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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Paisley Babe V-Neck Midi Dress
Look like a babe in this paisley midi dress to bring those retro vibes! It features a sleeveless V-neck, adjustable spaghetti straps, a bodycon silhouette, and an asymmetrical midi-hem with a trendy ruched seam. Complete the look in block heels for happy hour.
Fit & Features
- Sleeveless V-neck, adjustable spaghetti straps
- Bodycon silhouette
- Ruched side seam
- Asymmetrical midi-length hem
- Paisley pattern
- Stretchy and soft knit fabric
- Runs true to size
Style Number/Barcode: 05102-4380
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spotted In Floral Mesh Ruffle Hem Dress
Spotted in floral for spring! Refresh your closet with this flirty mini dress featuring a ruffle trim v-neck, adjustable spaghetti straps, a bodycon silhouette, ruffled hem, and a trendy front drawstring so you can customize the length. Composed of mesh-lined fabric with a moderate stretch. Finish the look in mules for a day date.
Fit & Features
- Sleeveless, ruffle trim v-neck
- Adjustable spaghetti straps
- Side ruched seams, front drawstring
- Bodycon silhouette
- Mini-length ruffled hem
- Floral pattern, mesh-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05101-1453
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flower Power Skater Dress
Elevate your spring style with this pretty floral printed skater dress. It features a subtle sweetheart neckline with ruching at the bust, short puff sleeves, a high waist, and a fit and flare silhouette with a short skater skirt with a ruffled hem. Style this lightweight chiffon dress with cute mules.
Fit & Features
- Sweetheart neckline, ruching at the bust
- Short puff sleeves, elasticized hems
- Back zipper, hook and eye closure
- High waist seam, fit and flare silhouette
- Short skater skirt, ruffled hem
- Floral print
- Sheer chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1406
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetie Puff Sleeve Mini Dress
You'll look so sweet in this mini dress for a cute brunch fit. It features adorable short puff sleeves along the sweetheart neck with a cutout bust tie. The side ruched seams accentuate your curves on slinky knit-lined fabric with a moderate stretch. Complete the look in PVC mules.
Fit & Features
- Short puff sleeves, elastic cinched hems
- Sweetheart neck, cutout bust tie
- Side ruched seams, bodycon fit
- Mini-length hem
- Slinky knit-lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4361
Category Name: Casual Dresses
Price: $5.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Retreat Chiffon Sweetheart Midi Dress
Ready for a floral retreat? Feel the sunshine on your shoulders in this floral chiffon midi dress featuring dainty spaghetti straps, a sweetheart neckline with a bust tie, a fitted bodice, and a side slit accent. Complete the look in simple heels.
Fit & Features
- Sleeveless sweetheart neckline, bust tie accent
- Spaghetti straps
- Fitted bodice, back zipper, hook and eye closure
- Midi-length hem, side slit
- Ditsy floral pattern
- Sheer chiffon fabric, knit lining
- A-line silhouette, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4356
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral State Scoop Neck Mini Dress
Got a floral state of mind? Then this mini dress is just what you need! It features a sleeveless, scoop neck, spaghetti straps, and ruched bust seam that leads to a bodycon silhouette. Complete the look in chic wedges for a cute picnic date.
Fit & Features
- Sleeveless, scoop neck, spaghetti straps
- Ruched bust seam
- Bodycon silhouette
- Mini-length hem
- Floral print
- Stretchy rib-knit fabric, lined
- Fits true to size
Style Number/Barcode: 05102-4601
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dinner Downtown Sleeveless Ruched Midi Dress
The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch.
Fit & Features
- Smooth knit fabric, stretchy knit lining
- Sleeveless crew neck
- Side ruched seams
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6066
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sway With Me Floral Chiffon Dress
Sashay and sway in this adorable floral chiffon dress featuring a sleeveless, scoop neck, adjustable spaghetti straps, smocked back panel, and a flowy, ruffled tiered short hem. Complete the look in trendy sandals for your next getaway.
Fit & Features
- Sleeveless, scoop neck, adjustable spaghetti straps
- Smocked back panel
- Flowy, tiered short hem
- Floral pattern
- Chiffon-lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 05102-4495
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Coastal Chic Striped Mesh Tunic
Create chic beachside looks with this on-trend mesh tunic. It features a V-neckline, long fitted sleeves with flared hems, center ruched detailing, and a short, curve-hugging fit. Style this striped tunic as a cover-up over your fave bikini.
Fit & Features
- V-neckline
- Long fitted sleeves, flared hems
- Center ruching, adjustable drawstring
- Mini-length, form-fitting silhouette
- Striped pattern
- Semi-sheer mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4195
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stylish Stunner Striped Halter Short Dress
Keep it stylish in a short sweater dress that wows and keeps it effortless. The dress features a halter neck with an adjustable neck tie, a striped pattern, and a short-length hem. The dress is composed of an unlined knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with wedges.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Halter neck
- Adjustable neck ties
- Striped pattern
- Short-length hem
- Knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1231
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Splash Of Style Twist Mini Dress
Your summer closet could use this stylish swirl print mini dress perfect for adding in brighter hues! It features a sleeveless, v-neck atop a twisted bust, spaghetti straps, bodycon silhouette, and side ruched seams to accentuate your natural curves. Complete the look in stiletto heels for a dinner with friends.
Fit & Features
- Sleeveless, v-neck, twisted bust, spaghetti straps
- Bodycon silhouette
- Side ruched seams
- Mini-length hem
- Swirl print
- Stretchy soft knit fabric
- Fits true to size
Style Number/Barcode: 05102-4596
Category Name: Casual Dresses
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Too Sweet Floral Ruffled Skater Dress
These florals are too sweet not to fall for! Twirl all day in this chiffon skater dress featuring a sleeveless, v-neck, ruffled trim straps, waist tie, open-back design with tie closure, and a tiered ruffled skirt. Complete the look in statement earrings.
Fit & Features
- Sleeveless, v-neck, ruffled trim straps
- Open-back with tie closure
- Tie waist, tiered ruffled skirt
- Skater silhouette
- Floral pattern, back zipper closure
- Chiffon fabric, inner knit lining, no stretch
- Fits true to size
Style Number/Barcode: 05101-1481
Category Name: Casual Dresses
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Trendsetter Ruched Mini Dress
Keep your look sweet and trendy with this adorable bodycon mini dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruched side detailing, a short, curve-hugging fit, and an all-over butterfly print. Style this dress with a pair of cute mules for an outing with the girls.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruched side detailing
- Mini-length, form-fitting silhouette
- Butterfly print
- Brushed knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4370
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Puff Love Square Neck Skater Dress
There's a lot to love about this puff sleeve skater dress! Features a square neck, smocked bodice, a trendy waist cutout, and a tiered short skirt. Composed of linen woven fabric with an inner lining. Finish the look in floral earrings for a cute spring fit.
Fit & Features
- Short puff sleeves, square neckline
- Smocked bodice, waist cutout
- Tiered short skirt
- Skater silhouette
- Linen woven fabric, inner lining, no stretch
- Fits true to size
Style Number/Barcode: 05102-4343
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Breeze Linen Halter Skater Dress
Feel the breeze this spring! This linen skater dress is perfect for your next daytime soiree featuring a sleeveless halter V-neckline, open-back design, dual tie-back closure, and a flowy, A-line skater silhouette. Composed of linen fabric with an inner knit lining with minimal stretch. Style with strappy heels.
Fit & Features
- Sleeveless, halter V-neck
- Open-back design, dual tie-back closure, lower back elasticized waistband
- Flowy, A-line skater silhouette
- Above-the-knee length hem
- Linen fabric, inner knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4414
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Eye On The Eyelet Lace Mini Dress
Keep your eye on this prize! Bring the flirty allure in this eyelet lace mini dress featuring short puff sleeves, a ruffle sweetheart neck with tie, and a babydoll-style bodice on a form-fitting silhouette. Complete the look in lace-up sandals for a cute picnic look.
Fit & Features
- Short puff sleeves
- Ruffle sweetheart neck with tie
- Babydoll-style bodice
- Form-fitting silhouette
- Mini-length hem
- Eyelet lace knit lined fabric
- Fits true to size, moderate stretch
Style Number/Barcode: 05102-4429
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Knits Halter Midi Dress
The cooler spring days call for your best knits! Set the tone in this halter midi sweater dress featuring a sleeveless high neck, adjustable spaghetti straps, space-dye knit pattern, bodycon silhouette, and a side slit accent to showcase some leg. Complete the look in cute mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless high neck, halter design
- Adjustable spaghetti straps
- Bodycon silhouette
- Side slit, midi-length hem
- Space-dye knit pattern
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1257
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wild Vibes Sleeveless Short Dress
Channel those wild vibes with a short dress that showcases your free-spirited side! The dress features a trendy zebra print, a sleeveless square neckline, bungee spaghetti straps, and a short-length hem. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a moto jacket for a night-out look.
Fit & Features
- Zebra print
- Sleeveless square neckline
- Bungee spaghetti straps
- Short length hem
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4572
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Earn Your Stripes Sweater Midi Dress
Earn your stripes in style rocking this sweater midi dress for all-day slays! It features a sleeveless square neck, adjustable spaghetti straps, a striped pattern, and a bodycon silhouette. Composed of a rib-knit fabric with a moderate stretch. Style with chic booties.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Striped pattern
- Bodycon midi-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1240
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutest Look Floral Mini Dress
Get the cutest look for the spring season with this adorable floral mini dress! It features a sleeveless sweetheart neckline with shirring at the bust, spaghetti straps, a short, curve-hugging fit, and an all-over dainty floral print pattern. Style this dress with a cropped denim jacket and strappy sandals.
Fit & Features
- Sleeveless sweetheart neckline
- Shirring at the bust
- Spaghetti straps
- Mini-length, form-fitting silhouette
- Floral print
- Brushed knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4612
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Easy Breezy Eyelet Skater Dress
Easy, breezy, and flirty! This eyelet skater dress is perfect for your next spring fling. It features a sleeveless, square neck, spaghetti straps, high waist seam, and a trendy open-back with twist detail on the flared short silhouette. The dress is composed of a lined lightweight woven knit fabric that offers a flattering form hugging fit with a moderate stretch. Complete the look in espadrille sandals.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- High waist seam
- Open-back with twist detail
- Flared short silhouette
- Eyelet pattern
- Lined lightweight woven knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4415
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smooth Talker Strapless Bodycon Midi Dress
Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion!
Fit & Features
- Rib knit fabric, sewn-in knit lining, moderate stretch
- Strapless neckline
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000724
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BROWN-2, IVORY
Available Size: XS, S, M, L
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Beachside Brunch Swim Coverup Dress
Strut down the pier looking so fab in this maxi coverup dress featuring a sleeveless V-neckline, tank straps, and a form-fitting silhouette with a sultry front slit. The coverup dress is composed of an unlined semi-sheer knit fabric that offers a form-hugging fit. Perf for layering over your bikinis, complete the look in sandals.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless V-neckline, tank straps
- Surplice accent
- Form-fitting silhouette
- Front slit
- Maxi-length hem
- Unlined, semi-sheer sweater-knit fabric, no stretch
- Runs true to size
Style Number/Barcode: 06005-1250
Category Name: Casual Dresses
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sunday Girl Eyelet Lace-Up Skater Dress
This eyelet skater dress is perfect for Sunday brunch! It features adorable short puff sleeves, a square neck, an elasticized waist, an open-back design with lace-up closure, and a flared skirt. Composed of breathable cotton fabric with an inner lining. Finish the look in strappy sandals.
Fit & Features
- Short puff sleeves
- Squareneck
- Elasticized waist
- Open-back design, lace-up closure
- Flared, skater silhouette, short-length hem
- Eyelet lace cotton fabric, inner lining
- Fits true to size, no stretch
Style Number/Barcode: 05102-4428
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale