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.

  • Floral Chic Mini Dress

    Add some floral chic to your pretty look with this adorable mini dress! It features a sleeveless bodice, tie shoulder spaghetti straps, a sweetheart neckline with a tie front detail, a square back with a hidden zipper and hook and eye closure, a high waist seam, and a flowy A-line skirt. The dress is composed of a woven fabric with a skirt lining, and offers no stretch.

    Style Number/Barcode: 05102-0224

    Category Name: Casual Dresses

    Price: $15.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flow With It Maxi Dress

    Go with the flow of this pretty summer maxi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline, a stretchy smocked square back, a front crochet top with sheer insets at the waist, and a long, floor length flowy maxi skirt with a front high thigh slit. The dress is composed of a linen fabric with no stretch.

    Style Number/Barcode: 05102-0085

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beauty So Bold Floral Mesh Maxi Dress

    Stroll like a bold beauty in this floral mesh maxi dress for any occasion! Its strapless design and curve-hugging fit accentuate your natural beauty, while the flowing maxi hem adds elegant movement.

    Fit & Features

    • Bold floral print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000058

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ruffled And Rowdy Dress

    Dance around and get rowdy in ruffles! This adorable mini dress features a v-neckline with a snap and hook closure. The bodice of this dress is line with a ruffled trim, thick ruffled straps that lead to a low back, with a hidden zipper and a self tie bow. The skirt is adorned with a tiered ruffle effect. The dress is composed of a chiffon style material and offers no stretch yet, a flowy fit and includes a smooth inner lining. Now take a twirl! 

    Style Number/Barcode: 05102-0206

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Color Wheel Striped Mini Dress

    Rendered in bright stripes, this mini makes an impact. Dress features a fitted bodice with off-the-shoulder neckline, contrast gently pleated, A-line skirt, and a gathered elasticized waist with decorative tie. Dress is made from a soft, lightweight woven material with stretch through the bodice and waist.

    Style Number/Barcode: 05102-0000

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Connection Mini Dress

    Make a sweet connection in florals! This must have mini dress features a sleeveless bodice, a cowl neck, spaghetti straps and a mini length silhouette to show glowing gams! The neutral tone is complemented with pretty florals throughout! Dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch.

    Style Number/Barcode: 05102-0086

    Category Name: Casual Dresses

    Price: $13.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keeping Knit Cute One-Shoulder Long Sleeve Mini Dress

    Keep it cute for any plans in this bodycon mini dress featuring a sassy one-shoulder neckline, long fitted sleeves for comfort, and crafted on soft hacci brushed knit fabric. Complete the look with sleek heels.

    Fit & Features

    • Soft hacci knit fabric, high stretch
    • One-shoulder neckline
    • Long fitted sleeves
    • Ruched side seams
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5965

    Category Name: Casual Dresses

    Price: $18.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • New Leaf Linen Mini Dress

    A lovely leaf print lends this green and white linen mini its easy sweetness. Dress features adjustable tie straps, a seamed bodice with ruffle trim and back zip, and a slight A-line skirt with ruffle hem. Dress is lined and made from a lightweight cotton blend with little to no stretch.

    Style Number/Barcode: 05102-0266

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffle Things Up Satin Mini Dress
    Make their hearts beat a little faster in this sexy light blue mini dress! It features a sweetheart neckline with a ruffle trim, narrow sleeves with a complementing ruffle trim, bustier style cups with underwire, a hidden back zipper closure, and a body-hugging silhouette. Dress is composed of a lined, satin knit fabric with minimal stretch. 

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

    Style Number/Barcode: 05103-0071

    Category Name: Casual Dresses

    Price: $10.00 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Knotch It Up Mini Dress
    This dress is a cute versatile a piece, dress it up with some strappy heels or throw on your favorite sneaks. This piece features a sleeveless bodice, with U shaped neckline, a knotch cut out at the center of the bust area. The dress has a smooth inner lining and is composed of a soft knit material that is ribbed for a casual style. The hem hits above mid thigh, and is form fitting with a moderate stretch.

     Model is 5'7" with a 32" bust,  23" waist and 34.5" hips. She is wearing a size small.  

    Style Number/Barcode: 06002-0107

    Category Name: Casual Dresses

    Price: $8.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Catch The Bouquet Dress

    This neutral ditsy flower pattern dress has us swooning! With a floral bouquet pattern it features a square neckline, ruffled stretchy spaghetti straps, a square back with a hidden zipper and double straight hem down the middle. This mini dressed has a ruched side detailing and an inner linen lining.  

