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.
HomeCasual Dresses

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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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Paradise Pick V-Neck Cutout Tropical Maxi Dress
Enjoy the fun and sun on your paradise vacay in this tropical maxi dress! This flowy maxi silhouette features adjustable spaghetti straps, a flirty V-neckline with a keyhole, and a sultry cutout back. With a front slit, you'll steal the show with every step. Complete the look with sunnies and a straw handbag.
Fit & Features
- Tropical print, mesh fabric lined with stretchy knit
- Adjustable spaghetti straps
- V-neckline, keyhole
- Cutout back
- Front slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5692
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Scene Crew Neck Midi Dress
Your next casual plans call for this t-shirt midi dress for grabbing coffee or running errands in style! It features a classic crew neck, short sleeves, a cutout waist with a knot accent, a bodycon silhouette, and a flirty front slit on smooth cotton knit fabric. Complete the look in cute strappy sandals.
Fit & Features
- Crew neck, short sleeves
- Cutout waist, knot accent
- Bodycon silhouette
- Front slit, midi-length hem
- Smooth cotton knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5765
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute And Casual Knit Hoodie Dress
This cute and casual knit hoodie dress is perfect for styling up for your weekend plans! It features a hoodie with a front drawstring, long fitted sleeves, and a mini-length, form-hugging fit. The soft ribbed knit fabric offers plenty of stretch for ultra comfortable wear. Complete the look in this short dress with a plaid shacket and combat boots.
Fit & Features
- Hoodie, front drawstring
- Long fitted sleeves
- Mini-length hem
- Form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4798
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The One You Need Mini Dress
Step out in style with this sexy ribbed knit mini dress, perfect for brunch with your besties or a relaxed weekend outing. Its minimalist bodycon silhouette pairs effortlessly with an oversized denim jacket or a fitted blazer for a look that's polished yet effortlessly chic. The dress's flattering V-neckline is ideal for showcasing delicately layered necklaces, adding a sweet and enchanting touch to your ensemble.
Fit & Features
- Sleeveless V-neckline
- Thin bungee straps
- Strapless bra recommended
- Mini-length bodycon silhouette
- Ribbed knit fabric
- Figure-hugging fit, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-0500
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Best Spot To Be Off-The-Shoulder Polka Dot Mini Dress
Wherever you are in this off-the-shoulder polka dot mini dress is the best spot to be! The ruffled neckline with non-slip grip lining adds a flirty touch while the stretchy smocked bodycon silhouette highlights your curves. The tiered ruffle mini-length hem and polka print add a playful and chic vibe to this woven dress. Complete the look with earrings and cute booties!
Fit & Features
- Polka dot print, lined woven fabric
- Ruffled off-the-shoulder neckline
- Stretchy smocked bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5553
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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What You Want Strappy Cutout Slit Midi Dress
This sleeveless midi dress is just what you want to elevate your everyday style! Featuring a flattering square neckline, spaghetti straps, and a strappy cutout twist back, this bodycon dress will make you stand out in any crowd. The side slit adds a touch of sexiness to the midi-length hem. Complete the look in sleek stiletto heels for upcoming weekend plans!
Fit & Features
- Double-lined rib knit fabric, moderate stretch
- Spaghetti straps
- Square neckline
- Strappy cutout twist back
- Side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5663
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darling Delight Sleeveless Lace Trim Skater Dress
When the occasion calls for flair, this sleeveless skater dress delivers with darling delight! Perfect for bridal showers, rehearsal dinners, and graduations. Made from a smooth chiffon fabric, the lace trim straps and hem add a delicate touch. Featuring a square neckline and ruched bust, the flattering skater silhouette will have you twirling all day! Complete the look in block heels.
Fit & Features
- Smooth chiffon fabric, stretchy knit lining
- Square neckline, lace trim straps
- Back zipper and hook-eye closure
- Skater silhouette
- Lace trim short-length hem
- Runs true to size
Style Number/Barcode: 05101-3563
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Cute And Cool Denim Mini Dress
Weekend plans? Sorted. This zip-front denim mini dress keeps it casual but still put-together, with a belted waist that flatters every move. Pair with sleek boots for the perfect edgy fall vibe.
Fit & Features
- Denim fabric
- Sleeveless collared neckline
- Zip-up front closure
- Belted waist
- Front pockets
- Bodycon fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000223
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Whimsical Beauty Strappy Back Textured Knit Skater Dress
Radiate whimsical beauty in this gorgeous textured knit skater dress perfect for graduations or parties! The sheer textured knit fabric includes a full-length knit lining and offers plenty of stretch. The dress is shaped with a sleeveless square neckline and dual spaghetti straps leading to a bold open back with a cross-back strappy design. The high waist flows out to a short skater skirt with an adorable fit and flare silhouette. Style with hoop earrings and espadrille sandals.
