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.

  • Sweetly Tied Skater Dress

    Sweeten up your look with this adorable red skater dress! It features a sleeveless bodice, adjustable halter straps that lead to a button back closure with a keyhole cut out below, a back zipper and hook and eye closure, a V neckline, a cute tie front detail, and a flowy skater skirt. The dress is composed of a lightweight linen fabric with a short knit lining.

    Style Number/Barcode: 05102-3826

    Category Name: Casual Dresses

    Price: $13.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

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  • Ruffled And Rowdy Dress

    Dance around and get rowdy in ruffles! This adorable mini dress features a v-neckline with a snap and hook closure. The bodice of this dress is line with a ruffled trim, thick ruffled straps that lead to a low back, with a hidden zipper and a self tie bow. The skirt is adorned with a tiered ruffle effect. The dress is composed of a chiffon style material and offers no stretch yet, a flowy fit and includes a smooth inner lining. Now take a twirl! 

    Style Number/Barcode: 05102-0206

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

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  • Botanical Beauty Midi Dress
    This botanical print dress features a square ruffled neckline, elastic ruffle straps and a straight bodice. The backing of the dress has a hidden zipper and  stretch smock detailing.This piece has a dark toned floral print and is mid-length with a smooth inner lining and a side slit.It is composed of a sheer chiffon-like material that offers a relaxed fit with minimal stretch. On a stroll through the park or a gals brunch date, this dress is bound to have heads turning!

    Model is 5'9" with a 32" bust, a 24" waist, and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0210

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Color Wheel Striped Mini Dress

    Rendered in bright stripes, this mini makes an impact. Dress features a fitted bodice with off-the-shoulder neckline, contrast gently pleated, A-line skirt, and a gathered elasticized waist with decorative tie. Dress is made from a soft, lightweight woven material with stretch through the bodice and waist.

    Style Number/Barcode: 05102-0000

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

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  • Simply Wrapped Mini Dress

    Keep it simply sophisticated in this statement mini dress! The dress features a plunging wrap V neckline with pleated accents, adjustable spaghetti straps and an asymmetrical hem with ruched detailing. Dress is composed of a lined smooth knit fabric that offers a curve hugging fit with a moderate stretch. Includes a back zipper closure.

    Style Number/Barcode: 05102-3948

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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  • Classic Chic Shirt Dress

    This classic chic mini shirt dress is everything you need and more. It features a collar, a plunging wrap front V neckline, long sleeves with buttons to cuff, a high waist seam, side ruched detailing, and a short fit. The dress is composed of a woven fabric with no stretch.

    Model is 5'9" with a 33" bust, 24" waist and 35.5 hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0293

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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  • Smocked And Stylin' Mini Dress

    This adorable floral printed mini is smocked and stylin'! The dress features a sleeveless bodice, tie shoulder spaghetti straps, a square neckline with a bust keyhole cut out, a square back, pleated details, and a stretchy and smocked fit. The dress is composed of a lightweight linen fabric that offers a form hugging fit.

    Style Number/Barcode: 05102-0283

    Category Name: Casual Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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  • Floral Stunner Midi Dress

    Be a stylish stunner in this gorg floral midi dress! It features a sleeveless bodice, adjustable spaghetti straps that cross in the back, a V neckline, side ruched detailing, and an asymmetrical hem. The dress is composed of a knit fabric that offers plenty of stretch.

    Style Number/Barcode: 05102-3848

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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  • Knotch It Up Mini Dress
    This dress is a cute versatile a piece, dress it up with some strappy heels or throw on your favorite sneaks. This piece features a sleeveless bodice, with U shaped neckline, a knotch cut out at the center of the bust area. The dress has a smooth inner lining and is composed of a soft knit material that is ribbed for a casual style. The hem hits above mid thigh, and is form fitting with a moderate stretch.

     Model is 5'7" with a 32" bust,  23" waist and 34.5" hips. She is wearing a size small.  

    Style Number/Barcode: 06002-0107

    Category Name: Casual Dresses

    Price: $8.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Steal The Scene Skater Dress
    Steal the scene and turn heads in this captivating skater dress! It features a sleeveless bodice, spaghetti straps that lead to an open cross back and lattice details, vertical seams that run down the bust, a high waist seam, and a flowy high low skater skirt. The dress is composed of a crepe fabric that offers moderate stretch.

    Style Number/Barcode: 05101-8831

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Floral Connection Mini Dress

    Make a sweet connection in florals! This must have mini dress features a sleeveless bodice, a cowl neck, spaghetti straps and a mini length silhouette to show glowing gams! The neutral tone is complemented with pretty florals throughout! Dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch.

    Style Number/Barcode: 05102-0086

    Category Name: Casual Dresses

    Price: $13.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Fresh Blooms Side Slit Maxi Dress

    It's time to refresh and reset for the szn! This spring-ready maxi will be your go-to piece for daytime events! Slip into some mules and add some layered necklaces for a pretty OOTD! 

    Fits & Features

    • Spaghetti Straps
    • Scoop Neckline 
    • Thigh High Side Slit
    • Maxi Length Silhouette 
    • Form Hugging Fit
    • Zipper Not Included 

    Model is 5'9" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0289

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Knit Mini Dress

    This mini dress is composed of a very soft knit material. It is form fitting, hugs your curves and has a maximum stretch, and the hem meets mid thigh. It features a round neckline and spaghetti straps that lead to a round back. This dress will pair well with sneakers and a jean jacket or a leather jacket and heels! Play dress up with it, it goes with everything!

    Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0232

    Category Name: Casual Dresses

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sultry Sweater Dress

    Keep it classy in a sweater dress! This dress features a v neckline, and long sleeves that puff at the wrist with the help of a thick wristband. Bodice meets skirt high waist with a belt that ties at the side. Back of the garment has a tie detail below the neck.The hem of this dress hits mid thigh, and dress is composed of a knit material that offers a comfortable form fit with moderate stretch.

    Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06005-0076

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Off Shoulder Sweater Dress

    It's sweater time! We love a good sweater dress, just slip it on and you are ready! Designed with an off shoulder fold over neckline, long sleeves, and a form fitting silhouette. Dress is composed of a soft knit woven fabric that offers moderate stretch.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06005-0068

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casual Knit Open Back Tunic

    Keep it casual cutie with pretty knits! The tunic features a turtle neck, long sleeves with ribbed cuff, a partial open back and a short form hugging fit. Tunic is composed of knit fabric that offers a moderate stretch. 

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06005-0053

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Mod Mini Belted Dress

    Get retro glam in this sunny, striking mini! Dress has a body con cut and features thick, tank-style straps, a square neckline, seam detail at bust, an attached fabric belt with oversize buckle, and a pencil skirt. Dress is lined, slips on, and is made from a woven crepe material with a fair amount of stretch.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0171

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fine In Florals High Neck Maxi Dress

    Florals are DEF your color, bb girl! Show off your curves in our Fine In Florals maxi dress! 

    Fits & Features

    • Spaghetti Straps That Cross & Lace-Up At The Back 
    • High Neckline 
    • Maxi Length Silhouette 
    • Dual Side Slits 
    • Smooth Jersey Knit Fabric 
    • Form Hugging Fit I Ample Stretch 

    Style Number/Barcode: 05102-0277

    Category Name: Casual Dresses

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Wild Child Bodycon Mini Dress

    Stay fierce in a dress as wild as you! This bodycon features elasticized spaghetti straps and a square neckline. Cut to a flirty mini length, this piece is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Dress also includes a knit lining.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0152

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Daring In Denim Mini Dress

    We dare you to be bold in this hot denim mini! The dress features a sleeveless strapless square neckline, double vertical seam detailing down the front and back, and a short, raw hem. The dress is composed of a jean fabric that offers moderate stretch and a curve hugging fit.

    Model is 5'9" with a 33" bust, 24" waist and 35.5 hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0162

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Ready To Ruffle Mini Dress
    You'll be ready to ruffle in this flirty little mini dress! It features a sleeveless bodice, a V neckline with an adorable tie closure followed by a front cut out, button detailing starting at the waist, a hidden back zipper and hook and eye closure, and a cute tiered ruffle hem. The dress is composed of a linen fabric with no stretch.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0149

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Beauty Eyelet Mini Dress
    Showcase your effortless beauty in this beyond gorgeous eyelet mini dress! It features a square neck and back, short sleeves with ruffle detailing, a hidden back zipper and hook and eye closure, mini side cut outs at the waist seam, and a short, mid-thigh length. The dress is composed of a woven fabric with a full lining and has no stretch.

    Style Number/Barcode: 05102-0150

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On Knit Mini Dress
    You're always on it when it comes to style, and this basic knit mini will make for such a cute 'fit. The dress features a sleeveless bodice, tank-like shoulder straps, a square neck and back, and a short, form hugging fit. The dress is composed of a soft knit that offers plenty of stretch.

    Style Number/Barcode: 05102-0095

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Darling In Denim Mini Dress

    This darling denim mini is the new dress you need! It features a sleeveless, sweetheart neckline with a built-in padded bust, adjustable spaghetti straps, piping detailing down the front, and a short, curve-hugging fit. Complete the look in PVC strap mules.

    Fit & Features

    • Sleeveless, sweetheart neckline, built-in padded bust
    • Adjustable spaghetti straps
    • Back zipper closure
    • Piping detail down the front and back
    • Short, curve-hugging fit
    • Denim fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-0120

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale