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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Trendy Stunner Plaid Mini Dress
You'll be a total trendy stunner in this sultry sleeveless plaid mini dress! It features a square neckline, spaghetti straps, an open back with a strappy design, and a short, curve-hugging silhouette. Complete the look with chic mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open back, strappy design
- Mini-length, form-hugging fit
- Plaid print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4205
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Essential Sleeveless Midi Dress
The perfect sleeveless midi sweater dress for every occasion! It features a V-neck, tank straps, and a bodycon silhouette on ribbed knit fabric with a moderate stretch. Complete the look in sleek hoops and heels.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless V-neckline, tank straps
- Bodycon silhouette
- Midi-length hem
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1239
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Oh Snap Mock Neck Ribbed Midi Dress
Oh, snap, imagine how cute you'd look in this ribbed midi dress! It features long sleeves, a mock neck, bodycon silhouette, and side snap-button closures on ribbed knit fabric with a moderate stretch. Complete the look in suede booties.
Fit & Features
- Long sleeves
- Mock neck
- Bodycon silhouette
- Side snap-button closures
- Midi-length hem
- Ribbed knit fabric
- Fits true to size, moderate stretch
Style Number/Barcode: 06005-1124
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Born To Rock Lace-Up Graphic Tunic
Feel the rockstar vibes in this trendy graphic tunic for all of your jam sessions! It features a sleeveless mock neck, dual side lace-up detail, and a front graphic script that reads, 'Let's Make Some Noise/Born To Be A Rockstar'. Complete the look in lug booties.
Fit & Features
- Sleeveless, mock neck
- Dual side lace-up detail
- Graphic reads, 'Let's Make Some Noise/Born To Be A Rockstar'
- Form-fitting bodice
- Short hem
- Cotton knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1149
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Be Mine Button-Down Ribbed Midi Dress
One look at this midi dress and you'll want it to be yours! It features short sleeves, a scoop neck, button-down front closures, a sultry front slit, and a bodycon silhouette. Composed of rib-knit fabric with a moderate stretch. Finish the look in chic hoop earrings.
Fit & Features
- Short sleeves, scoop neck
- Button-down front closures
- Front slit, midi hem
- Bodycon silhouette
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4292
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shamrock Shake Ruched Mini Dress
Look like a treat this St. Patrick's Day! This sleeveless mini dress features an on-trend square neck, spaghetti straps, and dual side ruching with adjustable ties, a shamrock pattern, and a bodycon silhouette. Composed of a brushed knit fabric with a moderate stretch. Finish the look in strappy sandals.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Dual side ruching, adjustable ties
- Shamrock pattern
- Bodycon silhouette
- Mini hem
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4430
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Moves Midi Dress
Make the trendiest of moves in this cool printed midi dress. It features a sleeveless halter neckline with spaghetti straps that lead to an open back with a strappy lattice design, a fitted bodice leading to a subtle flowy silhouette with a thigh-high front slit, and an all-over splattered tie-dye print. Style this dress with clear mules.
Fit & Features
- Sleeveless halter neckline, spaghetti straps
- Open back, strappy lattice design, tie closure
- Fitted bodice, flowy silhouette, high front slit
- Spattered tie-dye print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4371
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Mood Ribbed Knit Midi Dress
Keep it lowkey in a dress that brings those casual vibes! The dress features a crew neckline, short sleeves, and a sexy open back with a tie-back accent. The midi dress is composed of a lined ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sneakers and a denim jacket for those girl next door vibes!
Fit & Features
- Crew neckline
- Short sleeves
- Open back
- Tie-back accent
- Midi-length, high side slit
- Lined ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4526
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rodeo Rebel Faux Suede Mini Dress
Cowgirl, but make it hot. This faux suede mini dress brings western vibes with curve-hugging fit, embroidery details, and a button-front that’s strictly for show.
Fit & Features
- Western-embroidery, faux suede fabric, sewn-in knit lining
- Moderate stretch
- Strapless tube neckline
- Side zipper and hook-and-eye closure
- Faux front buttons
- Bodycon fit, mini hem
- Runs true to size
Style Number/Barcode: 05102-000148
Category Name: Casual Dresses
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty And Flowy Woven Mini Dress
Flirty and flowy, this adorable woven mini dress is perfect for day dates! It features a V-neckline, long blouson sleeves, a high waist seam, and an A-line silhouette with tiered ruffle detailing. The lightweight woven fabric includes a knit lining. Complete the look with a denim jacket and mules.
Fit & Features
- V-neckline
- Long blouson sleeves, tapered hems
- Back zipper and hook and eye closure
- High waist seam
- A-line silhouette, tiered ruffle detailing
- Woven fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4280
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ditsy Floral Scoop Mini Dress
Fall for this ditsy floral mini to revive your springtime wardrobe! It features puff short sleeves, a scoop neckline, a bodycon silhouette, and a short-length hem. Complete the look in chic mules for brunch.
Fit & Features
- Puff short sleeves
- Scoop neckline
- Bodycon silhouette
- Short-length hem
- DItsy floral pattern
- Fits true to size
Style Number/Barcode: 05102-4336
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Own It Ribbed Knit Midi Dress
Own your look with a ribbed dress that makes a head-turning impression! The dress features a crew neckline, long sleeves, a sexy cutout at the waist, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties and a teddy jacket.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Cutout at the waist
- Midi-length silhouette
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1079
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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In The Wild Leopard Mini Dress
Flaunt your wild side in a leopard mesh mini dress for your next prowl! It features a sleeveless, square neck bodice with spaghetti straps and side ruched seams on a bodycon silhouette. Complete the look in heels.
Fit & Features
- Sleeveless bodice, square neck
- Spaghetti straps
- Side ruched seams
- Mini-length bodycon silhouette
- Leopard print pattern
- Sheer mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4470
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Everyday Perfection Ribbed Knit Mini Dress
This comfortable ribbed knit mini dress is perfect for everyday 'fits! It features a classic crew neckline, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric offers a moderate stretch. Keep it casual with sneakers and a denim jacket, or elevate the look with sleek hoops and strappy mules.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Form-fitting silhouette
- Mini-length hem
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1272
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Collared And Chic Button Down Dress
Keep it chic with a dress that is part trendy, part casual. The dress features a collared neckline, a button-down front, ruching, long sleeves, 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 clear mules and gold earrings.
Fit & Features
- Collared neckline
- Button-down front
- Ruching
- Long sleeves
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4235
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Double Take Knit Mini Dress
Wow in a mini dress that makes them all take a double take! The dress features a mock neck, long sleeves, a sexy cutout at the back, and a mini-length hem. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a trench coat.
Fit & Features
- Mock neck
- Long sleeves
- Cutout at the back
- Mini length hem
- Lined ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1252
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Cutie Puff Sleeve Mini Dress
Look cute in this mini floral dress for a picnic date or brunch with friends. It features puff short sleeves, a sweetheart neck with keyhole tie, and a short-length hem. Complete the look in trendy sandals.
Fit & Features
- Short puff sleeves
- Sweetheart neck, keyhole tie
- Dainty floral pattern
- Short-length fitted hem
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4337
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Winter Florals Ruched Bodycon Dress
Florals for winter? Absolutely! This bodycon dress features a sleeveless, bungee spaghetti strap on a scoop neck, ruched sides, and a fitted hem. Composed of soft-knit fabric with a moderate stretch. Perfect for styling with a moto jacket.
Fit & Features
- Sleeveless, bungee spaghetti straps
- Scoop neck
- Ruched sides, fitted hem
- Floral pattern throughout
- Soft knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4445
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Show Your Floral Smocked Chiffon Dress
Show your florals off in this chiffon mini dress for your next girl's day! It features long peasant sleeves, a sweetheart neck with a front knot-tie and keyhole accent, and a smocked short-length hem. Complete the look in chic sunglasses and heels.
Fit & Features
- Long peasant sleeves
- Sweetheart neck
- Front knot-tie, keyhole accent
- Floral pattern
- Smocked mini-length hem
- Chiffon fabric
- Fits true to size
Style Number/Barcode: 05101-1378
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Thinking About Knit Cutout Midi Dress
You've got knit on the mind, show off in a midi dress that stuns! The dress features a crew neckline, short sleeves, a knot accent at the center with dual cutouts at the waist, and a midi-length silhouette that is accented with a high side slit. The dress is composed of a cotton knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and a clutch.
Fit & Features
- Crew neckline
- Short sleeves
- Twist knot accent
- Dual cutouts at the waist
- Midi-length silhouette, high side slit
- Cotton knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4261
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Go With The Flow Chiffon Skater Dress
Go with the flow and keep it casual with a dress that can be dressed up or down for a date with bae. The dress features a square neckline, long balloon sleeves, an empire waist with pleating, and a skater length silhouette with a ruffled hem. The dress is composed of a lined chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with block heels and hoops.
Fit & Features
- Square neckline
- Long balloon sleeves
- Empire waist with pleating
- Skater length silhouette, ruffled hem
- Lined chiffon fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1133
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Girl Next Door Slip Dress
Show off your trendy style in this adorable cow print slip dress! It features a sleeveless V-neckline, bungee spaghetti straps, a stylish small front slit, and a short fitted silhouette. Complete the look with ankle booties.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Short front slit
- Mini-length fitted silhouette
- Brushed knit fabric, moderate stretch
- Cow print
- Runs true to size
Style Number/Barcode: 05102-4325
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetest Frame Long Sleeve Midi Dress
Bring the sweetness in this long sleeve midi dress featured in a sweetheart neck, bodycon silhouette, and midi-length hem. The dress is composed of a rib-knit fabric offering a moderate stretch. Complete the look with chic booties.
Fit & Features
- Long sleeves
- Sweetheart neckline
- Bodycon silhouette
- Midi-length hem
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1179
Category Name: Casual Dresses
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Twist Off-The-Shoulder Soft Knit Mini Dress
The cashmere-like soft knit mini dress features an off-the-shoulder neckline, a popover accent with twist detail, long bell sleeves, faux wrap ties at the waist, and a fitted short-length hem. Complete a cozy stylish outfit with clear heels or ankle booties.
Fit & Features
- Soft cashmere-like knit fabrication
- Off-the-shoulder neckline
- Popover accent with twist detail
- Long bell sleeves
- Faux wrap ties at the waist
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-6003
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free