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.

  • So Irresistible Mesh Midi Dress

    You'll be a vision in this simply irresistible mesh midi dress perfect for an engagement party or cocktail soiree! It features a sleeveless plunge v-neck, adjustable straps, a back slit accent, and ruched seams that accentuate your curves along the bodycon silhouette. Complete the look in stiletto heels.

    Fit & Features

    • Sleeveless plunge v-neck
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Ruched seams, back slit accent
    • Bodycon, midi-length hem
    • Mesh fabric, sewn-in knit lining, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05101-1857

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Must-Have Ribbed Knit Mini Dress

    This ribbed knit mini dress is a basic must-have that needs to be in your wardrobe! It features a classic crew neckline, long fitted sleeves, and a short, form-hugging fit. The ribbed knit fabric offers a moderate stretch. Style with hoop earrings and knee-high boots.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Mini-length hem, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1407

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Floral Vibes Ruched Mini Dress

    Capture a sweet romantic look in this flirty floral mini dress! It features a sleeveless V-neckline with ruching at the bust, spaghetti straps, a mini-length hem, and a form-hugging fit. The stretchy ribbed knit fabric features an all-over ditsy floral print for an adorable summer style. Pair with espadrille sandals for a day date.

    Fit & Features

    • Sleeveless V-neckline
    • Ruching at the bust
    • Spaghetti straps
    • Mini-length hem, form-hugging fit
    • Ditsy floral print
    • Ribbed knit fabric, smooth knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4760

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Add Some Spice Mini Dress

    This fiery bodycon mini dress will add some spice to your night-out look! It features a sleeveless square neckline, trendy chain-link shoulder straps, and a short, curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Style this sexy mini dress with platform heels.

    Fit & Features

    • Sleeveless square neckline
    • Chain-link shoulder straps
    • Mini-length hem, bodycon silhouette
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4755

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Happily In Love Scoop Neck Mini Dress

    You'll be happily in love with how stunning you look in this sleeveless mini dress for a graduation or birthday brunch! It features a scoop neck with a flirty bust tie, spaghetti straps, and a bodycon silhouette on rib knit fabric with a stretchy knit lining. Complete the look in trendy wedges.

    Fit & Features

    • Sleeveless scoop neck, spaghetti straps
    • Bust tie
    • Bodycon silhouette
    • Mini-length hem
    • Rib knit, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4754

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty In Paradise Strappy Cutout Maxi Dress

    You'll be pretty in paradise in this stunning maxi dress for vacation or a bachelorette weekend! The dress features a sleeveless V-neckline, spaghetti straps that lace up along the open back, flirty waist cutouts, and a high front slit along the flowy hem. Complete the look with earrings and clear block heels for a chic style!

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Lace-up open back
    • Waist cutouts, high front slit
    • Maxi-length hem
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4752

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • One Love Sweetheart Sweater Dress

    The sweater dress your wardrobe needs! It features a sleeveless, sweetheart neckline, shoulder straps, a ruched bust seam, and a flirty cutout waist leading to the bodycon, mini-length silhouette. Complete the look in statement earrings.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, sweetheart neckline, shoulder straps
    • Ruched bust seam
    • Cutout waist
    • Bodycon silhouette
    • Mini-length hem
    • Hacci ribbed-knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4751

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fall Ritual Poplin Shirt Dress

    Your new fall favorite for wearing all season! This poplin shirt dress features long sleeves with buttoned cuffs, a collared neckline, front button-down closures, a fitted waist, a lower open-back design with lace-up, and a pleated, short skater silhouette. Complete the look in chic Panama hat and booties. 

    Fit & Features

    • Long sleeves with buttoned cuffs
    • Collared neckline
    • Front button-down closures
    • Fitted waist, lower open-back, lace-up
    • Pleated, short skater silhouette
    • Non-stretch poplin fabric
    • Fits true to size

    Style Number/Barcode: 05101-1771

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wonderful Winter Sweater Midi Dress

    Slay all season no matter the weather in this sweater midi dress perfect for casual or dressy events! It features fitted long sleeves, a mock neck, a bust cutout, and a form-hugging silhouette with a flirty front slit. The dress is composed of a stretchy rib-knit fabric. Pair with booties to complete the look.

    Fit & Features

    • Fitted long sleeves, mock neck
    • Bust cutout
    • Form-hugging silhouette
    • Front slit accent
    • Midi-length hem
    • Rib-knit sweater fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1579

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Winter Chic Off-The-Shoulder Sweater Dress

    This adorable ribbed knit sweater dress will give you a chic look for the winter season! It features an off-the-shoulder neckline with a fold-over design, long fitted sleeves, a midi-length, curve-hugging silhouette, and a high front slit. The knit fabric offers a moderate stretch for comfortable wear. Style with knee-high boots.

    Fit & Features

    • Off-the-shoulder neckline, fold-over design
    • Long fitted sleeves
    • Midi-length hem, fitted bodycon silhouette
    • High front slit
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1578

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Style Warm Up Sweater Knit Dress

    Cozy up this season in style! This sweater mini dress is the best of both worlds featuring cozy dolman sleeves, a surplice v-neckline, belted tie-front waist, and a bodycon silhouette. The dress is composed of soft cable and rib-knit fabric that offers plenty of stretch. Style with knee-high boots to complete the look!

    Fit & Features

    • Dolman sleeves
    • Surplice v-neckline
    • Belted tie-front waist, belt loop accents
    • Bodycon silhouette, mini-length
    • Cable and rib-knit sweater fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1572

    Category Name: Casual Dresses

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Adorable Mock Neck Mini Dress

    So adorable and perfect for chilly days, this long sleeve mini dress is what your closet needs! The mini dress features a mock neck and a bodycon silhouette composed of hacci rib-knit fabric with moderate stretch. Complete the look in over-the-knee boots for a movie date!

    Fit & Features

    • Long fitted sleeves
    • Mock neck
    • Bodycon silhouette
    • Mini-length hem
    • Hacci rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5227

    Category Name: Casual Dresses

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Flirt Polka Dot Two Tone Mini Dress

    Showcase your flirty side with a mini dress that brings some seriously sultry appeal! The dress features a sleeveless sweetheart neckline with mesh trim, a plunging lace-up front, bungee spaghetti straps, ruching throughout, and a stylish swiss dot design. The dress is composed of a lined mesh fabric that reveals a two-tone effect. Complete date night outfit with heels and rhinestone duster earrings. 

    Fit & Features

    • Sleeveless sweetheart neckline, mesh trim 
    • Adhesive bra recommended, bungee spaghetti straps
    • Lace-up front 
    • Ruching
    • Swiss dot design 
    • Lined mesh fabric, two-tone color 
    • Form hugging fit, minimal stretch, runs true to size 

    Style Number/Barcode: 05102-4746

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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