Explore the array of casual dresses perfect for brunch with your besties to stroll around the farmers market on the weekends. Discover a variety of casual fabrics like ribbed knit, denim, mesh, linen, or cotton gauze. Browse the variety of skater dresses, sundresses, t-shirt dresses, and boho-inspired maxis. Look out for off-the-shoulder mini dresses, tropical print shift dresses, and tie-dye ribbed dresses perfect for a laid-back vibe but always with a chic aesthetic.

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STYLE SPOTLIGHT

Cute Work Dresses

Floral Print Dresses

Everyday Ease: Casual Dresses for Warm-Weather Plans

From weekend brunches to spontaneous getaways, 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 farmer’s market or catching golden hour with friends.

Laid-Back & Versatile

Lightweight cotton, knit, and chiffon dresses bring comfort and style to sun-filled days. Slip into playful mini dresses, breezy midi styles, or long casual dresses in soft florals, neutrals, and vibrant hues. Tunic and t-shirt dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.

Chic from Day to Night

Swap sneakers for strappy sandals to take your favorite midi dress from errands to evening hangs. A flowy maxi in a muted pastel or black adds relaxed elegance—just add a denim jacket and slides for an effortless finish.

Ready to reset your daily 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!

Covetable Charm Strapless Mini Skater Dress
From casual outings to chic occasions, this strapless skater dress is one you'll covet for charming looks every time! The non-slip grip lining along the strapless neckline ensures a secure fit while the ruched bodycon bodice flatters your figure. The skater silhouette and pleated short-length hem add a playful touch to this poplin dress! Complete the look in sandals and sunnies.

Fit & Features
- Poplin stretchy fabric, sewn-in knit lining
- Back zipper and hook-eye closure
- Strapless square neckline
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-000035

Category Name: Casual Dresses

Price: $46.90

Availability: In Stock

Available Color: NAVY

Available Size: XXS, XS, S, M, L
Perfectly Stylish Sleeveless Ribbed Knit Midi Dress
Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules.

Fit & Features
- Stretchy ribbed knit fabric
- V-neckline
- Spaghetti straps
- High front slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-1645

Category Name: Casual Dresses

Price: $38.90

Availability: In Stock

Available Color: WHITE, BLACK

Available Size: S, M, L, XS
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Bold New Look Corset Lace-Up Linen Skater Dress
Make a bold impression in this corset linen skater dress all season long! The sweetheart neckline with a bust tie and adjustable straps provides a flattering fit while the flexible boning supports your shape. The strappy lace-up back adds a touch of playfulness to the skater silhouette and short-length hem. Complete the look in wedge sandals and a handbag.

Fit & Features
- Linen blend fabric lined with stretchy knit
- Sweetheart neckline with bust tie
- Adjustable straps, side zipper and hook-eye closure
- Strappy lace-up back
- Flexible boning
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3791

Category Name: Casual Dresses

Price: $49.90

Availability: In Stock

Available Color: BLACK, LIGHT, BLUE, WHITE

Available Size: XS, S, M, L
Product Badge:
- Sale
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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