Casual Dresses

Loading...

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.

  • Sun Kissed Strapless Floral Bodycon Mini Dress

    Bare your sun kissed shoulders on vacay in this strapless mini dress with a statement floral print and flattering bodycon fit that flaunts your curves!

    Fit & Features

    • Mesh fabric, floral print, stretchy knit lining
    • Strapless neckline
    • Bodycon fit
    • Mini-length hem
    • Runs small

    Style Number/Barcode: 05102-6112

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Attract And Allure Marble Print Midi Dress

    Attract and allure in this marble print midi dress that puts your curves on display! It features a high crew neckline, long fitted sleeves, a midi-length hem with a form-hugging silhouette, and an all-over trendy marble print pattern. The sheer mesh fabric includes a full-length sleeveless knit lining. Style this mid-length dress with clear heel mules for a cool-girl vibe for a rooftop bar!

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Midi-length hem, form-hugging fit
    • Marble print, sheer mesh fabric
    • Full-length sleeveless knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5403

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gorgeous Silhouette Sleeveless Bodycon Midi Dress

    Flaunt your gorgeous figure in this midi dress designed with smooth nylon fabric offering plenty of stretch. It features a sleeveless scoop neck and back design, tank straps, and a midi-length bodycon silhouette to showcase your curves.

    Fit & Features

    • Smooth nylon fabric with plenty of stretch
    • Scoop neck and back
    • Tank shoulder straps
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5931

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Abstract Moment Mesh Mock Neck Midi Dress

    Step out in this stylish mesh midi dress and not miss a single moment to have all eyes on you! The knee-length dress features a feminine mock neck with back button closures, fitted sheer long sleeves, and bodycon silhouette with abstract print on mesh fabric. Complete the look with gold hoop earrings for an art gallery opening and dinner downtown!

    Fit & Features

    • Mock neck, back button closures
    • Fitted sheer long sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Abstract print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5294

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Silhouette Midi Sweater Dress

    This curve-hugging sweater dress was made for sunset happy hour! It features a sleeveless V-neckline with a twist-front design, a center cutout under the bust, tank shoulder straps, and a midi-length, form-fitting silhouette with a chic high side slit. Style with classic hoop earrings and clear mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline, twist-front accent
    • Center cutout under the bust
    • Tank shoulder straps
    • Midi-length hem, form-fitting silhouette, high side slit
    • Ribbed sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1462

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Here To Flirt Drop Waist Ruffled Skater Dress

    This adorable skater dress features a ribbed knit top with a sleeveless crew neckline and tank shoulder straps, a trendy V-shaped drop waist, and a tiered ruffled chiffon A-line silhouette for a flirty accent. Style with mules for a date night or sneakers to keep it casual!

    Fit & Features

    • Ribbed knit and chiffon fabrics, moderate stretch
    • Crew neckline, tank shoulder straps
    • V-shaped drop waist
    • Tiered ruffled design
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5910

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Fun Chain Strap Midi Dress

    Perfect for your next getaway, this tropical midi dress is a must to pack in your carry-on! It features a sleeveless square neck, half chain and adjustable spaghetti straps, a bodycon silhouette, and a flirty side slit. the dress is composed of a tropical print slinky-knit fabric with a sewn-in knit lining. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless square neck
    • Half chain, adjustable spaghetti straps
    • Bodycon silhouette
    • Side slit, midi-length hem
    • Tropical print
    • Slinky knit fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5070

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Beauty Strappy Back Knit Midi Dress

    This chic sleeveless midi dress is designed with a jacquard patterned sweater knit fabric and features a square neckline, halter spaghetti straps, and a bold open back with cross-back straps and tie-back straps. The midi-length form-hugging silhouette is detailed with a high front slit.

