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.

  • Doesn't Get Better Knit Midi Dress

    It doesn't get better than having this knit midi dress in your rotation! The dress features a trendy one-shoulder crew neckline with a long sleeve, spaghetti strap, and cutout bust that leads to the form-hugging silhouette with a sultry side slit hem. Complete the look in chic marabou heels.

    Fit & Features 

    • One-shoulder crew neckline
    • Long sleeve, spaghetti strap
    • Cutout bust
    • Form-hugging silhouette
    • Side slit hem, midi-length 
    • Smooth knit double-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4850

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Walk The Line Crepe Geo Mini Dress

    Walk the line into this artsy geometric print crepe dress to give your closet must needed prints! It features a sleeveless V-neckline, sleek bungee spaghetti straps, a bodycon silhouette, and a flirty slit along the mini-length hem. Complete the look in heeled sandals for a casual brunch downtown!

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Bodycon silhouette
    • Front slit, mini-length hem
    • Geometric print
    • Stretchy crepe fabric
    • Runs true to size

    Style Number/Barcode: 05102-4849

    Category Name: Casual Dresses

    Price: $6.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty In Fall Cable Knit Dress

    Stay flirty and cozy this fall in this cable knit midi dress! It features long sleeves, a mock neck, a bodycon silhouette, and a sultry open-back design. Perfect for styling with faux suede booties for your weekend plans!

    Fit & Features

    • Long sleeves
    • Mock neck
    • Bodycon silhouette
    • Open-back design
    • Midi-length hem
    • Soft cable knit sweater fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1614

    Category Name: Casual Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simple Chic Style Satin Mini Dress

    The simple chic style of this satin mini dress is perf for the babe who loves a classic look. It features a sleeveless V-neckline, bungee spaghetti straps, a fitted A-line silhouette, and a mini-length hem with an alluring front slit. The lightweight satin-knit fabric offers a moderate stretch. Complete the outfit with strappy heels.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Fitted A-line silhouette
    • Mini-length hem
    • Front slit
    • Satin-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1965

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Go With The Scoop Neck Midi Dress

    You'll be wearing this midi dress on repeat! It features long sleeves, a scoop neck, and a bodycon silhouette with a sultry side slit. The dress is composed of a stretchy rib-knit fabric. Style with pointed-toe booties to complete your cute look!

    Fit & Features

    • Long sleeves
    • Scoop neck
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4846

    Category Name: Casual Dresses

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made For You Marble Mesh Mini Dress

    This eye-catching marble mesh mini dress was made for you to style up and create a chic 'fit! It features a crew neckline, sheer long fitted sleeves, a mini-length hem, a bodycon silhouette that will hug your curves, and an all-over alluring marble print pattern. The partially lined mesh fabric offers plenty of stretch. Complete your look with strappy stilettos.

    Fit & Features

    • Crew neckline
    • Sheer long fitted sleeves
    • Mini-length hem
    • Bodycon silhouette
    • Marble print
    • Sheer mesh fabric, partial knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4847

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You're The One Tie-Front Midi Dress

    This rib knit midi dress will be the one you'll adore for casual outings and more! The dress features long sleeves, a surplice v-neckline, a faux wrap bust atop a flirty cutout bodice with a tie-front closure, and a bodycon silhouette. Style with faux suede booties for the perf autumn look!

    Fit & Features

    • Long sleeves
    • Surplice v-neckline
    • Faux wrap bust
    • Cutout bodice, tie-front closure
    • Bodycon, midi-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4843

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Everyday Style Midi Dress

    This form-fitting midi dress is perfect for creating that chic everyday style! It features a sleeveless V-neckline with a matching V-back design, tank shoulder straps, a fitted silhouette that will hug your curves, and a midi-length hem. The ribbed knit fabric offers plenty of stretch. Complete the look with strappy mules.

    Fit & Features

    • Sleeveless V-neckline, V-back design
    • Tank shoulder straps
    • Form-hugging fit
    • Midi-length hem
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4844

    Category Name: Casual Dresses

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Cable Knit Tie-Front Mini Dress

    Bring all the cozy vibes this season in this adorable cable knit mini dress! It features a V-neck and back with wrap designs, long balloon sleeves with tapered hems, a high waist with a tie-front accent, and a short, form-hugging fit. Style with knee-high boots.

    Fit & Features

    • V-neck and back, wrap design
    • Long balloon sleeves, tapered hems
    • High waist seam, tie-front
    • Mini-length hem, form-hugging fit
    • Cable knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4842

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Contemporary Girl Sweater Midi Dress

    Breeze in looking like a chic contemporary girl in this sweater midi dress! It features an on-trend cold shoulder with adjustable halter spaghetti straps, fitted long sleeves, a bodycon silhouette, and a front-side slit accent. Complete the look with lace-up heels for a dinner date!

    Fit & Features

    • Cold shoulder
    • Adjustable halter spaghetti straps
    • Fitted long sleeves
    • Bodycon silhouette
    • Front side slit, midi-length hem
    • Sweater rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1613

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Edgy Stunner Graphic T-Shirt Dress

    Show off an edgy style with this on-trend graphic t-shirt dress! It features a crew neckline with a notched design with safety pin detailing, short sleeves, a mini-length, fitted silhouette, and a motorcycle and eagle graphic with the script "American Motorcycles Road Lifestyle 1974." Complete your 'fit with combat boots.

    Fit & Features

    • Crew neckline, notched design, safety pin detailing
    • Short sleeves
    • Mini-length hem, form-hugging fit
    • Motorcycle and eagle graphic
    • Script that reads, "American Motorcycles Road Lifestyle 1974"
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1445

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sight To See V-Neck Slip Dress

    You'll be a sight to see in this casual slip dress perfect for dinner and drinks with your bae! It features a sleeveless v-neck, bungee spaghetti straps, a curve-hugging silhouette, and a short-length hem.  Style with earrings and heels to complete the look!

    Fit & Features

    • Sleeveless v-neck
    • Bust lining
    • Bungee spaghetti straps
    • Curve-hugging silhouette
    • Short-length hem
    • Texture knit design, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4840

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Head-Turning Chic Marble Print Midi Dress

    Make heads turn in this eye-catching chic bodycon midi dress! It features a sleeveless square neckline, spaghetti straps, bold front and back waist cutouts, ruched detailing down the side seams, and a midi-length, curve-hugging silhouette. The stretchy knit fabric features an all-over abstract marble print pattern for a trendy vibe. Complete the look with clear heels.

     Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Front and back waist cutouts
    • Ruching down the side seams
    • Midi-length hem, fitted bodycon silhouette
    • Abstract marble print pattern
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4837

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Weekend Vibes Ribbed Knit Mini Dress

    This cute and cozy ribbed knit mini dress is perf for your weekend plans! It features a crew neckline, long fitted sleeves, ruched detailing down the side seams, and a short, curve-hugging silhouette. The soft ribbed knit fabric offers plenty of stretch. Style with knee-high boots to grab coffee with your friends.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Ruching down the sides
    • Mini-length hem, fitted bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4839

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Style Strappy Back Midi Dress

    Simple yet so alluring, you'll love the sultry style of this strappy back midi dress. It features a sleeveless V-neckline, spaghetti straps that lead to an open back with cross-back lace-up straps, a midi-length hem, and a bodycon silhouette that will hug your natural curves. The ribbed knit fabric offers plenty of stretch. Complete your look with clear heels and a chic handbag.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Open back, cross-back lace-up straps, tie closure
    • Midi-length hem
    • Bodycon silhouette
    • Ribbed knit fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4835

    Category Name: Casual Dresses

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Color Me Pretty Ombre Midi Dress

    Give your closet some pretty color with this ombre knit midi dress perfect for dressing up! The dress features a sleeveless scoop neck, sleek spaghetti straps, an open lace-up back with tie closure, a bodycon silhouette, and an asymmetrical side slit cutout to showcase some chic strappy heels.

    Fit & Features

    • Sleeveless scoop neck, spaghetti straps
    • Open lace-up back, tie closure
    • Bodycon silhouette
    • Asymmetrical side slit cutout
    • Midi-length hem
    • Ombre lined knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4825

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Back Of My Mind Crepe Slip Dress

    You'll be unforgettable once they see you in this crepe slip dress perfect for casual parties and celebrations! It features a sleeveless V-neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the midi-length hem. Style with simple hoop earrings to complete the look!

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Form-hugging silhouette
    • Front slit accent
    • Midi-length hem
    • Crepe fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4826

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take A Trip Sweater Halter Dress

    Taking a trip somewhere fab? You're gonna need this sweater halter dress perfect for looking chic on the go! It features a sleeveless bodice, cross straps with neck-tie closure, a bodycon silhouette, and a mini-length hem. Complete the look in linear earrings.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless halter neck
    • Cross straps, neck-tie closure
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1605

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Abstract Idea Mesh Printed Dress

    Wear your art! This abstract mesh mini dress features a sleeveless square neck, adjustable spaghetti straps, front cutouts with rhinestone button accents, side ruched seams, and a bodycon silhouette. Complete the look in glitzy heels and earrings.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Front cutouts with rhinestone button accents
    • Side ruched seams
    • Bodycon, mini-length hem
    • Abstract print, lined-mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4824

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mesmerizing Swirl Mesh Midi Dress

    Captivate the room with your unique style! Unveil this swirl print midi dress featuring a sleeveless V-neckline with sleek spaghetti straps, a bodycon silhouette, and an asymmetrical hem with a side slit cutout. Complete the look in strappy heels for a birthday party.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Asymmetrical midi hem, side slit cutout
    • Swirl print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4823

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrap It Up Cable Knit Sweater Dress

    Wrap yourself up in style this season! Cue compliments whenever you're in this cable knit sweater midi dress featuring long balloon sleeves, a v-neckline, and a surplice bodice with a tie-front waist belt and a bodycon silhouette. Style with pointed-toe booties to complete the look!

    Fit & Features

    • Long balloon sleeves
    • V-neckline
    • Surplice bodice
    • Tie-front waist belt
    • Bodycon silhouette
    • Midi-length hem
    • Cable knit fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05102-4818

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wear Your Art Striped Midi Dress

    Wear this fine work of art and every eye will be on you! This marble striped midi dress features long sleeves, front and back v-necklines, a bodycon silhouette, and a tie-front waist. Complete the look in PVC mules for a casual lunch!

    Fit & Features

    • Long sleeves
    • Front and back v-necklines
    • Bodycon silhouette
    • Tie-front waist
    • Midi-length hem
    • Marble striped print, stretch-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4821

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Marvelous Mod Mesh Short Dress

    So marvelously mod, this marble print mesh dress has entered the chat. It features a sleeveless square neckline, spaghetti straps, and side ruched seams to accentuate your curves along the bodycon silhouette. Complete the look in chunky platform heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Marble print, mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4819

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shape Of Me Backless Mini Dress

    You'll fall in love with the shape of your curves in this body-hugging mini dress perfect for bachelorettes or going wine-tasting! It features a sleeveless V-neck, bungee spaghetti straps, and a backless design with a lower ruched seam to accentuate your assets on the bodycon silhouette. Complete the look in platform wedges.

    Fit & Features

    • Sleeveless V-neck
    • Bungee spaghetti straps
    • Backless design, lower ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Brushed double-lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5026

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale