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!

  • Such A Daydream Mesh Mini Dress

    You'll look like such a daydream in this trendy tie-dye mini dress! It features a sleeveless scoop neckline, spaghetti straps, a twist-back design, a short, curve-hugging silhouette, and a subtle all-over tie-dye print in pretty pastel hues. Style this dress with mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Twist-back design
    • Mini-length, form-hugging fit
    • Mesh fabric, tie-dye print, pastel hues
    • Runs true to size

    Style Number/Barcode: 05102-4131

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet For The Summer Babydoll Dress

    Sweet and chic, this babydoll dress is perf for the summer season. It features a square neckline, three-quarter length puff sleeves with cute ruffled hems, a high waist seam, and a short, flowy, flared-out silhouette. Style this dress with a trendy shoulder bag and mules for a weekend brunch.

    Fit & Features

    • Square neckline
    • Three-quarter length puff sleeves, ruffled elastic cinched hems
    • Stretchy smocked back detail, high waist seam
    • Mini-length silhouette
    • Flowy, flared-out fit
    • Twill fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4109

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry-Chic Style Mini Dress

    Elevate your style with this sultry-chic mini dress! It features a sleeveless deep V-neckline, spaghetti straps, sexy cutouts at the waist, and a short, form-hugging fit that will hug your curves. Complete the look with sleek earrings and cute mules.

    Fit & Features

    • Sleeveless deep V-neckline
    • Spaghetti straps
    • Cutouts at the waist
    • Mini-length, form-hugging silhouette
    • Ribbed knit fabric, smooth knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4119

    Category Name: Casual Dresses

    Price: $5.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Summer Vibes Maxi Dress

    Get those chic sultry vibes this summer in this stunning maxi dress. It features a sleeveless V-neckline, spaghetti straps, dual waist cutouts, a floor-length, fitted silhouette, and an all-over tropical floral print. Style this dress with sleek hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual waist cutouts
    • Floor-length, form-hugging silhouette
    • Knit fabric
    • Tropical floral print
    • Runs true to size

    Style Number/Barcode: 05102-4112

    Category Name: Casual Dresses

    Price: $6.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • X Marks The Spot Denim Mini Dress

    Step up in a stylish denim dress that hits the style mark! The dress features a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and a mini side slit. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops. 

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps, cross at back 
    • Mini length silhouette
    • Mini side slit
    • Denim fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-1311

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dare Me Denim Mini Dress

    We dare you to strut your style in this dress! The dress features a sleeveless scoop neckline, corset seams at the bust, adjustable spaghetti straps, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops. 

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Corset seams the bust
    • Mini length silhouette 
    • Denim fabric 
    • Form hugging fit, runs true to size

    Style Number/Barcode: 05102-1288

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Instincts Basic Tube Dress

    Tap into your stylish instincts with a basic tube dress. The dress features a sleeveless square neckline and a midi-length silhouette. The dress is composed of a knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a jelly purse

    Fit & Features

    • Sleeveless square neckline
    • Midi length silhouette
    • Knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0975

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fiercely Stylish Lace-Up Leopard Maxi Dress

    Keep it fiercely stylish with a maxi dress that is part bold, part glam! The dress features a leopard print, a sleeveless square neckline with racer bust, spaghetti straps, lace-up straps at back, and a flowy A-Line silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with sandals and metal bangles. 

    Fit & Features 

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up back 
    • A-line silhouette
    • Leopard print
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1195

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Girl Next Door Denim Mini Dress

    Channel those girl next door vibes with a mini dress that is part casual, part stylish! The dress features a sleeveless square neckline, tank shoulder straps, vertical seams along the body, and a mini center slit at the back. The dress is composed of form-hugging denim fabric. Complete look with clear mules and rhinestone rings

    Fit & Features 

    • Sleeveless square neckline
    • Tank shoulder straps
    • Vertical seams 
    • Mini center slit at back
    • Mini length silhouette
    • Form hugging denim fabric
    • Runs true to size

    Style Number/Barcode: 05102-0478

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Chic Snake Print Ruched Mini Dress

    Keep it sassy with a snake print mini dress! The dress features a sleeveless square neckline, spaghetti straps, snake print, dual ruched drawstrings, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Snake print
    • Dual ruched drawstrings
    • Mini length silhouette
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-1093

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Charm Sleeveless Mini Dress

    Bring the floral charm with a pretty mini dress! The dress features a sleeveless square neckline, smocked tie-shoulder straps, a floral print, and a mini-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with sandals

    Fit & Features

    • Sleeveless square neckline
    • Smocked tie-shoulder straps
    • Floral print
    • Mini length silhouette
    • Lightweight woven fabric, knit lining
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1905

    Category Name: Casual Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Status Strapless Midi Dress

    Elevate your chic status with this simple yet stunning midi dress. It features a strapless square neckline, a high waist seam, a mid-length, curve-hugging silhouette, and a sultry side slit. Style this dress with strappy heels for a night out.

    Fit & Features

    • Strapless square neckline
    • High waist seam
    • Mid-length, form-hugging fit
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-4210

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Laced In Love Corset Mini Dress

    She’s giving drama, curves, and just the right amount of trouble. This corset mini dress hugs you in all the right places with a flirty ruffle that finishes the look with a wink.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Strapless sweetheart neckline
    • Built-in underwire padded but
    • Corset bodice, flexible boning, back zipper and hook-eye closure
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000256

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling And Chic Floral Mini Dress

    Darling and chic, this ditsy floral printed mini dress is a summer must-have. It features short puff sleeves, a sweetheart neckline with a tie at the bust, a front waist cutout, and a short, curve-hugging silhouette. Style this dress with hoop earrings and cute wedges for a party.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline, tie at the bust
    • Front waist cutout
    • Mini-length, form-hugging fit
    • Ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-2343

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Sweetheart Striped Mini Dress

    Bring the sweet vibes to your summer look with this adorable mini dress. It features a sleeveless square neckline, spaghetti straps, a tie-back detail, and a short, curve-hugging silhouette. The ribbed knit fabric has a cute all-over striped print. Style this dress with casual sneakers.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Tie-back detail
    • Mini-length, form-hugging fit
    • Ribbed knit fabric, striped print
    • Runs true to size

    Style Number/Barcode: 05102-0443

    Category Name: Casual Dresses

    Price: $7.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Essential Ribbed Knit Midi Dress

    This ribbed knit midi dress is a basic essential you need in your closet that you can dress up or down. It features a sleeveless square neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a stylish side slit. Keep this dress casual with sneakers, or elevate the look with chic mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Form-hugging fit
    • Side slit, midi-length hem
    • Double-lined rib knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4961

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Free-spirited Floral Beauty Sleeveless Maxi Dress

    Let your natural beauty glow in this pretty maxi dress! The dress features a floral print, V-neckline, spaghetti straps that cross at the back, a lace-up back, and a high side slit. The dress is composed of an airy chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and hoops. 

    Fit & Features

    • Floral print 
    • Sleeveless V-neckline
    • Spaghetti straps, cross at back 
    • Lace-up back 
    • High side slit
    • Maxi length silhouette
    • Chiffon fabric, relaxed fit, runs true to size

    Style Number/Barcode: 05101-0974

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Classic Chic Vibes Mini Dress

    Elevate your everyday style with this mini dress that will give you those classic chic vibes! It features a V-neckline with a wrap-front design, shirring at the bust, flowy half-length sleeves, a cinching high waist seam, and a short, curve-hugging silhouette. Complete the look with heels and a cute clutch.

    Fit & Features

    • V-neckline, wrap-front design
    • Shirring at the bust
    • Flowy half-length sleeves
    • Cinching high waist seam
    • Mini-length, form-hugging fit
    • Knit fabric, ruched detailing
    • Runs true to size

    Style Number/Barcode: 05101-0997

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy And Chic Floral Mini Dress

    This floral mini dress will have you looking dreamy and chic for a summer date night with bae! It features a sleeveless sweetheart neckline with a ruffle trim at the bust, adjustable spaghetti straps, ruched detailing, a short, form-hugging fit, and a ruffled hem with a tie at the front. Style this dress with cute mules.

    Fit & Features

    • Sleeveless sweetheart neckline, ruffle trim at the bust
    • Adjustable spaghetti straps
    • Ruching
    • Mini-length, form-hugging silhouette
    • Ruffled hem, tie at the front
    • Mesh fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05101-1008

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Floral Moment Woven Mini Dress

    Have a major floral moment in this adorable woven mini dress! It features a sleeveless sweetheart neckline with ruching at the bust, thin ruffle-detail shoulder straps, a smocked back, and a short, curve-hugging silhouette. The all-over ditsy floral print is perf for summer. Style this dress with casual sneakers.

    Fit & Features

    • Sleeveless sweetheart neckline, ruching at the bust
    • Thin ruffle-detail shoulder straps
    • Smocked back
    • Mini-length, form-hugging fit
    • Woven fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-0451

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Twirl Ruffled Skater Dress

    Create a twirl-worthy moment with a floral dress that brings the romance! The dress features a sleeveless V-neckline, spaghetti straps, a strappy back, a ditsy floral print, and a skater silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with no stretch. Complete look with wedges and a clutch.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Strappy back, back zipper and hook and eye closure
    • Ditsy floral print
    • Skater silhouette 
    • Lined gauze knit fabric, relaxed fit, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4101

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Denim Days Button Up Mini Dress

    Button up in a denim dress that is part stylish, part edgy! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a button-down front, side pockets, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit. Complete look with mules and hoops.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Button-down front
    • Side pockets
    • Mini-length silhouette, form-hugging fit
    • Denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0499

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Splash Of Style Tie Dye Midi Dress

    Add a splash of style with a pretty midi dress! The dress features a sleeveless cowl neckline, spaghetti straps, a strappy back design, a tie-dye print, and a midi-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with clear mules

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Strappy back design 
    • Tie-dye print
    • Midi length silhouette
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1659

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Romance Ruched Mini Dress

    Start a floral romance with this pretty mini dress! The dress features an off-the-shoulder neckline, ruching at the bust, short sleeves, a cutout at the midriff, a ditsy floral print, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and earrings. 

    Fit & Features

    • Off the shoulder neckline
    • Ruching at bust
    • Short sleeves
    • Cutout at the midriff
    • Ditsy floral print
    • Smooth knit fabric, form-hugging fit, runs true to size
    • Mini length silhouette

    Style Number/Barcode: 05102-1103

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale