Casual Dresses

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Everyday Ease: Casual Dresses for Transitional-Weather Plans

From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.

Laid-Back & Versatile

Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.

Chic from Day to Night

Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in nuetral or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.

Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.

What Makes a Dress Casual?

Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.

Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.

How Do I Style a Dress Casually?

Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.

For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!

  • 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: 05102-0159

    Category Name: Casual Dresses

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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:
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  • 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