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.

  • Sway With Me Fringe Mini Dress

    Add a little sway to your step in this cute mini dress! 

    Fits & Features

    • Adjustable Spaghetti Straps 
    • Back Zipper With Hook & Eye Closure 
    • Mini Length Silhouette I Ruffle Hem 
    • Subtle Fringe Detailing Along Square Neck, Bodice, & Skirt 
    • Woven Fabric With Knit Lining 
    • Minimal Stretch 

    Style Number/Barcode: 05101-0719

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep It Chic Mini Dress

    Keep it simple & chic in this perf LBD! Dress it up with some strappy mules or down with a jean jacket and a casual slip on sneaker.

    Fit & Features

    • Turtleneck
    • Tank-like shoulder straps
    • Short, flowy fit
    • Crepe fabric
    • Plenty of stretch

    Style Number/Barcode: 06001-2487

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Eyelet Breeze Sleeveless Skater Dress

    Spring into the season with this twirl-worthy skater dress! Throw on some pumps and dainty deets to complete a brunch-ready look! 

    Fit & Features 

    • V-Neckline 
    • Spaghetti Straps 
    • Floral Eyelet Design 
    • Skater Silhouette
    • Lined Lightweight Woven Fabric
    • Relaxed Fit 
    • Minimal Stretch 

     


    Style Number/Barcode: 05102-0599

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Get Drawn In Mini Dress

    Get drawn into this must-have dress! Pair this mini dress with wedges and hoops for a head-turning look!

    Fit & Features

    • V-Neckline
    • Spaghetti Straps
    • Ruched Drawstring Center 
    • Lined Ribbed Fabric
    • Form Hugging Fit
    • Moderate Stretch 

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

    Style Number/Barcode: 05102-0598

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get A Move On Crepe Midi Dress

    You need to get a move on with making those GNO plans with your girlfriends! Make sure you pick up this party-ready dress and elevate your style with some bold earrings!

    Fits & Features

    • Spaghetti Straps 
    • Scoop Neckline 
    • Midi Length Silhouette I Front Slit 
    • Crepe Fabric 
    • Form Hugging Fit I Plenty Of Stretch 
    • Zipper Not Featured

    Style Number/Barcode: 05103-0851

    Category Name: Casual Dresses

    Price: $13.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ruffle Square Neck Smocked Midi Dress

    Show off your figure in this body-lovin' midi dress! Add a cute pair of heels to level up your 'fit. 

    Fits & Features 

    • Short Sleeves I Elastic Shoulders & Cuffs
    • Square Neckline 
    • Tiered Ruffle Trim Along The Bodice & Skirt 
    • Midi Length Silhouette I Ruffle Hem
    • Smocking All Over
    • Woven Fabric 
    • Form Hugging Fit I Plenty Of Stretch 

    Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0597

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Off Shoulder Puff Sleeve Mini Dress

    With puff sleeves and an off-shoulder neckline, you'll be making a trendy and stylish statement in this romantic little number! 

    Fits & Features 

    • Off Shoulder Neckline I No-Slip Interior Slip 
    • Puff Long Sleeves With Ruffle Accents At The Cuffs & Shoulders
    • Smocked Back I Zipper With Hook & Eye Closure
    • Mini Length Silhouette 
    • Woven Fabric I Smooth Knit Lining 
    • Ties At The Hem 
    • Relaxed Fit I Minimal Stretch 

    Style Number/Barcode: 05102-0596

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic And Captivating Mesh Maxi Dress

    Keep it chic and captivating with a mesh dress that wows! The dress features a sleeveless square neckline, adjustable spaghetti straps, a ruched drawstring at the hem, a high side slit, and a mini length lining with a sheer mesh maxi-length hem. Complete look with rhinestone heels. 

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps 
    • Ruched drawstring at the hem 
    • High side slit
    • Mini length lining, maxi-length hem
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0594

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Into The Ruched Mini Dress

    Get into this ruched trend girl! Pair this curve-hugging mini dress with glitzy pumps and a statement clutch! 

    Fit & Features

    • Plunging Wrap V-Neckline  
    • Spaghetti Straps 
    • Ruched Drawstring Seam 
    • Lined Smooth Knit Fabric 
    • Curve Hugging Fit 
    • Moderate Stretch 


    Style Number/Barcode: 05102-0593

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Start Fresh Ruffle And Ruched Mini Dress

    It's time to refresh your wardrobe with this adorable mini dress! It features spaghetti straps, a ruffled V neckline, center ruching, and a short, curve-hugging fit. The lined knit fabric offers plenty of stretch for comfortable wear. Accessorize your look with cat-eye sunglasses and heeled mules.

    Fit & Features

    • Spaghetti straps
    • Ruffled V neckline
    • Ruching down the center front
    • Mini-length silhouette
    • Form-hugging fit
    • Fully lined knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-0591

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off Shoulder Ruffle Mini Dress

    Pretty layered ruffles and a sweetheart neckline are just a few of the fab details on this cute mini dress! 

    Fits & Features

    • Off Shoulder Short Sleeves With Puff & Ruffle Accents 
    • Sweetheart Neckline With No-Slip Interior Strip I Padded Bust 
    • Back Zip With Hook & Eye Closure 
    • Cut Out At The Center Waist 
    • Mini Length I Ruched Skirt I Layered Ruffle Hem
    • Woven Fabric I Fully Lined  
    • Minimal Stretch

     

    Blue Dress: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    White Dress: Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0753

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty And Chic Paisley Printed Mini Dress

    Showcase a pretty and chic vibe in this on-trend paisley printed mini dress. It features a sleeveless V-neckline, a tie accent at the bust, ruffle detailed shoulder straps, and a mini-length, curve-hugging silhouette. Style this dress with wedges for weekend brunch with the girls.

    Fit & Features

    • Sleeveless V-neckline
    • Tie-front at the bust
    • Ruffled shoulder straps
    • Smocked back
    • Short, form-hugging fit
    • Paisley printed chiffon fabric
    • Runs true to size

    Style Number/Barcode: 05102-0571

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Romance Chiffon Floral Mini Dress

    It's a match babe! Add this dreamy dress to cart and you'll be sweeping them off their feet! 

    Fits & Features 

    • Sweetheart Neckline I Lace-Up Bodice 
    • Square Back With Zipper & Hook And Eye Closure 
    • Sheer Long Sleeves I Elastic Cuffs
    • Mini Length Silhouette With Self Ties At The Front
    • Ruffle-Trim  At Shoulders, Neckline, Hem 
    • Lined Chiffon Fabric With Romantic Floral Print
    • Form Flattering Fit I Minimal Stretch 

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0707

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Knit Girl Turtleneck Mini Dress

    You'll be a major it girl in this adorable ribbed knit mini dress! It features a cozy turtleneck, long fitted sleeves, and a mini length, curve-hugging silhouette. This dress is perf for a holiday party, styled with thigh-high boots for a chic look.

    Fit & Features

    • Turtleneck
    • Long fitted sleeves
    • Short, form-hugging fit
    • Ribbed knit fabric
    • Moderate stretch

    Style Number/Barcode: 05102-0589

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dreamy Vacay Vibes Midi Dress

    Get those dreamy vacay vibes in this stunning midi dress! It features a sleeveless V neckline, adjustable spaghetti straps, an asymmetric mid-length hem with a side slit, and a curve-hugging silhouette. The knit fabric has a gorgeous all-over tropical floral print. Complete the look with strappy sandals and some cute sunnies.

    Fit & Features

    • V neckline
    • Adjustable spaghetti straps
    • Asymmetric mid-length hem
    • Side slit
    • Form-hugging fit
    • Knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05102-0586

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty In Plaid Knit Mini Dress

    Look oh-so-pretty in plaid in this adorable knit mini dress! Featuring a trendy square neckline and a short, form-hugging fit, this dress is a fall must-have. Pair with strappy heels and layer on a chic faux leather jacket for a date night.

    Fit & Features

    • Spaghetti straps
    • Square neck and back
    • Mini length silhouette
    • Form-hugging fit
    • Plaid print
    • Knit fabric

    Style Number/Barcode: 05102-0585

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take Me Away Tropical Tie-Dye Maxi Dress

    Get carried away in this laid-back maxi dress! The dress features a tropical tie-dye print, a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a smocked waist, and a maxi-length silhouette with a high side slit. 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

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, cross at back 
    • Smocked waist
    • Maxi length silhouette, high side slit
    • Smooth knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-0576

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Second Take Denim Lace-Up Mini Dress

    Make them all take a second look at you in this stunning mini dress! The dress features a sleeveless square neckline, a backless design with a lace-up back, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Backless, lace-up straps
    • Mini length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

     

    Style Number/Barcode: 05102-0577

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Zipper Key Hole Ribbed Knit Mini Dress

    This ribbed mini dress features a zippered keyhole that adds an element of sexiness! We love to see you pairing this look with some booties or heels! 

    Fits & Features

    • Ribbed Crew Neck 
    • Front Zipper Opens To Keyhole Cut Out 
    • Mini Length Silhouette
    • Ribbed Fabric
    • Form Hugging Fit I Plenty Of Stretch 

    Style Number/Barcode: 05102-0574

    Category Name: Casual Dresses

    Price: $10.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleeveless Crossback Floral Ruffled Mini Dress

    Get crossed up in a floral mini dress. Make a statement this season in a mini dress that features a charming floral print, a scoop neckline, and spaghetti straps. The back features an open back design with cross-strap ties. The relaxed fit waist features a ruffled hem and leads to a mini length silhouette with matching ruffled hem. The dress is composed of a lightweight woven fabric that offers a relaxed fit with a slight stretch.  Complete your look with neutral-hued wedges and a floppy hat. 

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Floral print 
    • X-back 
    • Ruffles 
    • Mini length silhouette
    • Lightweight woven fabric, slight stretch 

    Style Number/Barcode: 05102-0581

    Category Name: Casual Dresses

    Price: $15.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Getaway Sleeveless Asymmetrical Ruched Midi Dress

    Head to the tropics in this midi dress that brings a tropical burst of color. This vacation-ready dress features a sleeveless bodice, a plunging V-neckline and adjustable spaghetti straps that lead to an X-back design. The relaxed fit waist leads to a midi length silhouette with a ruched side seam and an asymmetrical high slit to show off a hint of skin. The all-over tropical print features bright hues that perfectly complement the neutral background. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete your look with a pair of heels and golden hoop earrings. 

    Fit & Features

    • Plunging V-neckline
    • Adjustable spaghetti straps
    • X-back 
    • Midi length silhouette 
    • Tropical print
    • Asymmetrical high side slit
    • Form hugging fit

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

    Style Number/Barcode: 05102-0579

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty Vibes Off The Shoulder Floral Mini Dress

    Channel those flirty vibes with a pretty mini dress! The vibrant dress features an off-the-shoulder neckline with short puff sleeves, a mini tie-front, a ditsy floral print, a smocked back, and a mini-length silhouette. The dress is composed of a crepe fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules. 

    Fit & Features

    • Off the shoulder neckline, short puff sleeves
    • Mini tie-front smocked back
    • Ditsy floral print
    • Mini length silhouette 
    • Crinkle-crepe fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0573

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lace Up Sweetheart Neck Denim Mini Dress

    Lace-up in classic denim to impress. This denim dress is designed with a sweetheart neckline, a corset-like bodice complemented with lace-up straps for a customized fit, and adjustable spaghetti straps. The curve-hugging mini length dress is composed of breathable medium-wash denim fabric. Pair this head-turning dress with statement earrings and bold heels to dress up this look. 

    Fit & Features

    • Sweetheart neckline
    • Corset-like seams at bodice
    • Lace-up ties at center of the bodice
    • Adjustable spaghetti straps
    • Mini length silhouette 
    • Denim fabric 

    Style Number/Barcode: 05102-0565

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Mesmerizing Beauty Floral Mini Dress

    Showcase your mesmerizing beauty in this chic floral mini dress. It features a sleeveless wrap-front V-neckline, spaghetti straps, a wrap skirt with an asymmetric hem, and a curve-hugging silhouette. Style this dress with clear heels and a sleek clutch for a summer date night.

    Fit & Features

    • Sleeveless wrap-front V-neckline
    • Spaghetti straps
    • Wrap skirt, asymmetric hem
    • Form-hugging fit
    • Floral printed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-0567

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free