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.

  • Chic Glimpse Floral Tube Midi Dress

    Romantic but make it bodycon. This floral mesh midi dress is the perfect mix of dreamy and daring—made for slow dances, date nights, and second glances. 

    Fit & Features:

    • Sheer floral mesh fabric, stretchy knit lining
    • Strapless tube neckline
    • Curve-hugging bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000206

    Category Name: Casual Dresses

    Price: $7.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

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  • Flirt Factor Belted Denim Dress

    From brunch to concert nights, this strapless denim dress delivers instant style. The cinched belt and playful skater skirt keep the vibe equal parts sweet and sassy.

    Fit & Features

    • Denim fabric
    • Strapless neckline
    • Back zipper closure
    • Belted waist
    • Form-hugging bodice
    • Skater mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000207

    Category Name: Casual Dresses

    Price: $9.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

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  • Serving Looks Mock Neck Ponte Mini Dress

    Not your average court-side fit. This contrast-trim mini dress serves preppy energy with a flirty twist—perfect for brunch, errands, or wherever the vibe is “cute but casual.”

    Fit & Features

    • Black has contrast-trim
    • Smooth ponte knit fabric with stretch
    • Mock neckline
    • Keyhole cutout with button closure
    • A-Line silhouette
    • Front slit accent, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000205

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Boss Babe Strapless Blazer Mini Dress

    Giving boardroom meets bottle service in the chicest way. This strapless mini dress doubles as a statement piece that’s perfect for cocktail hour or styled up with sneakers for a cool-girl twist.

    Fit & Features

    • Woven fabric
    • Strapless neckline, back zipper closure
    • Faux button front accents
    • Faux flap pocket accents
    • Fitted silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000398

    Category Name: Casual Dresses

    Price: $7.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

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  • Petals with a Plot Twist Floral Maxi Dress

    Soft? Yes. Sweet? Sure. But this maxi dress is not here to behave—with a side slit that demands attention and a form-hugging fit that doesn’t miss.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Tube strapless neckline
    • High side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000381

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Soft Focus Cable Knit Midi Dress

    Knits, but make it chic—this tube cable knit midi dress hugs your shape while keeping it cozy. Perfect for layering with a jacket or going solo for an effortlessly polished vibe.

    Fit & Features

    • Cable knit fabric, stretchy knit lining
    • Tube strapless neckline
    • Form-hugging silhouette
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000203

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Street Chic Faux Suede Mini Dress

    A little jacket inspo, a lot of city attitude. This faux suede mini dress brings structure and edge to your fall lineup. Perfect for styling with a long sleeve top and boots on crisp autumn days.

    Fit & Features

    • Soft, smooth faux suede fabric
    • Mock neckline, dual snap-button closures
    • Front zip-up closure
    • A-line fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000202

    Category Name: Casual Dresses

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

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  • So Sleek Strappy Back Maxi Dress

    A dress that does the flirting for you—sleek, slinky, and unforgettable. With a curve-loving fit and sultry strappy back, it’s your go-to for nights that demand a little drama.

    Fit & Features

    • Slinky knit fabric, high stretch
    • Sleeveless V-neckline
    • Dual bungee spaghetti straps
    • Open back, cross-back strappy design
    • Maxi-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000368

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Romance Floral Lace-Up Maxi Dress

    Evoke chic romance on date night in this gorgeous floral maxi dress designed with an open lace-up strappy back and floor-length form-hugging silhouette. Style with a sleek handbag and stiletto heels.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Large floral print
    • Sleeveless deep V-neckline
    • Spaghetti straps
    • Open cross-back lace-up strappy design
    • Maxi-length hem, form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000111

    Category Name: Casual Dresses

    Price: $7.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Fierce Flirt Animal Print Mini Dress

    This animal print mini dress was made for turning heads. With its draped cowl neckline, strappy halter fit, and flouncy layered hem, it’s a party dress with untamed vibes.

    Fit & Features

    • Animal print, mesh-lined stretchy fabric
    • Halter cowl neckline with adjustable belted strap
    • Open back
    • Form-hugging fit
    • Layered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000320

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Back At It Twist Back Midi Dress

    You didn’t plan to stand out, but here we are. This sleeveless midi dress hugs in all the right places with a twist cutout back and side slit that catches every eye.

    Fit & Features

    • Soft rib knit fabric, smooth knit lining
    • Square neckline
    • Tank shoulder straps
    • Twist cutout back
    • Side slit
    • Form-hugging, midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000201

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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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
  • 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:
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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:
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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:
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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:
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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:
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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:
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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:
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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:
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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:
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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

    Product Badge:
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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