Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, 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 dinner date, these casual dresses are made to move with your mood—and your calendar.
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Casual Dresses Made for Everyday Fall Plans
Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.
Easy Prints, Textures & Layers for the Season
Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.
What Makes a Dress Casual?
A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.
How Do You Transition a Casual Dress From Summer to Fall?
Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.
Which Fabrics Work Best for Everyday Dresses?
Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.
How Can You Style One Casual Dress for Different Plans?
Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.
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Feelin' Wild Sleeveless Slip Dress
Showcase a chic wild style in this sleeveless slip dress! It features a lined V-neckline, spaghetti straps, a cute tie-back detail, and a flirty short silhouette with a subtle flared-out hem. The lightweight woven fabric has a trendy all-over animal print. Complete the look with strappy mules.
Fit & Features
- Sleeveless lined V-neckline
- Spaghetti straps
- Tie-back detail
- Mini-length silhouette
- Woven fabric, no stretch, animal print
- Runs true to size
Style Number/Barcode: 05102-4245
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendsetting Stunner Slinky Knit Midi Dress
Show off your trendy stunner status in this of-the-moment slinky knit midi dress. It features a collared neckline, long sleeves, a complete button-down front, ruching at the waist, and a mid-length, curve-hugging silhouette. Complete the look with sleek hoop earrings.
Fit & Features
- Collared neckline
- Long fitted sleeves
- Complete button-down front
- Ruching at the waist
- Mid-length, form-hugging fit
- Slinky knit fabric
- Runs true to size
Style Number/Barcode: 05102-4222
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cool Girl Vibes Tie-Dye Mini Dress
Bring those effortless cool girl vibes in this fab tie-dye mini dress. It features a square neckline, short sleeves, and a short, curve-hugging silhouette. Style this knit dress with sneakers to keep it casual or clear heels for an elevated glam look.
Fit & Features
- Square neckline
- Short sleeves
- Mini-length, form-hugging fit
- Tie-dye print
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-4249
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Perfectly Plaid Knit Mini Dress
You'll look perfectly stylish in this plaid mini dress that you can take from day to night! It features a sleeveless square neckline, spaghetti straps, and a short, form-fitting silhouette that will hug your curves. Style with sneakers for a casual daytime look, and layer on a faux leather jacket and style with ankle booties for night.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Mini-length, form-hugging fit
- Lined knit fabric, moderate stretch
- Plaid print
- Runs true to size
Style Number/Barcode: 05102-1687
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Baddie Chic Tie Front Mini Dress
Rock on like the baddie you are with a tie-front mini dress that is part edgy, part chic! The dress features a plunging V-neckline, short sleeves, a sexy tie-front, cutout at the midriff, and a mini-length silhouette. The dress features an image of eagle wings, roses, and a script that reads: "American Motorcycles. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with chunky sneakers.
Fit & Features
- Plunging V-neckline, short sleeves
- Tie-front, cutout at the midriff
- Mini length silhouette
- Image of eagle wings, roses
- Script: "American Motorcycles"
- Cotton knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06002-0943
Category Name: Casual Dresses
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Born To Ride Lace Up Mini Dress
Let this mini dress let everyone know that you were born to be wild! The dress features a crew neckline, a plunging keyhole at the bodice, a chain-link lace-up front, short sleeves, and a mini-length silhouette. The dress features a graphic that reads: "Riders, Motorcycle" with an image of eagle wings. The dress is composed of a cotton knit fabric. Complete look with sneakers.
Fit & Features
- Crew neckline
- Keyhole at bodice
- Chain link lace-up front
- Short sleeves
- Mini length silhouette
- Graphic: "Riders, Motorcycle", image of eagle wings
- Form hugging fit, moderate stretch
Style Number/Barcode: 06002-0944
Category Name: Casual Dresses
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Start A Spark Ruched Mini Dress
Start a spark with a mini dress that showcases your luxe style! The dress features a sleeveless square neckline, bungee spaghetti straps, a ruched body, and a mini-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with lucite heels and gold jewelry.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ruched body
- Mini length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4191
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Set It Off Ruffled Bodycon Dress
Set off your night with a head-turning bodycon that raises the heat! The dress features a sleeveless wrap V-neckline, spaghetti straps, a ruched body, and a mini-length silhouette with a ruffled hem. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with rhinestone heels and a clutch.
Fit & Features
- Sleeveless wrap V-neckline
- Spaghetti straps
- Ruched body
- Mini length silhouette, ruffled hem
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4464
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Uniquely Darling Strapless Pleat Skater Denim Mini Dress
Darling and adorable, this denim mini dress brings flirtiness to any scene with a skater silhouette and pleated mini-length hem perfect for pairing with cowboy boots!
Fit & Features
- Denim fabric, stretchy knit shorts lining
- Strapless sweetheart neckline, non-slip grip lining
- Back zipper and hook-eye closure
- Skater silhouette
- Pleated mini-length hem
- Runs small
Style Number/Barcode: 05102-000683
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: DARK, DENIM, LIGHT
Available Size: S, M, L, XS
Product Badge:- Sale
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Making My Mark Ribbed Mini Dress
Make your style mark with a mini dress that is part casual, part glam! The dress features a sleeveless crew neckline, tank shoulder straps, and an open back with criss-cross straps. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Open back, criss-cross straps
- Lined ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4270
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island It Girl One-Shoulder Cutout Maxi Dress
Giving tropical baddie with a side of luxury, this one-shoulder maxi brings the heat with a bold leaf print, cutout waist, and gold hardware that says, "I didn’t come to play." It's made for vacation slays, beach weddings, or poolside parties!
Fit & Features
- Tropical leaf print, smooth stretchy knit fabric, short lining
- One-shoulder neckline with hardware trim
- Side cutout bodice
- High side slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000082
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Baroque Bohemian Glam Mini Dress
Stand out like the glam trendsetter you are with a mini dress that is a true one of a kind! The dress features a sleeveless cowl neckline, spaghetti straps, a bohemian paisley print with baroque-inspired accents, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Bohemian paisley print
- Baroque print
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4148
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Trendsetter Ruched Knit Mini Dress
Showcase casual trendsetting looks in this stylish knit mini dress. It features a square neckline, short sleeves, ruched side detailing with drawstrings, and a short, form-hugging silhouette. Pair this dress with a denim jacket and cute mules for an effortless everyday outfit.
Fit & Features
- Square neckline
- Short sleeves
- Ruched side detailing
- Adjustable drawstrings
- Mini-length, form-hugging fit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4333
Category Name: Casual Dresses
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruched Ribbed Knit Cutout Mini Dress
Keep it casually chic with a mini dress that stuns with stylish details! The dress features a crew neckline, long sleeves, a cutout at the midriff with criss-cross straps, ruched drawstrings, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and statement earrings.
Fit & Features
- Crew neckline
- Long sleeves
- Cutout at the midriff
- Criss-cross straps, ruched drawstrings
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4242
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off The Shoulder Ribbed Knit Mini Dress
Button up in a chic mini dress that is perf to dress up or dress down in for your next outing! The dress features an off-the-shoulder neckline, short sleeves, a faux button-down front, and a mini-length silhouette. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and denim jacket.
Fit & Features
- Off the shoulder neckline
- Short sleeves
- Faux button down front
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1911
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Endless Summer Halter Cutout Dress
Embrace the summer vibes in this chic curve-hugging dress! It features a sleeveless halter neckline, an open back, a center knot detail with dual waist cutouts, and an ankle-length, form-fitting silhouette. Style this dress with sleek hoop earrings.
Fit & Features
- Sleeveless halter neckline
- Open back
- Center knot detail
- Dual waist cutouts
- Long, form-hugging fit
- Ribbed sweater knit fabric
- Runs true to size
Style Number/Barcode: 06005-1216
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutie In Floral Puff Sleeve Mini Dress
You'll look like such a cutie in this adorable floral mini dress! It features a subtle sweetheart neckline with a mini tie-front at the bust, short puff sleeves, and a mini-length, curve-hugging silhouette. Style this dress with your fave pair of sandals.
Fit & Features
- Sweetheart neckline
- Mini tie-front at the bust
- Short puff sleeves
- Back zipper and hook and eye closure
- Short, form-hugging fit
- Floral print, knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4153
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Daring Diva Open Back Midi Dress
Dare to go bold with a midi dress that wows! The dress features a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and a midi-length silhouette. Complete look with stilettos and door knocker earrings.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps, cross at back
- Open back
- Midi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1210
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Staple Ribbed Knit Mini Dress
This comfy ribbed knit mini dress will be a new casual staple in your closet. It features a sleeveless scoop neckline, adjustable spaghetti straps, and a short, curve-hugging silhouette with a rounded hem. Style this dress with a denim jacket and sneakers for the perf everyday look.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Mini-length, form-hugging fit
- Rounded hem
- Ribbed sweater knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-0968
Category Name: Casual Dresses
Price: $4.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Crew Ribbed Knit Mini Dress
Show em' all that you roll with the chic crew in this fab mini dress! The dress features a crew neckline with a racer bust, a ruched body, and a mini side slit. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a denim jacket.
Fit & Features
- Sleeveless crew neckline
- Racer bust
- Ruching
- Mini side slit
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4240
Category Name: Casual Dresses
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Chic Ditsy Floral Mini Dress
Bring the charm with a floral mini dress that is perf for date night! The dress features a sleeveless sweetheart neckline with a lace trim, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless sweetheart neckline, lace trim
- Spaghetti straps
- Ditsy floral print
- Mini-length silhouette, lace trim at the hem
- Smooth knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4196
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Stunner Cutout Midi Dress
Stand out like the major stunner you are with a midi dress that brings the style! The dress features a plunging halter neck with a V-neck bust, a cutout at the midriff with sleek straps, and a midi-length silhouette with a high side slit. The dress is composed of a lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Halter neck, V-neck bust
- Cutout at the midriff with straps
- Midi length silhouette
- High side slit
- Lurex knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4157
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blooming Beauty Ditsy Floral Cutout Mini Dress
Let your beauty bloom with a gorge mini dress that reveals your sweet side! The dress features a ditsy floral print, a sleeveless V-neckline, a ruched drawstring at the center, spaghetti straps, a cutout at the midriff, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a denim jacket.
Fit & Features
- Ditsy floral print
- Sleeveless V-neckline
- Ruched drawstring at the bodice
- Spaghetti straps
- Cutout at midriff
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4126
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Flowy A-Line Mini Dress
Get an effortless look in this flowy boho-chic mini dress. It features a sleeveless subtle square neckline, adjustable spaghetti straps that lead to a cross-back design, a short A-line silhouette, and a drop hem with a cute ruffle detail. Style this dress with your fave pair of wedges.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Cross-back design
- Mini-length, A-line silhouette
- Drop hem, ruffle detail
- Double-lined gauze fabric
- Runs true to size
Style Number/Barcode: 05102-3099
Category Name: Casual Dresses
Price: $20.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale