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
Discover New Skater Dress Styles
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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Darling Twirl Crepe Ruffle Skater Dress
Delight with your darling twirls in this crepe skater dress perfect for family parties or brunch! It features adorable puff short sleeves, a V-neckline, and a ruffled layered short-length hem with a fit-and-flare silhouette. Complete the look in this skater dress with sleek hoop earrings.
Fit & Features
- Puff short sleeves
- V-neckline
- Back zipper and hook-eye closure
- Skater silhouette
- Ruffled layered short-length hem
- Crepe fabric, partial stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5064
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Desert Princess Halter Maxi Dress With Pockets
Experience the effortless beauty of this boho maxi dress! The sleeveless halter neckline and spaghetti strap tie create a flowy silhouette, while the hidden side pockets add functionality. The front slit and ruffled maxi-length hem in a chic bohemian print will make you feel like a true desert princess! Complete the look in sandals and sunnies.
Fit & Features
- Bohemian print, woven fabric, no stretch
- Halter neckline, spaghetti strap tie
- Hidden side pockets
- Flowy ruffled silhouette
- Runs true to size
Style Number/Barcode: 05102-5804
Category Name: Casual Dresses
Price: $16.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darling Vibe Ditsy Floral A-Line Midi Dress
Look oh-so-darling at weekend brunch in this ditsy floral A-line midi dress! The sleeveless sweetheart neckline is detailed with a dainty lace trim and tie-front design.
Fit & Features
- Woven fabric
- Ditsy floral print
- Sleeveless sweetheart neckline, dainty lace trim, lace trim spaghetti straps
- Tie-front detail, underbust seam
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5989
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Swept Off Your Feet Button Ruffle Maxi Dress
Oh-so-breezy! Sweep the room off their feet when you enter in this maxi dress featuring a sleeveless V-neckline, adjustable spaghetti straps, button-down front closures, and a flowy ruffled hem with a skin-flaunting front slit. The dress is composed of a smooth woven fabric with a sewn-in knit stretchy lining. Complete the look in espadrille wedges for a trip to the coast!
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Button-down front closures
- Front slit design
- Flowy ruffled maxi-length hem
- Smooth woven fabric, sewn-in knit stretchy lining
- Runs true to size
Style Number/Barcode: 05102-5061
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Alluring Bloom Flocked Floral Mesh Maxi Dress
This dress is giving sultry garden goddess. The strapless neckline and body-hugging mesh silhouette keep it sleek, while the flocked floral detail adds just the right amount of romance. Perfect for whenever you want to turn a subtle moment into the moment.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Flocked floral print pattern
- Strapless straight-across neckline
- Back zipper closure
- Ruching
- Fitted silhouette, midi-length flared hem
- Runs true to size
Style Number/Barcode: 05101-000180
Category Name: Casual Dresses
Price: $54.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Most Alluring Strapless Corset Abstract Mini Dress
Feel your most alluring in this corset mini dress providing a cinched look you'll love flaunting out on the town! Featuring a flattering strapless neckline and flexible boning, this bodycon dress creates a sleek silhouette. The mini-length hem and abstract print add a touch of playfulness, while the mesh fabric keeps you on trend. Complete the look in platform heels.
Fit & Features
- Abstract print, mesh fabric lined with stretchy knit
- Back zipper and hook-eye closure
- Flexible boning
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5359
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirt And Twirl Puff Sleeve Tie-Back Skater Dress
Flirt and twirl in this cute skater dress at parties and day dates! The puff short sleeves and square neckline add a touch of charm, while the tie-back design and skater silhouette create a flattering fit. Complete the look with hoop earrings.
Fit & Features
- Crepe woven fabric, stretchy knit lining
- Square neckline
- Tie-back detail
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3243
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flawless Beauty Eyelet A-Line Mini Dress
Make every heart flutter in this eyelet mini dress boasting a flirty bust tie and flattering A-line silhouette. Perfect for shower celebrations or brunch!
Fit & Features
- Eyelet knit stretchy fabric, stretchy knit lining
- V-neckline, spaghetti straps
- Bust tie
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6037
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love's In The Air Floral Chiffon A-Line Dress
Slip into romance! This dainty floral chiffon short dress features a sweetheart neckline and bust tie to accentuate your figure while the wide shoulder straps and underwire bust provide support. The corset-trim bodice and back lace-up design add a touch of romance along the flattering A-line silhouette and short-length hem. Complete the look with a ring set and sandals for a date or brunch!
Fit & Features
- Sleeveless sweetheart neckline
- Wide shoulder straps
- Underwire bust, tie front, side zipper and hook-eye closure
- Corset-trim bodice, lace-up back design
- A-line silhouette, short-length hem
- Dainty floral print, chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-3007
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Enchanted Floral Slit A-Line Midi Dress
Turn heads in this enchanting floral midi dress boasting a flattering A-line silhouette and a front slit for effortless sashays all day!
Fit & Features
- Ditsy floral print, knit fabric lined with stretchy knit
- V-neckline, bust tie
- Spaghetti straps
- Front slit
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6048
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tell Me About It Stud Strapless Denim Mini Dress
Be the talk of the night in this strapless denim mini dress at parties or concerts! With a strapless neckline and non-slip grip lining, this bodycon dress ensures a perfect fit. The studded trim adds a touch of edgy charm, while the mini-length hem accentuates your legs. Complete the look in knee-high boots and a cowboy hat!
Fit & Features
- Denim fabric, slight stretch
- Strapless neckline, non-slip grip lining
- Back zipper and hook-eye closure
- Studded trim along the front
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5473
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Crush Marble Print Maxi Dress
They'll totally be crushing on you in this alluring abstract marble print maxi dress! It features a strapless straight-across neckline, ruching down one side seam with an adjustable drawstring, a sultry high-cut side slit, and an asymmetric maxi-length hem. The fitted bodice leads to a flowy silhouette. The marble-printed sheer mesh fabric includes a mini-length knit lining. Style with gemstone earrings.
Fit & Features
- Strapless straight-across elastic-banded neckline
- Ruching down one side seam, adjustable drawstring
- High-cut side slit, asymmetric maxi-length hem, lettuce-edge trim
- Fitted bodice, flowy silhouette
- Abstract marble print
- Sheer mesh fabric, mini-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5276
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bubbly Love Corset Skater Party Dress
You'll always have people falling for you in this corset skater party dress at parties! The square neckline and adjustable spaghetti straps keep it trendy while the corset bodice and hidden front hook and eye fasteners provide a flattering silhouette. The stretchy smocked back and embroidered woven fabric add style to this playful bubble hem dress. Complete the look with earrings.
Fit & Features
- Embroidered woven fabric, sewn-in knit lining
- Adjustable spaghetti straps
- Square neckline
- Hidden front hook and eye fasteners
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2979
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Soft Focus Cable Knit Midi Dress
Knits, but make it chic—this tube cable knit midi dress hugs your shape while keeping it cozy. Perfect for layering with a jacket or going solo for an effortlessly polished vibe.
Fit & Features
- Cable knit fabric, stretchy knit lining
- Tube strapless neckline
- Form-hugging silhouette
- Center back slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000203
Category Name: Casual Dresses
Price: $28.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Divine Cutie Tie-Back Ruffled Skater Dress
You'll look positively cute and divine in this short skater dress at brunch or graduations! Designed with a flattering square neckline, adjustable spaghetti straps for the perfect fit, and a tie-back design, this dress is perfect for every girlie. The skater silhouette and ruffled layer add a playful touch, while the short-length hem offers comfort and versatility. Complete the look in strappy mules.
Fit & Features
- Airy woven fabric, sewn-in knit lining
- Adjustable spaghetti straps
- Ruffled
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5733
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Enchanting Look V-Neck Button Down Skater Dress
Your day just got sweeter in this sleeveless skater dress perfect for spring and summer occasions! This V-neck skater dress boasts adjustable spaghetti straps and button closures that allow for the perfect fit while the skater silhouette and short-length hem elevate your style. Complete the look with sandals and sunnies!
Fit & Features
- Woven fabric with lining, no stretch
- Adjustable spaghetti straps
- V-Neckline
- Button down front
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5555
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off To A Chic Start One-Shoulder Mini Dress
Your night will be looking oh-so-chic in this one-shoulder mini dress featured in a flattering bodycon fit that accentuates your curves!
Fit & Features
- Smooth knit-lined fabric, moderate stretch
- One-shoulder neckline
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5976
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Paradise Babe Lace Up Tropical Floral Maxi Dress
Look like a babe in paradise in this tropical floral maxi dress perfect for your next getaway or beach day! Embrace the warm, tropical vibes in this maxi-length hem dress on an airy mesh fabric bursting with a tropical floral print. With its flowy silhouette and high slit, you'll feel like you're walking on clouds. The V-neckline and spaghetti straps add a trendy vibe while the lace-up detail adds a touch of playfulness. Complete the look in sandals and sunnies!
Fit & Features
- Tropical floral print
- Mesh fabric lined with knit, moderate stretch
- Lace-up
- Spaghetti straps
- High slit
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05101-3241
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Exceptional Bliss Lace-Up Floral Chiffon Maxi Dress
Answer that invite in exceptional blissful style in this floral chiffon maxi dress perfect for showers, graduations, or vacations! With spaghetti straps, a lace-up back, and a flowy ruffled silhouette, this maxi dress is both comfortable and stylish. The stretchy smocked waist and maxi floor-length hem provide a flattering look for any occasion. Complete the look with dainty earrings.
Fit & Features
- Floral print, chiffon fabric lined with woven fabric
- Spaghetti straps
- Lace-up back
- V-Neckline
- Flowy ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-3345
Category Name: Casual Dresses
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Modern Minimalist Long Sleeve Midi Dress
Keep it sleek in a smooth knit dress that features a square neckline, fitted long sleeves, and a midi-length hem. Channel those casual vibes when you pair this midi dress with statement sneakers.
Fit & Features
- Smooth knit fabrication
- Square neckline
- Fitted long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5966
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweetest Style Puff Sleeve Floral Chiffon Skater Dress
Show off the sweetest style in this breezy floral chiffon skater dress! The airy sheer chiffon fabric is detailed with an adorable dainty floral print for a charming vibe. The short dress features a square neckline with ruching and a small tie-front detail, short puff sleeves, dual high waist seams, and a fit-and-flare skater silhouette. Style with espadrille wedges for weekend brunch!
Fit & Features
- Sheer chiffon fabric, stretchy knit lining
- Dainty floral print
- Ruched square neckline, tie-front detail
- Short puff sleeves
- High waist seams, back zipper with hook and eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3027
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Flair Ditsy Floral Mini Dress
Show off a charming flair in this adorable ditsy floral mini dress designed with eyelet knit fabric. The sweet vibes of the print are the perfect pairing with the sassy short bodycon silhouette.
Fit & Features
- Sheer eyelet knit fabric with knit lining, high stretch
- Ditsy floral print
- Sleeveless square neckline, dainty rosette detail, eyelet trim
- Adjustable spaghetti straps
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5999
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Artsy Mood Asymmetric Abstract Knit Midi Dress
Play up your going-out look adding an artsy vibe with this abstract midi dress! The stretchy knit fabric showcases a trendy abstract print for that cool-girl aesthetic. The mid-length dress features a sleeveless square neckline and spaghetti straps, ruched detailing down the side seam to accentuate your curves on the bodycon silhouette, and a high-cut asymmetric hem creating a sultry slit. Style with clear heels for a rooftop bar.
Fit & Features
- Abstract printed stretchy knit fabric, knit bust lining
- Sleeveless square neckline
- Spaghetti straps
- Ruched side seam
- Asymmetric hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5511
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Abstract printed stretchy knit fabric, knit bust lining
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Artful Drama Floral Open Back Maxi Dress
Serve artful drama in this halter maxi dress featuring a draped cowl neckline, sultry open back, and a watercolor-inspired floral print. Made for cocktail receptions, weddings, and statement entrances into parties.
Fit & Features
- Watercolor floral print, mesh-lined fabric, stretchy
- Cowl halter neckline, tie closure
- Open back with tie closure
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000690
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: BLUE
Available Size: S, M, L