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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Effortless Perfection Bodycon Striped Mini Dress
With this striped mini dress and sunnies, you'll be effortlessly cute for a perfect weekend out or vacation! Featuring a square neckline with a twist and spaghetti straps, this dress is designed to hug your body and accentuate your natural curves. The mini-length hem adds a flirty touch. Complete the look with sandals and sunnies!
Fit & Features
- Striped pattern, texture knit fabric, moderate stretch
- Spaghetti straps
- Square neckline with twist
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5675
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Charm Crew Neck Bodycon Midi Dress
The perfect basic midi dress for any occasion! It features a classic crew neck, cap sleeves, and a bodycon silhouette that flatters your curves. Pair with sleek heels and earrings.
Fit & Features
- Smooth jersey knit fabric, double-lined
- Crew neck
- Cap sleeves
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5661
Category Name: Casual Dresses
Price: $28.90
Availability: Out of Stock
Product Badge:- Sale
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Pleasant Cutie Collared V-Neck Belted Midi Dress
Make your look sweet and simple in this sleeveless midi dress perfect for summer plans! The collared V-neckline and button-down closures offer a classic touch, while the adjustable belted waist gives you a flattering A-line silhouette complete with a midi-length hem. Style this midi dress with wedges and earrings.
Fit & Features
- Woven fabric with lining, no stretch
- Collared V-neckline
- Button-down closures
- Adjustable belted waist with buckle
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3347
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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What You Want Strappy Cutout Slit Midi Dress
This sleeveless midi dress is just what you want to elevate your everyday style! Featuring a flattering square neckline, spaghetti straps, and a strappy cutout twist back, this bodycon dress will make you stand out in any crowd. The side slit adds a touch of sexiness to the midi-length hem. Complete the look in sleek stiletto heels for upcoming weekend plans!
Fit & Features
- Double-lined rib knit fabric, moderate stretch
- Spaghetti straps
- Square neckline
- Strappy cutout twist back
- Side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5663
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Done In One Ribbed Knit Bodycon Midi Dress
Be ready in a flash with this done-in-one bodycon midi dress perfect for styling up or down! Made with stretchy ribbed knit fabric, it's also soft and comfortable to wear all day. It features a flattering scoop neckline and tank shoulder straps for a comfortable and stylish fit. With a bodycon silhouette and midi-length hem, this dress will hug your curves! Complete the look in a crop denim jacket and sandals.
Fit & Features
- Ribbed knit fabric, sewn-in knit lining, moderate stretch
- Scoop neckline
- Tank shoulder straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5666
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Admired Scoop Neck A-Line Mini Dress
You'll always admire having this sleeveless mini dress for dressing up or down! Made from lined stretchy rib knit fabric, this dress hugs your curves in a flattering A-line silhouette. The scoop neckline and thin spaghetti straps add a flattering look. Style with a cute jacket and your favorite sneakers!
Fit & Features
- Stretchy rib knit fabric, full knit lining
- Spaghetti straps
- Curve-hugging, A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5652
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Fling High Slit Ditsy Floral Knit Midi Dress
Embrace your flirtatious side in this adorable floral knit midi dress! The lightweight stretchy knit fabric is detailed with the cutest ditsy floral print pattern for the spring season. The mid-length dress features a crew neckline, short sleeves, a small back keyhole cutout, a large lower back cutout to add some allure, a high-cut front slit, and a bodycon silhouette to flaunt your curves. Style with hoop earrings and a charm necklace.
Fit & Features
- Stretchy knit fabric
- Ditsy floral print
- Crew neckline, short sleeves
- Back keyhole cutout, lower back cutout
- High front slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5653
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Strolls In The Sand V-Neck Tropical Skater Mini Dress
Getaway in this tropical skater mini dress to the beach or on vacay! Featuring adjustable spaghetti straps and a flattering V-neckline, this dress hugs your silhouette with an elasticized waist and side cutouts. Its skater silhouette and mini-length hem make it perfect for any daytime adventure. Complete the look in cute sandals.
Fit & Features
- Tropical print, woven fabric lined with stretchy knit
- Adjustable spaghetti straps
- V-neckline
- Elasticized waist with side cutouts
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5656
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Vibes Collared Striped Woven Skater Dress
Sweet and stylish, this striped woven skater dress is spring-time perfection! The lightweight woven fabric features a chic vertical striped pattern for a polished look. The short dress has a collared V-neckline for that touch of sophistication, leading to a partial button-down front. The short puff sleeves add an adorable detail. The high waist is accented with a tie-back design, and flows out to a fit-and-flare skater silhouette. Pair this short dress with wedges for weekend brunch!
Fit & Features
- Non-stretch cotton-blend woven fabric, woven skirt lining
- Vertical striped pattern
- Collared V-neckline, button-down front
- Short puff sleeves with elastic cinched hems
- High waist with back elastic band, tie-back design
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5657
Category Name: Casual Dresses
Price: $6.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crushing On You Strapless Denim Corset Mini Dress
This sexy denim corset mini dress will have them all majorly crushing on you! The denim fabric features a contrasting light and dark wash design for a trendy vibe. The strapless sweetheart neckline shapes the top, leading to a corset-style bodice with angled seams for a snatched look. The bodycon fit along the mini-length silhouette will flaunt your gorgeous curves. Complete the look with cowboy boots for a country concert or festival.
Fit & Features
- Denim fabric with contrast wash design, moderate stretch
- Strapless sweetheart neckline
- Corset bodice, angled seams
- Back zipper with hook and eye closure
- Bodycon fit
- Style runs small
Style Number/Barcode: 05102-5659
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fall Into Fashion Crew Neck Open Back Maxi Dress
You'll be the cutest thing around in this sleeveless maxi dress all season! With its sleek crew neckline, alluring strappy open back, and flattering form-hugging fit, this dress is both stylish and versatile. Complete with a side slit and maxi-length hem, it's the perfect piece for any occasion. Style this maxi dress with earrings and sandals.
Fit & Features
- Stretchy rib knit fabric
- Crew neckline
- Strappy open back
- Side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5654
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Striped Halter Crochet Midi Dress
Stay stylish in this striped crochet midi dress for a sunny day by the beach or on vacation! It features a flattering halter neckline, adjustable spaghetti strap ties, and a bodycon fit that accentuates your curves along the midi-length hem. Complete the look with sunglasses and a tote bag!
Fit & Features
- Striped pattern, crochet fabric, short knit stretchy lining
- Halter neckline with spaghetti strap ties
- Bodycon fit
- Midi-length silhouette
- Runs true to size
Style Number/Barcode: 06005-2032
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Confident Cutie Sleeveless V-Neck A-Line Mini Dress
Get ready to feel confident and cute in this basic A-line mini dress perfect for styling up or down! The soft and stretchy rib knit fabric includes a full knit lining for added coverage. This dress is perfect for any occasion with a flattering V-neckline, delicate spaghetti straps, and a stylish A-line silhouette. Complete the look in a chunky choker and sneakers!
Fit & Features
- Soft and stretchy rib knit fabric, full knit lining
- V-neckline
- Spaghetti straps
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5651
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Main Style Ribbed Knit Tank Mini Dress
This adorable tank mini dress will be your new main style to create the cutest everyday looks! Designed with a stretchy ribbed knit fabric for comfortable wear, it features a sleeveless scoop neck and back, thin tank shoulder straps, and a bodycon silhouette to flaunt your figure. Pair this short dress with a denim jacket and sneakers for a coffee date with friends.
Fit & Features
- Stretchy ribbed knit fabric
- Scoop neck and back
- Thin tank straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1975
Category Name: Casual Dresses
Price: $8.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutest Of All Ribbon Bow Bodycon Mini Dress
You'll be the cutest of all in this bodycon mini dress out on dates or brunch! Crafted from a woven fabric lined with stretchy knit, this dress features a flattering square neckline and a satin ribbon bow that adds an elegant touch. The bodycon silhouette hugs your curves beautifully, while the mini-length hem gives a playful and flirty vibe. Complete the look in sandals and sunnies!
Fit & Features
- Woven fabric lined with stretchy knit
- Square neckline
- Satin ribbon bow
- Back zipper and hook-eye closure
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5655
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Day To Night Charm Lace-Up Ditsy Floral Mini Dress
Be effortlessly charming in this ditsy floral mini dress day to night! This dress features a flattering sweetheart neckline, sleek spaghetti straps, and a mini bow along the bust to accentuate your figure. The open lace-up back and bodycon silhouette add a touch of sexiness, while the ditsy floral print on stretchy ribbed knit fabric keeps you comfortable and looking cute! Complete the look in boots to edge up your allure.
Fit & Features
- Stretchy ribbed knit fabric, knit lining
- Ditsy floral print
- Sweetheart neckline, mini bow detail
- Spaghetti straps
- Open lace-up back
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5650
Category Name: Casual Dresses
Price: $6.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love Impression Crew Neck Tie-Dye Bodycon Mini Dress
This tie-dye mini dress will have you falling head over heels! It features classic short sleeves and a crew neckline, a bodycon fit to flaunt your curves, and a mini-length hem. Complete the look with earrings and stiletto heels for any occasion!
Fit & Features
- Tie-dye print, mesh fabric, partial lining
- Crew neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5646
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Read All About It Newspaper Bodycon Mini Dress
Extra, extra read all about how fine you'll look in this newspaper print mini dress! This dress features a sweetheart neckline with lace trim and adjustable spaghetti straps for a perfect fit. The built-in padded underwire bust ensures support while the bodycon fit and mini-length hem create a flattering silhouette. Complete the look in a crop denim jacket.
Fit & Features
- Newspaper print, knit fabric with stretchy lining
- Adjustable spaghetti straps
- Sweetheart neckline with lace trim
- Back zipper and hook-eye closure
- Built-in padded underwire bust
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5578
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Attention Getter Strapless Newspaper Print Mini Dress
Capture attention with all eyes on you in this fab newspaper print mini dress! The textured lined woven fabric features a newspaper print with rose print accents for that trendy-girl vibe. The strapless straight-across neckline is detailed with an eyelet lace and thin velvet ribbon trim, tying at the center. The bodice features a bust seam outline with ruching to accentuate your figure. The flexible side boning adds structure, while the hidden back zipper offers effortless styling. The form-hugging fit on the mini-length hem will flaunt your stunning curves. Style with a layered choker necklace.
Fit & Features
- Non-stretch textured lined woven fabric, rose newspaper print
- Strapless straight neckline with no-slip strip
- Eyelet lace and velvet ribbon trim, tie-front, bust seam outline with ruching
- Flexible side boning, hidden back zipper with hook and eye closure
- Form-hugging fit
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05102-5644
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lovely In Lace Ruffled Puff Sleeve Mini Dress
You'll be looking oh-so-lovely in this adorable ruffled puff sleeve mini dress! The sheer floral lace fabric gives that dainty-chic vibe, while the partial knit lining provides coverage. The mini-length dress features a square neckline and sheer short puff sleeves with the cutest ruffle trim, a small bust cutout with a sleek ribbon tie-front design, and a flattering empire waist seam. The flowy A-line silhouette adds that effortless flair. Style this short dress with heeled mules for date night.
Fit & Features
- Sheer floral lace fabric with knit lining, minimal stretch
- Square neckline, ruffle trim
- Sheer short puff sleeves, ruffle trim
- Bust cutout, tie-front design
- Empire waist seam, hidden side zipper closure
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3338
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ocean Breeze Cowl Neck Low Back Tropical Maxi Dress
Relax poolside with a drink in hand and this tropical mesh maxi dress on! Featuring a playful cowl neckline, adjustable spaghetti straps, and a low back with criss-cross straps for a touch of intrigue. Its curve-hugging silhouette and maxi-length hem will make you feel like a tropical goddess on vacation! Complete the look in sunnies and sandals!
Fit & Features
- Tropical palm print, mesh fabric lined with stretchy knit
- Cowl neckline
- Adjustable spaghetti straps
- Low back with criss-cross straps
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5645
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Babe With Taste Buckle Strap Pleated Mini Dress
Let everyone know you're a babe with taste in this pleated mini dress! Made from a twill woven fabric for structure and has a stretchy knit lining for coverage. With a square neckline and seam detailing, this dress exudes style. The adjustable buckle shoulder straps provide a customizable fit, while the fitted bodice and pleated mini-length hem flatter your figure. Complete the look with sunglasses and a purse!
Fit & Features
- Twill woven fabric, stretchy knit lining
- Square neckline
- Back zipper closure
- Adjustable buckle shoulder straps
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5629
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tuscan Charm Strapless Slit Eyelet Maxi Dress
You'll be so charming in Tuscan wearing this eyelet maxi dress as the stunning new bride or chic traveler! The eyelet fabric adds a touch of delicacy, making it the perfect dress for any occasion. With a form-hugging fit and a high-side slit, this dress exudes confidence and elegance! Complete the look with earrings.
Fit & Features
- Eyelet fabric, sewn-knit lining, minimal stretch
- Strapless neckline
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5637
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Artsy Scene Mock Neck Abstract Mini Dress
Indulge in the artsy scene in this mock neck abstract mini dress for downtown art walks! This sleeveless dress boasts a figure-flattering bodycon silhouette with side ruching, while the mini-length hem adds a flirty touch. The abstract print adds a bold and unique touch to this must-have dress. Complete the look in edgy boots and a shoulder bag.
Fit & Features
- Abstract print
- Mesh fabric, sewn-in knit lining, stretchy
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5630
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free