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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Ditsy Floral Daze Mini Dress
Ditsy florals are the trendy print of the season! This floral printed dress features a sleeveless square neckline with ruffle spaghetti straps, ruched detailing down the side, and a mini-length, curve-hugging silhouette. Pair this adorable dress with some cute strappy sandals for the perf daytime 'fit!
Fit & Features
- Ruffle spaghetti straps
- Square neck and back
- Ruched side detailing, adjustable drawstring at hem
- Short, form-hugging fit
- Ditsy floral print
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-0524
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Puff Sleeve Leopard Print Mini Dress
Puff sleeves and leopard print - this mini dress couldn't get any trendier!
Fit & Features
- Off the shoulder neckline
- Short puff sleeves
- High waist seam
- Short, form hugging fit
- Leopard print
- Knit fabric | Plenty of stretch
- Form hugging fit
Style Number/Barcode: 05102-0521
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Puff It Up Crepe Mini Dress
Pump up the jams and get your night going in this LBD with statement puff sleeves!
Fits & Features
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Puff Shoulder Short Sleeves
- Plunging V Neckline I Padded Bust
- Square Back I Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0624
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Puff Shoulder Short Sleeves
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As Good As Knit Gets Mini Dress
This chic white knit mini dress is as good as it gets! Paired with some glam earrings and strappy heels, you'll be lookin' fine bb!
Fit & Features
- Spaghetti straps
- Wrap front V neckline
- Ruched side detailing
- Short envelope hem
- Ribbed knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0620
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Fleur Love Scuba Mini Dress
Wrap yourself up in florals with this oh-so-lovely and charming mini dress! Easily dress your look up or down by pairing it with some sneakers or heels.
Fits & Features
- Spaghetti Straps
- Square Neckline
- Mini Length Silhouette I Front Slit
- Scuba Knit Fabric
- Form Hugging Fit I Plenty Of Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0626
Category Name: Casual Dresses
Price: $11.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flow With The Floral Skater Dress
Go with the flow of this pretty floral skater dress! Pair with some everyday sandals for an effortless, spring ready vibe.
Fit & Features
- Off the shoulder elastic banded neckline
- Three quarter length flowy sleeves
- High waist seam
- Skater skirt
- Sheer chiffon fabric | Knit lining
- Rose print
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0410
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Summer-Coded Crochet Halter Mini Dress
Serve all the summer vibes in this crochet knit mini dress designed with a halter V-neck with a beaded trim on the straps. Style with espadrille wedges for sunset happy hour.
Fit & Features
- Sheer crochet knit fabric with knit lining, moderate stretch
- Sleeveless V-neckline
- Tie-back halter straps, beaded trim
- Partially open back
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6114
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Burnout Floral Mock Neck Mini Dress
We can't get enough of these burnout floral dresses! This mini version is complete with a trendy mock neck and a short, curve hugging fit.
Fit & Features
- Mock neckline
- Back zipper closure
- Long sheer fitted sleeves
- Sheer insets at the neckline
- Sheer back
- Mesh burnout floral sheer fabric | Knit lining
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0597
Category Name: Casual Dresses
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ready Or Not Ruched Mini Dress
Ready or not, you're showing up to slay in this ruched mini dress!
Fit & Features
- Long billowy sleeves | Elastic banded cuffs
- Square neckline
- Complete stretchy smocked back
- Front ruched detailing | Dual drawstrings at hem
- Short, curve hugging fit
- Smooth woven fabric
Pink: Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Black: Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0627
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Own The Moment Tube Floral Maxi Dress
Ready to shut down the vacation pics? This strapless floral maxi dress brings effortless chic with a curve-hugging fit and leg-baring side slit.
Fit & Features
- Floral print, mesh-lined fabric, moderate stretch
- Strapless tube neckline
- High side slit
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000237
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Puff Sleeve Floral Mini Dress
Puff sleeves are so of the moment. Pair that with spring time florals and you've got yourself an adorably trendy fit! Pair this mini dress with some cute clear mules and wear either off the shoulder or on.
Fit & Features
- Short puff sleeves | Merrow edge trim
- Square neckline | Faux tie front detail
- High elastic banded waist
- Ruched side detailing
- Short, form hugging fit
- Small floral print
- Brushed knit fabric | Plenty of stretch
Model is 5'6.5" with 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0420
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dreamy In Denim Button Front Mini Dress
Look ever so dreamy in denim in this spring ready mini dress! Pair with some wedges and trendy sunnies and you'll be ready to go!
Fit & Features
- Long sleeves | Single buttons to cuff | Puff shoulders
- Sweetheart neckline | Bust seam detailing
- Partial stretchy smocked back
- Button down front
- Slanted front pockets
- Short, form-fitting style
- Jean fabric | Moderate stretch
Style Number/Barcode: 05102-0653
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Curves Ahead Bodycon Dress
Showcase your curves in this bodycon and flaut a confident look with statement heels!
Fit & Features
- Wired Sweetheart Neckline
- Adjustable Spaghetti Straps
- Lined Jersey Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0633
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vacay Vibes Skater Dress
Escape on vacay in this gorg tropical printed skater dress! Pair with some heels and accessorize with a cute woven bag and live it up!
Fit & Features
- Off the shoulder square neckline | Ruffle trim
- Long sleeves | Elastic banded hems
- High rise elastic banded waist
- Tie front belt
- Flowy skater skirt | Woven lining
- All over colorful palm print
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0603
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off The Shoulder Button Front Midi Dress
The perf midi dress that has major spring time vibes! With its short puff sleeves, button front detailing, and flowy feel, this dress is a must for your wardobe.
Fit & Features
- Off the shoulder sweetheart neckline
- Short puff sleeves
- Faux button down front
- Stretchy smocked back
- Front slit | Ruffle hem
- Flowy fit
- Woven fabric | Short knit lining
Style Number/Barcode: 05102-0637
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adore Me Floral Mini Dress
Walk right into any room and everyone will be falling head over heels for this floral look!
Fits & Features
- Spaghetti Straps
- V Neckline
- Mini Length Silhouette
- Woven Fabric I Floral Print Throughout
- Curve Hugging Fit I Ample Stretch
- Zipper Not Featured
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0399
Category Name: Casual Dresses
Price: $9.97 $23.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Asymmetric Ruched Midi Dress
Add some flower power to your look with this bold and beautiful midi dress! Goes amazing with some strappy heels

Fits & Features
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Adjustable Spaghetti Straps That Cross At The Back
- V Neckline | Lined At The Bust
- Midi Length Asymmetric Hemline
- Side Ruching
- Woven Fabric With Floral Prints
- Plenty Of Stretch | Form Hugging Fit
- Zipper Not Featured
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0333
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adjustable Spaghetti Straps That Cross At The Back
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Floral Dreaming Satin Midi Dress
We're dreaming of romance in this floral beauty! This midi dress perfectly pairs with stilettos and clutch for the perfect date night look!
Fit & Features
- V-Neckline
- Adjustable Spaghetti Straps | Cross-Back
- Floral Print
- Lined Satin Fabric
- Midi Length Silhouette
- Front Slit
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05101-0367
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fleur Paradise Chiffon Smocked Mini Dress
Slip-on this pretty mini dress and enchant them all with the bold and beautiful floral prints!
Fits & Features
- Ruffle-Trim At Square Neckline, Cuffs & Hem
- Sheer, Roomy Chiffon Long Sleeves I Elastic Cuffs
- Smocked Bodice & Mini Length Silhouette
- Curve Hugging Fit
- Ample Stretch
Style Number/Barcode: 05101-0509
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Garden Parties Pleated Midi Dress
Get ready for garden parties, backyard brunches, bridal showers, and spring weddings with this spring staple! Pair with wrap heels, or strappy mules!
Fit & Features
- Tie halter neckline
- Pleated bodice with keyhole cut out
- Smocked stretchy waist line
- Pleated flowy skirt
- Mid-length hemline
- Lightweight sheen polyester material
- Unlined | Moderate stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0724
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Heatwave Floral Halter Mini Dress
Cause a major heatwave in this sultry mini dress designed with a large floral print on smooth, stretchy knit fabric. The plunging halter V-neck and short, curve-hugging silhouette are alluring details you'll love.
Fit & Features
- Lined knit fabric, high stretch
- Large floral print
- Sleeveless plunging V-neckline
- Halter strap, partially open back
- Ruching
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000639
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE-2
Available Size: XS
Product Badge:- Sale
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Boho Breeze Tiered Mini Dress
Breeze on by like the boho babe you are in this spring ready mini dress! Paired with some strappy sandals, you'll have the best 'fit.
Fit & Features
- Tank-like shoulder straps
- Square neck and back
- Parital button down front
- Hidden back zipper | Hook and eye closure
- Stretchy smocked waist
- Tiered flowy skirt
- Lightweight woven fabric | Woven skirt lining
Style Number/Barcode: 05102-0626
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kiernan Glittering Mesh Party Dress
Get ready for a night that you will never forget, when you start the party in our glittering Kiernan skater dress that is fit for a princess!
Fit & Features
- V-neckline
- Adjustable spaghetti straps
- Square back | Zipper closure
- Fully lined with double layered glitter overlay
- Banded high waist line
- Pleated bodice
- Flowy mini hemline | Lightweight feel | Minimal stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0305
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Fling Floral Chiffon Ruffle Dress
Embrace the florals and ruffles in this romantic mini dress! It features peasant long sleeves, a plunge v-neckline, and a babydoll style silhouette with flirty ruffle trim on floral chiffon-lined fabric. Complete the look in a boho ring set.
Fits & Features
- Plunging V Neckline
- Sheer Roomy Long Sleeves I Elastic Cuffs
- Back Zipper With Hook & Eye Closure
- Dual Buton Detail At Nape Of Neck I Cut Out At Back
- Mini Length Hemline
- Lined Chiffon Fabric With Floral Print I Ruffle-Trim Detail
- Minimal Stretch
Style Number/Barcode: 05102-0470
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale