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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Signature Stripes Strapless A-Line Maxi Dress
Show off your signature style in this striped maxi dress perfect for casual summer plans! Features a strapless neckline, a stretchy smocked bodice for a comfortable fit, and a flattering A-line midi silhouette with hidden side pockets to keep your hands warm. Complete the look with sunglasses and trendy sandals.
Fit & Features
- Striped pattern, cotton woven fabric, no stretch
- Strapless neckline
- Stretchy smocked bodice
- Hidden side pockets
- A-line midi silhouette
- Runs true to size
Style Number/Barcode: 05102-5802
Category Name: Casual Dresses
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Favorite Fleur V-Neck Floral Chiffon Skater Dress
Give them a twirl in this adorable floral chiffon skater dress at birthdays or graduation parties! Featuring puff short sleeves, a tie front bust, and a stretch smocked empire waist, this dress will hug your curves in all the right places. The skater silhouette and ruffled hem add a playful touch to this flowy chiffon dress. Complete the look with teardrop earrings.
Fit & Features
- Floral print, chiffon fabric lined with stretchy knit
- V-Neckline, tie front
- Skater silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05101-3135
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly Chic Ribbed Knit Skater Dress
When your outfit says polished but still playful, this is the skater dress. The mock neck and fit-and-flare silhouette keep it chic, flirty, and ready for any plans on your calendar.
Fit & Features
- Ribbed sweater knit fabric, moderate stretch
- Sleeveless mock neckline
- Tank shoulder straps
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 06005-000085
Category Name: Casual Dresses
Price: $36.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Looking Long Sleeve Denim Mini Dress
A denim mini dress features long sleeves, a classic collar neckline, flap pockets for style, and a flattering bodycon silhouette. Perfect for back-to-school and styling with sneakers or boots.
Fit & Features
- Denim fabric, minimal stretch
- Long sleeves with button cuffs
- Collar neckline
- Front zipper closure
- Flap pockets
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5448
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Feels Off-The-Shoulder Sweater Mini Dress
Feel cute in this off-the-shoulder sweater mini dress all year round! The folded off-the-shoulder neckline adds a flirty touch, while the bodycon fit accentuates your curves perfect for a day or night on the town. Complete the look in block heels.
Fit & Features
- Sweater knit fabric, moderate stretch
- Off-the-shoulder neckline
- Bodycon fit
- Mini-length
- Runs true to size
Style Number/Barcode: 06005-1947
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Special Stunner One-Shoulder Cutout Ombre Maxi Dress
Leave everyone in awe when you're in this ombre maxi dress for sunset cocktails! Featuring a unique one-shoulder neckline with an adjustable spaghetti strap and flirty side cutout, this dress hugs your curves and shows off your legs with a high-side slit along the maxi-length hem and form-hugging silhouette. Complete the look with sparkly bracelets.
Fit & Features
- Ombre mesh fabric, stretchy knit lining
- One-shoulder neckline, adjustable spaghetti strap
- Side cutout
- High side slit
- Form-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5708
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly Trendy Striped Slit Maxi Dress
A trendy maxi dress features a flattering square neckline, form-hugging fit, and a high front slit to show off your shoes. Perfect for styling with a denim jacket and sandals.
Fit & Features
- Striped pattern, stretchy knit fabric
- Square neckline, spaghetti straps
- High front slit
- Form-hugging maxi-length fit
- Runs true to size
Style Number/Barcode: 05102-5867
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Be My Forever Ribbon Bow Bodycon Mini Dress
Flattery will get you everywhere in this sleeveless mini dress perfect for boasting an adorable look! The scoop neckline is adorned with delicate lace and charming bow detail, while the tank shoulder straps give a flirty touch. The bodycon silhouette and mini-length hem finish this flawless dress. Complete the look in platform high heels for a party.
Fit & Features
- Woven fabric with minimal stretch
- Scoop neckline, lace and ribbon trim, bow
- Back zipper and hook-eye closure
- Tank shoulder straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5817
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Little Wild One-Shoulder Zebra Print Maxi Dress
Your next night out just got a little wild in this sassy zebra print maxi dress perfect for vacation or the weekend! This form-hugging dress features a one-shoulder neckline and spaghetti strap, with a side drawstring cutout to show some skin. The high side slit and maxi-length hem add a flirty touch to this fierce and flattering piece. Complete the look with heeled sandals and earrings.
Fit & Features
- Zebra printed knit fabric, plenty of stretch
- One-shoulder neckline, spaghetti strap
- Side drawstring cutout
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5821
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Always Strapless Cutout Ruffle Maxi Dress
Have all eyes on you in this strapless maxi dress boasting a sweetheart twist neckline and a cutout bodice. The smooth knit fabric hugs your curves along the form-hugging silhouette and creates a front center ruffle design.
Fit & Features
- Smooth knit lined fabric, moderate stretch
- Strapless sweetheart twist neckline
- Cutout bodice
- Center front ruffle design
- Form-hugging, maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3601
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darling Details Floral Eyelet Mini Dress
This floral eyelet mini dress has darling details that make it perfect for spring and summer looks! Made from a beautiful floral printed woven eyelet fabric, this dress will make you feel like a blooming flower. With a flirtatious square neckline and bust keyhole tie, this dress is perfect for any occasion. The adjustable spaghetti straps ensure a perfect fit while the curve-hugging silhouette and mini-length hem show off your figure. Complete the look with a ring set.
Fit & Features
- Floral printed woven eyelet fabric with knit lining
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Square neckline, keyhole tie
- Curve-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-3013
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Garden Of Romance Tie Back Rose Floral A-Line Dress
Let your love bloom for this rose floral chiffon midi dress perfect for garden parties and weddings! Featuring a square neckline, adjustable spaghetti straps, and a tie-back for the perfect fit, this flowy A-line silhouette dress will have you feeling flirty and feminine. With a front slit and midi-length hem, it's perfect for styling with chic stiletto heels.
Fit & Features
- Rose floral print, chiffon fabric lined with stretchy knit
- Square neckline
- Adjustable spaghetti straps
- A-Line silhouette
- Front slit
- Runs true to size
Style Number/Barcode: 05101-3257
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bloom Season Floral Mesh Maxi Tube Dress
Meet your new obsession for dinner dates and chic soirées. This floral mesh maxi dress hugs in all the right places with a strapless neckline that feels effortlessly elevated.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Floral print
- Strapless straight-across neckline
- Ruching
- Maxi-length hem, back slit
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000252
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L, XL
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Covetable Charm V-Neck Ruffled Maxi Dress
You'll covet the charm of this sleeveless maxi dress all season! With a flattering V-neckline and adjustable spaghetti straps, this dress will hug you in all the right places. The crisscross and smocked back add a trendy touch, while the flowy silhouette and ruffled long-length hem offer a breezy style. Complete the look in sandals.
Fit & Features
- Woven fabric, bust lining, no stretch
- Adjustable spaghetti straps
- Crisscross and smocked back
- Flowy silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5546
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sure To Love Floral Woven Puff-Sleeve Skater Dress
You'll love wearing this sweet floral puff-sleeve skater dress all summer long! The lightweight woven fabric is detailed with a soft floral print for a pretty feminine look. The short dress features a scoop neckline with ruching and a tie-front accent, short puff sleeves with elastic cinched hems, a stretchy smocked high waist, and an adorable fit-and-flare silhouette with a ruffled hem for a flirty vibe. Style with sneakers for a cute and casual outfit.
Fit & Features
- Floral print
- Woven fabric with smooth woven lining
- Ruched scoop neckline with tie-front detail
- Short puff sleeves with elastic cinched hems
- Stretchy smocked high waist
- Fit-and-flare silhouette, ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5716
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Graceful Presence Sweetheart Floral Skater Dress
Have a graceful presence in this floral skater dress at showers or graduations! A charming dress with a sweetheart neckline and tie spaghetti straps, the skater silhouette flatters your figure, while the short-length hem adds a playful touch. Complete the look in wedge sandals.
Fit & Features
- Floral print, woven fabric lined with stretchy knit
- Tie spaghetti straps
- Sweetheart neckline
- Back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3194
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Babe Floral Woven Puff Sleeve Skater Dress
Create a darling day date look with this floral puff sleeve skater dress! Made with a lightweight woven fabric, it is detailed with a charming dainty floral print for those sweet feminine vibes. The short dress features a V-neckline with a cute tie-front detail, short puff sleeves with a ruffled trim, a high waist seam, and a skater hem with a flirty fit-and-flare silhouette. Style with a dainty charm necklace and heels.
Fit & Features
- Dainty floral print
- Woven fabric
- V-neckline, tie-front detail
- Short puff sleeves, ruffled trims
- Back zipper closure, high waist seam
- Short skater skirt, fit-and-flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3466
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Show Off Your Glow Tropical Lace-Up Midi Dress
Show off your vacation glow in this tropical midi dress all over the island or resort! With a square neckline, spaghetti straps, and a lace-up back, this side slit dress hugs your body in all the right places with side ruched seams and a bodycon fit. Complete the look in sandals.
Fit & Features
- Tropical print, mesh fabric, sewn-in knit lining, moderate stretch
- Spaghetti straps
- Square neckline
- Lace-up back
- Ruched side seams, bodycon fit
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5866
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfectly Poised Sweetheart Polka Dot A-Line Dress
Always put your best sweet self forward in this sleeveless polka dot dress at parties or on day dates! The sweetheart neckline with bust tie and spaghetti strap shoulder ties elevate your look, while padded bra cups provide support and comfort. The A-line silhouette and mini-length hem create a flattering style. Complete the look with hoop earrings.
Fit & Features
- Polka dot print, lined woven fabric, no stretch
- Spaghetti strap shoulder ties
- Sweetheart neckline with bust tie
- Padded bra cups
- Back zipper and hook-eye closure
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5822
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty In Plaid Drop Waist A-Line Mini Dress
This halter dress will make you feel pretty in plaid and flattering with its halter neckline and pleated A-line silhouette.
Fit & Features
- Plaid-printed linen-blend woven fabric with woven lining, no stretch
- Plunge V-neckline
- Tie-back halter straps
- Partially open back, hidden zipper with hook-eye closure
- Drop waist
- Mini-length pleated A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5852
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fiji Feeling Sleeveless Lace-Up Tropical Maxi Dress
Escape to the island or look like you did in this tropical maxi dress for an effortless summer style! With a flattering V-neckline and delicate spaghetti straps, this dress will keep you stylish all day long. The lace-up back adds a touch of playful detail, while the A-line silhouette and maxi-length hem create a flowy and romantic look.
Fit & Features
- Palm leaf tropical and border print, woven fabric with lining, no stretch
- V-neckline
- Spaghetti straps
- Lace-up back
- A-line maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5864
Category Name: Casual Dresses
Price: $11.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Breezy Chic Floral Embroidered Chiffon Skater Dress
This breezy chic floral chiffon skater dress is perfect for your summer parties! The airy sheer embroidered chiffon fabric is detailed with a dainty floral print and includes a stretchy full-length knit lining. The short dress features a sleeveless sweetheart neckline, a bustier-style bodice with a padded bust and structured underwire, and ruched cups. The adjustable spaghetti straps lead to a partially smocked back design for added stretch with a secure back zipper closure. The front faux buttons lead to a high waist seam flowing out to a short skater skirt with a flirty fit and flare A-line silhouette. Complete your look with strappy sandals.
Fit & Features
- Sheer embroidered chiffon fabric, floral print, stretchy knit lining
- Sweetheart neckline, bustier bodice, padded bust with underwire, ruching
- Adjustable spaghetti straps
- Partial stretchy smocked back, zipper with hook and eye closure
- Front faux buttons, high waist seam
- Fit and flare A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3009
Category Name: Casual Dresses
Price: $49.90
Availability: Out of Stock
Product Badge:- Sale
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Lovely Look Cold Shoulder Bodycon Lace Mini Dress
Nothing can compare to your lovely look in this lace mini dress as a stunning bride-to-be or birthday girlie! Featuring a trendy cold shoulder V-neckline, feminine flutter short sleeve cuffs, and delicate spaghetti straps, this dress hugs your curves for a bodycon fit that will turn heads. Complete the look with earrings and clutch.
Fit & Features
- Lace fabric lined with stretchy knit
- Cold shoulder V-neckline
- Flutter short sleeve cuffs, spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3423
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Think Sunshine Long Sleeve Cutout Crochet Mini Dress
Get in the summer vibe with this crochet mini dress perfect for pool parties or vacation! Featuring sheer flared long sleeves for a trendy touch, a sexy V-neckline, and a cutout waist and back for a daring look. The hoop insert adds a unique twist and the tie-back design creates a flattering look along the bodycon silhouette. Complete the look with sunglasses and sandals!
Fit & Features
- Crochet fabric, sewn-in knit lining, slight stretch
- Sheer flared long sleeves
- V-neckline
- Hoop insert, cutout waist and back
- Tie-back design
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5732
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale