Casual Dresses

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STYLE SPOTLIGHT

Cute Sweater Dresses

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Everyday Ease: Casual Dresses for Cool-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.

Laid-Back & Versatile

Knit, ribbed, and sweater dresses bring comfort and style to crisp fall 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 burgundy 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!

  • Cool Girl Casual Knit Mini Dress

    Show off a cool girl style in this casual knit mini dress! It features a mock neckline with a partial zip-front design, long fitted sleeves, and a short, curve-hugging silhouette. The soft ribbed knit fabric offers plenty of stretch for comfortable wear. Complete the look with combat boots.

    Fit & Features

    • Mock neckline
    • Partial zip-front
    • Long fitted sleeves
    • Mini-length hem, fitted bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4789

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stir Up The Cuteness Lace Ruffled Mini Dress

    With romantic lace, ruffled edges, and a bold western-style belt buckle, this halter mini dress is ready to stir up trouble—in the cutest way!

    Fit & Features

    • Lace fabric, stretchy knit lining, bodysuit lining with snap-button closures
    • Halter V-neckline, tie closure
    • Back zipper and hook-and-eye closure
    • Skater silhouette
    • Western-style buckle waist belt design
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000235

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BURGUNDY-2

    Available Size: XS, S

  • Morning Brew Henley Midi Dress

    Serve major looks in the morning slaying it in this midi dress featuring long sleeves, a collared v-neckline, a button-down front, a bodycon silhouette, and a slit hem. Style with a Panama hat and booties!

    Fit & Features

    • Long sleeves
    • Collared v-neckline
    • Button-down front
    • Bodycon silhouette
    • Midi-length slit hem
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4797

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Hole Package Sweater Mini Dress

    Babe, you'll be looking stunning from all angles in this sweater mini dress featuring a crew neck, long sleeves, front keyhole cutouts, button accents, and a bodycon silhouette on rib-knit fabric. Style with knee-high boots to complete the look.

    Fit & Features

    • Crew neck, long sleeves
    • Front keyhole cutouts
    • Button accents
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit sweater fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1542

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Babe For The Weekend Mini Dress

    Be a bold babe in this classy stunner! This long sleeve mini dress features a wide scoop neckline on the front and back on a bodycon silhouette. Composed of a rib-knit fabric. Style with statement earrings for weekend soirees. 

    Fit & Features

    • Long sleeves
    • Wide scoop neck on the front and back
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4099

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twist It Up Sweater Midi Dress

    Spice up your everyday look with this sweater midi dress that brings eye-catching detail! It features long sleeves, a v-neck, a twisted bust and cutout, a side slit, and a form-hugging silhouette. Complete the look in a crop denim jacket for lunch!

    Fit & Features

    • Long sleeves
    • V-neck
    • Twisted bust and cutout
    • Form-hugging silhouette
    • Side slit, midi-length hem
    • Sweater rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1517

    Category Name: Casual Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • You're The One Tie-Front Midi Dress

    This rib knit midi dress will be the one you'll adore for casual outings and more! The dress features long sleeves, a surplice v-neckline, a faux wrap bust atop a flirty cutout bodice with a tie-front closure, and a bodycon silhouette. Style with faux suede booties for the perf autumn look!

    Fit & Features

    • Long sleeves
    • Surplice v-neckline
    • Faux wrap bust
    • Cutout bodice, tie-front closure
    • Bodycon, midi-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4843

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Go With The Scoop Neck Midi Dress

    You'll be wearing this midi dress on repeat! It features long sleeves, a scoop neck, and a bodycon silhouette with a sultry side slit. The dress is composed of a stretchy rib-knit fabric. Style with pointed-toe booties to complete your cute look!

    Fit & Features

    • Long sleeves
    • Scoop neck
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4846

    Category Name: Casual Dresses

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sight To See V-Neck Slip Dress

    You'll be a sight to see in this casual slip dress perfect for dinner and drinks with your bae! It features a sleeveless v-neck, bungee spaghetti straps, a curve-hugging silhouette, and a short-length hem.  Style with earrings and heels to complete the look!

    Fit & Features

    • Sleeveless v-neck
    • Bust lining
    • Bungee spaghetti straps
    • Curve-hugging silhouette
    • Short-length hem
    • Texture knit design, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4840

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step It Up Collared Mini Sweater Dress

    Step up your everyday fall 'fits with this trendy mini sweater dress. It features a johnny collar, a V-neckline with a partial button-down front, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric offers a moderate stretch. Style with sleek hoop earrings and knee-high boots.

    Fit & Features

    • Johnny collar
    • V-neckline, partial button-down front
    • Long fitted sleeves
    • Mini-length hem
    • Fitted bodycon silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1534

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Alluring Trendsetter Halter Midi Dress

    Show off your alluring trendy style in this sleek curve-hugging midi dress! It features a cross-front halter neckline with tie-back straps, a cold-shoulder design with long fitted sleeves, and a midi-length asymmetric hem creating a chic high side slit. The smooth knit fabric includes a full lining. Complete the look with your fave mules.

    Fit & Features

    • Cross-front halter neckline, tie-back straps
    • Cold-shoulder design
    • Long fitted sleeves
    • Midi-length asymmetric hem, high side slit
    • Form-hugging silhouette
    • Knit fabric, full lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4904

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Perfection Mock Neck Sweater Dress

    Showcase chic perfection in this classic ribbed knit sweater dress. It features a mock neckline, long fitted sleeves with puff accents at the shoulders, and a short, curve-hugging silhouette. The knit fabric offers plenty of stretch. Style with knee-high boots.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Puff shoulders
    • Mini-length hem
    • Form-hugging silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1681

    Category Name: Casual Dresses

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Doesn't Get Better Knit Midi Dress

    It doesn't get better than having this knit midi dress in your rotation! The dress features a trendy one-shoulder crew neckline with a long sleeve, spaghetti strap, and cutout bust that leads to the form-hugging silhouette with a sultry side slit hem. Complete the look in chic marabou heels.

    Fit & Features 

    • One-shoulder crew neckline
    • Long sleeve, spaghetti strap
    • Cutout bust
    • Form-hugging silhouette
    • Side slit hem, midi-length 
    • Smooth knit double-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4850

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On A Roll Turtleneck Midi Dress

    The styling possibilities are endless with this turtleneck midi dress! It features long sleeves, a bodycon silhouette, and a sultry side slit on stretchy rib-knit fabric. Complete the look in suede booties for the perf autumn outfit!

    Fit & Features

    • Long sleeves
    • Turtleneck
    • Bodycon silhouette
    • Side slit
    • Midi-length 
    • Rib-knit, lined, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4855

    Category Name: Casual Dresses

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Head-Turning Chic Marble Print Midi Dress

    Make heads turn in this eye-catching chic bodycon midi dress! It features a sleeveless square neckline, spaghetti straps, bold front and back waist cutouts, ruched detailing down the side seams, and a midi-length, curve-hugging silhouette. The stretchy knit fabric features an all-over abstract marble print pattern for a trendy vibe. Complete the look with clear heels.

     Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Front and back waist cutouts
    • Ruching down the side seams
    • Midi-length hem, fitted bodycon silhouette
    • Abstract marble print pattern
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4837

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Midi Long Sleeve Slit Dress

    You can't be disturbed cause you'll be busy admiring yourself in this rib knit midi dress featuring long sleeves, a sweetheart neckline, bust seam detail, and a form-hugging silhouette with a sultry side slit. Complete your cute look in faux suede booties for a Friendsgiving! 

    Fit & Features

    • Long sleeves
    • Sweetheart neck
    • Bust seam detail
    • Form-hugging silhouette
    • Midi-length hem, side slit
    • Ribbed knit fabric, partial lining, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4853

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Iconic And Chic Tube Mini Dress

    Effortlessly stunning, no extras needed. This strapless mini dress hugs your curves with a clean, bodycon fit and a subtle slit that keeps it sleek and modern for date nights or dressy celebrations.

    Fit & Features

    • Ponte fabric, minimal stretch
    • Strapless tube neckline
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Front slit accent
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000426

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Trendy Style Cutout Sweater Dress

    Show off a fab trendy style in this long sleeve sweater dress! It features a scoop neckline, a bold cutout at the bust with a tie-front design, dual front cutouts at the waist, and a short, curve-hugging silhouette. The knit fabric offers a moderate stretch. Pair with knee-high boots for a cute everyday 'fit.

    Fit & Features

    • Long fitted sleeves
    • Scoop neckline
    • Bust cutout, tie-front design
    • Dual front cutouts at the waist
    • Mini-length hem, form-hugging fit
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1596

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ribbed Knit Tie-Front Mini Sweater Dress

    Wrap yourself in the cozy elegance of this long-sleeve mini sweater dress. The dress features a flattering wrap design with a side tie that cinches at the waist, enhancing your silhouette. Crafted from a soft ribbed knit fabric, it offers both warmth and style, making it perfect for chilly days. The plunging V-neckline adds a touch of allure, while the Dolman-shaped sleeves maintain a chic and sophisticated look. Ideal for any autumn or winter occasion, this sweater dress pairs beautifully with boots or heels for a stylish seasonal ensemble.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Wide V-neckline
    • Long sleeves
    • Backstrap accent
    • Wrap front and back
    • High waist seam with tie-front detail
    • Short, form-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1555

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chain Effect Midi Dress With Belt

    You'll make a chain reaction by stepping out in this rib knit tank midi dress featuring a sleeveless square neck, tank shoulder straps, a detachable chain belt with lobster clasp closure, and a form-hugging silhouette. Complete the look in a chic blazer for happy hour!

    Fit & Features

    • Sleeveless square neck
    • Tank shoulder straps
    • Detachable chain belt with lobster clasp closure
    • Form-hugging silhouette
    • Midi-length hem
    • Double-lined rib knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4882

    Category Name: Casual Dresses

    Price: $19.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fall For Surplice Sweater Dress

    This autumn, you'll fall for this surplice sweater dress that's cozy and stylish! The mini dress features long sleeves, a plunge v-neckline, a bodycon silhouette, and a side ruched seam leading to the asymmetrical wrap hem. Complete the look in tall boots and a coat for a perf fall vibe.

    Fit & Features

    • Long sleeves
    • Plunge v-neckline
    • Surplice bodice
    • Side ruched seam, bodycon fit
    • Asymmetrical wrap mini hem
    • Smooth knit nylon-blend fabric
    • Runs true to size

    Style Number/Barcode: 06005-1473

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Adorable Mock Neck Mini Dress

    So adorable and perfect for chilly days, this long sleeve mini dress is what your closet needs! The mini dress features a mock neck and a bodycon silhouette composed of hacci rib-knit fabric with moderate stretch. Complete the look in over-the-knee boots for a movie date!

    Fit & Features

    • Long fitted sleeves
    • Mock neck
    • Bodycon silhouette
    • Mini-length hem
    • Hacci rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5227

    Category Name: Casual Dresses

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fine Details Twist V-Neck Dress

    Turn heads in the sultry details of this mini dress featuring long sleeves, a v-neck, twisted bust, and side ruched seams that flaunt your curves along the bodycon silhouette. Complete the look in knee-high boots for apple picking!

    Fit & Features

    • Long sleeves, v-neck
    • Twisted bust
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4562

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wear Your Art Striped Midi Dress

    Wear this fine work of art and every eye will be on you! This marble striped midi dress features long sleeves, front and back v-necklines, a bodycon silhouette, and a tie-front waist. Complete the look in PVC mules for a casual lunch!

    Fit & Features

    • Long sleeves
    • Front and back v-necklines
    • Bodycon silhouette
    • Tie-front waist
    • Midi-length hem
    • Marble striped print, stretch-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4821

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale