Casual Dresses
Casual dresses that keep up with your plans—brunch, game day, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and sweater knits, these pieces prove laid-back can still look styled. Play it polished with a shirt dress or belted A-line, lean comfy-cute in a fitted bodycon, 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 outing, these casual dresses are built to move with your mood—and your calendar.
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STYLE SPOTLIGHT
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Everyday Ease: Casual Dresses for Cool-Weather Plans
From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends.
Laid-Back & Versatile
Knit, ribbed, and sweater dresses bring comfort and style to crisp fall days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.
Chic from Day to Night
Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in burgundy or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.
Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.
What Makes a Dress Casual?
Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.
Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.
How Do I Style a Dress Casually?
Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.
For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!
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Elevated Cutout Mini Sweater Dress
This elevated mini sweater dress is a trendy staple for this fall season! It features a mock neckline, long fitted sleeves, waist cutouts that lead to the back, and a short, curve-hugging, bodycon silhouette. Style with strappy heels.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Waist cutouts that lead to the back
- Mini-length hem
- Fitted bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1469
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All Business Sweater Mini Dress
All business with some pleasure! Take this sweater mini dress from office hours to happy hour. It features a sleeveless, v-neck, and a form-fitting silhouette. Complete the look with a chic clutch.
Shop More Styles: The Sweater Collection
Fit & Features
- Sleeveless, v-neck
- Form-fitting silhouette
- Mini-length hem
- Sweater rib-knit
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1529
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Struck By Sultry Halter Mini Dress
Get struck by this sultry halter mini dress sure to capture every eye in the room! The knit dress features a sleeveless halter neck with tie closure, a strappy cutout waist, and a form-hugging silhouette. Complete the look in sassy platform heels.
Fit & Features
- Sleeveless halter neck with tie closure
- Strappy cutout waist
- Form-hugging silhouette
- Mini-length hem
- Lined slinky knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4776
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Cool Slit Maxi Dress
Stroll outside looking casually cool and cute in this basic maxi dress design with a sleeveless scoop neck with bungee spaghetti straps, a form-hugging silhouette, and a high-cut side slit. Complete the look in a crop denim jacket and sneakers.
Fit & Features
- Sleeveless scoop neck
- Bungee spaghetti straps
- Form-hugging
- High-cut side slit
- Maxi-length hem
- Rib-knit fabric, lined, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4883
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Timeless Trend Collared Mini Dress
Totally timeless and trending, this collared mini dress will be such a staple in your year-round closet! It features long fitted bell sleeves with split cuffs, a V-neckline, a bodycon silhouette, and side and center front ruching that puts your curves on display! Complete the look in chic booties.
Fit & Features
- Long fitted bell sleeves with split cuffs
- Collared V-neckline
- Bodycon silhouette
- Center and side ruching
- Mini-length hem
- Stretchy smooth knit fabric
- Runs true to size
Style Number/Barcode: 05102-4899
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off The Scale Snake Mini Dress
This snake mini dress will take your style to a new scale! It features a sleeveless square neck with sleek spaghetti straps and side ruched seams to accentuate your curves along the bodycon silhouette. Complete the look in a choker necklace.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Snake print, knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4695
Category Name: Casual Dresses
Price: $9.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruched Babe Mock Neck Bodycon Dress
Flaunt your babe status in this bodycon dress! It features long sleeves, a mock neckline, a ruched front, and a short-length hem. The dress is composed of a soft knit fabric with a moderate stretch
Fit & Features
- Long sleeves
- Mock neckline
- Ruched front
- Short-length hem, bodycon style
- Soft knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4290
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Highly Sophisticated Sweater Dress
This sleeveless sweater dress brings sultry-sophistication to every occasion! It features a halter neckline, side cutouts on the bodice, and a form-fitting silhouette on a mini-length hem. Complete the look in a classy blazer and heels.
Fit & Features
- Sleeveless, halter neckline
- Side cutouts
- Form-fitting silhouette
- Mini-length hem
- Soft sweater knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1377
Category Name: Casual Dresses
Price: $3.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Good For You Sweater Maxi Dress
Cause you like looking good for yourself! This sweater maxi dress is the perfect staple for your seasonal closet. It features long sleeves, a collared v-neckline, a form-hugging silhouette, and a flirty front cutout slit. Style with booties for an afternoon lunch.
Fit & Features
- Long sleeves
- Collared v-neckline
- Form-hugging silhouette
- Front cutout slit
- Maxi-length hem
- Ribbed knit fabric
- Fits true to size
Style Number/Barcode: 06005-1482
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On Top Of The Trends Cutout Mini Dress
Stay on top of the latest trends this fall with this casual yet chic mini dress! It features a sweetheart neckline with a center knot accent at the bust, dual asymmetric front cutouts at the waist, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric has a moderate stretch for comfortable wear. Style with knee-high boots for a fall festival.
Fit & Features
- Sweetheart neckline, center knot detail at the bust
- Dual asymmetric front waist cutouts
- Long fitted sleeves
- Mini-length hem
- Fitted bodycon silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4320
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Marvelous Mod Mesh Short Dress
So marvelously mod, this marble print mesh dress has entered the chat. It features a sleeveless square neckline, spaghetti straps, and side ruched seams to accentuate your curves along the bodycon silhouette. Complete the look in chunky platform heels.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Marble print, mesh-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4819
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rock Legend Graphic Choker Tunic
Showcase your rock babe status in this edgy graphic tunic top featuring short sleeves, a choker neck with a cutout accent and slash details, and a front script that reads, "Vintage Rock N Roll" along the form-fitting short hem. Complete the look in combat boots for a concert.
Fit & Features
- Short sleeves
- Choker neck with cutout accent
- Slash details
- Graphics front script "Vintage Rock N Roll"
- Form-fitting, short hem
- Jersey knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1414
Category Name: Casual Dresses
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Take A Look Sweater Midi Dress
Let everyone take a look at you in this sweet sweater midi dress perfect for the autumn season! This dress features a sleeveless halter neck with tie closure, a bodycon silhouette, and a cutout waist with a front slit along the hem. Complete the look in pointy-toe booties.
Fit & Features
- Sleeveless halter neck with tie closure
- Bodycon silhouette
- Cutout waist, front slit
- Midi-length hem
- Rib-knit sweater fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1416
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Romance Floral Lace-Up Maxi Dress
Evoke chic romance on date night in this gorgeous floral maxi dress designed with an open lace-up strappy back and floor-length form-hugging silhouette. Style with a sleek handbag and stiletto heels.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Large floral print
- Sleeveless deep V-neckline
- Spaghetti straps
- Open cross-back lace-up strappy design
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000111
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L, XL
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Swirl Of Splash Crew Mini Dress
A splash of this swirl print mini dress will instantly give your closet a fresh look! The dress features long fitted sleeves, a crew neckline, and a bodycon silhouette on smooth knit fabric with a moderate stretch. Complete the look in a crop denim jacket for a day out with friends!
Fit & Features
- Long fitted sleeves
- Crew neckline
- Bodycon silhouette
- Mini-length hem
- Swirl print
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4779
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Knit Your Average Sweater Dress
Level up in this curve-flaunting sweater dress featuring a sleeveless, scoop neckline, spaghetti straps, a bodycon silhouette, and a mini-length hem on ribbed knit fabric with plenty of stretch. Complete the look in a crop cardigan and booties.
Shop More Styles: The Sweater Collection
Fit & Features
- Sleeveless, scoop neckline
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Ribbed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1450
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
- Sleeveless, scoop neckline
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Edgy Stunner Graphic T-Shirt Dress
Show off an edgy style with this on-trend graphic t-shirt dress! It features a crew neckline with a notched design with safety pin detailing, short sleeves, a mini-length, fitted silhouette, and a motorcycle and eagle graphic with the script "American Motorcycles Road Lifestyle 1974." Complete your 'fit with combat boots.
Fit & Features
- Crew neckline, notched design, safety pin detailing
- Short sleeves
- Mini-length hem, form-hugging fit
- Motorcycle and eagle graphic
- Script that reads, "American Motorcycles Road Lifestyle 1974"
- Cotton-blend fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1445
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Coffee Date Ribbed Knit Midi Dress
This soft ribbed knit midi dress is perfect for fall coffee dates! It features a collared V-neckline, long fitted sleeves, a partial faux button-down front, a midi-length hem with a high front slit, and a form-hugging fit. Style with knee-high boots for a chic autumn look.
Fit & Features
- Collared V-neckline
- Long fitted sleeves
- Partial faux button-down front
- Midi-length hem, front slit
- Fitted silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4740
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Chic Ribbed Knit Midi Dress
Style up this casual chic ribbed knit midi dress for every day! It features a mock neckline, short sleeves, a midi-length hem, a form-hugging fit, and a high front slit. Complete the look with hoop earrings and ankle booties.
Fit & Features
- Mock neckline
- Short sleeves
- Midi-length hem
- Fitted bodycon silhouette
- Front slit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4739
Category Name: Casual Dresses
Price: $19.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Animal Kingdom Zebra Satin Dress
You'll be the head of the animal kingdom in this fierce and femme zebra satin mini dress! It features a sleek and sleeveless cowl neck, spaghetti straps, and a curve-hugging silhouette. Complete the look in strappy heels for a wild night out!
Fit & Features
- Sleeveless cowl neck
- Spaghetti straps
- Curve-hugging silhouette
- Mini-length hem
- Zebra pattern
- Smooth satin with minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4532
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fall Ritual Poplin Shirt Dress
Your new fall favorite for wearing all season! This poplin shirt dress features long sleeves with buttoned cuffs, a collared neckline, front button-down closures, a fitted waist, a lower open-back design with lace-up, and a pleated, short skater silhouette. Complete the look in chic Panama hat and booties.
Fit & Features
- Long sleeves with buttoned cuffs
- Collared neckline
- Front button-down closures
- Fitted waist, lower open-back, lace-up
- Pleated, short skater silhouette
- Non-stretch poplin fabric
- Fits true to size
Style Number/Barcode: 05101-1771
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simple Life Crew Tank Midi Dress
All a girl needs is this basic crew tank midi dress perfect for dressing up or down! It features a sleeveless bodice, wide tank shoulder straps, a midi-length hem, and a bodycon silhouette on lined ribbed knit fabric with plenty of stretch. Style this mid-length dress with a jacket and suede booties.
Fit & Features
- Sleeveless crew neckline
- Wide tank shoulder straps
- Midi-length hem
- Bodycon silhouette
- Lined ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4772
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Everyday Ribbed Knit Midi Dress
Effortlessly chic for every day, this ribbed knit midi dress is a must-have for fall. It features a V-neckline, a combination of front spaghetti straps and long fitted sleeves, and a midi-length, curve-hugging silhouette. Style with ankle booties for coffee dates this season.
Fit & Features
- V-neckline
- Front spaghetti straps, long fitted sleeves
- Midi-length hem
- Fitted bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4975
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Good Turtleneck Maxi Dress
Look and feel good in this rib knit maxi dress perfect for everyday styling! It features long sleeves, a turtleneck, a form-hugging silhouette, and a side-slit accent. Complete the look in mules for a dinner date.
Fit & Features
- Long fitted sleeves
- Turtleneck
- Form-hugging silhouette
- Side slit
- Maxi-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4861
Category Name: Casual Dresses
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale