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.

  • Floral Soiree Puff Sleeve Mini Dress

    Heading to an afternoon soiree? This floral mini dress is perfect! It features adorable short puff sleeves, a sweetheart neckline, a front bust tie with a keyhole accent, and a bodycon silhouette. Complete the look with a crossbody bag.

    Fit & Features

    • Short puff sleeves, elasticized hems
    • Sweetheart neckline
    • Front bust tie, keyhole accent
    • Bodycon silhouette
    • Mini-length hem
    • Floral pattern
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4608

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachside Beauty Floral Mini Dress

    You'll be a total beachside beauty on your summer vacay in this floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, dual front verticals seams with ruched detailing, and a short, curve-hugging silhouette. The lined mesh fabric features an all-over tropical floral print. Complete the look with espadrille sandals.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Dual front vertical seams, ruched detailing
    • Mini-length, form-fitting, bodycon silhouette
    • Tropical floral print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4609

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set The Style Marble Print Dress

    Set the style you desire! This marble print mini dress features side ruched drawstrings that let you customize the length depending on your preference, a square neck, spaghetti straps, and a form-hugging fit. Complete the look in strappy heeled mules. 

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Side ruched customizable drawstrings
    • Marble print 
    • Form-hugging fit
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4605

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good Marbles Lace-Up Mini Dress

    Turn your day into a fashion slay! Stay trending in this sleeveless mini dress featuring a square neck, spaghetti straps that lace up on the open back, and Venecia marble print on stretch-knit fabric that offers a form-hugging fit. Complete the look in doorknocker earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lace-up design
    • Form-hugging fit
    • Mini-length hem
    • Venecia marble print, stretch knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4607

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Poised And Chic Sweater Dress

    Keep it poised and chic with a sweater dress that is perf for every day! The dress features a sleeveless collared neckline, a button-down front, and a bodycon fit through the hip and thigh. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules and hair clips.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features 

    • Sleeveless collared neckline
    • Button-down front 
    • Bodycon fit
    • Short-length hem 
    • Ribbed knit fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size  

    Style Number/Barcode: 06005-1451

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Occasion Ruched Side Mini Dress

    Your next daytime occasion calls for this floral mini dress featuring a sleeveless, square neck, spaghetti straps, and side ruched seams that accentuate your curves on the soft-knit fabric. Complete the look with a cropped jacket.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Floral print
    • Soft-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4606

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knit Your Average Sweater Dress

    Level up in this curve-flaunting sweater dress featuring a sleeveless, scoop neckline, spaghetti straps, a bodycon silhouette, and a mini-length hem on ribbed knit fabric with plenty of stretch. Complete the look in a crop cardigan and booties.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, scoop neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1450

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feel The Heat V-Neck Midi Dress

    Sizzle and stun in this midi dress perf to bring up the temps! It features a sleeveless plunge V-neckline with a center O-ring insert, cutout bodice, form-fitting silhouette, and a side slit accent. Complete the look in lucite mules for a night out.

    Fit & Features

    • Sleeveless, plunge V-neck
    • Center O-ring
    • Cutout bodice
    • Form-fitting silhouette
    • Side slit accent, midi-length hem
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1448

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flatter Me Cutout Maxi Dress

    You won't need anyone flattering you in this sexy maxi dress! Featuring a sleeveless, scoop neck, spaghetti straps, a cutout bodice, partial open-back, a form-fitting silhouette, and a sultry slit perfect for showcasing heels.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Cutout bodice
    • Partial open-back
    • Form-fitting silhouette
    • Front slit
    • Maxi-length hem
    • Slinky knit fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4603

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fine Lines Chambray Skater Dress

    Flirty and fine! Look and feel effortlessly cute in this chambray striped skater dress featuring a sleeveless, v-neck, ruffled trim, and a babydoll-style seam that leads to the flowy short-length hem. Complete the look in braid strap mules.

    Fit & Features

    • Sleeveless, v-neck, ruffled trim
    • Babydoll-style seam
    • Flowy short-length hem
    • Chambray striped fabric, lining, no stretch
    • Back keyhole accent, button closure
    • Fits true to size

    Style Number/Barcode: 05102-4602

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Have We Met Lace-Up Mini Dress

    Say hello to your new fave mini dress for day-to-night soirees! Featuring a sleeveless, square neck, spaghetti straps, high waist seam, side ruched seams, and an open-back with lace-up closure. Composed of brushed soft and stretchy knit fabric that hugs your curves like an hourglass. Finish the look in a sleek cropped jacket.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • High waist seam
    • Side ruched seams
    • Open-back, lace-up closure
    • Bodycon silhouette, mini-length hem
    • Brushed soft and stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4593

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Smooth Knit Mini Dress

    Style up this simple smooth knit mini dress for adorable date looks! It features a sleeveless square neckline, spaghetti straps, ruching down the side seams, a wrap-front design, and a short, curve-hugging, bodycon silhouette. Complete the outfit with strappy mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down the side seams
    • Wrap-front
    • Mini-length hem, bodycon silhouette
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4594

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral State Scoop Neck Mini Dress

    Got a floral state of mind? Then this mini dress is just what you need! It features a sleeveless, scoop neck, spaghetti straps, and ruched bust seam that leads to a bodycon silhouette. Complete the look in chic wedges for a cute picnic date.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Ruched bust seam
    • Bodycon silhouette
    • Mini-length hem
    • Floral print
    • Stretchy rib-knit fabric, lined
    • Fits true to size

    Style Number/Barcode: 05102-4601

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You'll Be Back Twist Bodycon Dress

    You'll be back wearing this sultry bodycon dress on repeat! It features a sleeveless square neckline, sleek spaghetti straps, a mini-length hem, and an open back with dual twist accents that add sultry detail to your look. Style with a necklace and heels for a daytime party.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Open-back, dual twist accents
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4592

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Splash Of Style Twist Mini Dress

    Your summer closet could use this stylish swirl print mini dress perfect for adding in brighter hues! It features a sleeveless, v-neck atop a twisted bust, spaghetti straps, bodycon silhouette, and side ruched seams to accentuate your natural curves. Complete the look in stiletto heels for a dinner with friends.

    Fit & Features

    • Sleeveless, v-neck, twisted bust, spaghetti straps
    • Bodycon silhouette
    • Side ruched seams
    • Mini-length hem
    • Swirl print
    • Stretchy soft knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4596

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Choice Halter Midi Dress

    This casual-chic midi dress will make styling so effortless. It features a sleeveless crew neckline with halter straps, an open back with a cross-back strap design, a midi-length, curve-hugging silhouette, and an alluring high side slit. Complete the look with a classic pair of hoops.

    Fit & Features

    • Sleeveless crew neckline
    • Halter straps
    • Open back, cross-back strap design 
    • Bodycon silhouette, side slit accent
    • Midi-length hem
    • Ribbed knit fabric, lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4588

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry Mood Snake Print Mini Dress

    This sultry mini dress was made for nights out with the squad! It features an asymmetrical one-shoulder neckline, a tank shoulder strap, ruching down the side seams, and a short, curve-hugging, bodycon silhouette. The mesh fabric features an all-over snake print pattern. Complete the look with sleek hoop earrings.

    Fit & Features

    • Sleeveless asymmetrical one-shoulder neckline
    • Single tank shoulder strap
    • Ruching down the side seams
    • Mini-length hem, fitted bodycon silhouette
    • Mesh fabric, moderate stretch
    • Snake print
    • Runs true to size

    Style Number/Barcode: 05102-4590

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Cutest Denim V-Neck Mini Dress

    Show off your cute figure in this stylish denim mini-dress! It features a sleeveless sweetheart neck, wide shoulder straps, a front exposed zipper closure, and a bodycon silhouette. Complete the look in lace-up heels for a birthday party!

    Fit & Features

    • Sleeveless sweetheart neck
    • Wide shoulder straps
    • Front exposed zipper closure
    • Bodycon silhouette
    • Mini-length hem
    • Denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05102-4591

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Reap The Rewards Cutout Mini Dress

    You'll be reaping the rewards of this rib mini dress all season long! It features long fitted sleeves and a crew neckline, a twist accent bust with a cutout waist, side ruched ties that let you customize the length, and a bodycon silhouette. Complete the look in booties.

    Fit & Features

    • Long fitted sleeves
    • Crew neckline
    • Twist accent bust, cutout waist
    • Side ruched ties to customize the length
    • Bodycon mini silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4583

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Muse Chiffon Skater Dress

    Showcase your effortless beauty in this airy chiffon skater dress. It features a sweetheart neckline with ruffled trim and a pleated bust, long bishop sleeves, a fitted high waistband, and a tiered skater skirt with a short hem and a fit and flare silhouette. Style this skater dress with your fave mules.

    Fit & Features

    • Sweetheart neckline, ruffled trim, pleated bust
    • Long sheer bishop sleeves, cinched hems
    • Smocked back design, fitted high waistband
    • Fit and flare silhouette
    • Tiered skater short-length skirt
    • Chiffon fabric fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1650

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild Blooms Floral Short Dress

    Tame your wild side and showcase this flirtatious floral short dress perfect for a casual picnic date! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a cutout back accent. Complete the look in wedges.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Bodycon silhouette
    • Cutout back accent
    • Short-length hem
    • Floral print knit fabric, knit lining at the bust, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4579

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twirl-Worthy Moment Skater Dress

    Get ready to have a total twirl-worthy moment in this adorable skater dress. It features a sleeveless square neckline, spaghetti straps that lead to a lace-up back design, a high waist seam, and a short skater skirt with a flirty fit and flare silhouette. Style this dress with your fave platform heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Cross-back, lace-up design, tie closure
    • High waist
    • Short skater skirt, fit and flare silhouette
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4578

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Days Square Neck Mini Dress

    Give your jeans a break but keep the denim spirit! You'll find yourself reaching for this denim mini dress of those days spent with friends or exploring the city. It features a sleeveless, square neck, adjustable spaghetti straps, princess seam detailing on the bodycon silhouette, and a back zipper closure. Complete the look in simple earrings and sneakers.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Back zipper closure
    • Princess seam detailing
    • Bodycon silhouette
    • Mini-length hem
    • Denim fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4571

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's Trendy Tie-Dye Mini Dress

    Showcase your trendy style in this tie-dye printed mini dress. It features a sleeveless square neckline, adjustable spaghetti straps, ruching down one side leading to an adjustable drawstring at the hem, and a short, curve-hugging silhouette. Complete your cool-girl look with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • High waist seam, ruching down one side, adjustable drawstring
    • Mini-length, form-fitting silhouette
    • Tie-dye print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4573

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale