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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Picturesque Cutie Corset Lace-Up A-Line Midi Dress
Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette.
Fit & Features
- Woven fabric lined with stretchy knit
- Sweetheart neckline, tie-front detail
- Thin adjustable straps
- Corset bodice, lace-up back
- High waist seam
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3069
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plant One On Floral Skater Dress
Featuring pretty floral graphics throughout, this fab floral dress is the perfect partner in crime for all your daytime outings.
Fits & Features
- Adjustable spaghetti straps
- Surplice V neckline
- Zipper & hook and eye closure at back
- Removable waist tie
- Wrapped and layered skater skirt
- Crepe composition I Fully lined
- Form-fitting, limited stretch
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0223
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Prettiest Pick Sweetheart Ruched Mini Dress
Girl, this dress is the right pick for that girl's brunch you got planned! Add a pair of statement-making earrings and some cute strappy heels.
Fits & Features
- Off Shoulder Sleeves I Elastic Shoulders & Back
- Lace-Up Design At Center Front Bodice
- Ruching Throughout
- Mini Length Silhouette
- Woven Fabric With Mesh Lining
- Ruffle-Trim At The Cuffs & Hem
- Minimal Stretch
Style Number/Barcode: 05102-0604
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Easy Does It Puff Sleeve Ruched Mini Dress
Fall for this sweet mini dress that'll have you ready for the warmer days ahead! Pair with slip-on mules and a cute mini purse for the perf daytime OOTD!
Fits & Features
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Surplice V Neckline
- Puff, Short Sleeves
- Mini Length Silhouette
- Ruching Along The Sides
- Brushed Knit Fabric
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0663
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Surplice V Neckline
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Off Shoulder Ruffle Mini Dress
Pretty layered ruffles and a sweetheart neckline are just a few of the fab details on this cute mini dress!
Fits & Features
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Off Shoulder Short Sleeves With Puff & Ruffle Accents
- Sweetheart Neckline With No-Slip Interior Strip I Padded Bust
- Back Zip With Hook & Eye Closure
- Cut Out At The Center Waist
- Mini Length I Ruched Skirt I Layered Ruffle Hem
- Woven Fabric I Fully Lined
- Minimal Stretch
Blue Dress: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
White Dress: Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0753
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Off Shoulder Short Sleeves With Puff & Ruffle Accents
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Pretty In Plaid Mini Dress
Keep it pretty in plaid with this brunch ready mini dress! This season-ready dress only needs a pair of wedges and a pop of jewel tones for a complete look!
Fit & Features
- Square Neckline
- 3/4 Puff Sleeves
- Plaid Print
- Lined Lightweight Fabric
- Mini Length Silhouette
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05102-0680
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Moment Maxi Dress
Create a charming moment in florals in this sweet maxi dress! Perfect for brunch when paired with fab heels and a neutral handbag!
Fit & Features
- Wrap V-Neckline
- Spaghetti Straps
- Elastic Waist
- Floral Print
- Maxi Silhouette
- Lined Knit Fabric | Mini Skirt Length Lining
- Relaxed Fit | Moderate Stretch
Style Number/Barcode: 05101-0530
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Moment Asymmetrical High Slit Midi Dress
Make a fab impression in a floral dress, perfect for a first date. The midi dress features a gorgeous floral print, a wrap V-neckline for a flattering fit, and an asymmetrical high slit. Complete your look with strappy heels and hoop earrings to complement this fab print.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Bodycon silhouette
- Asymmetrical high slit
- Midi-length hem
- Floral print, knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-0562
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Zipper Key Hole Ribbed Knit Mini Dress
This ribbed mini dress features a zippered keyhole that adds an element of sexiness! We love to see you pairing this look with some booties or heels!
Fits & Features
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Ribbed Crew Neck
- Front Zipper Opens To Keyhole Cut Out
- Mini Length Silhouette
- Ribbed Fabric
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0574
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Crew Neck
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Floral Bliss Smocked Mini Dress
Bring out the floral prints and wave those gloomy winter-blues goodbye! Radiate that early springtime energy in this cute mini dress!
