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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Call of The Wild Midi Slit Dress
Answer the call in a fierce midi dress! Showcase your unique style in this geometric crepe midi dress featuring a sleeveless, V-neck, sleek spaghetti straps, and a slim-fit silhouette with a front slit accent. Complete the look in lattice booties.
Fit & Features
- Sleeveless, V-neck, spaghetti straps
- Slim-fit silhouette
- Front slit accent
- Midi-length hem
- Geometric print
- Crepe knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4649
Category Name: Casual Dresses
Price: $4.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Life's A Breeze Floral Cutout Midi Dress
This floral cutout midi dress makes getting ready a breeze! It features short puff sleeves and a ruched sweetheart bodice with a flirty waist cutout that leads to a flowy, midi-length silhouette with a slit accent. Composed of a chiffon-lined fabric with no stretch. Style with a trendy mini tote.
Fit & Features
- Short puff sleeves
- Ruched sweetheart bust
- Waist cutout, smocked back
- Midi-length silhouette with slit accent
- Floral pattern
- Chiffon fabric, inner lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1551
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Meet Me in the Meadow Chiffon Floral Maxi Dress
Easy, breezy, and made for photoshoots and parties. This strapless chiffon maxi dress with a smocked bodice and floral print gives off-carefree weekend energy with a soft, boho vibe.
Fit & Features
- Floral print, chiffon fabric, short woven lining
- Strapless smocked bodice
- Flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000107
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, L
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Island Views Tropical Cowl Mini Dress
You may be in paradise but you'll be the main view in this tropical mini dress! Features a sleeveless, cowl neck, sleek spaghetti straps, bodycon silhouette, and an asymmetrical mini-length hem with a side ruched tie. Complete the look in hoop earrings and heels.
Fit & Features
- Sleeveless, cowl neck, spaghetti straps
- Bodycon silhouette
- Asymmetrical mini-length hem
- Side ruched tie
- Tropical pattern
- Texture knit fabric, moderate stretch, fits true to size
Style Number/Barcode: 05102-4366
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Paradise Calls Tropical Midi Dress
Vacation on the mind? You're going to need this tropical midi dress with paradise written all over it! Features a sleeveless, v-neck, adjustable spaghetti straps, a form-fitting silhouette, and a side ruched seam on an asymmetrical midi hem. Complete the look in lace-up sandals for a dinner with a view.
Fit & Features
- Sleeveless, v-neck, adjustable spaghetti straps
- Form-fitting silhouette
- Side ruched seams
- Asymmetrical midi hem
- Tropical pattern
- Texture knit fabric, moderate stretch. fits true to size
Style Number/Barcode: 05102-4367
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wrapped In Chic Style Midi Sweater Dress
Get wrapped up in chic style in this ribbed knit sweater dress. It features a sleeveless V-neckline, tank shoulder straps, a trendy knot-front design with a small center keyhole cutout, and a mid-length, curve-hugging fit. Complete the look with strappy mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Knot-front design, center keyhole cutout
- Midi-length, form-fitting silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1256
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Beauty Floral Bodycon Dress
Hey beauty! Showcase your charm in this blooming floral bodycon dress. It features a sleeveless square neckline, spaghetti straps, chic ruching down the sides, and a short, curve-hugging silhouette. Style this dress with sparkly stud earrings and cute mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ruched detailing down the sides
- Mini-length, form-fitting, bodycon silhouette
- Floral print
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4549
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cold Brew Collared Mini Dress
For coffee dates and everything else, you'll adore this collared v-neck mini dress designed to flatter your figure on a bodycon silhouette with a faux button-down accent and all-over ruching. Composed of sleek knit fabric with a moderate stretch. Finish the look in cute booties.
Fit & Features
- Sleeveless, collared v-neck
- Faux button-down placket
- All-over ruching
- Bodycon silhouette
- Mini-length hem
- Sleek knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4482
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Glam Lattice Short Dress
Bring it back to basics to make a glam impression in a short sweater dress that stuns! This must-have dress features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a lace-up back design, and a short-length hem. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross back
- Lace-up back
- Short-length hem
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1332
Category Name: Casual Dresses
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Soiree Puff Sleeve Mini Dress
Heading to an afternoon soiree? This floral mini dress is perfect! It features adorable short puff sleeves, a sweetheart neckline, a front bust tie with a keyhole accent, and a bodycon silhouette. Complete the look with a crossbody bag.
Fit & Features
- Short puff sleeves, elasticized hems
- Sweetheart neckline
- Front bust tie, keyhole accent
- Bodycon silhouette
- Mini-length hem
- Floral pattern
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-4608
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy-Chic Style Halter Midi Dress
Showcase your trendy-chic status in this of-the-moment midi dress! It features a sleeveless halter neckline, spaghetti straps that lead to a cross-back lace-up strappy design, a sleek front O-ring accent, a midi-length, curve-hugging silhouette, and an all-over geometric striped pattern. Style this dress with heeled mules.
Fit & Features
- Sleeveless halter neckline, spaghetti straps
- Open back, strappy cross-back lace-up design, tie closure
- Front O-ring detail
- Midi-length, form-fitting silhouette
- Geometric striped pattern
- Knit fabric, partial front knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4411
Category Name: Casual Dresses
Price: $4.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chasing Sunsets Floral Maxi Dress
This floral maxi dress is perfect for sunset dinners while on vacay! It features sleeveless, v-neck, sleek spaghetti straps, and a slim-fit silhouette with a front side slit to showcase some skin. Complete the look in trendy sandals.
Fit & Features
- Sleeveless, V-neck, sleek spaghetti straps
- Slim-fit silhouette
- Front side slit
- Maxi-length hem
- Floral pattern
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1393
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Poised And Chic Sweater Dress
Keep it poised and chic with a sweater dress that is perf for every day! The dress features a sleeveless collared neckline, a button-down front, and a bodycon fit through the hip and thigh. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules and hair clips.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless collared neckline
- Button-down front
- Bodycon fit
- Short-length hem
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1451
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Destination Dinner Paisley Halter Mini Dress
Dinner plans? You're gonna need this perfect halter mini dress! It features a sleeveless bodice on an open-back with dual tie-back closure, a front slit accent, bodycon silhouette, and a paisley pattern throughout. Complete the look in lace-up heels.
Fit & Features
- Sleeveless, halter neckline
- Dual tie-back closure
- Front slit accent
- Bodycon silhouette
- Mini-length hem
- Paisley pattern
- Knit fabric, partial front knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4410
Category Name: Casual Dresses
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Places To Go One Shoulder Midi Dress
You've got places to go and this one-shoulder midi dress will have you looking stylish! It features a spaghetti strap, bodycon silhouette, and an asymmetrical midi-length hem with a high side slit to showcase some legs. Composed of stretchy texture knit fabric. Finish the look in platform heels.
Fit & Features
- Sleeveless, one-shoulder, spaghetti strap
- Bodycon silhouette
- Asymmetrical midi-length hem
- High side slit
- Texture knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4358
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Nothing Bud Fun Floral Halter Dress
Have nothing but fun in this flirty floral halter dress perfect for a brunch date! It features a sleeveless, halter v-neck with adjustable neck tie, a babydoll style bodice leading to a flowy, ruffled short hem. Showcase some skin in the open-back with tie closure. Complete the look in lace-up sandals.
Fit & Features
- Sleeveless, halter v-neck, adjustable necktie
- Babydoll style bodice
- Flowy ruffled short hem
- Open-back, tie closure
- Ditsy floral print, woven-lined fabric
- Fits true to size, no stretch
Style Number/Barcode: 05102-4364
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Let It Flow Crochet V-Neck Skater Dress
Flowy and flirty! Twirl all day in this crochet V-neck skater dress featuring a sleeveless bodice with adjustable spaghetti straps, an open back with tie closure, and a tiered short hem. Composed of a gauze woven fabric with an inner lining. Finish the look in trendy mules.
Fit & Features
- Sleeveless bodice, crochet V-necklined
- Adjustable spaghetti straps
- Open-back, tie closure
- Tiered short hem
- Skater silhouette
- Airy gauze woven fabric, inner lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4397
Category Name: Casual Dresses
Price: $21.97 $47.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Timeless Romance Open Back Lace Romper
Enter your forever romantic era in this lace long sleeve romper boasting a flirty open back and ruffled short-length hem.
Fit & Features
- Lace-lined fabric
- Scoop neckline
- Sheer fitted long sleeves
- Open back
- Form-hugging fit
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 06503-1276
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Day To Night Snap Button Midi Dress
Go from office hours to happy hour in a snap with this classy sweater midi dress! It features long sleeves, a rounded neckline, a bodycon silhouette, and a side slit with snap button accents. Composed of a ribbed knit fabric with a moderate stretch. Style with a chic jacket and heels.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Long fitted sleeves
- Round neckline
- Bodycon silhouette
- Side slit, snap button accents
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1219
Category Name: Casual Dresses
Price: $18.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruffle Party Chiffon V-Neck Babydoll Dress
Make a ruffle at the party in this chiffon babydoll dress featuring a sleeveless V-neckline, adjustable spaghetti straps, criss-cross back, flowy silhouette, and a ruffled trim throughout. Composed of a chiffon woven fabric with an inner skirt lining. Perfect for styling with a mini tote bag.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Criss-cross back
- Babydoll flowy silhouette
- Ruffled trim throughout
- Chiffon woven fabric, inner lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1465
Category Name: Casual Dresses
Price: $6.67 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunday Girl Floral Chiffon Skater Dress
Look cute for Sunday brunch in this floral chiffon skater dress featuring three-quarter length puff sleeves, a square neck, and a pleated waistband on the skater silhouette. Showcase a peek of skin in the open-back design with tie closure and ruffled short-length hem. Composed of a chiffon floral lined fabric with no stretch. Perfect for styling with knee-high boots.
Fit & Features
- Three-quarter length puff sleeves, elastic cinched hems
- Square neckline
- Pleated waistband, skater silhouette
- Ruffled short-length hem
- Open-back, tie closure, back zipper, hook and eye closure
- Chiffon floral lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-1706
Category Name: Casual Dresses
Price: $25.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Prepped For Anything Cutout Mini Dress
With this mini dress, you'll be ready for whatever plans come up! It features long sleeves, a collared neck, button-down closures, a sultry cutout bodice on a bodycon silhouette. Composed of stretchy rib-knit fabric. Style with mules.
Fit & Features
- Long sleeves, collared neck
- Button-down closures
- Cutout bodice
- Bodycon silhouette
- Mini-length hem
- Stretchy rib-knit fabric
- Fits true to size
Style Number/Barcode: 05102-4354
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fab And Wild Slip Dress
Keep it fab with a slip dress that showcases your wild side! The dress features a snake print, a sleeveless cowl neckline, adjustable spaghetti straps that cross at the back, a tie-back accent, and a short-length hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with a minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps, cross at back
- Tie back ties
- Snake print
- Short length hem
- Lined lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-4345
Category Name: Casual Dresses
Price: $4.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Always On Point Ruched Mini Dress
You'll always look on point in this trendy ruched mini dress! It features a sleeveless square neckline, bungee straps, a high waist seam, side ruched detailing with adjustable drawstrings, and a short, curve-hugging fit. Style this dress with sleek hoop earrings and strappy sandals.
Fit & Features
- Sleeveless square neckline
- Bungee straps
- High waist seam
- Side ruching, adjustable drawstrings
- Mini-length, form-fitting silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4472
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale