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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Keeping Knit Basic Ruched Midi Dress
Keep it basic with a midi dress that can be dressed up for your next date night! The dress features a sleeveless square neckline, tank-shoulder straps, a ruched high side slit with a drawstring 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 and hoops.
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Ruched high side slit
- Drawstring
- Midi length silhouette
- Ribbed knit fabric
- Form hugging, moderate stretch, runs true to size
Style Number/Barcode: 05102-2181
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In A Snap Long Sleeve Ribbed Dress
Look stylish in a snap with this long sleeve dress as your base for creating fire styles! It features a v-neckline with snap-button closures, a bodycon silhouette, and a mini-length hem. Composed of a rib-knit fabric with a moderate stretch. Complete the look with booties and a cropped jacket.
Fit & Features
- Long sleeves
- V-neckline, snap-button closure
- Bodycon silhouette
- Mini-length hem
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1034
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Just Like That Mini Dress
Show them you've got your style locked down just like that! This mini dress features a sleeveless scoop neckline, spaghetti straps, and a short, curve-hugging silhouette. The lined stretchy knit fabric has contrasting exposed seams on the front for a trendy vibe. Complete the outfit with sneakers to keep it casual, or style with clear heels for an elevated look.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Mini-length, form-hugging fit
- Lined stretchy knit fabric
- Contrasting exposed seams
- Runs true to size
Style Number/Barcode: 05102-2180
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off-The-Shoulder Ribbed Knit Mini Dress
Channel those effortless chic vibes with this sweater mini dress that slays! The dress features an off-the-shoulder neckline, a faux button-down front, long sleeves, 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.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Off-the-shoulder neckline
- Faux button-down front
- Long fitted sleeves
- Lettuce edge hems
- Mini-length silhouette
- Ribbed knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1015
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy And Chic Floral Mini Dress
This floral mini dress will have you looking dreamy and chic for a summer date night with bae! It features a sleeveless sweetheart neckline with a ruffle trim at the bust, adjustable spaghetti straps, ruched detailing, a short, form-hugging fit, and a ruffled hem with a tie at the front. Style this dress with cute mules.
Fit & Features
- Sleeveless sweetheart neckline, ruffle trim at the bust
- Adjustable spaghetti straps
- Ruching
- Mini-length, form-hugging silhouette
- Ruffled hem, tie at the front
- Mesh fabric, floral print
- Runs true to size
Style Number/Barcode: 05101-1008
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Pop Ruffled Mini Dress
Add a pop of florals to your look with a mini dress that brings the romance! The dress features an off-the-shoulder neckline, a sweetheart bust with ruffled trim, short sleeves, and a ditsy floral print. 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
- Off the shoulder neckline, padded cups
- Sweetheart bust, ruffled trim
- Short sleeves
- Ditsy floral print
- Mini length silhouette
- Lined mesh fabric
- Form hugging, moderate stretch, runs true to size
Style Number/Barcode: 05101-1009
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vintage Grunge Distressed Graphic Tunic
Showcase those trendy vintage grunge vibes in this distressed graphic tunic! It features a V-neckline, short sleeves, a center eagle and stars graphic with the script "Born Free, Unknown Destination," slashed detailing, and a short, curve-hugging fit. Style this tunic with sneakers to keep it casual, or combat boots for an edgy look.
Fit & Features
- V-neckline, short sleeves
- Center eagle and stars graphic
- Script "Born Free, Unknown Destination"
- Slashed detailing
- Mini-length, form-hugging fit
- Cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-0823
Category Name: Casual Dresses
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortlessly Enchanting Floral Maxi Dress
You will look effortlessly enchanting in this stunning floral maxi dress! It features adjustable spaghetti straps, a square neckline with a ruffled trim, a stretchy smocked bodice, and a lace-up back. The elastic-banded high waist flows out to a floor-length skirt with an A-line silhouette and a thigh-high slit. Complete the look with dainty earrings and cute wedges.
Fit & Features
- Adjustable spaghetti straps
- Square neckline, ruffled trim
- Stretchy smocked bodice, lace-up back
- Elastic-banded high waist
- Floor-length skirt, A-line silhouette, high slit
- Floral printed sheer chiffon fabric, knit lining
- Runs true to size
Style Number/Barcode: 05101-0998
Category Name: Casual Dresses
Price: $9.97 $52.90
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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Flowy Floral Woven Halter Dress
Perfect for the warmer months, this flowy floral woven dress is a must-have for weekend brunches and picnic dates! It features a sleeveless square neckline, halter tie straps, a back bar strap design, a fitted stretchy smocked bodice, and a flowy skirt with an A-line silhouette. Pair this ditsy floral printed dress with cute wedges and a trendy straw tote.
Fit & Features
- Square neckline
- Halter tie straps
- Back bar strap design
- Fitted stretchy smocked bodice
- Flowy skirt, A-line silhouette
- Ditsy floral print
- Woven fabric, knit lining
- Runs true to size
Style Number/Barcode: 05101-1001
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Classically Chic Button Up Mini Dress
Button up in a chic mini dress that is oh so chic! The dress features a collared neckline, a button-down front, long sleeves, 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 heels.
Fit & Features
- Collared neckline
- Button-down front
- Long sleeves
- Ruched body
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4190
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Put A Ring On It Cutout Mini Dress
Put a ring on this cute mini dress that is a must for your next night out! The dress features a plunging sleeveless V-neckline, dual cutouts at the waist, an O-Ring at the center of the bodice, 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 mules.
Fit & Features
- Sleeveless V-neckline
- Cutouts at the waist
- O-Ring
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2139
Category Name: Casual Dresses
Price: $19.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Trendsetter Status Mini Dress
Showcase your major trendsetter status in this knit mini dress! It features short sleeves, a deep V neckline, a front waist cutout design, and a mini-length, curve-hugging silhouette. Wear the dress with the cutout in the back for a versatile look. Complete the outfit with cute sneakers.
Fit & Features
- Short sleeves
- V neckline
- Waist cutout design
- Short, form-hugging fit
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-2122
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spotted In Style Leopard Mini Dress
Get spotted in this mini dress that brings the bold factor to your look! The dress features a sleeveless V-neckline, bungee spaghetti straps, a leopard print, a mini side slit, and a mini-length silhouette. The dress is composed of a lightweight knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops.
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Leopard print
- Mini side slit
- Mini length silhouette
- Lightweight knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-2138
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Romance Ditsy Floral Mini Dress
Fall in love with this adorable ditsy floral mini dress that is perfect for summer date nights. It features short puff sleeves, a sweetheart neckline with a center criss-cross bust detail, and a mini-length, curve-hugging silhouette. Complete the outfit with a charm necklace and clear heels.
Fit & Features
- Short puff sleeves
- Sweetheart neckline
- Center criss-cross bust detail
- Short, form-hugging fit
- Knit fabric, ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-2103
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Dream Lace-Up Maxi Dress
Get carried away in this tropical maxi dress that will have you ready for that cabana life! The dress features a tropical floral print, a sleeveless V-neckline, a double row of spaghetti straps that cross at the back, a lace-up back, and a maxi-length silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and hoops.
Fit & Features
- Tropical floral print
- Sleeveless V-neckline
- Double-row of spaghetti straps, cross at back
- Lace-up back
- High side slit
- Maxi length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-2104
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Feels Ruffled Mini Dress
This pretty floral dress has us in our feels, bby! The dress features a floral print, an off-the-shoulder neckline with a ruffled popover, ruffled short sleeves, 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 wedges and a metal cuff.
Fit & Features
- Ditsy floral print
- Off the shoulder neckline
- Ruffled popover, ruffled short sleeves
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2096
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Fever Ribbed Knit Mini Dress
Keep it stylish with a floral dress that is all the rage! The dress features a sleeveless sweetheart neckline, spaghetti straps, a tie-front at the bust, 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 wedges.
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Tie-front
- Ditsy floral print
- Mini-length silhouette
- Ribbed knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2032
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vintage Racing Sleeveless Mini Dress
This on-trend vintage-inspired mini dress is perfect for weekend outings with the squad. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette with side drawstrings at the hem. The dress has a cool center car graphic with the script "Vintage Racing." Complete the outfit with edgy combat boots.
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Short, form-hugging fit
- Side drawstrings
- Car graphic with the script "Vintage Racing"
- Runs true to size
Style Number/Barcode: 06002-0803
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Summer Daydream Floral Mini Dress
You'll look like such a daydream in this adorable floral mini dress. It features a sleeveless V-neckline, bungee spaghetti straps, a mini-length fitted silhouette, and a slightly flared-out hem with a front slit. Complete the look with hoop earrings and strappy sandals.
Fit & Features
- V-neckline
- Bungee spaghetti straps
- Short, fitted silhouette
- Slightly flared-out hem, front slit
- Knit fabric, plenty of stretch
- Ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-4172
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ride Or Die Baddie Mini Dress
Here's looking at you baddie! Keep it bold in a mini dress that features a sleeveless scoop neckline, tank shoulder straps, a graphic that reads: "Old Motorcycle, Extraordinary Performance", an image of a motorcycle with wings, ruched drawstrings at the hem, 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 a moto jacket and ankle booties.
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Graphic: "Old Motorcycle, Extraordinary Performance"
- Image of a motorcycle with wings
- Ruched drawstrings at hem
- Mini length silhouette
- Ribbed knit fabric, form-hugging fit, moderate stretch
Style Number/Barcode: 06002-0802
Category Name: Casual Dresses
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Edgy Destruction American Motorcycle Graphic Tunic
Channel an edgy look with a tunic that plays up your rocker side! The tunic features a V-neckline, short sleeves, eagle wings graphic, a script that reads: "American Motorcycles", destructed detailing, and a mini length. Complete look with combat boots.
Fit & Features
- V-neckline
- Short sleeves
- Eagle wings
- "American Motorcycles" script
- Destructed detailing
- Cotton knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06002-0801
Category Name: Casual Dresses
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Retro Babe Sleeveless Colorblock Mini Dress
Channel a retro moment with a mini dress that makes a stylish statement. The dress features a sleeveless crew neckline, a colorblock design accented with exposed seams, 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 crew neckline
- Colorblock pattern with exposed seams
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2064
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Dreamy Ditsy Floral Mini Dress
Keep it dreamy with a floral mini dress that brings the romance. The dress features a sleeveless V-neckline with a ruched center, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a lined ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline with ruched center
- Spaghetti straps
- Ditsy floral print
- Mini-length silhouette
- Lined ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2047
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free