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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Desert Princess Halter Maxi Dress With Pockets
Experience the effortless beauty of this boho maxi dress! The sleeveless halter neckline and spaghetti strap tie create a flowy silhouette, while the hidden side pockets add functionality. The front slit and ruffled maxi-length hem in a chic bohemian print will make you feel like a true desert princess! Complete the look in sandals and sunnies.
Fit & Features
- Bohemian print, woven fabric, no stretch
- Halter neckline, spaghetti strap tie
- Hidden side pockets
- Flowy ruffled silhouette
- Runs true to size
Style Number/Barcode: 05102-5804
Category Name: Casual Dresses
Price: $16.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunshine Romance Floral Babydoll Dress
Indulge in the romantic allure of this floral dress for dressy events! With delicate ruffled shoulder straps and a charming babydoll silhouette, this dress offers a flirty and feminine look.
Fit & Features
- Floral print, chiffon fabric
- Square neckline
- Ruffled shoulder straps
- Babydoll silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3467
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Babe Floral Woven Puff Sleeve Skater Dress
Create a darling day date look with this floral puff sleeve skater dress! Made with a lightweight woven fabric, it is detailed with a charming dainty floral print for those sweet feminine vibes. The short dress features a V-neckline with a cute tie-front detail, short puff sleeves with a ruffled trim, a high waist seam, and a skater hem with a flirty fit-and-flare silhouette. Style with a dainty charm necklace and heels.
Fit & Features
- Dainty floral print
- Woven fabric
- V-neckline, tie-front detail
- Short puff sleeves, ruffled trims
- Back zipper closure, high waist seam
- Short skater skirt, fit-and-flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3466
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cheerful Cutie Strapless Gingham Skater Dress
Spread your sunshine in this gingham skater dress for the sweetest look all summer! The strapless neckline, lace trim, and stretchy smocked waist create a flirty and comfortable look. The skater silhouette and ruffled mini-length hem with lace trim add a touch of cuteness to your look. Complete the look with a crossbody purse and sandals for any casual plans!
Fit & Features
- Gingham print, cotton fabric with woven lining
- Strapless lace trim neckline
- Stretchy smocked waist
- Skater silhouette
- Ruffled lace trim hem
- Runs true to size
Style Number/Barcode: 05102-5801
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Passion V-Neck Color Block Maxi Dress
Dress to impress in this V-neck maxi dress to make a chic impression at parties or rehearsal dinners! The flowy silhouette and color block panels give you a stunning look, while the spaghetti straps and neck tie add a trendy touch. Complete the look with a clutch and heels.
Fit & Features
- Woven fabric, no stretch
- V-neck
- Spaghetti straps, spaghetti strap neck tie
- Color block panels, flowy silhouette
- Maxi length
- Runs true to size
Style Number/Barcode: 05102-5803
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Signature Stripes Strapless A-Line Maxi Dress
Show off your signature style in this striped maxi dress perfect for casual summer plans! Features a strapless neckline, a stretchy smocked bodice for a comfortable fit, and a flattering A-line midi silhouette with hidden side pockets to keep your hands warm. Complete the look with sunglasses and trendy sandals.
Fit & Features
- Striped pattern, cotton woven fabric, no stretch
- Strapless neckline
- Stretchy smocked bodice
- Hidden side pockets
- A-line midi silhouette
- Runs true to size
Style Number/Barcode: 05102-5802
Category Name: Casual Dresses
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Flirt Sweetheart Lace Trim Skater Dress
This sleeveless chiffon skater dress features a lace trim sweetheart neckline and bodice for flirty flair while the drop waist seam accentuates your curves along the mini-length skater silhouette. Perfect for a dressy brunch or party.
Fit & Features
- Sheer chiffon woven fabric with stretchy knit lining
- Lace trim sweetheart neckline with bow detail, bust underwire
- Adjustable lace trim shoulder straps
- Partially smocked back with zipper and hook-eye closure
- Lace trim bodice, drop waist seam
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3461
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Dreams Hanky Hem Floral Mini Dress
Sweet and dreamy will be your vibe in this adorable floral mini dress! Designed with a stretchy sheer mesh fabric with a knit lining for coverage, the short dress showcases a blooming floral print for the prettiest look. It features a sleeveless V-neckline with dainty lace trim for a feminine touch, spaghetti straps, a trendy drop waist silhouette, and a mini-length asymmetric hanky hem with a flowy A-line fit. Style with bow hair pins and strappy mules.
Fit & Features
- Floral print
- Stretchy sheer mesh fabric with knit lining
- V-neckline with lace trim
- Spaghetti straps
- Drop waist silhouette
- Asymmetric hanky hem, A-line fit
- Runs true to size
Style Number/Barcode: 05101-3462
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cherry On Top Lace Trim V-Neck Mesh Mini Dress
This mesh mini dress is the cherry on top of your perfect summer! Featuring delicate lace trim V-neckline, adjustable spaghetti straps, and a cherry print on mesh fabric, this mini-length bodycon dress will hug your curves and flaunt your style. Complete the look in platform heels.
Fit & Features
- Cherry print, mesh fabric, stretchy knit lining
- Lace trim V-neckline
- Adjustable spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5798
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Getaway Girl Halter Open Back Tropical Mini Dress
Getaway to paradise in this tropical mini dress! Featuring a sultry cowl halter neckline and an open back with dual spaghetti strap ties, this dress will show plenty of skin on vacay while the bodycon silhouette and mini-length hem flatter your figure. Complete the look with doorknocker earrings and heels.
Fit & Features
- Tropical print, mesh fabric lined with stretchy knit
- Halter cowl neckline
- Open back with dual spaghetti strap ties
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5795
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Babe Cutout Ruffle Hem Chiffon Midi Dress
Show up and stun at a summer party like the bold babe you are in this fab midi dress! Designed with a crinkled chiffon fabric, the mid-length dress features a smocked body for added stretch along the figure-flaunting bodycon silhouette. The sleeveless bodice is shaped with a sweetheart neckline with the cutest tie-front design at the bust, a sultry waist cutout to reveal some skin, and adjustable spaghetti straps to find your perfect fit. The layered ruffled hem adds a flirtatious allure to the iconic look. Style this midi dress with hoop earrings and espadrille sandals!
Fit & Features
- Crinkled chiffon fabric, knit bust lining, moderate stretch
- Sweetheart neckline, tie-front bust
- Waist cutout
- Adjustable spaghetti straps
- Smocked body, layered ruffled hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3454
Category Name: Casual Dresses
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Perfection Scoop Neck Bow Skater Dress
You'll look like cute perfection in this sleeveless skater dress at soirees! With adjustable spaghetti straps, a flattering scoop neckline, and three adorable bows with ruffle trim, this skater dress will have you feeling confident and stylish in its short-length hem. Complete the look in trendy sandals and a hair accessory.
Fit & Features
- Airy chiffon fabric, woven lining, no stretch
- Adjustable spaghetti straps
- Scoop neckline
- Back zipper and hook-eye closure
- Three bows with ruffle trim
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3453
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Picking Flowers Halter Strappy Back Daisy Skater Dress
This daisy print skater dress will have you dreaming of sunny days picking flowers! The halter spaghetti strap neckline perfectly frames your shoulders while the cutout bodice adds a touch of allure. The strappy open back creates a stunning statement and the skater silhouette and tiered ruffled short-length hem give you a playful and fun look. Complete the look in sandals for a brunch or day date!
Fit & Features
- Daisy print, woven fabric with lining, no stretch
- Spaghetti strap
- Strappy open back
- Ruffles
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5794
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Artistic Sensation Strapless Abstract Bubble Mini Dress
Anytime you step out in this artsy abstract strapless mini dress you'll attract all the attention! The strapless neckline highlights your curves, while the A-line silhouette flatters your figure. The fun and flirty bubble short-length hem adds a playful touch to any occasion. Complete the look with hoop earrings.
Fit & Features
- Abstract print, poplin woven fabric, sewn-in knit lining
- Strapless neckline, non-slip grip lining
- A-line silhouette
- Bubble short-length hem
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Runs small and short, recommend sizing up if needed
Style Number/Barcode: 05101-3450
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Confident Moves Crew Neck Ruffled Mini Dress
Get ready to make confident moves in this sleeveless mini dress perfect for office days and after work play! Featuring a crew neckline and bodycon fit, this dress will have you feeling fabulous. The tiered ruffled mini-length hem adds a playful touch that will have heads turning. Complete the look in stiletto pumps and a blazer.
Fit & Features
- Smooth double-lined knit fabric, moderate stretch
- Crew neck
- Bodycon fit
- Tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5792
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bohemain Charm Halter Open Back Tie Dye Maxi Dress
Meet the bohemian charm of this tie dye maxi dress for summer soirees and parties! Featuring a halter cowl neckline and an alluring open back with tie closure, this dress exudes sensuality. The side ruched seams and form-hugging fit accentuate your curves, while the front slit and sheer maxi-length hem add a chic touch! Complete the look with earrings and a clutch.
Fit & Features
- Tie dye print, stretchy mesh fabric, sewn-in knit lining
- Halter cowl neckline
- Open back with tie closure
- Form-hugging fit
- Front slit
- Runs true to size
Style Number/Barcode: 05101-3445
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ultimate Chic Choice Floral Tie-Back Short Dress
For the ultimate chic choice, pick this floral short dress for all your summer plans! The sweetheart neckline and spaghetti straps give a flirty touch, while the dual tie-back design ensures a perfect fit. The underwire bust and flexible boning offer support and structure, with a short-length hem for a stunning silhouette. Complete the look with dainty chic earrings.
Fit & Features
- Ditsy floral print, woven fabric lined with stretchy knit
- Sweetheart neckline, underwire bust
- Spaghetti straps
- Dual tie-back design
- Flexible boning
- Short-length silhouette
- Runs true to size
Style Number/Barcode: 05101-3447
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bright Beauty Halter Cutout Tropical Maxi Dress
You'll look bright and beautiful in this tropical maxi dress on vacation or at a weekend pool party! The halter neckline with a spaghetti strap tie highlights your shoulders, while the U-ring insert adds some structure. The cutout back with smocked detail flatters your figure along the flowy maxi-length silhouette. Complete the look with sunglasses and sandals for a chic vibe!
Fit & Features
- Tropical print, chiffon fabric, short stretchy knit lining
- Halter neckline with spaghetti strap tie, U-ring insert
- Cutout back with smocking
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5791
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Make An Impression Cowl Neck Bodycon Mini Dress
Make an impression in this abstract print mesh mini dress for an artsy vibe! With a halter cowl neckline and a spaghetti strap tie, you'll turn heads wherever you go. Side ruched seams create a flattering, bodycon fit that accentuates your curves along the mini-length hem. Complete the look in hoop earrings and a clutch!
Fit & Features
- Abstract print, mesh fabric, sewn-in knit lining
- Halter cowl neckline, spaghetti strap tie
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5785
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Here Comes The Sun Strapless Ruffled Mini Dress
Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The short tube dress features ruched sides and a ruffled hem, adding a playful touch to the bodycon silhouette.
Fit & Features
- Double-lined brushed knit fabric, moderate stretch
- Strapless straight neckline
- Ruched side seams
- Bodycon silhouette
- Mini-length tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5784
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Express Your Style V-Neck Ruffle Bodycon Mini Dress
Express your devotion to style in this charming sleeveless mini dress perfect for casual showers or brunch! This dress features adjustable spaghetti straps for the perfect fit, a flirty V-neckline with a bust tie for added charm, and a bodycon fit to accentuate your curves. The mini-length hem and ruffle trim throughout add a touch of romance to this head-turning dress. Complete the look with earrings.
Fit & Features
- Ruffle trim throughout, knit fabric lined with stretchy knit
- Adjustable spaghetti straps
- V-neckline with bust tie
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5789
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Amazing Strapless Tie-Dye Mini Dress
Keep things casual and cute in this tie-dye mini dress for upcoming summer fun! Boasting a trendy tie-dye print on soft knit fabric, this dress brings an effortless boho charm featuring a strapless neckline and bodycon fit. Complete the look in sandals.
Fit & Features
- Tie-dye print, soft knit fabric with stretchy knit lining
- Strapless neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5788
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Iconic Abstract Print Ruched Mini Dress
Step out like the icon you are in a mini dress that features a plunging cowl neckline with halter neck ties for a secure fit, an abstract floral print, and ruching throughout to enhance curves. Style with clear heels.
Fit & Features
- Fitted mesh fabrication, moderate stretch
- Cowl neckline
- Open back, halter neck ties
- Abstract floral print
- Mini length hem
- Ruching
- Runs true to size
Style Number/Barcode: 05102-5786
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Looking Cute Strapless Tie-Dye Bodycon Mini Dress
Looking cute is easy with this tie-dye mini dress for summer! This mini-length dress will effortlessly enhance your curves and flatter your figure featuring a trendy strapless neckline and bodycon silhouette. Complete the look with earrings and heels for a party!
Fit & Features
- Tie-dye print, mesh fabric lined with stretchy knit
- Strapless neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5782
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale