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.

  • Viper Vixen Snake Print Mini Dress

    You'll be a total stylish vixen in this trendy snake print mini dress! It features a flattering square neckline and a curve-hugging fit. Keep it chic with some dazzling duster earrings and heels for a night out.

    Fit & Features

    • Spaghetti straps
    • Square neck and back
    • Short, form-hugging fit
    • All over snake print
    • Knit fabric

    Style Number/Barcode: 05102-0837

    Category Name: Casual Dresses

    Price: $10.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Twist of Glamour Brushed Knit Mini Dress

    Bring a twist of glam to this mini dress! The dress features a plunging V-neckline with a twist knot accent, a midriff keyhole, and a mini length silhouette with an envelope hem. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules. 

    Fit & Features

    • V-neckline
    • Twist-knot accent at the center of the bodice
    • Long sleeves
    • Mini length silhouette with an envelope hem 
    • Brushed knit fabric
    • Form hugging fit, moderate stretch

    Style Number/Barcode: 05102-0830

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylishly Ruched Ribbed Knit Mini Dress

    This stylish ruched ribbed knit mini is the perf everyday dress you need in your closet! Featuring trendy ruched detailing and double ties at each side, this dress can be worn as a mini or a midi. Pair with some sleek booties for your new fave fall 'fit.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Ruched detailing
    • Double ties at each side
    • Ribbed knit fabric
    • Form-hugging fit

    Style Number/Barcode: 05102-0838

    Category Name: Casual Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Ribbed Knit Basic Mini Dress

    Basic yet still so chic, this ribbed knit mini dress is an everyday essential! It features a doubled ribbed knit fabric for comfortable wear and a form-hugging fit to enhance your curves. Pair this adorable dress with some chunky sneakers to get that effortless vibe.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Doubled ribbed knit fabric

    Style Number/Barcode: 05102-0841

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feelin' Fresh In Floral Ruffle Hem Mini Dress

    Get a fresh look in this gorg floral ruffle hem mini dress! It features woven tie shoulder straps and cute ruffle detail at the hem for a fun and flirty vibe. A must-have for your next backyard bbq, style it up with clear slide on mules and sleek gold hoop earrings.

    Fit & Features

    • Tie shoulder straps
    • Slight sweetheart neckline
    • Partially smocked back with a hidden zipper closure
    • Short ruffle hem
    • Floral print
    • Woven fabric

     

    Model is 5'9" with a 34" bust,  24" waist and 35.5" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0833

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tie-Dye Satin Cowl Neck Mini Dress

    Keep it chic in a tie-dye dress to brighten your cute summer fits girl! The dress features a sleeveless bodice, a cowl neckline, sleek spaghetti straps, and a pretty pastel tie-dye print. Complete your look with a chic scrunchie and a dainty charm necklace.

    Fit & Features

    • Sleeveless bodice
    • Cowl neckline
    • Tie-dye print
    • Mini length silhouette
    • Satin fabric
    • Relaxed fit 

     

    Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0812

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Romanced in Ruffles A-Line Mini Dress

    Fall for this ruffled dress as you have em' fall for you girl! Step out for a day-date in this mini dress that features a ruffled off the shoulder neckline with a sweetheart bust, a cute tie-front accent, and an A-line mini length silhouette with ruffled hem. Complete your look with sunnies and wedges. 

    Fit & Features

    • Ruffled off the shoulder neckline
    • Sweetheart bust with tie-front accent
    • Mini length A-line silhouette
    • Ruffled hem 
    • Form hugging fit

     

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0811

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Double Drawstring Floral Mini Dress

    Bring the charm in a floral dress that brings a sweet vibe this season. The mini dress features a sweetheart neckline, adjustable spaghetti straps, and a floral print. Complete your look with cute cork wedges and dainty anklets. 

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Floral print
    • Drawstring at the side seams
    • Mini length silhouette
    • Form hugging fit

     

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small. 

    Style Number/Barcode: 05101-0878

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flowy Fall Feels Off The Shoulder Tunic

    Get those fall feels in this adorable flowy off the shoulder tunic! It features long flowy flared sleeves and a cinched elastic waist. The lightweight woven fabric features a gorgeous allover bohemian floral print. Pair this tunic with some heeled mules for the perfect date night look.

    Fit & Features

    • Off the shoulder boat neckline
    • Long flowy flared sleeves
    • Cinched elastic waist
    • Short, ruffle hem
    • Woven fabric with allover floral print

    Style Number/Barcode: 06003-1017

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Belted Sophistication Sleeveless Mini Dress

    Keep it chic in a belted dress that elevates you to a sophisticated and polished look. The dress features a sleeveless square neckline, spaghetti straps, side slit, and a belted waist with a rectangular buckle. Complete look with clear heels. 

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Belted waist with rectangular buckle
    • Mini length silhouette
    • Side slit
    • Ribbed knit fabric

     

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06005-0684

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Charm Puff Sleeve Floral Mini Dress

    Keep it charming and chic in a floral mini dress that keeps you looking gorge! The mini dress features an elastic square neckline, short puff sleeves, a ditsy floral print, and a mini length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules. 

    Fit & Features

    • Square neckline 
    • Short puff sleeves
    • Ditsy floral print 
    • Mini length silhouette
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch 
    • Fits true to size

    Style Number/Barcode: 05102-0787

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blooming Floral Knit Maxi Dress

    Showcase your beauty as the best-dressed wedding guest in this blooming floral knit maxi dress! Designed with a gorgeous floral print design, it features a sleeveless V-neckline, spaghetti straps that lead to a bold open back with a lace-up strappy design, a thigh-high front slit to show off your heels, and a slim-fit silhouette. Complete your look with sleek hoop earrings.

    Fit & Features

    • Floral printed knit fabric
    • V-neckline, spaghetti straps
    • Open back, cross-back lace-up straps
    • Fitted floor-length skirt
    • High front slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05101-0851

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Vibes Smocked Mini Dress

    Channel those floral vibes with a smocked mini dress that nails those lowkey vibes just right! The dress features a sleeveless square neckline, spaghetti straps, a floral print, a mini-length silhouette, and a smocked body throughout. The dress offers a form-hugging fit with a moderate stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Floral print
    • Mini length silhouette with ruffled hem
    • Smocked fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0802

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Fierce Ribbed Knit Mini Dress

    Keep it fab and fierce in a mini dress that keeps your look on point! The ribbed mini dress features a plunging sweetheart neckline, bust seams at the cups, adjustable spaghetti straps, and composed of a form-hugging ribbed knit fabric. Complete your look with hoop earrings and wedge heels. 

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps 
    • Bust seams at the cups
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 

     

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0792

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Can't Live Without Glam Ruched Mini Dress

    Channel a glam look with a mini dress that showcases your fab taste! The dress features a sleeveless V-neckline, spaghetti straps, a backless design, a ruched body, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules. 

    Fit & Features

    • Sleeveless V-neckline
    • Backless
    • Spaghetti straps 
    • Ruched body
    • Mini-length silhouette
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05103-2928

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stripe It Down Ribbed Button Down Midi Dress

    Keep it stunning in a striped dress that wows. Step out for brunch in this midi dress that features an off the shoulder neckline with a sweetheart bust, short sleeves, a button-down front, and narrow horizontal stripes. Complete your look with strappy mules and sleek hoops. 

    Fit & Features

    • Off the shoulder neckline
    • Sweetheart bust
    • Short sleeves
    • Button-down front
    • Narrow horizontal stripes
    • Midi length silhouette with center front slit
    • Ribbed knit fabric, form-hugging fit


    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0795

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfect Look Plaid Knit Mini Dress

    Get the perfect look for date night in this adorable plaid knit mini dress! It features a square neckline and a mini length, curve-hugging silhouette. Pair this chic dress with heeled booties and sleek hoop earrings.

    Fit & Features

    • Spaghetti straps
    • Square neck and back
    • Short, form-hugging fit
    • Allover plaid print
    • Knit fabric

    Style Number/Barcode: 05102-0801

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • For The Love of Florals Mini Dress

    Show off your love of florals in this frilly and flirty mini dress! Throw on your favorite wedges and dainty pieces for a brunch ready look!

    Fit & Features 

    • Sweetheart Neckline
    • Sheer Chiffon Long Sleeves
    • Smocked Bodice 
    • Ruched Drawstring 
    • Daisy Floral Print
    • Smocked and Chiffon Fabric 

     

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small.  

     


    Style Number/Barcode: 05101-0845

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fresh As A Daisy Mini Dress

    Keep your look fresh as a daisy this season with a pretty floral mini that brings the flutters! Pair this must-have mini dress with a pair of strappy heels for a head-turning look! 

    Fit & Features 

    • Square Neckline 
    • Bungee Straps 
    • Embroidered Daisy Print 
    • Lined Mesh Fabric 
    • Mini Length Silhouette 
    • Form Hugging Fit 

     

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small. 

     

     


    Style Number/Barcode: 05102-0791

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Good Vibes Tie-Dye Mini Dress

    Bring the good vibes to your summer style with this adorable tie-dye mini dress! It features a sleeveless sweetheart neckline, spaghetti straps, front ruched detailing, and a mini-length, curve-hugging silhouette. Complete the look with clear heels.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Ruching
    • Short, form-hugging fit
    • Mesh fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-0784

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Center Of Attention Mini Dress

    All eyes will be on you in this casual-chic mini dress. It features a wide sweetheart neckline, short sleeves, seam details that run down the center, ruching, and a mini-length, curve-hugging silhouette. Style this dress with clear heels and a trendy shoulder bag.

    Fit & Features

    • Wide sweetheart neckline
    • Short sleeves
    • Center seam details
    • Ruching
    • Short, form-hugging fit
    • Ribbed knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0786

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bring The Heat Maxi Dress

    Bring the heat to your next vacay in this tropical printed maxi dress! It features an off-the-shoulder neckline, a flowy overlay with short sleeves, a high waist, a floor-length silhouette with a relaxed fit, and a thigh-high side slit. The all-over tropical palm leaf print is perf for your summer getaway! Style this dress with strappy sandals.

    Fit & Features

    • Off-the-shoulder neckline
    • Flowy overlay with short sleeves
    • High waist
    • Floor-length silhouette, relaxed fit, high side slit
    • Knit fabric, tropical palm leaf print
    • Runs true to size

    Style Number/Barcode: 05102-0778

    Category Name: Casual Dresses

    Price: $22.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim and Lace Open Back Mini Dress

    Give our denim dress a glam touch with a little lace. The mini dress features a plunging v-neckline with lace trim, adjustable spaghetti straps that offer support, and a bold open back with bar strap ties. Complete your head-turning look with cork heels. 

    Fit & Features

    • Sleeveless v-neckline with lace trim
    • Adjustable spaghetti straps
    • Open back with bar strap ties
    • Mini length hem with lace trim
    • Denim fabric 
    • Form hugging fit 


    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0774

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rose Darling Sweetheart Neck Mini Dress

    Enchant in this gorg mini dress that will make hearts flutter! The dress features a sweet ditsy rose print, a sweetheart neckline, a tie-front at the bust, short sleeves, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Style dress with dainty heart charm necklaces and mules for the perfect brunch date with bae.

    Fit & Features

    • Sweetheart neckline
    • Tie-front at the bust
    • Short sleeves
    • Ditsy floral print
    • Mini-length silhouette, form-hugging fit
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0775

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale