Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on 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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A Bold Move Mini Dress
Make a major bold move and absolutely stun in this vibrant mini dress! The bright coral hue is perf for spring break!
Fit & Features
- Bungee spaghetti straps
- Square neckline
- Dart seam detailing
- High waist | Front cut out
- Short, ruffle hem
- Form hugging fit
- Crepe fabric | Moderate stretch
Style Number/Barcode: 05101-0780
Category Name: Casual Dresses
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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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Wild In Lace Leopard Dress
Unlock your wild side in this fierce mini dress! Pair this bold print with sleek hoops and stilettos for stand out lewk!
Fit & Features
- V-Neckline | Lace Trim
- Spaghetti Straps
- Side Slit | Lace Trim
- Leopard Print
- Lined Smooth Knit Fabric
- Relaxed Fit
- Moderate Stretch
Style Number/Barcode: 05102-0710
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feeling Floral Eyelet Mini Dress
We’re always in the mood for a little floral print! Pair this mini dress with sandals and layered dainty jewelry.
Fit & Features
- All Over Eyelet Design
- Ditsy Floral Print
- Mini Length
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0709
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spot Me Woven Ruffle Mini Dress
Get spotted in this chic & stylish woven LBD, perf paired with some strappy sandals and a denim jacket.
Fit & Features
- Short sheer sleeves
- Wrap front V neckline
- Sheer back | Hidden zipper closure
- High waist
- Front ruched detailing | Faux drawstring
- Short, ruffle hem
- Sheer swiss dot woven fabric | Stretchy knit lining
Style Number/Barcode: 05101-0775
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Got A Flair For It Ruffle Hem Mini Dress
Add some flair to your movement with this ruffle mini dress! Pair with some block heels and hoop earrings!
Fits & Features
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Spaghetti Straps
- Square Neckline I Princess Seams
- Back Zipper With Hook & Eye Closure
- Side Ruching
- Mini Length Silhouette I Ruffle Trim Hemline
- Smooth Textured Woven Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0698
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spaghetti Straps
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Falling For Florals Mini Dress
Fall for this pretty print this season as you charm them all! Pair this beauty with fab pumps and butterfly accessories for an unforgettable look!
Fit & Features
- Sweetheart Neckline with Built-In Boning
- Lace-Up Bodice
- Adjustable Spaghetti Straps
- Floral Print
- Lined Lightweight Woven Fabric
- Mini Skirt Length Knit Lining
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05102-0700
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Daisy Days Smocked Mini Dress
Keep it fab in florals this season with this charming mini dress! Pair with wedges and a cute tote for the perf lewk honey!
Fit & Features
- Square Neckline | Smocked Trim
- Inset | Tie at Bust
- Spaghetti Tie Straps
- Daisy Floral Print
- Smocked Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 05102-0684
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Felt Cute Button Off Shoulder Mini Dress
Felt cute, probably leaving on! Show off those curves in this sweet mini! Opt for some strappy mules and a pair of chic earrings for an adorable attire!
Fits & Features
- Off Shoulder Design I Short Sleeves
- V Neckline
- Snap Button-Front
- Ribbed Knit Fabric
- Mini Length Hem
- Figure Hugging I Plenty Of Stretch
Style Number/Barcode: 06005-0636
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleeveless Ruched Midi Dress
Yessssss girl! She's classy and curvy. Up your midi game with this form-hugging dress! Pair it with your fav block heels.
Fits & Features
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Crew Neckline
- Dual Button Closure At Nape I Keyhole Opening
- Midi Length Silhouette
- Ruching Throughout
- Smooth Jersey Knit Fabric I Fully LIned
- Form Hugging Fit I Moderate Stretch
- Zipper Not Featured
Style Number/Barcode: 05102-0699
Category Name: Casual Dresses
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Crew Neckline
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Girly In Gingham Smocked Mini Dress
Look oh so gorgeous and girly in this gingham smocked mini dress babe! Pair with some cute wedges and you'll have a spring ready look!
Fit & Features
- Tie shoulder spaghetti straps
- Notched V neckline | Ruffle trim
- Stretchy smocked body
- Short, form hugging fit
- All over gingham print
Style Number/Barcode: 05102-0683
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Tie shoulder spaghetti straps
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Got A Flair For It Ruffle Hem Mini Dress
Add some flair to your movement with this ruffle mini dress! Pair with some block heels and hoop earrings!
Fits & Features
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Spaghetti Straps
- Square Neckline I Princess Seams
- Back Zipper With Hook & Eye Closure
- Side Ruching
- Mini Length Silhouette I Ruffle Trim Hemline
- Smooth Textured Woven Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0697
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spaghetti Straps
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Be Amazed Ruched Off Shoulder Mini Dress
Not your typical LBD. They're going to be amazed once they see you strutting in with this mini dress! Dust your neckline with some sparkling rhinestone accents to go for that extra glow!
Fits & Features
- Off Shoulder Neckline I Elastic Interior Band
- Fitted Long Sleeves
- Drawstring Bust
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette I Mesh Lined Fabric
- Ruching Throughout I Ruffle Trim Neckline & Hem
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0767
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Love Lace Up Front Mini Dress
We've all got love for leopard print in our wardrobe! Make your presence be known in this fierce mini dress!
Fits & Features
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Sheer Roomy Long Sleeves
- Ruffle-Trim At Sweetheart Neckline & Shoulders
- Lace-Up Front
- Back Zipper With Hook & Eye Closure
- Mini Length Hemline I Adjustable Dual Drawstrings At The Front
- Woven Lined Fabric
- Minimal Stretch
Style Number/Barcode: 05101-0768
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sheer Roomy Long Sleeves
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Dreamy Meadow Chiffon Ruffle Maxi Dress
Look like a dreamy meadow in this flowy and sweet midi dress! Slip into some block heels and you'll be ready for your spring soiree!
Fits & Features
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Adjustable Spaghetti Straps
- Surplice V Neckline I V Back
- Back Zipper
- Maxi Length Silhouette I Ruffle-Trim Hem I Partial Lining
- Adjustable Drawstring & Ruching At Front Side
- Chiffon Fabric I Floral & Botanical Prints
- Minimal Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0769
Category Name: Casual Dresses
Price: $21.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Adjustable Spaghetti Straps
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Center Of Attention Ruched Mini Dress
Be the center of attention in this sultry mini dress! Pair with some booties or heels for a chic look!
Fits & Features
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V Neckline
- Roomy Sheer Long Sleeves
- Elastic Shoulder & Cuffs
- Adjustable Drawstring Center Front
- Mini Length Silhouette
- Mesh Lined Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0696
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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V Neckline
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Purrfectly Fierce Smocked Mini Dress
Look purrfectly fierce in this so of the moment leopard printed mini dress! Its smocked detailing will flatter your curves.
Fit & Features
- Strapless sweetheart neckline
- Tie front detail
- Front cut out
- Stretchy smocked body
- Short, form hugging fit
- Leopard print
Style Number/Barcode: 05102-0682
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Knit Crew Neck Bodycon Mini Dress
Keep it casually chic in a mini dress that is a total must-have! The short dress features a crew neckline with a racerback design, a mini-length hem, and is composed of a form-hugging ribbed knit fabric. Put your hair in an updo and style with strappy mules for a cute look!
Fit & Features
- Crew neckline
- Sleeveless bodice
- Racerback design
- Mini-length hem
- Ribbed knit fabric, fully lined
- Form-hugging fit, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-0689
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Burst Ruffle Mini Dress
Burst into the season with fab florals bby! Pair this charming print with fab wedges and pop of color to complete a brunch-ready look!
Fit & Features
- Sweetheart Neckline | Drawstring
- Short Puff Sleeves
- Mid-Drift Cut Out
- Ruched Side Seam | Drawstring
- Floral Print
- Lined Chiffon
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05102-0676
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Smocked Sweetheart Gingham Mini Dress
Yes girl, it's the perfect daytime date dress! Perfectly pair the look with some clean white sneakers or heeled sandals!
Fits & Features
- Elastic Sweetheart Neckline & Cuffs
- Tie Design & Cut Out At The Bust
- Woven Short Sleeves I Can Be Worn Off Shoulder
- Smocking Throughout
- Mini Length Hemline With Ruffle Trim
- Gingham Print Design
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0688
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Friday Night Ruched Midi Dress
Get this dress now so you don’t have to worry about not having anything to wear next Friday! It looks great paired with clear heels and layered gold necklaces.
Fits & Features
- Square Neckline
- Ruched Detailing
- Form Hugging Fit
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0692
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortless Beauty Eyelet Mini Dress
You've got that effortless beauty babe! Wear this gorg eyelet mini dress and have the perfect spring time look!
Fit & Features
- Adjustable spaghetti straps
- Wrap front V neckline
- Hidden back zipper | Hook and eye closure
- Side tie detail
- Wrap front skirt
- Eyelet detail woven fabric | No stretch
Style Number/Barcode: 05102-0686
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Breeze On By A-Line Mini Dress
Breeze right through the crowd (and catch some glances doing it!) in this simply chic mini dress! Elevate your look adding some dainty jewels and a pair of strappy mules!
Fits & Features
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Surplice v neckline
- Short sleeves
- Mini length hem, A-line silhouette
- Smooth, stretchy knit fabric
- Form hugging fit, plenty of stretch
- Zipper not included
Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0687
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Surplice v neckline
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You're The One Bodycon Midi Dress
There's truly no one like you bb girl! With a statement single strap and a figure-hugging fit, you'll be feeling fierce in this basic ribbed dress!
Fits & Features
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One Shoulder Strap
- Slanted Neckline
- Midi Length Hem
- Ribbed Knit Fabric
- Figure Hugging I Moderate Stretch
Style Number/Barcode: 05102-0685
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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One Shoulder Strap