart neckline, ruffle trim
- Tie-front detail
- Short puff sleeves
- Ditsy floral print
- Brushed knit fabric, moderate stretch
- Short, form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-1430
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tie Dye Ruched Mini Dress
Keep it ruched and stylish with a dress that channels those retro vibes. The dress features a sleeveless square neckline, spaghetti straps, dual drawstrings, a tie-dye print, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Dual drawstrings
- Tie-dye print
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-1438
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love At First Sight Mini Dress
With you in this adorable ditsy floral dress, it will be love at first sight. The dress features thin ruffle shoulder straps, a V neckline with subtle ruching, and a short, curve-hugging silhouette. The lightweight knit fabric offers plenty of stretch. Complete your look with a classic denim jacket and sneakers.
Fit & Features
- Thin ruffle shoulder straps
- V neckline with ruching
- Mini-length, form-hugging fit
- Knit fabric with plenty of stretch
- Ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-1429
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Essential High Slit Ribbed Knit Maxi Dress
Create a chic moment with a maxi dress that brings the chic details! The dress features a crew neckline, short sleeves, dual side cutouts, and a maxi silhouette accented with a high side slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sneakers for a casual vibe.
Fit & Features
- Crew neckline
- Short sleeves
- Dual side cutouts
- Maxi length silhouette
- High side slit
- Ribbed knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1420
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Flirt Floral Mini Dress
Bring the flirtatious vibes in this adorable floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. Style this dress with sneakers for a cute and casual look.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruched detailing, drawstrings at the hem
- Short, form-hugging fit
- Ribbed knit fabric, floral print
- Runs true to size
Style Number/Barcode: 05102-1404
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free