Casual Dresses

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.

  • 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
  • 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

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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

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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

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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

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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

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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

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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

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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

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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

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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:
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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

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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:
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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:
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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

  • 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:
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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:
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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:
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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
  • 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:
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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:
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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:
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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:
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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:
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