    Fit & Features

    • Knit fabric with jacquard pattern, moderate stretch
    • Square neckline, halter spaghetti straps
    • Open back, cross-back straps, tie-back straps
    • Contrast seam design at the bodice
    • High front slit
    • Midi-length form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-2227

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spot Me In Leopard Slit Midi Dress

    You can be spotted all season in this leopard print midi dress perfect for a casual lunch or a wine night with friends! It features a sleeveless V-neckline, tank shoulder straps, and a form-hugging, slim silhouette with a flowy slit hem. Complete the look in sleek statement hoop earrings and sandals.

    Fit & Features

    • Sleeveless V-neckline, tank shoulder straps
    • Form-hugging, slim silhouette
    • Front slit
    • Midi-length flowy hem
    • Leopard print
    • Woven non-stretch fabric
    • Runs true to size

    Style Number/Barcode: 05102-4469

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty In Paradise Strappy Cutout Maxi Dress

    You'll be pretty in paradise in this stunning maxi dress for vacation or a bachelorette weekend! The dress features a sleeveless V-neckline, spaghetti straps that lace up along the open back, flirty waist cutouts, and a high front slit along the flowy hem. Complete the look with earrings and clear block heels for a chic style!

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Lace-up open back
    • Waist cutouts, high front slit
    • Maxi-length hem
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4752

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keeping Knit Chic Long Sleeve Midi Dress

    Keep it chic in this knit midi dress boasting an off-the-shoulder neckline and trendy button accents that lead to a flirty slit. Pair with boots.

    Fit & Features

    • Ribbed knit fabrication
    • Off-the-shoulder neckline, foldover accent
    • Long sleeves
    • Snap button accents at the hem
    • High side slit
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 06005-2137

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's The Main Rib Knit Strapless Midi Dress

    Flaunt your look with ease and chicness with this midi dress this season! The knee-length dress features a strapless neckline, a flattering bodycon silhouette, and a fitted maxi-length hem on soft and stretchy rib knit fabric with a short knit lining. Style with the matching bolero and heels for weekend plans!

    Shop Matching Bolero: She's The Main Rib Knit Slouchy Bolero

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Fitted midi-length hem
    • Soft and stretchy
    • Rib knit fabric, short knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5872

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Sweet Floral A-Line Mini Dress

    Sunny sweet will be your vibe in this cute floral mini dress designed with a strapless neckline, ruching, and a hanky hem A-line silhouette.

    Fit & Features

    • Knit fabric, high stretch
    • Small floral print
    • Strapless straight neckline
    • Ruching
    • Drop waist
    • Mini-length hanky hem, A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000008

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Chills Long Sleeve Slit Mini Dress

    Look cute in this mini dress for casual chills with friends or daytime outings! The mini dress features a classic crew neckline, bell long sleeves, a flattering bodycon silhouette, and a flirty front slit along the hem on rib knit fabric. Complete the look with booties and a handbag!

    Fit & Features

    • Bell long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Front slit, mini-length hem
    • Rib knit fabric
    • Minimal stretch
    • Style runs small

    Style Number/Barcode: 05102-5326

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Muse Square Neck Bodycon Mini Dress

    Show off your sleek chic style in this bodycon mini dress featuring a sleeveless square neckline, tank-like shoulder straps, and a short form-hugging silhouette. Style with stiletto heels for a rooftop bar!

    Fit & Features

    • Lined rayon knit fabric, plenty of stretch
    • Square neckline
    • Tank-like shoulder straps
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5970

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Night Out Abstract Print Mesh Midi Dress

    Create a chic vibe to grab drinks with the girls in this airy mesh midi dress designed with a bold abstract print pattern. The dress features a sleeveless mock neckline, tank shoulder straps, ruching at the waist, and a bodycon silhouette to flaunt your curves.

    Fit & Features

    • Sheer mesh fabric with brushed knit lining, plenty of stretch
    • Abstract print
    • Mock neckline
    • Tank shoulder straps
    • Ruched waist
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5929

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Ribbed Knit Long Sleeve Mini Dress

    Make a sleek statement with this long-sleeve mini dress, the epitome of chic simplicity. This figure-hugging silhouette, crafted from a soft ribbed knit fabric, offers both warmth and style. Featuring a high turtleneck for a touch of polished sophistication, this mini dress is perfect for transitioning from day to evening. Layer this ribbed knit mini-dress with an oversized faux leather blazer or stylish trench coat and knee-high boots for the perfected layered outfit.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Mini-length hem
    • Curve-hugging fit
    • Ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-0703

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Modern Stripes Ribbed Knit Long Sleeve Mini Dress

    Capture a modern vibe in this striped rib knit long sleeve mini dress designed with a chic mock neck and flattering bodycon fit. Pair with boots.

    Fit & Features

    • Ribbed knit fabrication
    • Mock neck
    • Fitted long sleeves
    • Multi-stripe pattern
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 06005-2095

    Category Name: Casual Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Fave Cable Knit Long Sleeve Mini Dress

    Cozy up in the cutest cable knit mini dress featuring a V-neckline, a surplice wrap front and back design, and long dolman-style sleeves. The tie-front high waist and form-hugging fit will highlight your curves, making it your fave dress of the season.

    Fit & Features

    • Cable knit fabric with plenty of stretch
    • V-neckline, surplice front and back design
    • Back bar strap
    • Long dolman sleeves
    • Tie-front waist
    • Mini-length form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-2101

    Category Name: Casual Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic And Sleek Knit Off-Shoulder Long Sleeve Midi Dress

    Classic and sleek, this stretchy knit midi dress features an asymmetric off-shoulder neckline with long fitted sleeves, ruching at the waist to accentuate your curves, and a bodycon silhouette. Style with stiletto heels for a chic outing!

    Fit & Features

    • Jersey knit fabric with plenty of stretch
    • Asymmetric off-shoulder neckline
    • Long fitted sleeves
    • Ruched waist
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5977

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Adored Sleeveless Bow Trim Crepe Mini Dress

    Embrace romance in this crepe mini dress that features a sleeveless square neckline with tank-like straps, a charming bow accented trim under the bust, and a flared mini-length hem with an A-line silhouette. Complete your look with sleek flats!

    Fit & Features

    • Crepe fabric with knit lining, moderate stretch
    • Sleeveless square neckline, dart seams
    • Tank-like shoulder straps
    • Bow accented trim under bust
    • Back zipper closure
    • Flared mini-length hem, A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3840

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out And About Long Sleeve Short Dress

    This adorable long sleeve short dress is ideal for those casual days where you're out and about! It features a square neckline with a ruched bust and an adjustable tie-front drawstring, long fitted sleeves, a fitted high waist seam, a short-length hem, and a flowy A-line silhouette. The lined brushed crepe fabric offers plenty of stretch. Style this short-length dress with a chunky knit cardigan and over-the-knee boots for a coffee date!

    Fit & Features

    • Square neckline
    • Ruched bust, tie-front drawstring
    • Long fitted sleeves
    • High waist seam
    • Short-length hem, A-line silhouette
    • Brushed crepe fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5395

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Match My Energy Eyelet Skater Dress

    This adorable dress will have you feeling cute and carefree for any fun plans! The strapless neckline, ruffled skater silhouette, and eyelet print add a touch of playfulness to your everyday look.

    Fit & Features

    • Eyelet fabric, sewn-in knit lining
    • Strapless neckline
    • Strappy back
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000108

    Category Name: Casual Dresses

    Price: $9.97 $65.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Elevated Chic Off-The-Shoulder A-Line Mini Dress

    Elevate any casual day in this off-the-shoulder mini dress! This stunning dress features a twisted bust accent for a trendy touch, an A-line silhouette, and a mini-length hem that creates a flattering fit on the smooth knit-lined fabric. Complete the look with luxe earrings for a dinner party!

    Fit & Features

    • Smooth knit lined fabric, moderate stretch
    • Off-the-shoulder neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5755

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free