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.

  • Natural Beauty Tropical Maxi Dress

    Explore a tropical island looking naturally beautiful in this palm print maxi dress featuring a sleeveless, square neck, halter straps, an open back with tie, bodycon silhouette, and a front twist accent atop a sultry slit. Complete the look in a straw floppy hat.

    Fit & Features

    • Sleeveless, square neck, halter straps
    • Open-back with tie
    • Bodycon silhouette
    • Front twist accent and slit
    • Maxi-length hem
    • Tropical palm print, knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4720

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Color Story Square Neck Short Dress

    Vibrant and bold, who doesn't want to hear the end of this story? This sleeveless tunic top features an on-trend, square neck, bungee spaghetti straps, a color block pattern, and a bodycon silhouette. Complete the look in large hoop earrings.

    Fit & Features

    • Sleeveless, square neck, bungee spaghetti straps
    • Color block pattern
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1317

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • LA Rider Graphic Seam Short Dress

    Born to ride? Cruise through the streets of LA in this graphic short dress featuring cap sleeves, a crew neck, a front script that reads, " Motorcycle/Born to Ride/LA/CA Rider Crew", exposed seam detailing, and a front slit accent along the fitted hem. Complete the look in sleek sunglasses.

    Fit & Features

    • Cap sleeves
    • Crew neck
    • Exposed seam detailing
    • Graphic script that reads, " Motorcycle/Born to Ride/LA/CA Rider Crew"
    • Front slit accent, fitted hem
    • Form-hugging fit, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1318

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Always Alluring Cutout Midi Dress

    Keep your night out look alluring and chic in this sleek knit midi dress. It features a sleeveless asymmetrical one-shoulder neckline with dual spaghetti straps, a ruched side cutout to add a sultry vibe, and a midi-length, curve-hugging silhouette. Style with hoop earrings and your fave mules.

    Fit & Features

    • Sleeveless asymmetrical one-shoulder neckline
    • Dual spaghetti straps
    • Ruched side cutout
    • Midi-length, form-fitting, bodycon silhouette
    • Smooth knit fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4716

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Street Riders Graphic Short Dress

    You're not the average Jane...show your edgy side in this graphic short dress for a night of riding! It features a sleeveless, one-shoulder neckline with chain straps, a cutout accent, and a front graphic script that reads, " The Street Riders/Motorcycle Company", a bodycon silhouette, and a short-length hem. Complete the look in combat boots.

    Fit & Features

    • One-shoulder neckline, chain straps, cutout accent
    • A front graphic script that reads, " The Street Riders/Motorcycle Company"
    • Bodycon silhouette
    • Short-length hem
    • Cotton knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1314

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Timeless Twist One Shoulder Dress

    Bring the allure in this one-shoulder maxi dress featuring a sleeveless bodice, a single spaghetti strap, and a form-hugging silhouette atop an asymmetrical slit hem with a timeless twist accent. Complete the look in dangly earrings and heels.

    Fit & Features

    • Sleeveless, one-shoulder
    • Single spaghetti strap
    • Form-hugging silhouette
    • Twist accent and slit
    • Asymmetrical maxi-length hem
    • Slinky knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4714

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty As A Rose Crew Mini Dress

    Look and feel pretty as a rose in this ditsy floral mini dress featuring a sleeveless crew neck, a bodycon silhouette, and adjustable ties at the hem that let you customize the length. Complete your look in a dainty bracelet for a backyard bbq.

    Fit & Features

    • Sleeveless, crew neck
    • Ruching down the side seams
    • Adjustable ties at the hem
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print
    • Rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4713

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutie In Cap Sleeve Midi Dress

    Cute has never looked so cozy! This rib-knit midi dress is designed with cap sleeves, dual v-necklines, a bodycon silhouette, and a flirty side slit along the hem. Complete the look in sandals for a day date.

    Fit & Features

    • Cap sleeves
    • Dual v-necklines
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4715

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Give A Twirl Linen Skater Dress

    Have your twirl-worthy moment in this linen skater dress perfect for casual parties! It features three-quarter-length puff sleeves with ruffled hems, a square neckline, a babydoll-style seam, a flirty open-back with an elasticized lattice strap, and a short-length hem with a flared-out skater silhouette. Complete the look in this skater dress with strappy stiletto heels.

    Fit & Features

    • Three-quarter-length puff sleeves, ruffled elastic cinched hems
    • Square neckline
    • Babydoll style seam
    • Open-back, elasticized lattice strap
    • Short skater silhouette
    • Plaid linen fabric, lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4717

    Category Name: Casual Dresses

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tending The Blooms Floral Midi Dress

    This floral midi dress needs no gardening skills to keep beautiful! It features a sleeveless cowl neckline, spaghetti straps, a form-hugging silhouette, and a flirty front slit. Complete the look in whimsical butterfly earrings for a garden party!

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Form-hugging silhouette
    • Front slit
    • Midi-length hem
    • Garden floral print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05101-1684

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Find Me In Floral Mini Dress

    They can find you in this floral mini dress wandering the gardens. It features an off-the-shoulder neckline, short-sleeve cuffs, a front bust tie, and a short, curve-hugging fit. Complete the look in platform heels for a day date.

    Fit & Features

    • Off-the-shoulder neckline
    • Short-sleeve cuffs
    • Front bust tie
    • Curve-hugging silhuoette
    • Mini-length hem
    • Floral print, rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4708

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Feels Halter Skater Dress

    Feel flirty in floral! This adorable halter skater dress will add funky freshness to your summer lineup. It features a sleeveless smocked bodice, open-back with elasticized lattice straps, and a flowy short-length hem. Complete the look in strappy heels for a birthday brunch.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • Smocked bodice
    • Open-back, elasticized lattice straps
    • Skater silhouette
    • Flowy short-length hem
    • Floral print, non-stretch woven fabric, knit lining
    • Fits true to size

    Style Number/Barcode: 05102-4707

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Trendsetter Mock Neck Mini Dress

    This adorable mini dress is a must-have for an everyday trendsetter like yourself. It features a sleeveless mock neckline, tank shoulder straps, and a short, form-hugging fit. The soft ribbed knit fabric offers plenty of stretch. Style with a cute shoulder bag and sneakers.

    Fit & Features

    • Sleeveless mock neckline
    • Tank shoulder straps
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4706

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Scene Satin A-Line Dress

    Set the scene for drinks at sunset in this satin a-line dress featuring a sleeveless, scoop neck, spaghetti straps, tie-front bust, and a form-fitting silhouette on marble print fabric. Complete the look in lucite heels.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Tie-front bust
    • Form-fitting, a-line silhouette
    • Mini-length hem
    • Marble print, satin fabric, inner lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4705

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek And Chic Leopard Print Mini Dress

    Elevate your everyday outfits with this sleek and chic satin mini dress. It features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, a flirty short A-line silhouette, and an all-over trendy leopard print pattern. Style with an oversized blazer and strappy mules.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • A-line silhouette
    • Mini-length hem
    • Leopard print
    • Smooth woven satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4701

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Color Story Crepe Mini Dress

    Tell the trendiest color story with this fab mini dress! It features a sleeveless, square neck, spaghetti straps, bodycon silhouette, and a color block pattern. Complete the look in sleek hoop earrings for a lunch date.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Color block pattern
    • Crepe-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4704

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Beach Babe Mini Dress

    This adorable retro floral mini dress will have you looking like a total beach babe! It features a sleeveless V-neckline, spaghetti straps, a short, curve-hugging silhouette, and an all-over bold floral print pattern. The lightweight ribbed knit fabric offers a moderate stretch. Complete the outfit with braided mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Mini-length, form-fitting, bodycon silhouette
    • Floral print
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4700

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sleek Zebra Print Midi Dress

    Keep your look so sleek with a midi dress that levels up your casual outfits! It features a sleeveless V-neckline with a knot-front design, a small keyhole cutout under the bust, spaghetti straps, a midi-length, fitted, A-line sihouette, and a chic front slit. The smooth knit fabric features an all-over zebra print pattern. Stye with strappy mules.

    Fit & Features

    • Sleeveless V-neckline, knot-front design
    • Keyhole cutout under the bust
    • Spaghetti straps
    • Midi-length hem, fitted A-line silhouette
    • High front slit
    • Knit fabric, plenty of stretch
    • Zebra print
    • Runs true to size

    Style Number/Barcode: 05102-4703

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendsetting Icon Mesh Mini Dress

    Show off your trendsetter status in this of-the-moment mini dress. It features a sleeveless square neckline, bungee spaghetti straps that lead to cross-back design, ruching down the side seams, and a short, curve-hugging, bodycon silhouette. The lined mesh fabric features an all-over marble print pattern. Style with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps, cross-back design
    • Ruching down the side seams
    • Mini-length hem, fitted bodycon silhouette
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Marble print
    • Runs true to size

    Style Number/Barcode: 05102-4702

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy-Chic Bodycon Mini Dress

    Showcase a beachy-chic vibe in this curve-hugging bodycon mini dress. It features a sleeveless square neckline, spaghetti straps, ruched detailing down the side seams, and a short, form-fitting silhouette. The stretchy brushed knit fabric features an all-over tropical palm leaf print. Style this dress with espadrille sandals.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down the side seams
    • Mini-length, form-fitting, bodycon silhouette
    • Tropical palm leaf print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4696

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off The Scale Snake Mini Dress

    This snake mini dress will take your style to a new scale! It features a sleeveless square neck with sleek spaghetti straps and side ruched seams to accentuate your curves along the bodycon silhouette. Complete the look in a choker necklace.

    Fit & Features

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

    Style Number/Barcode: 05102-4695

    Category Name: Casual Dresses

    Price: $9.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out Of Office Ruched Mini Dress

    Log off and get ready for a relaxing getaway in this ruched knit mini dress. It features a sleeveless cowl neckline, spaghetti straps, ruching down one side leading to an adjustable drawstring, and a mini-length, asymmetrical hem. The smooth knit fabric features an all-over tropical palm leaf print. Style with espadrille sandals and your favorite shades.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • High waist seam
    • Ruching down one side seam, adjustable drawstring
    • Short, curve-hugging, bodycon silhouette, asymmetrical hem
    • Stretchy knit fabric, tropical palm leaf print
    • Runs true to size

    Style Number/Barcode: 05102-4691

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wildflower Crew Neck Mini Dress

    Wander through the flower fields in this cute mini dress featuring cap sleeves, a crew neck, and adjustable side drawstrings on rib-knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look in caged sandals for a picnic date.

    Fit & Features

    • Cap sleeves, crew neck
    • Adjustable side drawstrings
    • Form-fitting design
    • Mini-length hem
    • Ditsy floral print
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4692

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picnic Perfect Gingham Mini Dress

    This gingham plaid mini dress is picnic-perfect! It features a sleeveless, sweetheart neck with adjustable bust tie and keyhole cutout, spaghetti straps, and a bodycon silhouette on stretchy knit-lined fabric. Complete the look in espadrille wedges for a day date.

    Fit & Features

    • Sleeveless, sweetheart neck, spaghetti straps
    • Adjustable bust tie, keyhole cutout
    • Bodycon silhouette
    • Mini-length hem
    • Gingham plaid print
    • Stretchy knit-lined fabric
    • Fits true to size

    Style Number/Barcode: 05102-4694

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale