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.

  • Alluring 'Fit Plunging Halter Mini Dress

    Create an alluring 'fit for sunset drinks in this textured knit mini dress featuring a plunging V-neck with a bust tie accent, halter straps, and a bold open back with a tie-back design. The short, bodycon silhouette will flaunt your gorgeous curves.

    Fit & Features

    • Sheer textured knit fabric with knit lining, high stretch
    • Sleeveless plunging V-neckline, bust tie accent
    • Tie-back halter spaghetti straps
    • Open back, tie-back spaghetti straps
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000020

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

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  • Cutie Style Striped Knit Bodycon Mini Dress

    Show off your cutie style in this adorable mini dress made with striped ribbed knit fabric with high stretch. The strapless sweetheart neckline features a knot detail at the bust and a small keyhole cutout for a trendy detail.

    Fit & Features

    • Striped ribbed knit fabric, knit bust lining, high stretch
    • Strapless sweetheart neckline, no-slip strip
    • Knot detail at the bust, small keyhole cutout
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000016

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • No You Hang Up Tube Mini Dress

    Get ready to wow in this tube mini dress for your next date! This dress is designed with an alluring twist bust with a keyhole cutout that shows some skin, while the form-hugging A-line silhouette accentuates your curves.

    Fit & Features

    • Texture knit stretchy fabric
    • Strapless tube sweetheart neckline
    • Twist bust, keyhole cutout
    • Form-hugging, A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000018

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

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  • Own The Room Striped Knit Midi Tube Dress

    Hot girl summer just got a little hotter. This striped midi tube dress hugs you in all the right places with a soft, textured knit that moves with you.

    Fit & Features

    • Striped textured cotton-blend knit fabric, lightweight knit lining
    • Moderate stretch
    • Strapless straight-across neckline
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000019

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

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  • Falling In Love V-Neck Lace A-Line Mini Dress

    Fall in love with how you'll look in this lace a-line mini dress for every romantic spree! 

    Fit & Features

    • Lace-lined fabric
    • V-neckline with ribbon bow trim
    • Adjustable spaghetti straps
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000017

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Going Out Strapless Lace Mini Dress

    Occasions made easy! This strapless lace mini dress is here to make you stand out at brunch or parties with a twirl-worthy hanky hem. 

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Strapless neckline
    • Side ruched seams, fitted bodice
    • Flared hanky mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-000015

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

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  • Cutest Icon Bow A-Line Mini Dress

    Draw everyone in with your posh and pretty aesthetic in this bow A-line mini dress! Perfect for shower celebrations or brunch.

    Fit & Features

    • Woven fabric, sewn-in woven lining
    • Square neckline, padded bra cups
    • Front bow
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000010

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Tropical Mood Strapless Midi Dress

    This tropical midi dress will have you looking like a warm weather cutie on vacation or a weekend escape!

    Fit & Features

    • Tropical print, knit fabric with stretchy knit lining
    • Strapless neckline
    • Form-hugging bodice
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000014

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

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  • Out In The Town Lace-Up Skater Dress

    Playful and daring, this skater dress showcases your best self with a lace-up back design and flowy short-length hem. 

    Fit & Features

    • Eyelet fabric
    • Scoop neckline
    • Adjustable spaghetti straps
    • Lace-up back design
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000013

    Category Name: Casual Dresses

    Price: $33.90

    Availability: Out of Stock

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  • Seashell Cove Strappy Back Crochet Mini Dress

    Channel beachy vibes with this crochet mini dress. The strappy back and bodycon silhouette enhance your curves while the wrap mini-length hem features a whimsical seashell trim. 

    Fit & Features

    • Crochet fabric, sewn-in knit lining
    • Strapless neckline, non-slip grip lining
    • Strappy back with tassel strings
    • Bodycon silhouette
    • Wrap mini-length hem with seashell trim
    • Runs true to size

    Style Number/Barcode: 05102-000012

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sunny Sweet Floral A-Line Mini Dress

    Sunny sweet will be your vibe in this cute floral mini dress designed with a strapless neckline, ruching, and a hanky hem A-line silhouette.

    Fit & Features

    • Knit fabric, high stretch
    • Small floral print
    • Strapless straight neckline
    • Ruching
    • Drop waist
    • Mini-length hanky hem, A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000008

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

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  • Cutesy Flair Ruffled Denim Mini Dress

    Show off a cutesy flair in this denim mini dress perf for festival season! You'll love the strapless ruffled neckline and matching ruffled A-line hem.

    Fit & Features

    • Denim fabric
    • Strapless straight neckline, ruffled trim
    • Vertical seams
    • Drop waist
    • Mini-length A-line silhouette, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-000006

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Effortless Days A-Line Midi Tube Dress

    Effortless days call for this woven midi tube dress designed with a smocked bodice with a geometric pattern and a flowy pleated A-line silhouette. Perfect for weekend plans, style with strappy sandals.

    Fit & Features

    • Poplin cotton woven fabric
    • Strapless sweetheart neckline
    • Smocked bodice, geometric pattern
    • High-rise waist
    • Side pockets
    • Midi-length pleated A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000007

    Category Name: Casual Dresses

    Price: $11.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sunset Girl Abstract Halter Slit Maxi Dress

    Need an unforgettable look? This abstract maxi dress will be the perfect companion for rooftop cocktails and parties, boasting a sultry halter neckline, cutout bodice, and high slit giving major sultry energy.

    Fit & Features

    • Abstract print, stretchy knit fabric, short knit stretch lining
    • Halter neckline with tie straps, hoop insert
    • Cutout bodice
    • High side slit
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000003

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

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  • Into The Sun V-Neck Maxi Dress

    Sun goddess maxi dress boasting a V-neckline with a unique metal accent and a body-skimming silhouette. Style with strappy sandals for a sunset dinner.

    Fit & Features

    • Textured knit fabric, soft knit stretchy lining
    • V-neckline with metal accent
    • Spaghetti straps
    • Body-skimming silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000002

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

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  • Catch Flights Tropical Lace-Up Slit Maxi Dress

    Booked the trip just for the outfit? Valid. This lace-up back maxi brings the heat with a tropical print and a leg-baring high slit that knows how to make an entrance.

    Fit & Features

    • Smooth knit stretchy fabric, tropical print, soft knit stretch lining
    • Square neckline with spaghetti straps
    • Bodycon silhouette
    • Lace-up open back with tie closure
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000005

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Effortless Era Woven A-Line Midi Dress

    Enter your effortless era in this woven A-line midi dress featuring a stretchy smocked bodice, hidden side pockets, and a pleated flowy silhouette with a side slit.

    Fit & Features

    • Poplin smooth cotton woven fabric with full-length woven lining
    • Sleeveless square neckline, adjustable spaghetti straps
    • Stretchy smocked bodice
    • V-shaped waist
    • Pleating, hidden side pockets
    • Midi-length flowy A-line silhouette, high side slit
    • Runs true to size

    Style Number/Barcode: 05102-000001

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Bold Beauty Floral Maxi Dress

    Just as bold as it is beautiful, this maxi dress is designed with a statement floral print on a body-skimming silhouette. It's perfect for your next vacation or weekend plans!

    Fit & Features

    • Floral print, mesh fabric, soft stretchy knit lining
    • Strapless neckline
    • Form-hugging bodice
    • Relaxed maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6118

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Island Hottie Tropical Halter Slit Maxi Dress

    Look hot to trot around the island on vacation in this tropical maxi dress! This stunning maxi features a crisscross halter neckline for a touch of elegance and a front slit to show off those curves.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, bust knit lining
    • Crisscross halter neckline, beaded
    • Front slit
    • Curve-hugging fit
    • Flowy maxi length hem
    • Runs true to size

    Style Number/Barcode: 05102-6117

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Petals and Plans Floral Lace-Up Maxi Dress

    For date nights, rooftop drinks, or weddings, this floral maxi dress is perfect for every event! The curve-hugging fit, flirty slit, and open lace-up back effortlessly flatters your figure and makes heads turn.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Square neckline
    • Spaghetti straps
    • Lace-up open back
    • High front slit
    • Curve-hugging fit, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4160

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Maui Nights Strapless Tropical Midi Dress

    Booked a vacation? This tropical midi dress is here to make you look stylish for your getaway! Designed with a flattering bodycon silhouette and side slit for effortless sultriness.

    Fit & Features

    • Tropical print, mesh knit-lined fabric
    • Strapless neckline
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6120

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Summer-Coded Crochet Halter Mini Dress

    Serve all the summer vibes in this crochet knit mini dress designed with a halter V-neck with a beaded trim on the straps. Style with espadrille wedges for sunset happy hour.

    Fit & Features

    • Sheer crochet knit fabric with knit lining, moderate stretch
    • Sleeveless V-neckline
    • Tie-back halter straps, beaded trim
    • Partially open back
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6114

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

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  • Getaway Girlie Halter Bead Crochet Mini Dress

    Your next getaway calls for this crochet mini dress! This dress has a stunning halter bead neckline that adds a touch of boho, a cutout accent, and a flattering bodycon silhouette.

    Fit & Features

    • Crochet lined fabric
    • Halter beaded neckline, spaghetti strap ties
    • Padded bra cups
    • Back zipper hook-eye closure, lower ruched seam
    • Cutout front accent
    • Bodycon silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6116

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Destination Summer Tropical Linen Mini Dress

    This cute mini dress was made for summer vacays featuring a contrast tropical print on lightweight linen fabric. The lace-up strappy back design offers a customized fit and a head-turning vibe.

    Fit & Features

    • Linen-blend woven fabric, woven lining
    • Tropical print
    • Sleeveless square neckline
    • Spaghetti straps
    • Open cross-back lace-up strappy design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6115

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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