Fit & Features
- Sheer textured knit fabric, full-length knit lining
- Plenty of stretch
- Square neckline, dual spaghetti straps
- Open back, cross-back strappy design
- High waist, short skater skirt
- Fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3142
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreaming Of Paradise Cowl Neck Tropical Midi Dress
Let your vacation or getaway be filled with sand and compliments when you're in this tropical midi dress! Featuring a cowl neckline and adjustable spaghetti straps for a perfect fit, this bodycon dress also boasts a side slit and midi-length hem. Complete the look with sunglasses and sandals!
Fit & Features
- Tropical print, stretchy knit fabric
- Adjustable spaghetti straps
- Cowl neckline
- Bodycon fit
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5613
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Arrival Rose Floral Chiffon Maxi Dress
Make a gorgeous arrival in this rose floral chiffon maxi dress for showers, birthdays, or family parties! The sweetheart neckline and adjustable spaghetti straps provide a flattering and comfortable fit, while the padded bra cups offer support and shape. The maxi-length hem and high front slit add a touch of sultry, making you feel so beautiful! Complete the look in chic wedge sandals and sunnies.
Fit & Features
- Rose floral print
- Chiffon fabric lined with stretchy knit
- Padded bra cups, adjustable spaghetti straps
- Back zipper and hook-eye closure
- High front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3128
Category Name: Casual Dresses
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tempting Allure Sweetheart A-Line Lace Mini Dress
A lace A-line mini dress that will captivate everyone in the room! With a playful sweetheart neckline, adjustable spaghetti straps, and an underwire bust, this dress accentuates your curves, while the A-line silhouette and ruffled tie mini-length hem add a touch of whimsy. Complete the look with a clutch for a dressy evening event.
Fit & Features
- Lace fabric lined with stretchy knit
- Sweetheart neckline, adjustable tie
- Adjustable spaghetti straps
- Underwire bust, back zipper and hook-eye closure
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3300
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romance That Wows Large Blossom Floral Maxi Dress
Make a stunning entrance in this large blossom floral maxi dress at dinner while on vacation or the weekend! Showcasing a statement blossoming floral print, this maxi dress is designed to turn heads. With a flattering V-neckline and delicate spaghetti straps, this dress hugs your curves in a bodycon silhouette and is finished with a maxi-length hem. Complete the look in strappy sandals and earrings!
Fit & Features
- Large blossoming floral print
- Mesh fabric lined with stretchy knit
- Spaghetti straps
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-3343
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Desirable Sultry Sweetheart Bow Bodycon Mini Dress
The heart wants what it wants and you need this bodycon mini dress! With adjustable spaghetti straps and a sweetheart neckline trimmed with delicate lace and a satin ribbon bow, this dress adds a touch of sweetness while flattering your curves in the bodycon fit. Complete the look in stiletto heels and a chic mini purse.
Fit & Features
- Woven fabric, minimal stretch
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Sweetheart neckline with lace and satin ribbon trim
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5813
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Garden Of Roses Chiffon Midi Dress
Frolic through the garden or your next soiree in this rose print chiffon midi dress! It features a sleeveless sweetheart neck, spaghetti straps, a ruched bust with a tie, and a slim A-line silhouette with a flirty front slit. Complete the look in strappy block heels.
Fit & Features
- Sleeveless sweetheart neck, spaghetti straps
- Ruched bust with tie
- Back zipper and hook-eye closure
- Slim A-line silhouette
- Front slit, midi-length hem
- Rose print, airy chiffon fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05101-2081
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pleasant Cutie Collared V-Neck Belted Midi Dress
Make your look sweet and simple in this sleeveless midi dress perfect for summer plans! The collared V-neckline and button-down closures offer a classic touch, while the adjustable belted waist gives you a flattering A-line silhouette complete with a midi-length hem. Style this midi dress with wedges and earrings.
Fit & Features
- Woven fabric with lining, no stretch
- Collared V-neckline
- Button-down closures
- Adjustable belted waist with buckle
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3347
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Artsy Flair Strapless Cutout Abstract Mini Dress
Showcase an artsy flair in this abstract mesh mini dress tonight! Featuring a striking strapless neckline, side ruched seams for a flattering fit, and a unique side cutout design, this bodycon mini-length dress is all about highlighting your curvaceous figure. Complete the look with stiletto heels.
Fit & Features
- Abstract print, mesh fabric, stretchy knit lining
- Strapless neckline
- Side cutout
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5693
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Think About Me Lace-Up Floral Skater Dress
Captivate everyone's thoughts in this floral skater dress sure to be the prettiest pick anyone has ever seen! With a square neckline and spaghetti straps, it's perfect for warmer days. The lace-up back and bow tie adds a playful touch, while the skater silhouette and mini-length hem flatter any figure. Complete the look with an adorable hair bow and sunglasses!
Fit & Features
- Floral print, woven fabric lined, no stretch
- Spaghetti straps
- Square neckline, bow tie
- Lace-up back
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5490
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Mode Tropical Floral Mesh Maxi Dress
Activate vacay mode and radiate dreamy vibes in this alluring tropical maxi dress! Designed with an airy sheer mesh fabric with a mini-length knit lining, this maxi-length dress is accented with a blooming tropical floral print for a stunning look. It features a sleeveless square neckline, spaghetti straps, ruched detailing at the waist to accentuate your curves, and a bodycon silhouette with a thigh-high side slit to showcase some leg. Style with stiletto heels for a sunset dinner!
Fit & Features
- Tropical floral print
- Sheer mesh fabric with mini-length knit lining, plenty of stretch
- Square neckline
- Spaghetti straps
- Ruched waist, side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5543
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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More Than Sweet Tie Strap Fit-And-Flare Dress
Who can imagine a look sweeter than this fit-and-flare dress? Showcase your darling side in this short eyelet dress at casual brunches or parties! This charming dress features a square neckline, tie shoulder straps, and a flattering fit-and-flare silhouette. With a tiered ruffled short-length hem and delicate eyelet lace fabric, this dress will have you looking and feeling your best. Complete the look in trendy sneakers for a cute style!
Fit & Features
- Sheer eyelet lace fabric with knit lining, moderate stretch
- Square neckline
- Tie shoulder straps
- Fit-and-flare silhouette
- Tiered ruffles
- Runs true to size
Style Number/Barcode: 05102-5532
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Allure Tie-Front Ruffled Skater Dress
Captivate with your charming allure in this pretty tie-front ruffled skater dress! Designed with a breezy gauze woven fabric, this short dress is the perfect lightweight style for weekend dates. It features a sleeveless V-neckline with the cutest tie-front bow design, a built-in padded bust, adjustable spaghetti straps so you can find your perfect fit, and a smocked back for added stretch. The high waist flows out to a tiered ruffled skater skirt with an adorable fit-and-flare silhouette. Complete your look with hoop earrings and heeled sandals.
Fit & Features
- Gauze woven fabric with woven lining, no stretch
- V-neckline with tie-front, padded bust
- Adjustable spaghetti straps
- High waist, smocked back
- Tiered ruffled design
- Fit-and-flare skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5720
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Enchanting A-Line Floral Chiffon Midi Dress
Have everyone under your spell in this floral chiffon midi dress as a stunning wedding guest or to attend a garden party! Featuring a square neckline with a bust tie, elasticized shoulder straps, and an A-line silhouette, this dress flatters any figure. The front slit and midi-length hem add a touch of sophistication. Complete the look in block heels and earrings!
Fit & Features
- Floral print, chiffon fabric, stretchy knit lining
- Elasticized shoulder straps
- Square neckline, bust tie
- Back zipper and hook-eye closure
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3304
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruffle Me Up Lace Halter Mini Dress
Serving flirty femme vibes—this lace mini dress with tiered ruffles is giving soft glam perfection. The halter neckline and curve-hugging fit make it your new go-to for bridal celebrations and dressy brunch plans.
Fit & Features
- Lace-lined fabric
- Halter V-neckline
- Bodycon silhouette
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000535
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: IVORY, BLACK
Available Size: L, XS, S, M
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Leave An Impression Twist Cutout Knit Midi Dress
Leaving an impression will be easy with this sleeveless knit midi dress! Perfect for vacation or a weekend spent at the beach, this dress features a flattering scoop neckline, spaghetti straps, a head-turning twist cutout back design, a bodycon fit, and a sultry side slit along the midi-length hem. Complete the look in strappy espadrille wedges.
Fit & Features
- Knit fabric, moderate stretch
- Scoop neckline
- Spaghetti straps
- Twist back cutout
- Side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1950
Category Name: Casual Dresses
Price: $17.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale