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!

  • Limelight Lace-Up Bandage Dress

    Look back at it. Flaunt your hourglass in this lace-up bandage dress featuring a sleeveless, boat neckline, spaghetti straps, a mini bodycon silhouette, and an open-back with an alluring lace-up design with tie-closure. Composed of a seamless bandage-knit fabric with minimal stretch. Finish the look in stiletto heels for a night out. 

    Fit & Features

    • Sleeveless, boat neckline
    • Spaghetti straps
    • Open-back, lace-up design with tie-closure
    • Mini bodycon silhouette
    • Seamless bandage-knit fabric
    • Fits true to size, minimal stretch

    Style Number/Barcode: 06005-1302

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Only The Best Cutout Sweater Dress

    Treat yourself to the best sweater midi dress to have this season! It features fitted long sleeves, an asymmetrical neckline with contrast trim, a form-hugging silhouette, and a flirty side waist cutout with contrast trim. Style with block heels to complete the look!

    Fit & Features

    • Fitted long sleeves
    • Asymmetrical neckline, contrast trim
    • Form-hugging silhouette
    • Side waist cutout, contrast trim
    • Midi-length hem
    • Rib-knit sweater fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1639

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Contemporary Girl Sweater Midi Dress

    Breeze in looking like a chic contemporary girl in this sweater midi dress! It features an on-trend cold shoulder with adjustable halter spaghetti straps, fitted long sleeves, a bodycon silhouette, and a front-side slit accent. Complete the look with lace-up heels for a dinner date!

    Fit & Features

    • Cold shoulder
    • Adjustable halter spaghetti straps
    • Fitted long sleeves
    • Bodycon silhouette
    • Front side slit, midi-length hem
    • Sweater rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1613

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rendezvous In Satin Slip Midi Dress

    Have a chic rendezvous in this satin slip midi dress featuring a sleeveless V-neck, bungee spaghetti straps, a fitted a-line silhouette, and a sultry front slit along the hem. The dress is composed of smooth, non-stretch satin fabric. Complete the look in lace-up stiletto heels.

    Fit & Features

    • Sleeveless V-neck
    • Bungee spaghetti straps
    • Fitted a-line silhouette
    • Front slit
    • Midi-length hem
    • Non-stretch woven satin fabric
    • Runs true to size

    Style Number/Barcode: 05101-2383

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wonderful Winter Sweater Midi Dress

    Slay all season no matter the weather in this sweater midi dress perfect for casual or dressy events! It features fitted long sleeves, a mock neck, a bust cutout, and a form-hugging silhouette with a flirty front slit. The dress is composed of a stretchy rib-knit fabric. Pair with booties to complete the look.

    Fit & Features

    • Fitted long sleeves, mock neck
    • Bust cutout
    • Form-hugging silhouette
    • Front slit accent
    • Midi-length hem
    • Rib-knit sweater fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1579

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Time To Slay Bodycon Midi Dress

    It's your time to slay in this simple yet chic bodycon midi dress! It features an asymmetrical boat neckline with a partial off-the-shoulder design, long fitted sleeves with thumb hole accents, a midi-length hem, and a curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Style with strappy heels.

    Fit & Features

    • Asymmetrical boat neckline, partial off-the-shoulder design
    • Long fitted sleeves, thumb hole accents
    • Midi-length hem
    • Curve-hugging fit
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5006

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swirls Of Style Satin Midi Dress

    Stylish marble swirls capture all the attention on this satin midi dress featuring a sleeveless v-neck, adjustable spaghetti straps, flexible boning inserts along the bodice, and a curve-hugging silhouette with a front slit accent. Complete the look in a casual crop jacket.

    Fit & Features

    • Sleeveless v-neck, adjustable spaghetti straps
    • Flexible boning inserts
    • Back zipper and hook-eye closure
    • Front slit, curve-hugging, midi-length hem
    • Marble print
    • Satin fabric, knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4867

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made For You Marble Mesh Mini Dress

    This eye-catching marble mesh mini dress was made for you to style up and create a chic 'fit! It features a crew neckline, sheer long fitted sleeves, a mini-length hem, a bodycon silhouette that will hug your curves, and an all-over alluring marble print pattern. The partially lined mesh fabric offers plenty of stretch. Complete your look with strappy stilettos.

    Fit & Features

    • Crew neckline
    • Sheer long fitted sleeves
    • Mini-length hem
    • Bodycon silhouette
    • Marble print
    • Sheer mesh fabric, partial knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4847

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winter Chic Style Midi Sweater Dress

    You'll adore the winter chic style of this midi sweater dress! Featuring a mock neckline, long fitted sleeves, a midi-length hem, and a form-hugging silhouette, this sweater dress is a perfect choice for casual holiday parties. The cozy brushed ribbed knit fabric offers plenty of stretch for comfortable wear. Style with ankle booties.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Midi-length hem
    • Form-hugging fit
    • Brushed ribbed knit fabric, knit lining down the body
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5039

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Perfection Ribbed Knit Mini Dress

    This ribbed knit mini dress will create perfect casual 'fits! It features a square neckline, long fitted bell sleeves with cute flared-out hems, and a mini-length, form-hugging silhouette. The lined knit fabric offers plenty of stretch for comfortable wear. Style with knee-high boots.

    Fit & Features

    • Square neckline
    • Long fitted bell sleeves, flared hems
    • Mini-length hem, form-hugging fit
    • Ribbed knit fabric, knit lining, plenty of stretch
    • Style runs small

    Style Number/Barcode: 05102-5217

    Category Name: Casual Dresses

    Price: $5.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet And Off-The-Shoulder Sweater Skater Dress

    Look sweet on chilly days in this darling sweater mini dress featuring a cute folded, off-the-shoulder neckline and forever flattering skater silhouette. 

    Fit & Features

    • Rib knit stretchy fabric
    • Folded off-the-shoulder neckline
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000013

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: RAISIN, NATURAL

    Available Size: XS, S, M, L

  • Back Of My Mind Crepe Slip Dress

    You'll be unforgettable once they see you in this crepe slip dress perfect for casual parties and celebrations! It features a sleeveless V-neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the midi-length hem. Style with simple hoop earrings to complete the look!

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Form-hugging silhouette
    • Front slit accent
    • Midi-length hem
    • Crepe fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4826

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wrap It Up Cable Knit Sweater Dress

    Wrap yourself up in style this season! Cue compliments whenever you're in this cable knit sweater midi dress featuring long balloon sleeves, a v-neckline, and a surplice bodice with a tie-front waist belt and a bodycon silhouette. Style with pointed-toe booties to complete the look!

    Fit & Features

    • Long balloon sleeves
    • V-neckline
    • Surplice bodice
    • Tie-front waist belt
    • Bodycon silhouette
    • Midi-length hem
    • Cable knit fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05102-4818

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Seasonal Surprise Color Block Dress

    Mix it up this season! Step out in this trendy color block mini dress featuring fitted long sleeves, a scoop neck, and a bodycon silhouette on stretchy rib-knit fabric. Style with over-the-knee boots to complete the look!

    Fit & Features

    • Fitted long sleeves
    • Scoop neck
    • Bodycon silhouette
    • Mini-length hem
    • Color block pattern
    • Rib-knit fabric, double-lined, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4952

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty In Fall Cable Knit Dress

    Stay flirty and cozy this fall in this cable knit midi dress! It features long sleeves, a mock neck, a bodycon silhouette, and a sultry open-back design. Perfect for styling with faux suede booties for your weekend plans!

    Fit & Features

    • Long sleeves
    • Mock neck
    • Bodycon silhouette
    • Open-back design
    • Midi-length hem
    • Soft cable knit sweater fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1614

    Category Name: Casual Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Love Mock Neck Midi Dress

    This midi dress is what dreams are made of! It features a cozy brushed rib-knit fabric designed with a mock neck, fitted long sleeves, and a bodycon silhouette. The knit fabric offers a moderate stretch. Style with a crop denim jacket to complete the look!

    Fit & Features

    • Mock neck
    • Fitted long sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Super soft brushed rib-knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5035

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • First Pick Henley Knit Maxi Dress

    Cute and stylish, this maxi dress will be your first pick for looking good always! It features fitted long sleeves, a v-neckline with button front closures, a bodycon silhouette, and is composed of stretchy rib-knit fabric. Style with booties to complete the look!

    Fit & Features

    • Fitted long sleeves
    • V-neckline
    • Button-front closures
    • Bodycon silhouette
    • Maxi-length hem
    • Rib-knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5036

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Cozy Turtleneck Mini Dress

    You'll forever be cozy in this soft and stretchy brushed knit mini dress! It features a turtleneck, long fitted sleeves, and a short, curve-hugging, bodycon silhouette. Style with a plaid blanket scarf and knee-high boots.

    Fit & Features

    • Turtleneck
    • Long fitted sleeves
    • Mini-length hem
    • Fitted bodycon silhouette
    • Double-lined brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4811

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Play The Game Checker Mini Dress

    Play the game of style with this checkered mini dress and you'll definitely get a checkmate! The sleeveless dress features a square neck, tank-style straps, flexible boning inserts, a bodycon silhouette, and a mini-length hem. Complete the look in a crop denim jacket for a casual daytime outing.

    Fit & Features

    • Sleeveless, square neck, tank-style straps
    • Flexible boning inserts
    • Back zipper and hook-eye closure
    • Bodycon fit, short-length hem
    • Checkered pattern
    • Rib-knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4877

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Style Warm Up Sweater Knit Dress

    Cozy up this season in style! This sweater mini dress is the best of both worlds featuring cozy dolman sleeves, a surplice v-neckline, belted tie-front waist, and a bodycon silhouette. The dress is composed of soft cable and rib-knit fabric that offers plenty of stretch. Style with knee-high boots to complete the look!

    Fit & Features

    • Dolman sleeves
    • Surplice v-neckline
    • Belted tie-front waist, belt loop accents
    • Bodycon silhouette, mini-length
    • Cable and rib-knit sweater fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1572

    Category Name: Casual Dresses

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In The Knit Cable Sweater Dress

    A fashionista like you needs to set the trends! Step it up this season in this staple cable knit sweater dress featuring a ribbed mock neck and long sleeves, a bodycon silhouette, and a short-length hem. Style with knee-high boots and a jacket to complete the look!

    Fit & Features

    • Ribbed mock neck and long sleeves
    • Bodycon silhouette
    • Short-length hem
    • Cable knit design
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1564

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Winter Chic Off-The-Shoulder Sweater Dress

    This adorable ribbed knit sweater dress will give you a chic look for the winter season! It features an off-the-shoulder neckline with a fold-over design, long fitted sleeves, a midi-length, curve-hugging silhouette, and a high front slit. The knit fabric offers a moderate stretch for comfortable wear. Style with knee-high boots.

    Fit & Features

    • Off-the-shoulder neckline, fold-over design
    • Long fitted sleeves
    • Midi-length hem, fitted bodycon silhouette
    • High front slit
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1578

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Classic Chic Mock Neck Sweater Dress

    This classic chic sweater dress is perfect for styling up or down this winter season. It features an on-trend mock neckline, long fitted sleeves, a short, curve-hugging silhouette, and a front slit accent. The knit fabric offers plenty of stretch. Pair with knee-high boots and sleek hoops.

    Fit & Features

    • Ribbed mock neckline
    • Long fitted sleeves
    • Mini-length hem, front slit
    • Curve-hugging silhouette
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1616

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cargo Without Plaid Short Dress

    You can't go without this plaid short dress perfect for autumn days and layering for winter nights! The dress features a sleeveless square neck, spaghetti straps, side flap pockets, and a bodycon silhouette. Complete the look in a basic long sleeve top and lug booties.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Side flap pockets
    • Bodycon silhouette
    • Short-length hem
    • Plaid pattern, knit fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05102-4898

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale