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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Wild West Glow Lace Up Mini Dress
Giving rodeo-ready meets it-girl chic. The faux suede finish and lace-up front serve sultry vibes that work from concerts to bachelorette trips to the country!
Fit & Features
- Micro faux suede fabric
- Halter V-neckline
- Front lace-up bust design
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000313
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Drama Meets Paradise Floral Maxi Dress
Giving goddess energy with every step you take. This mesh maxi dress clings in all the right places with a daring cowl neckline and a strappy open back made to be seen.
Fit & Features
- Floral print, mesh fabric, soft stretchy knit lining
- Plunging cowl neckline
- Strappy open back with hoop insert
- Form-hugging fit
- Flowy maxi hem and front slit
- Runs true to size
Style Number/Barcode: 05101-000352
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Western Style Horse Tapestry Mini Dress
Channel that western-chic style in this mini dress designed with a detailed horse tapestry fabric. The lace-up back offers a customized fit, while the short A-line silhouette is perf for pairing with cowboy boots.
Fit & Features
- Horse tapestry woven fabric, no stretch, knit lining
- Strapless straight-across neckline, no-slip strip
- Lace-up back design
- Lower back cutout, hidden zipper with hook-eye closure
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000200
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dinner With A View Abstract Open Back Maxi Dress
You'll be a gorgeous view at dinner in this abstract maxi dress! The cowl halter neckline with hoop insert adds a touch of elegance, while the open back design highlights your figure.
Fit & Features
- Abstract print, mesh fabric lined with stretchy knit
- Cowl halter neckline, hoop insert, tie straps
- Open back
- Form-hugging silhouette
- Floor-length hem
- Runs true to size
Style Number/Barcode: 05101-000114
Category Name: Casual Dresses
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stunning Always Bodycon Ruffle Mini Dress
You'll always be remembered as stunning in this mini dress, perfect for brunch or casual parties and plans! The flattering scoop neckline with a delicate rose accent adds a touch of romance, while the bodycon fit showcases your curves and is finished with a flirty ruffled hem.
Fit & Features
- Stretchy knit fabric, knit lining
- Scoop neckline with a rose accent
- Spaghetti straps
- Bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000152
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirt Alert Floral Slit Midi Dress
Leg pop approved. With a pleated waist and wrap-front slit, this floral midi dress brings the flirty vibes for any night out or dressed-up moment.
Fit & Features
- Stretch knit fabric with floral print
- Square neckline, spaghetti straps
- Side pleated seam
- Front wrap slit
- Bodycon silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000199
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summertime Heat Lace-Up Denim Mini Dress
Raise the temps, turning heads in this denim mini dress for a day out or night on the town! The strapless neckline with a front lace-up adds a touch of sexy to the bodycon silhouette that hugs your curves in all the right places.
Fit & Features
- Denim fabric
- Strapless neckline with a front lace-up
- Back zipper closure
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000196
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Captivated In Floral Halter Bodycon Midi Dress
Look captivating and contoured in this floral midi dress while on vacay! The twist halter neckline adds a unique touch while the bodycon silhouette accentuates your curves along the midi-length hem.
Fit & Features
- Floral print, mesh-lined fabric
- Twist halter neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000197
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ruffle Up And Go Tube Romper
Short, sweet, and kinda irresistible. This tube romper flirts with every step thanks to its strapless straight neckline, drop waist design, and adorable ruffled overlay.
Fit & Features
- Ponte knit fabric, moderate stretch
- Strapless straight-across neckline
- Drop waist design
- Tiered ruffled mini-length overlay, A-line silhouette
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000099
Category Name: Casual Dresses
Price: $14.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cut to the Chase Belted Denim Mini Dress
No time for small talk. This bodycon mini gets straight to the point with daring front cutouts, a plunge halter neckline, and belted straps that hit different.
Fit & Features
- Denim fabric, slight stretch
- Plunge halter neckline, dual button closures on the strap
- Front cutouts with belted straps
- Back zipper and hook-eye closure
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000195
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Glow Tube Floral Mini Dress
Sun, skin, and this dress—name a hotter trio. With bold blooms and a sleek bodycon fit, this strapless mini is your go-to for nights out or island dreams.
Fit & Features
- Floral print, knit fabric, moderate stretch
- Tube strapless neckline
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000194
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flawlessly Chic Strapless High Slit Maxi Dress
You'll look flawlessly chic in this textured knit maxi dress featuring a strapless neckline and high-cut side slit. Style with stiletto heels for a rooftop bar!
Fit & Features
- Sheer knit fabric, textured pattern, full-length lining
- Strapless straight neckline
- Back zipper closure
- High side slit
- Maxi-length fitted silhouette
- Runs true to size
Style Number/Barcode: 05102-000141
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 Loved Tube Bodycon Midi Dress
Love at first wear...this tube midi dress elevates your everyday look with curve-accentuating side ruched seams, a bodycon fit, and a side slit for movement.
Fit & Features
- Stretchy rib knit fabric, knit lining
- Strapless tube neckline
- Side ruched seams
- Bodycon silhouette
- Side slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000309
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Forever Fave Strapless Bodycon Mini Dress
This curve-flaunting mini dress will be a forever fave for rooftop bars or dressy date nights. The textured knit fabric adds a chic allure to the strapless bodycon silhouette.
Fit & Features
- Textured knit fabric, full-length knit lining, high stretch
- Strapless sweetheart neckline, no-slip strip
- Padded bust, bust seam outline
- Back zipper with hook-eye closure
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000190
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Steal The Scene Floral Corset Ruffle Mini Dress
This floral corset mini dress serves up ruffles, romance, and just the right amount of sass. With its curve-hugging bodice and flirty layered hem, it’s basically a love letter in dress form.
Fit & Features
- Flocked floral pattern, mesh-lined fabric
- Strapless sweetheart neckline, padded bra cups
- Corset-inspired bodice
- Back zipper and hook-eye closure
- Form-hugging fit
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001053
Category Name: Casual Dresses
Price: $59.90
Availability: In Stock
Available Color: IVORY-2
Available Size: M, L
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All Eyes On You Strapless Maxi Dress
Effortlessly sleek, this strapless maxi is giving luxe with zero effort. The body-hugging fit and flowy hem make it your go-to for dinner dates or rooftop hotel bars.
Fit & Features
- Rib knit stretchy fabric
- Strapless neckline
- Bodycon fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000088
Category Name: Casual Dresses
Price: $12.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Through The Meadow Floral Corset Dress
Too sweet to scroll past. This corset floral dress brings all the cottagecore charm with a flirty twist—yes, that oversized bow is doing the most. Perfect for shower celebrations or dressy events!
Fit & Features
- Floral print, woven texture fabric, lace trim woven lining
- Sweetheart lace trim neckline, bust tie
- Adjustable shoulder straps
- Corset bodice, flexible boning inserts, lace trim
- Back bow tie, zipper and hook-eye closure
- Drop waist seam, skater short-length silhouette
- Runs true to size
Style Number/Barcode: 05101-000269
Category Name: Casual Dresses
Price: $9.97 $62.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunkissed Curve Knit Midi Dress
This striped midi dress was made to highlight every curve with a sculpting rib texture, front cutout detail, and side slit. Dress it up with heels for a night out or keep it elevated with sandals for a chic daytime moment.
Fit & Features
- Striped print, rib knit fabric
- Sweetheart neckline, cutout bust accent
- Adjustable spaghetti straps
- Bodycon fit
- Dual side slits
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000084
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Chic Ribbed Knit Skater Dress
When your outfit says polished but still playful, this is the skater dress. The mock neck and fit-and-flare silhouette keep it chic, flirty, and ready for any plans on your calendar.
Fit & Features
- Ribbed sweater knit fabric, moderate stretch
- Sleeveless mock neckline
- Tank shoulder straps
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 06005-000085
Category Name: Casual Dresses
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bloom Season Floral Mesh Maxi Tube Dress
Meet your new obsession for dinner dates and chic soirées. This floral mesh maxi dress hugs in all the right places with a strapless neckline that feels effortlessly elevated.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Floral print
- Strapless straight-across neckline
- Ruching
- Maxi-length hem, back slit
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000252
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laced In Love Corset Mini Dress
She’s giving drama, curves, and just the right amount of trouble. This corset mini dress hugs you in all the right places with a flirty ruffle that finishes the look with a wink.
Fit & Features
- Lace fabric, stretchy knit lining
- Strapless sweetheart neckline
- Built-in underwire padded but
- Corset bodice, flexible boning, back zipper and hook-eye closure
- Form-hugging fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000256
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy Romance Floral Lace Skater Dress
Sweet? Always. Innocent? Rarely. This lace mini gives flirty vintage feels with a neckline made to be noticed and a hem made to be twirled.
Fit & Features
- Floral print, lace fabric, stretchy knit lining
- Adjustable spaghetti straps
- Ruched square neckline
- Skater silhouette, drop waist seam
- Flared mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000240
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Whirlwind Romance Floral Abstract Maxi Dress
This maxi dress is giving goddess in the wild. The sheer mesh and abstract floral print bring soft drama to any scene, whether it's brunch or rooftop party soirees!
Fit & Features
- Abstract floral print, mesh lined fabric
- Sweetheart neckline, padded bra cups, ruched bust seam
- Spaghetti straps
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-000242
Category Name: Casual Dresses
Price: $7.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Booked Floral Maxi Dress
Already picturing the dinner plans in this one. This tropical floral maxi dress features a soft cowl neckline and an open back that brings just the right amount of drama for your getaway lineup.
Fit & Features
- Tropical floral print, mesh-lined fabric, high stretch
- Cowl neckline
- Adjustable spaghetti straps
- Open strappy back
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000189
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free