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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Floral Passion Sleeveless Lace-Up Maxi Dress
The maxi dress features a sleeveless square neckline supported with additional built-in flexible boning, an abstract floral pattern, a lace-up back design, and a bold high-side slit. Complete the look with stiletto heels for the perfect date night outfit.
Fit & Features
- Mesh fabric, sewn-in knit lining
- Sleeveless square neckline
- Built-in-boning
- Floral pattern
- Lace-up back design
- High side slit
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05101-3773
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Romance Corset Lace-Up Floral A-Line Mini Dress
The flirty romantic allure of this floral mini dress will take you from brunch and garden party soirees! This mini dress boasts a cinched waist with a corset bodice and head-turning lace-up back design while the a-line silhouette flatters your figure. Pair with ballet flats.
Fit & Features
- Dainty floral print, poplin woven fabrication
- Sweetheart neckline with bust tie, underwire bust
- Adjustable spaghetti straps
- Corset bodice, lace-up back, flexible boning
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3768
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
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Kissed By Blooms Corset Skater Floral Dress
Blossom so cute in this skater floral dress boasting a corset bodice that flaunts your femme figure and a trendy lace-up back for added allure!
Fit & Features
- Floral print, woven fabric, tulle and woven linings
- Sweetheart neckline
- Adjustable spaghetti straps, side zipper and hook-eye closure
- Lace-up smocked stretchy back
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3769
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
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Sunshine Bliss Ditsy Floral Lace Corset Skater Dress
An adorable ditsy floral short dress for brunch, day dates, or celebration! The skater dress showcases a femme allure with a lace trim corset bodice designed to snatch your figure while the back bow tie and drop waist seam accentuate your figure. Pair with a ring set.
Fit & Features
- Ditsy floral print, woven fabric, woven lining with lace trim
- Lace trim sweetheart neckline
- Adjustable shoulder straps, back zipper closure
- Corset lace trim bodice, underwire bust, flexible boning
- Drop waist seam, skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3770
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
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Sealed With Charm Ponte Mini Dress
Seal your style with this charming ponte mini dress featuring an adorable strapless sweetheart neckline with a bow and a bodycon fit. Style with earrings.
Fit & Features
- Ponte knit fabric, plenty of stretch
- Strapless sweetheart neckline
- Bow tie front accent
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5897
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Adorable Drop Waist Bubble Hem Skater Dress
Adorable and trendy will be your vibe in this soft knit skater dress featuring a mock neckline, tank shoulder straps, ruched side seams to accentuate your curves, and a short ruched bubble hem. Style with platform heels for a cute party look!
Fit & Features
- Double-lined brushed knit fabric, plenty of stretch
- Mock neckline, tank shoulder straps
- Ruching
- Drop waist seam
- Short skater silhouette
- Ruched bubble hem
- Runs true to size
Style Number/Barcode: 05102-5902
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Trend Striped Knit Long Sleeve Mini Dress
This trendy striped knit mini dress features a scoop neckline, long fitted sleeves, an open lower back accent, and a short bodycon silhouette to hug your curves. Perfect for casual chic styling, pair with knee-high boots.
Fit & Features
- Striped ribbed knit fabric
- Scoop neckline
- Long fitted sleeves
- Open lower back
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 06005-2119
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Easily Gorgeous Strapless Cable Knit Midi Dress
Flaunt your gorgeous curves in this chic cable knit midi dress for brunch or a casual party. The dress boasts a flattering bodycon silhouette and a center back slit for movement.
Fit & Features
- Cable knit design, soft stretchy knit lining
- Strapless neckline
- Bodycon silhouette
- Center back slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5898
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shrug It Off One-Shoulder Bodycon Mini Dress
This is the perfect sleeveless mini dress for parties and cocktail hour! It features a sassy one-shoulder neckline and a sexy bodycon silhouette. Pair with boots.
Fit & Features
- Rib knit fabric, stretchy knit lining
- One-shoulder neckline
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5900
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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She's Stylish Mock Neck Cable Knit Midi Dress
A stylish sleeveless midi dress featuring a mock neck, a flattering form-hugging fit, and a side slit for movement. Complete the look with strappy heels.
Fit & Features
- Cable knit fabric, stretchy knit lining
- Mock neck
- Side slit
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5897
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Denim Darling Strapless Bodycon Mini Dress
A denim bodycon mini dress for a darling look paired with your fave boots at concerts and festivals!
Fit & Features
- Denim fabric, sewn-in knit lining, minimal stretch
- Strapless neckline
- Back zipper and hook-eye closure
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5901
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Luxe Long Sleeve Ribbed Knit Mini Dress
Part casual, part luxe, this long-sleeved mini dress is perfect for your next date night! The ribbed knit dress features a square neckline, long sleeves, and a mini-length hem. Complete look with knee-high boots!
Fit & Features
- Ribbed knit fabric with knit lining, plenty of stretch
- Square neckline
- Long fitted sleeves
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5899
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep It Cute Ruffled Drop Waist Skater Dress
Keep it cute every time in this strapless skater dress designed with a flirty ruffled short-length hem. Pair it with sleek heels.
Fit & Features
- Ponte knit fabric with partial knit lining, moderate stretch
- Strapless straight neckline, fold-over design
- Drop waist
- Mini-length tiered ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3756
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Chic Long Sleeve Midi Dress
Keep it chic in this knit midi dress boasting an off-the-shoulder neckline and trendy button accents that lead to a flirty slit. Pair with boots.
Fit & Features
- Ribbed knit fabrication
- Off-the-shoulder neckline, foldover accent
- Long sleeves
- Snap button accents at the hem
- High side slit
- Midi length hem
- Runs true to size
Style Number/Barcode: 06005-2137
Category Name: Casual Dresses
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Sweet Long Sleeve Drop Waist Skater Dress
Stay forever sweet in this skater dress featuring a sleek square neckline and ruching that flatters your figure. Pair with heels.
Fit & Features
- Stretchy smooth knit fabric
- Square neckline
- Long fitted sleeves
- Ruching
- Drop waist
- Mini-length tiered skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3745
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Silhouette Ribbed Knit Off-The-Shoulder Midi Dress
Showcase a sleek silhouette in this ribbed knit midi dress featuring an off-the-shoulder neckline with a fold-over design and a mermaid silhouette to highlight your curves. Style with knee-high boots for a chic look.
Fit & Features
- Ribbed knit fabric, plenty of stretch
- Off-the-shoulder neckline
- Fold-over design, short sleeves
- Midi-length mermaid silhouette
- Runs true to size
Style Number/Barcode: 05102-5896
Category Name: Casual Dresses
Price: $14.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Chic Icon Long Sleeve Knit Midi Dress
Become an instant chic icon in this bodycon midi dress adorned with flare cuff long sleeves with flirty tie accents and a V-neckline. Pair with mules.
Fit & Features
- Lined brushed knit fabric, plenty of stretch
- V-neckline
- Long fitted sleeves with ruched slit flare accents, adjustable drawstrings
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5895
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Curves Ribbed Knit Off-The-Shoulder Midi Dress
Showcase your perfect curves in this midi dress designed with soft ribbed knit fabric. It features an off-the-shoulder neckline with a chic fold-over design, long fitted sleeves, and a midi-length bodycon silhouette.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Off-the-shoulder neckline, fold-over design
- Long fitted sleeves
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5894
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Knit Off-The-Shoulder A-Line Mini Dress
Channel that cute and cozy vibe in this adorable soft ribbed knit mini dress featuring an off-the-shoulder straight neckline with a fold-over design, long fitted sleeves, and a short A-line silhouette. Style with knee-high boots for a fall date!
Fit & Features
- Soft ribbed knit fabric
- Off-the-shoulder straight neckline, fold-over design
- Long fitted sleeves
- Mini-length A-line fit
- Runs true to size
Style Number/Barcode: 05102-5892
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Sweetheart Smocked Gingham Cotton Skater Dress
This short skater dress features an adorable gingham print on lightweight lined cotton fabric. The smocked waist offers added stretch, while the fit-and-flare silhouette gives that flirty touch, perfect for a day date.
Fit & Features
- Gingham printed cotton fabric with woven lining, no stretch
- Scoop neckline with keyhole cutout and tie-front
- Adjustable spaghetti straps
- Stretchy smocked waist
- Short tiered skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5891
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Perfection Long Sleeve Knit Mini Dress
This ribbed knit mini dress will create perfect casual 'fits! It features a square neckline, long fitted bell sleeves with cute flared-out hems, and a mini-length, form-hugging silhouette. The lined knit fabric offers plenty of stretch for comfortable wear. Style with knee-high boots.
Fit & Features
- Ribbed knit fabric, knit lining, plenty of stretch
- Square neckline
- Long fitted bell sleeves, flared hems
- Form-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5889
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stripes In Style Off The Shoulder Mini Dress
Stay stylish in this trendy off-the-shoulder mini dress showcasing a classic striped pattern and a form-hugging fit. Pair with knee-high boots.
Fit & Features
- Ribbed knit fabrication
- Off-the-shoulder neckline
- Long dolman sleeves
- Stripes
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-5885
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Effortless Halter Bodycon Mini Dress
From brunch to dinner date plans, this halter bodycon mini dress will always collect compliments!
Fit & Features
- Mesh fabric, stretchy knit lining
- Halter sweetheart neckline, tie closure, padded bra cups
- Back zipper and hook-eye closure
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000189
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Find Me In Plaid A-Line Mini Dress
Tried and trendy, this plaid mini dress boasts a strapless folded neckline and a flattering A-line silhouette. Pair with boots.
Fit & Features
- Plaid pattern, soft knit fabric
- Strapless folded neckline
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5884
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free