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.

  • Feelin' Trendy Tie Dye Midi Dress

    This trendy tie dye knit midi dress is ready for you to style up! Featuring a sleeveless high neckline and a curve-hugging mid-length silhouette, you can easily take this dress from day to night. Layer on a denim jacket and some chunky sneakers for a casual-chic date look.

    Fit & Features

    • High rounded neckline
    • Mid-length silhouette
    • Form-hugging fit
    • Tie dye print
    • Knit fabric

     

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

    Style Number/Barcode: 05102-0866

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Dream Tie Dye Ruched Mini Dress

    You'll look like such a dream in this trendy tie dye mini dress! It features ruched detailing with side ties and a form-fitting style that will hug your curves. Pair this dress with some sleek gold hoops and chunky sneakers for that perf everyday vibe.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Ruched detailing
    • Side ties at hem
    • Short, form-hugging fit
    • Tie dye print
    • Knit fabric

    Style Number/Barcode: 05102-0867

    Category Name: Casual Dresses

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feelin' Basic V Neck Knit Mini Dress

    Sometimes it's a good thing to be basic! This knit mini dress features a deep V neckline and a short, flattering, curve-hugging fit. Keep it casual with some chunky sneakers and gold hoops for a day date with bae.

    Fit & Features

    • Spaghetti straps
    • V neckline
    • Square back
    • Mini length silhouette
    • Double-lined knit fabric

    Style Number/Barcode: 05102-0880

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tie Dye Frenzy Brushed Knit Mini Dress

    Make a splash in a tie-dye dress that brings the style to your next outing! The mini dress features a round neckline, a slash accent on the left side of the bodice, and a tie-dye print. Style this fun print with chunky sneakers and sleek hoops. 

    Fit & Features

    • Round neckline
    • Slashed detail on the left side of the bodice
    • Short sleeves
    • Tie-dye print
    • Mini length silhouette
    • Form hugging fit

    Style Number/Barcode: 06002-0581

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • A Chic Vibe Mini Sweater Dress

    Get a major chic vibe in this adorable sweater mini dress! It features a trendy mock neckline, long fitted sleeves, and a short form-hugging fit with a side slit. Pair this dress with over the knee boots for the perf fall date night look.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves with ribbed hems
    • Short, form-hugging fit
    • Side slit
    • Sweater knit fabric
    • Moderate stretch

    Style Number/Barcode: 06005-0734

    Category Name: Casual Dresses

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tie Front Wrap Mini Sweater Dress

    Get an adorable look perfect for a casual date night in this mini sweater dress! It features a wrap front and back with a front tie detail and a short, curve-hugging fit. Pair the dress with chic thigh-high boots for a gorgeous fall-time vibe.

    Fit & Features

    • Wrap front and back with a V neckline
    • Top tie back detail
    • Long sleeves with ribbed hems
    • Tie front belt
    • Short, form-hugging fit
    • Sweater knit fabric with plenty of stretch

    Style Number/Barcode: 06005-0719

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Off The Shoulder Ribbed Knit Cutout Mini Dress

    Stun in a mini dress that brings sultry appeal with cutout details! The mini dress features an off the shoulder neckline, cutout detail at the bust with matching cutout detail at the midriff, and a mini length silhouette. Complete look with clear mules.

    Fit & Features

    • Off the shoulder neckline 
    • Cutout detail at the bust
    • Cutout detail at the midriff
    • Long sleeves
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit

    Style Number/Barcode: 05102-0864

    Category Name: Casual Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Get On-Trend Tie Dye Knit Mini Dress

    Get on-trend in this adorable tie dye knit mini dress! It features an open back detail with a tie closure and ruched, form-hugging fit to enhance your curves. Pair this dress with chunky sneakers for a casual-chic everyday look.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Open back detail with tie closure
    • Ruched detailing
    • Short, form-hugging fit
    • Tie dye knit fabric

    Style Number/Barcode: 05102-0861

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Good Vibes Basic Ribbed Knit Maxi Dress

    Bring the good vibes in a maxi dress that can be dressed up for a chic day out. The dress features a scoop neckline, sleek bungee straps, and a maxi length silhouette with a high side slit. Style dress with chunky sneakers and sleek hoops.

    Fit & Features

    • Sleeveless scoop neckline
    • Bungee spaghetti straps
    • Maxi length silhouette 
    • High side slit
    • Ribbed knit fabric
    • Form hugging fit

    Style Number/Barcode: 05102-0863

    Category Name: Casual Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep Knit Cozy Mini Sweater Dress

    Keep your look cozy and chic in this mini sweater knit dress! It features a trendy mock neckline, long fitted sleeves, and a short, curve-hugging silhouette. Pair this dress with thigh-high boots for an adorable date night 'fit.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Front seam detailing
    • Short, form-hugging fit
    • Sweater knit fabric with moderate stretch

    Style Number/Barcode: 06005-0717

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Sweetheart Ribbed Mini Dress

    Show off your sweet side in a dress that brings the charm. The dress features a plunging sweetheart neckline, long sleeves, and a mini length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with faux fur jacket. 

    Fit & Features

    • Sweetheart neckline
    • Long sleeves
    • Mini length silhouette
    • Ribbed knit fabric 
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 06005-0707

    Category Name: Casual Dresses

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cozy Knit Long Sleeve Tunic

    You'll be so cozy and chic in this adorable knit tunic! It features a ribbed crew neckline, long sleeves with ribbed hems, a low V back with a strap detail, side slits, and a relaxed and comfortable fit. Pair this tunic with leggings and ankle booties or wear it as a dress with thigh-high boots.

    Fit & Features

    • Ribbed crew neckline
    • Long sleeves with ribbed hems
    • Low V back with strap detail
    • Side slits
    • Relaxed fit
    • Knit fabric with minimal stretch

    Style Number/Barcode: 06005-0716

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keeping Knit Casual Off the Shoulder Ribbed Mini Dress

    Keep it casual and fab in a mini dress that is so easy to style for your next day out with the squad. The dress features an off the shoulder neckline with a popover detail and composed of a ribbed knit fabric that enhances curves with a moderate stretch. Complete your casual outfit with ankle booties and hoop earrings. 

    Fit & Features

    • Off the shoulder neckline
    • Popover detail 
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch

    Style Number/Barcode: 05102-0859

    Category Name: Casual Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • All About Knit Mock Neck Mini Dress

    You'll be totally all about this chic mock neck mini dress! Featuring long fitted sleeves and a curve-hugging fit, this dress is perfect for the fall season. Pair with gold hoop earrings and chunky sneakers for that fab everyday 'fit.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Knit fabric

    Style Number/Barcode: 05102-0855

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Every Day Basic Knit Mini Dress

    Keep cute in a basic mini dress that is perfect for dressing up or dressing down for a casual day out. The dress features a sleeveless square neckline, tank-like straps that offer support,  and a mini length silhouette. Complete your casually cute outfit with sneakers and door knocker earrings. 

    Fit & Features

    • Sleeveless square neckline
    • Tank-like straps
    • Mini length silhouette
    • Knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0854

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stunning In Florals Sleeveless Midi Dress

    Be a stylish stunner in this gorg floral midi dress! Step out for brunch with the squad in this colorful midi dress. It features a sleeveless bodice, adjustable spaghetti straps that cross in the back, a V neckline, side ruched detailing, and an asymmetrical hem. Complete look with wedges.

    Fit & Features

    • Sleeveless v-neckline
    • Adjustable spaghetti straps
    • Crossback straps
    • Floral print
    • Ruched side seam
    • Midi length silhouette with asymmetrical hem 
    • Form hugging fit, plenty of stretch 

     

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

    Style Number/Barcode: 05102-0292

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Into You Basic Knit Midi Dress

    We're so into this dress that can be dressed up for a date night or keep it casual with layers. The dress features a sleeveless square neckline, tank-straps that offer support, and a curve-hugging midi-length silhouette. Complete look with ankle booties or mules. 

    Fit & Features

    • Sleeveless square neckline
    • Tank straps
    • Midi length silhouette
    • Smooth knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0912

    Category Name: Casual Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • She's A Showstopper Ruched Midi Dress

    Make them stop and stare at this stunning dress that commands attention! The sleek midi dress features a trendy square neckline, sleek bungee straps, and a curve-hugging ruched midi silhouette. Complete your look with duster earrings for your night-out outfit.

    Fit & Features

    • Sleeveless square neckline, bungee straps
    • Strapless bra recommended
    • Side ruched detailing
    • Midi-length bodycon silhouette
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0848

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovin' Knit Basic Midi Dress

    We love a knit dress to keep on trend this season! Throw on this must-have dress for a casual day out. The dress features a trendy square neckline, fitted long sleeves, and a midi length silhouette. Complete look with chunky sneakers for a casual vibe. 

    Fit & Features

    • Square neckline
    • Long sleeves
    • Midi length silhouette 
    • Knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0853

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep It Rosey Slip Midi Dress

    Keep it rosey in this cute slip dress that keeps your look effortlessly pretty! Step out this season in a slip dress that features a pretty floral print, a high side slit and a midi length silhouette. Complete your look with clear heels and fringe earrings. 

    Fit & Features

    • Plunging v-neckline
    • Adjustable spaghetti straps
    • Floral print
    • High side slit
    • Midi length silhouette
    • Lightweight woven fabric
    • Relaxed fit

     

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

    Style Number/Barcode: 05102-0836

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Strapless Tube Tie Dye Midi Dress

    Make a splash in a tie-dye dress that brings some serious summer vibes! Step out for that backyard bbq with the squad in this colorful midi dress. The dress features a strapless tube neckline, a tie-dye print, and a curve-hugging midi-length silhouette. Complete your summer outfit with clear heels. 

    Fit & Features

    • Sleeveless tube neckline
    • Tie-dye pattern
    • Midi length silhouette
    • Form hugging knit fabric
    • Moderate stretch 

     

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

    Style Number/Barcode: 05102-0831

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Open Back High Slit Floral Dress

    Show off your affinity for florals in a dress that creates major head-turning appeal! Step out for brunch with your squad in this pretty in pink dress! The dress features a high round neckline, cap sleeves, a lower back keyhole, and a high side slit. Complete look with clear heels and mini purse.

    Fit & Features

    • High round neckline
    • Cap sleeves
    • Lower back keyhole
    • Floral print 
    • High side slit
    • Midi-length silhouette
    • Lightweight woven fabric

     

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

    Style Number/Barcode: 05102-0834

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Twist Front Ribbed Knit Mini Dress

    Create a fab moment in a twist knot dress! The dress features a V-neckline with a twist knot accent, long sleeves, and a mini length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit. Complete your look with clear mules. 

    Fit & Features

    • V-neckline with twist front accent 
    • Long sleeves 
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit 

    Style Number/Barcode: 06005-0700

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Retro Feels Ruched Tie Dye Mini Dress

    Throw it back in a retro dress that gives us groovy feels. The dress features a sleeveless square neckline, a tie-dye print, and mini length silhouette with ruched drawstrings to customize fit or create an asymmetrical hem. Complete your outfit with trendy block heels and fringe earrings. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Tie-Dye print 
    • Mini length silhouette 
    • Ruched drawstring
    • Smooth knit fabric 

     

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

    Style Number/Barcode: 05102-0845

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance