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.

  • Pretty Lady Tie-Dye Cutout Dress

    Channel a certain pop culture character from everyone's favorite movie! Go as a Pretty Lady this Halloween wearing this iconic mini dress featuring a sleeveless scoop neck, tank-style straps, a cutout bodice with an o-ring insert, and a tie-dye skirt. Complete your costume with chic thigh-high boots and hoop earrings.

    Fit & Features

    • Sleeveless scoop neck
    • Tank-style straps
    • Cutout bodice, o-ring insert
    • Tie-dye mini skirt
    • Bodycon silhouette
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4745

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Muse Maxi Dress

    Show off your casual and trendy style in this sleek knit maxi dress. It features a sleeveless scoop neckline, spaghetti straps that lead to a cross-back design, a ruched wrap-front creating a high slit, and a curve-hugging fit with an asymmetrical hem. Complete the look with clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps, cross-back design
    • Ruched wrap-front, high slit
    • Maxi-length asymmetrical hem
    • Form-fitting silhouette
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1740

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep It In Check Plaid Mini Dress

    Keep your stylish look in check with this plaid knit mini dress. It features a collared V-neckline, short sleeves, and a mini-length hem with a form-hugging, bodycon silhouette. Complete the 'fit with a dainty layered necklace and booties.

    Fit & Features

    • Collared V-neckline
    • Short fitted sleeves
    • Mini-length hem, bodycon silhouette
    • Plaid print
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4743

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In The Knit Cable Sweater Dress

    A fashionista like you needs to set the trends! Step it up this season in this staple cable knit sweater dress featuring a ribbed mock neck and long sleeves, a bodycon silhouette, and a short-length hem. Style with knee-high boots and a jacket to complete the look!

    Fit & Features

    • Ribbed mock neck and long sleeves
    • Bodycon silhouette
    • Short-length hem
    • Cable knit design
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1564

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Throwback Halter Short Dress

    Channel your inner pop princess with this short dress that brings all the glam! The dress features a retro swirl print, a halter neckline with bungee spaghetti straps, dual ruching through hip and hem, and a short length. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete your look with butterfly clips and chrome heels.

    Fit & Features

    • Retro swirl print 
    • Halter neckline, bungee spaghetti straps
    • Dual ruching
    • Short length hem 
    • Bodycon fit 
    • Lined mesh fabric 
    • Moderate stretch, runs true to size

    Style Number/Barcode: 05102-4742

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coffee Date Ribbed Knit Midi Dress

    This soft ribbed knit midi dress is perfect for fall coffee dates! It features a collared V-neckline, long fitted sleeves, a partial faux button-down front, a midi-length hem with a high front slit, and a form-hugging fit. Style with knee-high boots for a chic autumn look.

    Fit & Features

    • Collared V-neckline
    • Long fitted sleeves
    • Partial faux button-down front
    • Midi-length hem, front slit
    • Fitted silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4740

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Varisty Babe Graphic Tunic

    Level up your look to varsity status with this adorable tunic! It features a crew neckline, short fitted sleeves, a center football helmet graphic with a script that reads "New Season," dual waist cutouts with a center O-ring cutout accent, and a short, form-hugging fit. Style with a cute shacket and sneakers.

    Fit & Features

    • Crew neckline, short sleeves
    • Football helmet graphic
    • Script that reads "New Season"
    • Dual waist cutouts, center O-ring cutout
    • Short, form-fitting silhouette
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1350

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Everyday Chic Ribbed Knit Midi Dress

    Style up this casual chic ribbed knit midi dress for every day! It features a mock neckline, short sleeves, a midi-length hem, a form-hugging fit, and a high front slit. Complete the look with hoop earrings and ankle booties.

    Fit & Features

    • Mock neckline
    • Short sleeves
    • Midi-length hem
    • Fitted bodycon silhouette
    • Front slit
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4739

    Category Name: Casual Dresses

    Price: $19.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Hole Package Sweater Mini Dress

    Babe, you'll be looking stunning from all angles in this sweater mini dress featuring a crew neck, long sleeves, front keyhole cutouts, button accents, and a bodycon silhouette on rib-knit fabric. Style with knee-high boots to complete the look.

    Fit & Features

    • Crew neck, long sleeves
    • Front keyhole cutouts
    • Button accents
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit sweater fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1542

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Style Goals Floral Mesh Midi Dress

    Showcase total style goals in this stunning floral mesh midi dress! It features a sleeveless square neckline, spaghetti straps, an open back with a strappy design, a midi-length, curve-hugging silhouette, and a thigh-high side slit. The lined mesh fabric features all-over floral embroidery for a pretty vibe. Complete the look with hoop earrings.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, horizontal strappy design
    • Midi-length hem, bodycon silhouette
    • High side slit
    • Floral embroidery
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4738

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Plans Ribbed Knit Maxi Dress

    This casual-chic maxi dress is perfect for your upcoming weekend plans. It features a sleeveless one-shoulder neckline for an effortless and trendy vibe, a single tank shoulder strap, an open back with a dual strap design, a fitted, maxi-length silhouette, and a high side slit. Style this dress with hoop earrings.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Single tank shoulder strap
    • Open back, dual strap design
    • Maxi-length hem, form-hugging fit, side slit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4737

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • One Night Of Chic Mesh Maxi Dress

    Have your chic moment in this mesh maxi dress featuring a sultry, one-shoulder neckline, a partial open-back, side and back ruching, and an asymmetrical maxi-length hem with a side slit cutout. Complete your dressy look in sleek heels.

    Fit & Features

    • Sleeveless, one-shoulder neckline, spaghetti strap
    • Partial open-back
    • Side and back ruching
    • Side slit cutout
    • Asymmetrical maxi-length hem
    • Form-hugging fit, partial lining, mesh fabric
    • Fits true to size

    Style Number/Barcode: 05102-4736

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Step It Up Collared Mini Sweater Dress

    Step up your everyday fall 'fits with this trendy mini sweater dress. It features a johnny collar, a V-neckline with a partial button-down front, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric offers a moderate stretch. Style with sleek hoop earrings and knee-high boots.

    Fit & Features

    • Johnny collar
    • V-neckline, partial button-down front
    • Long fitted sleeves
    • Mini-length hem
    • Fitted bodycon silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1534

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • All Business Sweater Mini Dress

    All business with some pleasure! Take this sweater mini dress from office hours to happy hour. It features a sleeveless, v-neck, and a form-fitting silhouette. Complete the look with a chic clutch.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, v-neck
    • Form-fitting silhouette
    • Mini-length hem
    • Sweater rib-knit
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1529

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Spring Into Floral Chiffon Skater Dress

    Transition your winter blues into fresh spring florals! This breezy chiffon skater dress is perfect for dressy brunches or engagement parties. It features a surplice V-neckline, sheer peasant sleeves, a tie-back belted waist, and a tiered ruffle short-length hem with an adorable ditsy floral print. Complete the look in lace-up heels.

    Fit & Features

    • Surplice V-neckline
    • Sheer peasant sleeves 
    • Tie-back belted waist, back zipper and hook-eye closure
    • Skater, fit and flare silhouette
    • Tiered ruffle short-length hem
    • Ditsy floral print, chiffon fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1711

    Category Name: Casual Dresses

    Price: $5.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Piece Of Me Crew Cutout Mini Dress

    Show off flirty peeks of skin on this sleeveless mini dress featuring a crew neck, bodycon silhouette, and cutout accents along the waist. Complete the look in strappy sandals for happy hour.

    Fit & Features

    • Sleeveless, crew neck
    • Bodycon silhouette
    • Cutout accents along the waist
    • Mini-length hem
    • Brushed knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4735

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Work Of Art Marble Midi Dress

    Girl, your taste is a work of art! Step out in a midi dress that features a gorge marble print, a sleeveless scoop neckline with bungee spaghetti straps, and a midi length hem with ruching throughout. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and a quilted crossbody. 

    Fit & Features

    • Sleeveless scoop neckline
    • Bungee spaghetti straps
    • Marble print
    • Ruching
    • Midi-length hem
    • Lined mesh fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4732

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step It Up Henley Knit Midi Dress

    Step up your basics with this rib knit midi dress with subtle detail for a cute, everyday style! The dress features long sleeves, a V-neck, a button-down front with a slit, and a form-hugging silhouette. Complete the look in strappy mules for weekend plans!

    Fit & Features

    • Long sleeves, V-neck
    • Front button-down
    • Slit accent
    • Form-hugging silhouette
    • Midi-length hem
    • Rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4726

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twist It Up Sweater Midi Dress

    Spice up your everyday look with this sweater midi dress that brings eye-catching detail! It features long sleeves, a v-neck, a twisted bust and cutout, a side slit, and a form-hugging silhouette. Complete the look in a crop denim jacket for lunch!

    Fit & Features

    • Long sleeves
    • V-neck
    • Twisted bust and cutout
    • Form-hugging silhouette
    • Side slit, midi-length hem
    • Sweater rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1517

    Category Name: Casual Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destination Dinner V-Neck Midi Dress

    Look fabulous in a flash wearing this sleeveless midi dress for dinner and drinks! It features a showstopping bodycon silhouette, a V-neck, tank straps, and side ruched seams that hug every curve like a glove. Complete the look with chic stiletto heels.

    Fit & Features

    • Sleeveless, V-neck, tank straps
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Slinky knit fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4834

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Nothing But Sultry V-Neck Midi Dress

    You'll be nothing but sultry in this midi dress for a party! It features a sleeveless, v-neck, bungee spaghetti straps, cutout bodice, open-back with tie closure, form-fitting silhouette, and a side slit accent along the hem. Complete the look with a sparkly bracelet and heels.

    Fit & Features

    • Sleeveless, v-neck, bungee spaghetti straps
    • Open-back, tie closure
    • Cutout bodice
    • Form-fitting
    • Side slit, midi-length hem
    • Slinky knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4724

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Everyday Ribbed Knit Midi Dress

    Effortlessly chic for every day, this ribbed knit midi dress is a must-have for fall. It features a V-neckline, a combination of front spaghetti straps and long fitted sleeves, and a midi-length, curve-hugging silhouette. Style with ankle booties for coffee dates this season.

    Fit & Features

    • V-neckline
    • Front spaghetti straps, long fitted sleeves
    • Midi-length hem
    • Fitted bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4975

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rare Marble Pattern Midi Dress

    Why blend in when you can stand out! Strut into the party in this marble midi dress featuring a trendy, sleeveless, square neck, bungee spaghetti straps, and a bodycon silhouette. Complete the look in doorknocker earrings.

    Fit & Features

    • Sleeveless, square neck
    • Bungee spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Marble pattern
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4723

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Basic High Slit Midi Dress

    This alluring basic midi dress will easily become one of your staple styles. It features a sleeveless sweetheart neckline with a built-in padded bust, adjustable spaghetti straps for a customized fit, a midi-length bodycon silhouette, and a high side slit. Pair with a moto jacket and mules.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Padded bust, bust seam outline
    • Adjustable spaghetti straps
    • Midi-length hem, fitted bodycon silhouette
    • High side slit
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4722

    Category Name: Casual Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale