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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Hidden Treasure Lace-Up Shell Accent Midi Dress
Discover your new signature look with this irresistible midi dress featuring a unique shell accent neckline, lace-up back offers undeniable allure, and a sultry side slit creates movement.
Fit & Features
- Texture knit fabric, moderate stretch, stretchy knit lining
- V-neckline with shell accent trim
- Spaghetti straps
- Lace-up back
- Side slit
- Bodycon silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6119
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blissful Darling Halter Lace Skater Mini Dress
Twirl with bliss in this darling lace skater mini dress with a flirty halter neckline and open back. It's perfect for shower celebrations or a dressy date night!
Fit & Features
- Lace knit fabric, stretchy knit lining
- Halter V-neckline, tie closure
- Open back
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4157
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Carefree Energy Halter Bodycon Mini Dress
Be a cute sight in this halter mini dress boasting a flattering bodycon fit that perfectly flaunts your curves on vacay or a chic staycation!
Fit & Features
- Texture knit stretchy fabric
- Halter neckline, spaghetti strap ties
- Knotted bust accent
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2302
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Falling For You Tropical Floral Slit Maxi Dress
Get the golden hour glow in this tropical floral maxi dress while on vacation! Featuring a chic square halter neckline and a form-hugging fit with a high side slit, this dress beautifully accentuates your silhouette.
Fit & Features
- Tropical floral print, mesh-lined fabric
- Square halter neckline, adjustable spaghetti straps
- Criss cross back
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6113
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On A Vacay Strapless Tropical Slit Maxi Dress
From sunny vacations to island getaways, this tropical maxi dress is destined to go with you on your next trip!
Fit & Features
- Tropical palm print, mesh fabric lined with stretchy knit
- Strapless neckline
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6110
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sun Kissed Strapless Floral Bodycon Mini Dress
Bare your sun kissed shoulders on vacay in this strapless mini dress with a statement floral print and flattering bodycon fit that flaunts your curves!
Fit & Features
- Mesh fabric, floral print, stretchy knit lining
- Strapless neckline
- Bodycon fit
- Mini-length hem
- Runs small
Style Number/Barcode: 05102-6112
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Picture Perfect Color Block Midi Dress
For a picture-perfect look you'll be reaching for this color block midi dress for any casual plans! The strapless fitted bodice accentuates your silhouette while the flowy midi-length hem creates an elegant movement as you walk. Plus, keep your hands warm in the convenient hidden side pockets!
Fit & Features
- Woven cotton-blend fabric, stretchy knit lining
- Strapless color block fitted bodice
- Hidden side pockets
- Back zipper and hook-eye closure
- Flowy midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6109
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kiss The Sun Tropical Lace-Up Slit Maxi Dress
Sipping a mai tai oceanside has never looked cuter in this tropical maxi dress! Made to turn heads, this maxi dress boasts a sexy lace-up back, form-hugging silhouette that shows off your curves, and a high front slit giving major allure.
Fit & Features
- Tropical print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Lace-up back
- Form-hugging silhouette, high front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6103
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Turn Heads Abstract Print Strapless High Slit Maxi Dress
Unveil a chic allure in this lined airy mesh maxi dress designed with an eye-catching abstract print to turn heads. It features a strapless straight-across neckline, a high-cut side slit to reveal some leg, and a fitted silhouette on the maxi-length hem.
Fit & Features
- Sheer mesh fabric with soft brushed knit lining, plenty of stretch
- Abstract print
- Strapless straight neckline
- High side slit
- Maxi-length fitted silhouette
- Runs true to size
Style Number/Barcode: 05102-6105
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Exceptional Cutie Striped Cutout Midi Dress
Strut like an exceptional cutie in this striped midi dress all season long! This strapless dress features a cutout bodice that adds a touch of playful sass, while the bodycon silhouette and midi-length hem hug your curves in all the right places.
Fit & Features
- Striped pattern, stretchy knit fabric
- Strapless neckline
- Cutout bodice
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2296
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Breezy Chic Belted A-Line Maxi Dress
Breezy chic, this A-line maxi dress is made with an airy gauze woven fabric accented with sheer lace insets. The belted waist leads to a long tiered flowy fit for that effortless vibe.
Fit & Features
- Gauze woven fabric with sheer lace insets
- Strapless sweetheart neckline with ruffled trim
- Bust cutout with tie-front detail, ruching, underbust seam
- Faux leather belted waist, gold metal buckle
- Maxi-length hem
- Tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6106
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Stunner Floral Mesh Strapless Maxi Dress
Turn heads your next vacay in this bold floral mesh maxi dress made to impress. The long bodycon silhouette will flaunt your gorgeous curves.