    Style Number/Barcode: 05102-0207

    Category Name: Casual Dresses

    Price: $9.97 $47.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wrapped In Beauty Mini Dress

    Wrap yourself in this gorgeous mini dress to showcase your beauty! The dress features a sleeveless bodice, a wrap V neckline, a tie waist belt and an asymmetrical mini skirt. Dress is composed of an unlined crepe fabric that offers a form hugging fit with a moderate stretch.

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

    Style Number/Barcode: 05102-0239

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simply Wrapped Mini Dress

    Keep it simply sophisticated in this statement mini dress! The dress features a plunging wrap V neckline with pleated accents, adjustable spaghetti straps and an asymmetrical hem with ruched detailing. Dress is composed of a lined smooth knit fabric that offers a curve hugging fit with a moderate stretch. Includes a back zipper closure.

    Style Number/Barcode: 05102-3948

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready To Ruffle Mini Dress
    You'll be ready to ruffle in this flirty little mini dress! It features a sleeveless bodice, a V neckline with an adorable tie closure followed by a front cut out, button detailing starting at the waist, a hidden back zipper and hook and eye closure, and a cute tiered ruffle hem. The dress is composed of a linen fabric with no stretch.

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

    Style Number/Barcode: 05102-0149

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Braid For Shade Maxi Dress
    Elegantly subdued hues and sophisticated cut lend this maxi its easy appeal. Dress features a halter neck with deep V, banded waist with cutout and two rows of braid trim, a braided clasp back, and an A-line skirt with back zip. Dress is partially lined and made from a soft, crepe-like woven material with little to no stretch.

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0181

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flawless Beauty Cutout A-Line Midi Dress

    Step out in this A-line midi dress for a flawless look all spring to summer! Designed with a sleek sweetheart neckline and underbust cutout, this dress makes a delightful impression.

    Fit & Features

    • Woven fabric
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Underbust cutout, back zipper closure
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6064

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Life's A Beach Mesh Dress

    Hit the pool, bask by the beach, or prep to party in this colorful mesh maxi! Dress features a vibrant tropical print, a strapless neckline, dramatic ruffle trim running from bust to hem, a high front slit, and built-in briefs. Dress bodice is semi-sheer and does not include a top. Maxi is made from a mesh blend material with moderate stretch.

    Style Number/Barcode: 05102-0158

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simply Stunning LBD
    Keep it sleek and stunning in this LBD! It features a sleeveless bodice, a square neckline and wide shoulder straps that lead to an open back design with multi narrow cross straps. The relaxed fit bodice leads to a curve accentuating midi length silhouette. Dress is composed of a ponte-like fabric that offers a moderate stretch.

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

    Style Number/Barcode: 05103-3528

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tied With Style Mini Dress
    Make your look all tied together with style with this summer ready mustard yellow mini dress! It features a sleeveless strapless bodice with a square neckline, a tie front belt, side ruched detailing, and a front envelope hem. The dress is composed of a crepe fabric with moderate stretch.

    Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.

    Style Number/Barcode: 05102-3919

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Vibes Gauzy Mini Dress
    Feel the heat while keeping it cool in this gauzy olive skater dress. Dress features a deep V at front and back, side bar cutouts, an elasticated waist, and an all-over crinkle effect. Dress is made from a rayon fabric with moderate stretch. Dress is semi-sheer and unlined.

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

    Style Number/Barcode: 05102-3847

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Second Look Open Back Dress
    This LBD is all you need to make them take a second look! It features a sleeveless bodice, a scoop neckline, narrow straps that lead to a cross design, an open back and lattice strap accents. Dress is composed of a knit fabric that offers a curve hugging fit with a moderate stretch.

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

    Style Number/Barcode: 05102-0061

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smocked In Spring Florals Dress
    Spring into the season with gorgeous florals! This dress features an ivory color, an off the shoulder neckline with a ruffled trim, a sweetheart bust and smocked side panels. The all over floral print features pink and green hues to create the perfect spring time look! Dress is composed a lightweight woven fabric that offers a curve hugging fit with minimal stretch. 

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

    Style Number/Barcode: 05102-0010

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Feels Maxi Dress

    Get all those floral feels with this beautiful printed maxi dress! It features a sleeveless bodice, spaghetti straps that cross in the back, a square neckline, a high side slit, and a long, fitted maxi length. The black floral printed dress is composed of a soft knit fabric that offers plenty of form hugging stretch.

    Style Number/Barcode: 05102-3749

    Category Name: Casual Dresses

    Price: $13.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Plaid Knit Mini Dress
    You'll be super pretty in plaid in this knit mini dress! It has a sleeveless bodice, adjustable spaghetti straps that lead to a straight across back, a rounded neckline, and a form hugging style. The chic dress is composed of a soft knit fabric that offers plenty of stretch and showcases a glen plaid pattern with a prominent hue of red.

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

    Style Number/Barcode: 05102-3761

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance