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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It's The Vibe Satin Cutout Maxi Dress
This maxi dress is the vibe for tonight! Going out has never looked so chic than on this sleeveless dress featuring a V-neckline, spaghetti straps, cutout sides and back, and a form-hugging silhouette with a flattering high side slit. Complete the look in lace-up stiletto heels.
Fit & Features
- Sleeveless V-neckline, spaghetti straps
- Cutout sides and back
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Smooth knit stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-5218
Category Name: Casual Dresses
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mix And Mingle Square Neck Mini Dress
Ready to mix and mingle? This chic little black mini dress will have you looking so stunning at cocktail mixers and dates! It features classic cap sleeves, a square neckline, a bodycon silhouette, a side slit accent, and a mini-length hem on smooth and stretchy rib knit fabric. Complete the look with an embellished clutch and simple block heels.
Fit & Features
- Cap sleeves
- Square neckline
- Bodycon silhouette
- Side slit accent
- Mini-length hem
- Smooth and stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5132
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Finders Keepers Tie Dye Mini Dress
Lucky you to have found this tie-dye mini dress! Perfect for summer fun, this sleeveless dress features a square neckline, spaghetti straps, adjustable side drawstrings let you customize the style, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in strappy sandals for a backyard dinner party!
Fit & Features
- Sleeveless square neckline, spaghetti straps
- Adjustable side drawstrings
- Bodycon silhouette
- Mini-length hem
- Unique tie-dye print
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5224
Category Name: Casual Dresses
Price: $6.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer In Tie Dye Cutout Midi Dress
Spend your summer in this tie-dye midi dress perfect for backyard dinners to sunset cocktails! It features a sleeveless V-neckline, spaghetti straps, a sexy cutout waist, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in trendy doorknocker earrings.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Cutout waist
- Bodycon silhouette
- Midi-length hem
- Tie-dye print, stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5225
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fierce And Fine Satin Leopard Midi Dress
Fierce, fine, and looking flawless in this satin leopard midi dress! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a knotted bust, and a relaxed slim silhouette. Complete the look with a dainty bracelet and strappy heels for a birthday lunch!
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Knotted bust
- Relaxed slim silhouette
- Midi-length hem
- Leopard print, smooth satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-5120
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Definite Yes High Slit Maxi Dress
This sleek high slit maxi dress is a definite yes for leveling up your casual looks! It features a sleeveless cowl neckline, spaghetti straps, a maxi-length hem with a thigh-high front slit to showcase some leg, and a slim-fit silhouette. The smooth knit fabric offers plenty of stretch. Style with strappy sandals for a lunch date!
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Maxi-length hem
- High front slit
- Slim-fit silhouette
- Smooth and stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5194
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fresh In Floral Ruched Mesh Midi Dress
Keep your summer style fresh with this pretty floral printed mesh midi dress! It features a sleeveless square neckline, adjustable spaghetti straps to customize the fit, all-over ruched detailing, a midi-length hem with a side slit accent, and a bodycon silhouette that will hug your natural curves. The airy floral printed sheer mesh fabric includes a smooth knit lining and offers plenty of stretch. Complete the look with strappy mules.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps, back zipper, hook and eye closure
- All-over ruching
- Midi-length hem, side slit, bodycon silhouette
- Floral print
- Sheer mesh fabric, smooth knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5267
Category Name: Casual Dresses
Price: $10.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dear Summer Eyelet Lace Open Back Dress
Make summer special looking so sweet in this eyelet lace mini dress for your upcoming daytime plans! It features adorable puff short sleeves, a square neckline, and an eye-catching open back with elasticized lattice straps and a bodycon silhouette. Complete the look in trendy platform wedges for brunch!
Fit & Features
- Puff short sleeves
- Square neckline
- Open back, elasticized lattice straps
- Bodycon silhouette
- Mini-length hem
- Eyelet lace fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5174
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Style Strappy Back Midi Dress
Simple yet so alluring, you'll love the sultry style of this strappy back midi dress. It features a sleeveless V-neckline, spaghetti straps that lead to an open back with cross-back lace-up straps, a midi-length hem, and a bodycon silhouette that will hug your natural curves. The ribbed knit fabric offers plenty of stretch. Complete your look with clear heels and a chic handbag.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Open back, cross-back lace-up straps, tie closure
- Midi-length hem
- Bodycon silhouette
- Ribbed knit fabric, full knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4835
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stand Out Marble Print Cutout Midi Dress
Stand out this season and have all eyes on you in this marble print midi dress perfect for weekend getaways or sunset cocktails! The dress features a sleeveless square neck, spaghetti straps, a cutout bodice, and side ruched seams that accentuate your curves along the bodycon silhouette. Complete the look with a sleek choker necklace.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Cutout bodice
- Side ruched seams, bodycon silhouette
- Midi-length
- Marble print, smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5235
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Living In Color Chiffon Halter Maxi Dress
Live life in color! Easy and breezy, this chiffon maxi dress is perfect for all of your summer activities. It features a sleeveless halter V-neckline, a unique braided neck strap with tie closure, a stretchy smocked back, and a flowy silhouette. The dress is designed with an airy chiffon fabric showcasing a watercolor print and a woven lining. Complete the look with a sleek arm cuff bracelet.
Fit & Features
- Sleeveless halter V-neckline
- Braided neck strap, tie closure
- Stretchy smocked back
- Flowy silhouette
- Maxi-length hem
- Airy chiffon fabric, watercolor print, woven lining
- Runs true to size
Style Number/Barcode: 05102-5269
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic And Simple Smooth Knit Mini Dress
This chic and simple smooth knit mini dress is the elevated basic you need! It features a sleeveless mock neckline, tank shoulder straps, a mini-length hem, and a bodycon silhouette that will hug your natural curves. The buttery-soft and smooth double-lined knit fabric offers plenty of stretch. Style with hoop earrings and clear mules.
Fit & Features
- Sleeveless mock neckline
- Tank shoulder straps
- Mini-length hem
- Bodycon silhouette
- Soft and smooth double-lined knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5198
Category Name: Casual Dresses
Price: $5.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Miss. Fashion Strapless Marble Print Mini Dress
They'll call you Miss. Fashion when you step out in this mesh mini dress! It features a strapless neckline, a bodycon silhouette, an adjustable side drawstring that lets you customize the style, a slit accent, and an asymmetrical hem. Style with lucite heels for a seamless-chic look!
Fit & Features
- Strapless neckline
- Bodycon silhouette
- Adjustable side drawstring, slit accent
- Asymmetrical mini-length hem
- Marble print
- Mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5268
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Art Of Style Abstract Print Midi Dress
Show everyone how it's done! This sleeveless midi dress features a square neck, spaghetti straps, a side ruched seam that accentuates your curves along the bodycon silhouette, and a high side asymmetrical slit. The dress is designed with an artsy abstract print on smooth knit fabric. Complete the look with earrings for an art gallery opening!
Fit & Features
- Sleeveless square neck, spaghetti straps
- Side ruched seam, bodycon silhouette
- High side asymmetrical slit
- Midi-length hem
- Abstract print, smooth knit fabric, moderate stretch
- Bust lining
- Runs true to size
Style Number/Barcode: 05102-5206
Category Name: Casual Dresses
Price: $5.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Own the Night One-Shoulder Cutout Maxi Dress
This dress isn’t subtle—and that’s the point. The sleek one-shoulder cut and bold side cutout bring drama, while the curve-hugging fit guarantees eyes on you at weddings, dressy parties, or date night!
Fit & Features
- Slinky knit-lined stretchy fabric
- One-shoulder neckline
- Side waist cutouts
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000249
Category Name: Casual Dresses
Price: $7.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Next Level Lace-Up Slit Maxi Dress
A next-level maxi dress to elevate your look for upcoming parties or date nights! It features a sleeveless square neckline, spaghetti straps that form the lace-up back with tie closure, a side ruched seam to show off your figure, a bodycon silhouette, and a sexy side slit on smooth knit stretchy fabric. Complete the look with fringe rhinestone earrings for a touch of glamour!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Lace-up back, tie closure
- Side ruched seam, bodycon silhouette
- High side slit, maxi-length hem
- Smooth knit stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-5147
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Enchanting Entrance Chiffon Floral Maxi Dress
Make an enchanting entrance into a tropical destination wedding in this effortless chiffon floral maxi dress! It features a sleeveless V-neckline, flirty ruffled spaghetti straps, a stretchy smocked back, a ruched bust, and a flowy tiered ruffled silhouette with a flattering front slit. Complete the look with a dainty layered choker necklace and heels.
Fit & Features
- Sleeveless V-neckline, ruffled spaghetti straps, adjustable
- Stretchy smocked back, ruched bust
- Flowy tiered ruffled silhouette, front slit
- Maxi-length hem
- Tropical floral print
- Airy chiffon fabric, short smooth woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-5270
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sun Ready Strapless High Slit Maxi Dress
If sandy beaches are what you seek this maxi dress is ready for fun under the sun! It features a strapless neckline, a side O-ring metal insert atop the sexy high slit, and a flowy long hem on slinky knit fabric. Complete the look in strappy sandals and sunglasses!
Fit & Features
- Strapless neckline
- Side O-ring insert, high side slit
- Flowy maxi silhouette
- Long hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5263
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Babe Satin A-Line Mini Dress
Embody the beauty of sunset hour in this satin marble print mini dress perfect for a rooftop lounge! It features a sleeveless front and back cowl neckline, adjustable spaghetti straps, crisscross back straps, and a flattering A-line silhouette. Complete the look in lace-up heels.
Fit & Features
- Sleeveless front and back cowl neckline
- Adjustable spaghetti straps
- Crisscross back straps
- A-line silhouette
- Mini-length hem
- Marble print, smooth satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-5273
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Lovely Off-The-Shoulder Ruffled Skater Dress
You'll look oh-so-lovely in this adorable ruffled skater dress! It features an off-the-shoulder sweetheart neckline with a ruffled trim and short sleeve cuffs, ruching at the bodice, a pointed high waist seam, a short skater skirt with a ruffled tiered design, and a fit and flare silhouette. The woven fabric has minimal stretch. Complete the look with rhinestone hoops and clear heels for a flirty date look.
Fit & Features
- Off-the-shoulder sweetheart neckline
- Ruffled trim, short sleeve cuffs
- Ruching at the bodice, pointed high waist seam
- Hidden back zipper, hook and eye closure
- Short skater skirt, ruffled tiered design, fit and flare silhouette
- Woven fabric, knit lining at the bodice, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5271
Category Name: Casual Dresses
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Curve Flaunter Mesh Ruched Midi Dress
Flaunt your best assets in this curve appeal of a midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a ruched bust with trim, a bodycon silhouette, a side slit, and all-over ruching. Complete the look in striking rhinestone sandals for an engagement party or birthday!
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Back zipper and hook-eye closure
- Ruched bust with trim
- Bodycon silhouette
- Side slit, midi-length hem, all-over ruching
- Mesh fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5266
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Invite Accepted Keyhole Slit Midi Dress
With this midi dress, you'll accept every invite just to show it off! Featuring a sleeveless scoop neckline, a spaghetti strap that cross in the back, a front keyhole bust cutout, a bodycon silhouette, and a flirty slit along the hem on smooth knit fabric. Complete the look in stiletto mules for a dinner date.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps, cross back
- Front keyhole bust cutout
- Bodycon silhouette
- Front slit, midi-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5215
Category Name: Casual Dresses
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Looking Marvelous One Shoulder Midi Dress
Step out looking marvelous in this one-shoulder midi dress for brunch or a family party! Featuring a sleeveless one-shoulder neckline with a tank shoulder strap, a flirty side ruched drawstring cutout with tie, a bodycon silhouette, and a flattering high side slit. The dress is designed with an eye-catching marble print on stretchy knit fabric. Complete the look with strappy stiletto heels.
Fit & Features
- Sleeveless one-shoulder neckline
- Tank shoulder strap
- Side ruched drawstring cutout with tie
- Bodycon silhouette
- High side slit, midi-length hem
- Marble print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5108
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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A Real Showstopper Lace-Up Maxi Dress
A real showstopper of a maxi dress! Flaunt your best self in this sleeveless dress featuring a square neckline, spaghetti straps, an open lace-up back design, a ruched side seam, and a bodycon silhouette with a flattering high side asymmetrical slit on sleek knit fabric. Complete the look in block heels for a dinner date.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open lace-up back design
- Ruched side seam, bodycon silhouette
- High side asymmetrical slit, maxi-length fitted hem
- Sleek knit and stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-5346
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free