Fits & Features
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Adjustable Spaghetti Straps
- Lettuce Edge Trim At Square Neckline & Hem
- Smocking Throughout
- Mini Length Silhouette
- Curve Hugging Fit
- Ample Stretch
Style Number/Barcode: 05102-0519
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adjustable Spaghetti Straps
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Sleeveless Bodycon Denim Midi Dress
Make a denim dress a work from home must. The bodycon dress features a sleeveless bodice with a square neckline, thick shoulder straps that offer plenty of support, and vertical seams that lead to a midi length silhouette. The dress is composed of denim fabric that offers a form hugging fit that enhances curves. Dress up this midi with colorful pumps and statement earrings.
Fit & Features
- Sleeveless square neckline
- Thick shoulder straps
- Front vertical seams that lead from bust to hem
- Midi length silhouette
- Denim fabric
- Form hugging fit
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 05102-0192
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Romance Chiffon Floral Mini Dress
It's a match babe! Add this dreamy dress to cart and you'll be sweeping them off their feet!
Fits & Features
- Sweetheart Neckline I Lace-Up Bodice
- Square Back With Zipper & Hook And Eye Closure
- Sheer Long Sleeves I Elastic Cuffs
- Mini Length Silhouette With Self Ties At The Front
- Ruffle-Trim At Shoulders, Neckline, Hem
- Lined Chiffon Fabric With Romantic Floral Print
- Form Flattering Fit I Minimal Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0707
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tropical Moment Sleeveless Asymmetrical Ruched Midi Dress
Create a tropical moment in a midi dress that brings the color this season. This vacation-ready dress features a sleeveless bodice, a plunging V-neckline and adjustable spaghetti straps that lead to an X-back design. The relaxed fit waist leads to a midi length silhouette with a ruched side seam and an asymmetrical high slit to show off a hint of skin. The all-over tropical print features bright hues that perfectly contrast the dark background. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete your look with a pair of heels and golden hoop earrings.
Fit & Features
- Plunging V-neckline
- Adjustable spaghetti straps
- X-back
- Midi length silhouette
- Tropical print
- Asymmetrical high side slit
- Form hugging fit
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0231
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Off Shoulder Puff Sleeve Mini Dress
With puff sleeves and an off-shoulder neckline, you'll be making a trendy and stylish statement in this romantic little number!
Fits & Features
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Off Shoulder Neckline I No-Slip Interior Slip
- Puff Long Sleeves With Ruffle Accents At The Cuffs & Shoulders
- Smocked Back I Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Woven Fabric I Smooth Knit Lining
- Ties At The Hem
- Relaxed Fit I Minimal Stretch
Style Number/Barcode: 05102-0596
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Off Shoulder Neckline I No-Slip Interior Slip
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Bungee Drawstring Side Seam Knit Mini Dress
Keep it casual in a knit mini dress. The dress features a round neckline, short sleeves, ruched side seams with bungee straps 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 hoops and heels to dress up this casual dress.
Fit & Features
- Crew neckline
- Short sleeves
- Ruched side seams with bungee cords
- Mini length silhouette
- Curve-hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0715
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Slit Floral Knit Maxi Dress
Upgrade your dress with a floral print. The floral maxi dress features a sleeveless bodice, a plunging V-neckline, and spaghetti straps that lead to a partially open back with a square neck. The relaxed fit waist leads to a curve-hugging maxi length silhouette that is accented with a high side slit to reveal a hint of leg. The dress is composed of a smooth knit fabric that offers a form hugging fit. Complete your brunch-ready look with statement heels and extra-large hoops.
Fit & Features
- Sleeveless v-neckline
- Spaghetti straps
- Partially open back
- Floral print
- Maxi length silhouette
- High side slit
- Knit fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0645
Category Name: Casual Dresses
Price: $21.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Speechless Strapless Floral Ruffle Mini Dress
Leave everyone speechless when you stroll in wearing this floral mini dress at parties or brunch! The strapless neckline and stretchy smocked bodice provide a comfortable and flattering fit, while the dainty floral print and embroidery add a touch of whimsy. Complete the look with sunnies.
Fit & Features
- Dainty floral print and embroidery
- Woven fabric, some stretch
- Fitted silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5456
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ribbed Knit Ditsy Floral Mini Dress
Keep it sweet in a ditsy floral dress. Perfect for brunch, this mini dress features a sleeveless bodice with a sweetheart neckline and supportive tank-like straps. The back features an open back with two ribbed bar back straps. The relaxed fit waist leads to a curve-hugging mini-length silhouette. Keep accessories minimal to let the ditsy floral print command attention.
Fit & Features
- Sleeveless bodice
- Sweetheart neckline
- Open back with bar straps
- Ditsy floral print
- Mini length silhouette
Style Number/Barcode: 05102-0439
Category Name: Casual Dresses
Price: $13.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleeveless V Neck Ruffled Floral Mini Dress
Get frilly in a ruffled floral dress. Celebrate with your squad in a floral mini dress that features a sleeveless bodice, a plunging V neckline, and spaghetti straps. The relaxed fit waist leads to a mini-length silhouette with a frilly ruffled hem. The all-over floral print features bright hues that contrast with the dark background. Complete your look with wedges and sunglasses.
Fit & Features
- Sleeveless V neckline
- Spaghetti straps
- Floral print
- Mini-length silhouette
- Ruffled hem
- Lightweight knit fabric with a moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0517
Category Name: Casual Dresses
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleeveless Crossback Floral Ruffled Mini Dress
Get crossed up in a floral mini dress. Make a statement this season in a mini dress that features a charming floral print, a scoop neckline, and spaghetti straps. The back features an open back design with cross-strap ties. The relaxed fit waist features a ruffled hem and leads to a mini length silhouette with matching ruffled hem. The dress is composed of a lightweight woven fabric that offers a relaxed fit with a slight stretch. Complete your look with neutral-hued wedges and a floppy hat.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Floral print
- X-back
- Ruffles
- Mini length silhouette
- Lightweight woven fabric, slight stretch
Style Number/Barcode: 05102-0581
Category Name: Casual Dresses
Price: $15.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Sleeveless Square Neck Ribbed Knit Midi Dress
Keep it sleek in this simple and stylish ribbed midi dress. Go for a minimal vibe with this dress that features a square neckline, spaghetti straps, and a high side slit to showcase some leg. The dress features a relaxed fit waist that leads to an at-the-knee midi-length silhouette. The dress is composed of a curve-hugging ribbed knit fabric that offers a moderate stretch. Complete look with strappy stilettos and extra-large hoops to dress up this minimal piece.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- High side slit
- Midi-length silhouette
- Ribbed knit fabric
- Curve-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0706
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bloom With Beauty Maxi Dress
Be a stunning blooming beauty in this floral printed maxi dress!
Fits & Features
- V Neckline
- Spaghetti Straps
- Sheer Lace Back With Zipper I Elastic Back Cut-Out
- High Waist Seam
- Flowy, Maxi Length
- Sheer Chiffon Fabric I Knit Lining
- Relaxed Fit I Minimal Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
*Also available in Plus.Style Number/Barcode: 05102-3887
Category Name: Casual Dresses
Price: $24.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Getaway Girl Floral Smocked Tube Maxi Dress
Girl, you'll look stunning on your weekend getaway in this floral tube maxi dress! It features a strapless square neckline, a smocked bodice, and a flowy maxi-length silhouette with a ruffle bottom hem. Don't forget to add a pair of wedges and a wide brim hat to your cart as well!
Fit & Features
- Strapless square neckline
- Stretchy smocked bodice
- Maxi-length silhouette, mini-length lining
- Ruffle bottom hem
- Floral printed woven fabric
- No stretch
- Runs true to size
Style Number/Barcode: 05101-0033
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Strapless square neckline