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

Cute Sweater Dresses

Floral Print Dresses

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!

Sun Kissed Strapless Floral Bodycon Mini Dress
Bare your sun kissed shoulders on vacay in this strapless mini dress with a statement floral print and flattering bodycon fit that flaunts your curves!

Fit & Features
- Mesh fabric, floral print, stretchy knit lining
- Strapless neckline
- Bodycon fit
- Mini-length hem
- Runs small
Style Number/Barcode: 05102-6112

Category Name: Casual Dresses

Price: $19.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Attract And Allure Marble Print Midi Dress
Attract and allure in this marble print midi dress that puts your curves on display! It features a high crew neckline, long fitted sleeves, a midi-length hem with a form-hugging silhouette, and an all-over trendy marble print pattern. The sheer mesh fabric includes a full-length sleeveless knit lining. Style this mid-length dress with clear heel mules for a cool-girl vibe for a rooftop bar!

Fit & Features
- Crew neckline
- Long fitted sleeves
- Midi-length hem, form-hugging fit
- Marble print, sheer mesh fabric
- Full-length sleeveless knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5403

Category Name: Casual Dresses

Price: $19.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Gorgeous Silhouette Sleeveless Bodycon Midi Dress
Flaunt your gorgeous figure in this midi dress designed with smooth nylon fabric offering plenty of stretch. It features a sleeveless scoop neck and back design, tank straps, and a midi-length bodycon silhouette to showcase your curves.

Fit & Features
- Smooth nylon fabric with plenty of stretch
- Scoop neck and back
- Tank shoulder straps
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5931

Category Name: Casual Dresses

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Abstract Moment Mesh Mock Neck Midi Dress
Step out in this stylish mesh midi dress and not miss a single moment to have all eyes on you! The knee-length dress features a feminine mock neck with back button closures, fitted sheer long sleeves, and bodycon silhouette with abstract print on mesh fabric. Complete the look with gold hoop earrings for an art gallery opening and dinner downtown!

Fit & Features
- Mock neck, back button closures
- Fitted sheer long sleeves
- Bodycon silhouette
- Midi-length hem
- Abstract print
- Mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5294

Category Name: Casual Dresses

Price: $19.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Silhouette Midi Sweater Dress
This curve-hugging sweater dress was made for sunset happy hour! It features a sleeveless V-neckline with a twist-front design, a center cutout under the bust, tank shoulder straps, and a midi-length, form-fitting silhouette with a chic high side slit. Style with classic hoop earrings and clear mules.

Shop More Sweater Dresses: Sweater Dress Collection

Fit & Features
- Sleeveless V-neckline, twist-front accent
- Center cutout under the bust
- Tank shoulder straps
- Midi-length hem, form-fitting silhouette, high side slit
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1462

Category Name: Casual Dresses

Price: $6.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Here To Flirt Drop Waist Ruffled Skater Dress
This adorable skater dress features a ribbed knit top with a sleeveless crew neckline and tank shoulder straps, a trendy V-shaped drop waist, and a tiered ruffled chiffon A-line silhouette for a flirty accent. Style with mules for a date night or sneakers to keep it casual!

Fit & Features
- Ribbed knit and chiffon fabrics, moderate stretch
- Crew neckline, tank shoulder straps
- V-shaped drop waist
- Tiered ruffled design
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5910

Category Name: Casual Dresses

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tropical Fun Chain Strap Midi Dress
Perfect for your next getaway, this tropical midi dress is a must to pack in your carry-on! It features a sleeveless square neck, half chain and adjustable spaghetti straps, a bodycon silhouette, and a flirty side slit. the dress is composed of a tropical print slinky-knit fabric with a sewn-in knit lining. Complete the look in heeled sandals.

Fit & Features
- Sleeveless square neck
- Half chain, adjustable spaghetti straps
- Bodycon silhouette
- Side slit, midi-length hem
- Tropical print
- Slinky knit fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5070

Category Name: Casual Dresses

Price: $9.97 $37.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Beauty Strappy Back Knit Midi Dress
This chic sleeveless midi dress is designed with a jacquard patterned sweater knit fabric and features a square neckline, halter spaghetti straps, and a bold open back with cross-back straps and tie-back straps. The midi-length form-hugging silhouette is detailed with a high front slit.

Fit & Features
- Knit fabric with jacquard pattern, moderate stretch
- Square neckline, halter spaghetti straps
- Open back, cross-back straps, tie-back straps
- Contrast seam design at the bodice
- High front slit
- Midi-length form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2227

Category Name: Casual Dresses

Price: $6.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Spot Me In Leopard Slit Midi Dress
You can be spotted all season in this leopard print midi dress perfect for a casual lunch or a wine night with friends! It features a sleeveless V-neckline, tank shoulder straps, and a form-hugging, slim silhouette with a flowy slit hem. Complete the look in sleek statement hoop earrings and sandals.

Fit & Features
- Sleeveless V-neckline, tank shoulder straps
- Form-hugging, slim silhouette
- Front slit
- Midi-length flowy hem
- Leopard print
- Woven non-stretch fabric
- Runs true to size
Style Number/Barcode: 05102-4469

Category Name: Casual Dresses

Price: $5.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pretty In Paradise Strappy Cutout Maxi Dress
You'll be pretty in paradise in this stunning maxi dress for vacation or a bachelorette weekend! The dress features a sleeveless V-neckline, spaghetti straps that lace up along the open back, flirty waist cutouts, and a high front slit along the flowy hem. Complete the look with earrings and clear block heels for a chic style!

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Lace-up open back
- Waist cutouts, high front slit
- Maxi-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4752

Category Name: Casual Dresses

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Keeping Knit Chic Long Sleeve Midi Dress
Keep it chic in this knit midi dress boasting an off-the-shoulder neckline and trendy button accents that lead to a flirty slit. Pair with boots.

Fit & Features
- Ribbed knit fabrication
- Off-the-shoulder neckline, foldover accent
- Long sleeves
- Snap button accents at the hem
- High side slit
- Midi length hem
- Runs true to size
Style Number/Barcode: 06005-2137

Category Name: Casual Dresses

Price: $7.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
She's The Main Rib Knit Strapless Midi Dress
Flaunt your look with ease and chicness with this midi dress this season! The knee-length dress features a strapless neckline, a flattering bodycon silhouette, and a fitted maxi-length hem on soft and stretchy rib knit fabric with a short knit lining. Style with the matching bolero and heels for weekend plans!

Shop Matching Bolero: She's The Main Rib Knit Slouchy Bolero

Fit & Features
- Strapless neckline
- Bodycon silhouette
- Fitted midi-length hem
- Soft and stretchy
- Rib knit fabric, short knit lining
- Runs true to size
Style Number/Barcode: 05102-5872

Category Name: Casual Dresses

Price: $19.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunny Sweet Floral A-Line Mini Dress
Sunny sweet will be your vibe in this cute floral mini dress designed with a strapless neckline, ruching, and a hanky hem A-line silhouette.

Fit & Features
- Knit fabric, high stretch
- Small floral print
- Strapless straight neckline
- Ruching
- Drop waist
- Mini-length hanky hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000008

Category Name: Casual Dresses

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casual Chills Long Sleeve Slit Mini Dress
Look cute in this mini dress for casual chills with friends or daytime outings! The mini dress features a classic crew neckline, bell long sleeves, a flattering bodycon silhouette, and a flirty front slit along the hem on rib knit fabric. Complete the look with booties and a handbag!

Fit & Features
- Bell long sleeves
- Crew neckline
- Bodycon silhouette
- Front slit, mini-length hem
- Rib knit fabric
- Minimal stretch
- Style runs small
Style Number/Barcode: 05102-5326

Category Name: Casual Dresses

Price: $19.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Muse Square Neck Bodycon Mini Dress
Show off your sleek chic style in this bodycon mini dress featuring a sleeveless square neckline, tank-like shoulder straps, and a short form-hugging silhouette. Style with stiletto heels for a rooftop bar!

Fit & Features
- Lined rayon knit fabric, plenty of stretch
- Square neckline
- Tank-like shoulder straps
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5970

Category Name: Casual Dresses

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Night Out Abstract Print Mesh Midi Dress
Create a chic vibe to grab drinks with the girls in this airy mesh midi dress designed with a bold abstract print pattern. The dress features a sleeveless mock neckline, tank shoulder straps, ruching at the waist, and a bodycon silhouette to flaunt your curves.

Fit & Features
- Sheer mesh fabric with brushed knit lining, plenty of stretch
- Abstract print
- Mock neckline
- Tank shoulder straps
- Ruched waist
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5929

Category Name: Casual Dresses

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Basic Ribbed Knit Long Sleeve Mini Dress
Make a sleek statement with this long-sleeve mini dress, the epitome of chic simplicity. This figure-hugging silhouette, crafted from a soft ribbed knit fabric, offers both warmth and style. Featuring a high turtleneck for a touch of polished sophistication, this mini dress is perfect for transitioning from day to evening. Layer this ribbed knit mini-dress with an oversized faux leather blazer or stylish trench coat and knee-high boots for the perfected layered outfit.

Fit & Features
- Mock neckline
- Long fitted sleeves
- Mini-length hem
- Curve-hugging fit
- Ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-0703

Category Name: Casual Dresses

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Modern Stripes Ribbed Knit Long Sleeve Mini Dress
Capture a modern vibe in this striped rib knit long sleeve mini dress designed with a chic mock neck and flattering bodycon fit. Pair with boots.

Fit & Features
- Ribbed knit fabrication
- Mock neck
- Fitted long sleeves
- Multi-stripe pattern
- Mini length hem
- Runs true to size
Style Number/Barcode: 06005-2095

Category Name: Casual Dresses

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Affair Long Sleeve Ruched Midi Dress
Make a casual-chic impression in this long sleeve ruched midi dress showcasing a folded off-the-shoulder neckline and a bodycon silhouette. Pair with heels.

Fit & Features
- Smooth knit fabrication, moderate stretch
- Off-the-shoulder neckline, foldover accent
- Fitted long sleeves
- Ruching
- Midi length hem
- Runs true to size
Style Number/Barcode: 05101-3723

Category Name: Casual Dresses

Price: $39.90

Availability: Out of Stock
Product Badge:
- Ships Free
Cozy Fave Cable Knit Long Sleeve Mini Dress
Cozy up in the cutest cable knit mini dress featuring a V-neckline, a surplice wrap front and back design, and long dolman-style sleeves. The tie-front high waist and form-hugging fit will highlight your curves, making it your fave dress of the season.

Fit & Features
- Cable knit fabric with plenty of stretch
- V-neckline, surplice front and back design
- Back bar strap
- Long dolman sleeves
- Tie-front waist
- Mini-length form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2101

Category Name: Casual Dresses

Price: $18.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Classic And Sleek Knit Off-Shoulder Long Sleeve Midi Dress
Classic and sleek, this stretchy knit midi dress features an asymmetric off-shoulder neckline with long fitted sleeves, ruching at the waist to accentuate your curves, and a bodycon silhouette. Style with stiletto heels for a chic outing!

Fit & Features
- Jersey knit fabric with plenty of stretch
- Asymmetric off-shoulder neckline
- Long fitted sleeves
- Ruched waist
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5977

Category Name: Casual Dresses

Price: $19.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Adored Sleeveless Bow Trim Crepe Mini Dress
Embrace romance in this crepe mini dress that features a sleeveless square neckline with tank-like straps, a charming bow accented trim under the bust, and a flared mini-length hem with an A-line silhouette. Complete your look with sleek flats!

Fit & Features
- Crepe fabric with knit lining, moderate stretch
- Sleeveless square neckline, dart seams
- Tank-like shoulder straps
- Bow accented trim under bust
- Back zipper closure
- Flared mini-length hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3840

Category Name: Casual Dresses

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Out And About Long Sleeve Short Dress
This adorable long sleeve short dress is ideal for those casual days where you're out and about! It features a square neckline with a ruched bust and an adjustable tie-front drawstring, long fitted sleeves, a fitted high waist seam, a short-length hem, and a flowy A-line silhouette. The lined brushed crepe fabric offers plenty of stretch. Style this short-length dress with a chunky knit cardigan and over-the-knee boots for a coffee date!

Fit & Features
- Square neckline
- Ruched bust, tie-front drawstring
- Long fitted sleeves
- High waist seam
- Short-length hem, A-line silhouette
- Brushed crepe fabric, knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5395

Category Name: Casual Dresses

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Match My Energy Eyelet Skater Dress
This adorable dress will have you feeling cute and carefree for any fun plans! The strapless neckline, ruffled skater silhouette, and eyelet print add a touch of playfulness to your everyday look.

Fit & Features
- Eyelet fabric, sewn-in knit lining
- Strapless neckline
- Strappy back
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000108

Category Name: Casual Dresses

Price: $9.97 $65.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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