Fit & Features
- Sheer mesh fabric with full-length brushed knit lining, high stretch
- Large floral print
- Strapless straight neckline
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-4149
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Make Your Debut Strapless Abstract Mesh Maxi Dress
Make your effortless debut in this abstract mesh maxi dress that hugs your curves in a flattering bodycon silhouette with a long-length hem. Pair with stiletto mules.
Fit & Features
- Abstract print, mesh fabric, soft and stretchy knit lining
- Strapless neckline
- Bodycon silhouette
- Long-length hem
- Runs true to size
Style Number/Barcode: 05101-4148
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feel The Sunshine Sweetheart A-Line Mini Dress
Step into the sunshine in this adorable sleeveless mini dress! With a captivating sweetheart neckline and hoop insert, this dress flatters your figure in an A-line silhouette and mini-length hem.
Fit & Features
- Woven fabric, stretchy knit lining
- Sweetheart neckline with hoop insert
- Wide shoulder straps
- Back zipper closure
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6100
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Sweetie Open Back Gingham Ruffle Skater Dress
Please, please, please envision how sweet you'll look in this gingham ruffle skater dress! Boasting a head-turning open back and flattering mini-length hem perf for pairing with boots!
Fit & Features
- Gingham print, woven fabric
- Sweetheart neckline, lace trim, bust tie
- Spaghetti straps
- Open back with spaghetti strap tie
- Skater silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6102
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweetest Outing Tie Back Ruffled Skater Mini Dress
Have the sweetest look in this tie back ruffled skater dress at bridal showers or graduations!
Fit & Features
- Woven fabric lined with stretch knit
- Sweetheart neckline with bust tie
- Adjustable spaghetti straps
- Tie-back cutout design, zipper and hook-eye closure
- Skater ruffled silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6101
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Easily Stunning Cutout Striped Midi Dress
This cutout striped midi dress was made for a laidback babe like you! With a bodycon fit and dual side slits for effortless allure, this dress is perfect for vacation or strolling the beach.
Fit & Features
- Striped print, stretchy knit fabric
- V-neckline with cutout
- Adjustable spaghetti straps
- Bodycon silhouette
- Dual side slits
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2290
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take Me There V-Neck Slit Bodycon Midi Dress
A perfectly flattering bodycon midi dress for any of your upcoming social plans!
Fit & Features
- Stretchy rib knit fabric
- V-neckline
- Spaghetti straps
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2286
Category Name: Casual Dresses
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Slay All Day Paisley Mesh Maxi Dress
Look good from every angle—this paisley mesh dress understood the assignment. The halter square neckline and high side slit bring all the heat for a night out or glam rooftop vibes.
Fit & Features
- Paisley print, mesh-lined fabric, moderate stretch
- Halter square neckline with spaghetti straps
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6099
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Total Attraction Cutout Bodycon Midi Dress
Look and feel like a babe in this bodycon midi dress with a flirty cutout twist back design and side slit for effortless movement! Pair with cute sandals.
Fit & Features
- Texture knit fabric, stretchy knit lining
- Scoop neckline, spaghetti straps
- Twist cutout back design
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2281
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Back In Stock
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Blissful Cutie Eyelet Bodycon Midi Dress
Enter every room like a blissful cutie in this eyelet bodycon midi dress perfect for brides-to-be or brunch!
Fit & Features
- Eyelet fabric lined with stretchy knit
- Square neckline, ruffle trim, bust tie
- Wide shoulder straps
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6098
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Charm Ruffled Chiffon Tube Skater Dress
Your go-to summer floral dress has arrived! With charming ruffles and skater silhouette, this short dress is perfect for shower celebrations, brunch, or day dates.
Fit & Features
- Floral print, chiffon fabric, stretchy knit lining
- Strapless tube neckline
- Stretchy, smocked fitted bodice
- Skater silhouette
- Ruffled short hem
- Runs true to size
Style Number/Barcode: 05101-4125
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Set For Vacay Tropical Floral Strapless Midi Dress
You'll be set for vacay in this strapless knit midi dress featuring a large tropical floral print for a bold allure. The form-hugging silhouette will flaunt your gorgeous curves.
Fit & Features
- Sleek knit fabric with full-length knit lining, high stretch
- Large tropical floral print
- Strapless straight-across neckline, no-slip strip
- Midi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-6097
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pleat The Way Scoop Neck Mini Dress
Make way for setting the trends in this sleeveless mini dress with trendy spaghetti strap ties and a layered pleated mini-length hem. Pair with sneakers.
Fit & Features
- Smooth twill woven fabric, stretchy knit lining
- Spaghetti strap ties
- Side zipper and hook-eye closure
- Scoop neckline
- Form-hugging fit
- Layered pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6096
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free