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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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
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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: XS, 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
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Tropical Beauty V-Neck Slit Midi Dress
Jet set on your next tropical getaway or weekend escape in this perfect slit midi dress! Featuring a bold metal insert and a flattering bodycon fit, this dress is perfect for any occasion.
Fit & Features
- Palm leaf tropical print, stretchy knit fabric, soft knit lining
- V-neckline with metal insert
- Spaghetti straps
- Side slit
- Bodycon silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6095
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Vision Halter Striped Crochet Midi Dress
The perfect blend of modern and retro! This halter striped crochet midi dress can easily be styled with sandals for the day and heels for night.
Fit & Features
- Striped design, crochet fabric, short stretchy knit lining
- Halter neckline, spaghetti strap tie
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2264
Category Name: Casual Dresses
Price: $8.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Timeless Romance Open Back Lace Romper
Enter your forever romantic era in this lace long sleeve romper boasting a flirty open back and ruffled short-length hem.
Fit & Features
- Lace-lined fabric
- Scoop neckline
- Sheer fitted long sleeves
- Open back
- Form-hugging fit
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 06503-1276
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cool Breeze Cutout Striped Knit Mini Dress
As the temps rise so will your style in this striped knit mini dress with a flirty cutout back and bodycon fit perfect for layering with a denim jacket on cooler nights.
Fit & Features
- Striped pattern, knit fabric
- Scoop neckline
- Wide shoulder straps
- Cutout back
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2268
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In The Cards Halter Skater Mini Dress
No matter the plans, this halter skater mini dress will have you looking fabulous!
Fit & Features
- Stretchy rib knit fabric
- Halter neckline
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2265
Category Name: Casual Dresses
Price: $12.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Like Me Scoop Neck Skater Mini Dress
Showcase your sweet side in this ribbed knit mini dress made to please the crowd! It features a sleek scoop neckline and a skater silhouette that flatters every figure. Style with a handbag.
Fit & Features
- Stretchy ribbed knit fabric
- Scoop neckline
- Tank shoulder straps
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000006
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Just Like A Dream Strappy Back Ruffled Maxi Dress
Make a jaw-dropping entrance in this gorgeous ruffled maxi dress at shower celebrations or on vacation! The flattering V-neckline draws the eye, while the intricate strappy back adorned with beaded insets creates an unforgettable exit view.
Fit & Features
- Airy woven gauze fabric, woven lining
- V-neckline
- Dual spaghetti straps
- Strappy back with beaded insets
- Cascading ruffles, flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000653
Category Name: Casual Dresses
Price: $59.90
Availability: In Stock
Available Color: RED, BROWN
Available Size: XS, S, M, L, XL
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Sweetest Poise Button Bodycon Midi Dress
Polished and poised, this sweet sleeveless midi dress will elevate your everyday style with chic button accents and a bodycon fit.
Fit & Features
- Stretchy rib knit fabric
- Square neckline
- Wide shoulder straps
- Button accents, front faux pockets
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2261
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutest Allure Ruffle Eyelet Knit Mini Dress
Bring the cutest allure to summer dates in this flirty eyelet knit mini dress that will get you all the compliments. The adorable dress features a plunging V-neck with a ruffled trim under the bust, ruffled spaghetti straps, and a short A-line silhouette.
Fit & Features
- Eyelet knit fabric, stretchy knit lining
- Sleeveless plunging V-neckline, bar strap detail, keyhole cutout
- Ruffled trim under the bust
- Ruffle trim spaghetti straps, adjustable
- Open back, tie-back strap design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6091
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft And Chic Ribbed Knit Off-The-Shoulder Mini Dress
Soft and chic, this mini dress is made with ribbed knit fabric offering plenty of stretch for comfortable wear. It features an off-the-shoulder straight neckline with a long fold-over design for a trendy look and a short bodycon silhouette to highlight your curves.
Fit & Features
- Ribbed knit fabric
- Off-the-shoulder straight neckline
- Long fold-over design
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-2259
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Style One-Shoulder Slit Tropical Maxi Dress
Get that tropical feeling when you're in this one-shoulder maxi dress, whether you're on vacay or having some weekend fun! The curve-hugging silhouette offers a show of skin with a side cutout and high slit.
Fit & Features
- Tropical print, stretchy knit fabric, short knit lining
- One-shoulder neckline
- Side cutout
- High side slit
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6089
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free