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!

In The Mood Scoop Neck Lace A-Line Mini Dress
Get in the mood to romance your look with this lace A-line mini dress perfect for a dressy soiree! This fun and flirty lace A-line mini features a scoop neckline and adjustable spaghetti straps for a perfect fit while the mini-length hem adds a touch of flirty. Complete the look with the matching bolero.

Shop Matching Bolero: In The Mood Long Sleeve Lace Bolero

Fit & Features
- Lace fabric lined with stretchy knit
- Adjustable spaghetti straps
- Scoop neckline
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3332

Category Name: Casual Dresses

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wild For Style Strapless Zebra Print Midi Dress
Let this strapless midi dress tame your worries over having nothing to wear! It features a strapless neckline, a figure-flaunting bodycon silhouette, and a midi-length hem on zebra print knit fabric that gives you a wild style. Complete the look with earrings for any occasion!

Fit & Features
- Zebra print, knit fabric, sewn-in knit lining, moderate stretch
- Strapless neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5820

Category Name: Casual Dresses

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Living A Dream Marble Off-The-Shoulder Midi Dress
This dreamy mesh midi dress is ready for you to take on any event! The stylish marble mesh fabric is sure to make a dramatic statement with its off-the-shoulder neckline, ruched fitted sheer long sleeves, flattering side ruched seams, and bodycon silhouette. Complete the look in stiletto heels for a birthday dinner or date night!

Fit & Features
- Off-the-shoulder neckline
- Ruched fitted sheer long sleeves
- Side ruched seams
- Bodycon silhouette
- Midi-length hem
- Marble print, mesh fabric, sewn-in knit lining
- Runs true to size
Style Number/Barcode: 05102-5332

Category Name: Casual Dresses

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Escape Lace-Up Tropical Midi Dress
Have the sweetest look in this tropical midi dress for your next vacay escape! With a flattering square neckline, delicate spaghetti straps, and a lace-up back, this bodycon dress will hug your curves down to the high-cut asymmetrical midi-length hem. Complete the look in espadrille wedges.

Fit & Features
- Tropical print, lined knit fabric, plenty of stretch
- Square neckline
- Spaghetti straps
- Lace-up back
- Asymmetric high-cut hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5564

Category Name: Casual Dresses

Price: $19.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
True Love In Floral V-Neck Corset Skater Dress
This sleeveless mini dress features a flattering V-neckline, adjustable spaghetti straps for a customizable fit, and a corset-inspired bodice. The skater silhouette and tiered ruffle hem gives this dress the perfect look with heels.

Fit & Features
- Floral print mesh fabric, stretchy knit lining
- V-neckline
- Adjustable spaghetti straps
- Corset-inspired bodice
- Skater silhouette
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3520

Category Name: Casual Dresses

Price: $9.97 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Unforgettable Cutie Bow A-Line Ponte Mini Dress
Bring an unforgettable cute vibe in this strapless ponte mini dress perfect for semi-formal events or brunch! Featuring a strapless neckline with a charming bow and contrast trim, this dress boasts an A-line silhouette and a mini-length hem for a flirty and flattering look. Complete the look with a necklace.

Fit & Features
- Ponte knit fabric, moderate stretch
- Strapless neckline, contrast trim and bow
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05101-3636

Category Name: Casual Dresses

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Good Looks Mock Neck Long Sleeve Knit Midi Dress
This mock neck midi dress will look so good on you! The midi dress features fitted long sleeves, a flattering form-hugging fit, and a center back slit on soft and stretchy ribbed knit fabric. Complete the look with a moto jacket for day or evening plans!

Fit & Features
- Soft and stretchy ribbed knit fabric
- Mock neckline
- Fitted long sleeves
- Form-hugging fit
- Center back slit
- Runs true to size
Style Number/Barcode: 05102-5221

Category Name: Casual Dresses

Price: $19.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sassy Style Ruched Knit Halter Skater Dress
Show off your sassy style at weekend outings in this adorable halter skater dress. Made with stretchy smooth knit fabric, it features a sleeveless V-neckline, trendy tie-back halter straps leading to a partially open back, ruched seams at the waist to accentuate your curves, a short double-layered skater skirt for a flirty vibe, and a fit-and-flare silhouette. Complete the look with a charm necklace and strappy mules!

Fit & Features
- Stretchy smooth knit, top knit lining
- V-neckline, tie-back halter straps
- Partially open back
- Ruched seams at the waist
- Double-layered skater skirt
- Fit-and-flare silhouette
- Runs true to size
Style Number/Barcode: 05102-5832

Category Name: Casual Dresses

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Girl Next Door Strapless Denim Mini Dress
Create a trendy girl next door vibe in this denim cargo mini dress! Made with a stretchy cotton-blend denim fabric, this dress features a strapless straight-across neckline, a secure back zipper closure, faux chest pockets, and large cargo-style flap pockets at the waist. The form-hugging silhouette will flaunt your gorgeous figure. Style this mini-length dress with cowboy boots for a country concert!

Fit & Features
- Cotton-blend denim fabric, moderate stretch
- Strapless straight neckline, front no-slip strip
- Back zipper with hook and eye closure
- Faux chest pockets
- Cargo flap pockets
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5524

Category Name: Casual Dresses

Price: $11.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Vacay Lace-Up Tropical Maxi Dress
Your summer vacay needs this tropical maxi dress! Made from a stretchy knit fabric adorned with a tropical print, this maxi dress features a flattering cowl neckline, spaghetti straps, and a lace-up back for head-turning allure. The form-hugging fit flaunts your figure while the high side slit offers a show of leg. Complete the look with sunglasses and a cocktail in hand!

Fit & Features
- Tropical print, stretchy knit fabric
- Cowl neckline
- Spaghetti straps, lace up back
- Form-hugging fit
- High side slit
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05102-5743

Category Name: Casual Dresses

Price: $19.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Destined For Love Lace-Up Short Skater Dress
You'll be destined for love in this short skater dress perfect for dressy parties! This flirty dress features a square neckline, adjustable spaghetti straps, and a lace-up back for a perfect fit. The skater silhouette and short-length hem add a playful touch, while the burnout pattern on the mesh fabric adds a touch of intrigue. Complete the look in block heels.

Fit & Features
- Burnout pattern, mesh fabric, tulle and stretchy knit lining
- Square neckline
- Adjustable spaghetti straps
- Lace-up, back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3319

Category Name: Casual Dresses

Price: $21.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Preppy-Chic Belted And Pleated Skater Dress
This preppy-chic twill skater dress features a collared neckline with a partial button-down front, short cap sleeves, and a subtle drop waist with a belted design. The mini-length pleated skater fit adds that flirty touch to the short silhouette.

Fit & Features
- Twill woven fabric, slight stretch
- Collared neckline, button-down front
- Cap sleeves
- Belted drop waist
- Mini-length pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5915

Category Name: Casual Dresses

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Abstract Babe Ruched Mesh Midi Dress
Let your look do the talking in this mesh midi dress! With an eye-catching abstract print and adjustable spaghetti straps, this midi dress will show off your style while the bodycon fit and side-ruched seams enhance your curves. Complete the look in trendy mules for an art show downtown!

Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Side ruched seams
- Bodycon silhouette, midi-length hem
- Abstract print, mesh fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5508

Category Name: Casual Dresses

Price: $9.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Artsy Scene Mock Neck Abstract Mini Dress
Indulge in the artsy scene in this mock neck abstract mini dress for downtown art walks! This sleeveless dress boasts a figure-flattering bodycon silhouette with side ruching, while the mini-length hem adds a flirty touch. The abstract print adds a bold and unique touch to this must-have dress. Complete the look in edgy boots and a shoulder bag.

Fit & Features
- Abstract print
- Mesh fabric, sewn-in knit lining, stretchy
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5630

Category Name: Casual Dresses

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bow Babe Strapless Pleated Ponte Romper
A strapless ponte romper features a form-hugging fit and a drop waist with an adorable ribbon bow and pleated short-length hem. Perfect for styling with a crop jacket and sandals.

Fit & Features
- Ponte knit fabric, slight stretch
- Strapless neckline
- Form-hugging fit
- Drop waist with ribbon bow trim
- Short pleated hem
- Runs true to size
Style Number/Barcode: 06503-1221

Category Name: Casual Dresses

Price: $17.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Blooming Beauty Floral Print Mesh Maxi Dress
Let your beauty bloom with a mesh maxi dress that features a sleeveless sweetheart neckline with lace trim, a bodycon-fit silhouette, and a pretty floral print throughout! Complete your date night look with stiletto heels!

Fit & Features
- Sheer mesh fabric with knit lining, plenty of stretch
- Floral print
- Sleeveless sweetheart neckline, lace trim
- Spaghetti straps
- Bodycon-like fit
- Long maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3785

Category Name: Casual Dresses

Price: $44.90

Availability: Out of Stock
Product Badge:
- Ships Free
Make Hearts Flutter Short Sleeve Cutout Maxi Dress
You'll instantly be crushing on this maxi dress perfect for weekend dinner parties or vacation! The flutter sleeves and plunging neckline create a playful vibe, while the elasticized waist and side cutouts show a hint of skin along the flowy maxi-length silhouette. Complete the look in strappy sandals.

Fit & Features
- Gauze woven fabric, short knit stretchy lining
- Flutter short sleeves
- Plunge V-neckline and V-cut back
- Elasticized strappy waist with side cutouts
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5719

Category Name: Casual Dresses

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Weekend Vibes High Slit Striped Knit Maxi Dress
This casual-chic striped knit maxi dress is perfect for your laid-back weekend vibes! Designed with stretchy ribbed knit with a thin striped pattern, it features a sleeveless scoop neckline with spaghetti straps, high-cut side slits on each side for added movement, and a form-hugging slim fit on the maxi-length silhouette. Style this long dress with strappy sandals.

Fit & Features
- Striped ribbed knit fabric, short knit lining, moderate stretch
- Scoop neckline
- Spaghetti straps
- High side slits
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5778

Category Name: Casual Dresses

Price: $19.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Confident Moves Crew Neck Ruffled Mini Dress
Get ready to make confident moves in this sleeveless mini dress perfect for office days and after work play! Featuring a crew neckline and bodycon fit, this dress will have you feeling fabulous. The tiered ruffled mini-length hem adds a playful touch that will have heads turning. Complete the look in stiletto pumps and a blazer.

Fit & Features
- Smooth double-lined knit fabric, moderate stretch
- Crew neck
- Bodycon fit
- Tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5792

Category Name: Casual Dresses

Price: $36.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
Lovely In Lace Ruffled Puff Sleeve Mini Dress
You'll be looking oh-so-lovely in this adorable ruffled puff sleeve mini dress! The sheer floral lace fabric gives that dainty-chic vibe, while the partial knit lining provides coverage. The mini-length dress features a square neckline and sheer short puff sleeves with the cutest ruffle trim, a small bust cutout with a sleek ribbon tie-front design, and a flattering empire waist seam. The flowy A-line silhouette adds that effortless flair. Style this short dress with heeled mules for date night.

Fit & Features
- Sheer floral lace fabric with knit lining, minimal stretch
- Square neckline, ruffle trim
- Sheer short puff sleeves, ruffle trim
- Bust cutout, tie-front design
- Empire waist seam, hidden side zipper closure
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3338

Category Name: Casual Dresses

Price: $19.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sway With Me Halter V-Neck Paisley Skater Dress
This breezy skater dress brings the romance with a halter neckline and swingy silhouette made to float with you. Perfect for golden hour snaps, weekend wandering, or spontaneous getaways!

Fit & Features
- Paisley print, woven fabric, bust lining
- Halter V-neckline with spaghetti strap ties
- Stretchy smocked bust
- Tie back design
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5575

Category Name: Casual Dresses

Price: $42.90

Availability: In Stock

Available Color: NAVY, OLIVE, RUST

Available Size: XS, S, M, L
City Of Love V-Neck Ruffle Babydoll Dress
Grab your baguette, passport, and this babydoll dress cause the city of love is calling your name! The playful ruffled shoulder straps and convenient side pockets add a touch of whimsy to this flirty dress. The babydoll silhouette and ruffled tiered hem make it perfect to sweep through Paris looking adorable! Complete the look in strappy sandals and a purse.

Fit & Features
- Woven fabric
- Ruffled shoulder straps
- Side pockets
- Babydoll silhouette
- Ruffled tiered short-length hem
- Runs true to size
Style Number/Barcode: 05102-5423

Category Name: Casual Dresses

Price: $21.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Coastal Dream Lace-Up Ruffled Maxi Dress
A dreamy sleeveless maxi dress perfect for styling for beach city days or coastal vacations! The scoop neckline and bust tie accentuate your figure, while adjustable spaghetti straps provide the perfect fit. The lace-up back adds a touch of charm, while the flowy ruffled silhouette and maxi-length hem exude effortless chicness! Complete the look with strappy sandals and sunglasses.

Fit & Features
- Woven fabric, short knit stretchy lining
- Scoop neckline with bust tie
- Adjustable spaghetti straps
- Lace-up back
- Flowy tiered ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5565

Category Name: Casual Dresses

Price: $9.97 $56.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Simple Staple Ribbed Knit Bodycon Mini Dress
Comfy and chic, this knit bodycon mini dress is the simple staple you need in your closet! Made with a stretchy ribbed knit fabric, it features a sleeveless scoop neckline, spaghetti straps, and a form-hugging fit to flaunt your curves along the bodycon silhouette. Style this mini-length dress with a denim jacket and sneakers for a cute and casual vibe.

Fit & Features
- Stretchy ribbed knit fabric
- Scoop neckline
- Spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1937

Category Name: Casual Dresses

Price: $29.90

Availability: In Stock

Available Color: BLACK, TAUPE

Available Size: M, S, L

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