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!

  • Feelin' Fresh In Floral Ruffle Hem Mini Dress

    Get a fresh look in this gorg floral ruffle hem mini dress! It features woven tie shoulder straps and cute ruffle detail at the hem for a fun and flirty vibe. A must-have for your next backyard bbq, style it up with clear slide on mules and sleek gold hoop earrings.

    Fit & Features

    • Tie shoulder straps
    • Slight sweetheart neckline
    • Partially smocked back with a hidden zipper closure
    • Short ruffle hem
    • Floral print
    • Woven fabric

     

    Model is 5'9" with a 34" bust,  24" waist and 35.5" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0833

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Persuasion Ruched Mini Dress

    Charm in a floral dress that brings major sweet appeal! Step out for your next lunch date with bae in this head-turning dress. The dress features a plunging v-neckline, quarter sleeves with a ruffled hem, a ruched center that runs bodice through the hem, and a cute floral print! Complete your look with cork wedges and sleek hoops

    Fit & Features

    • Plunging v-neckline
    • 3/4 sleeves with ruffled hem
    • Ruched center that runs bodice through the hem
    • Floral print
    • Mini length silhouette with ruffled hem

     

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

    Style Number/Barcode: 05102-0724

    Category Name: Casual Dresses

    Price: $18.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • A Splash Of This Tie-Dye Satin Mini Dress

    This trendy tie-dye satin mini dress will def expand your color palette babe! With its cowl neckline and slightly flared fit, you'll be serving looks. Perfect for a backyard photo shoot, add some sparkly earrings and slip into a pair of block heels to get the shot.

    Fits & Features

    • Adjustable spaghetti straps
    • Cowl neckline
    • Back zipper with hook and eye closure
    • Mini length silhouette
    • Satin-like fabric with a tie-dye print
    • Relaxed fit with minimal stretch

     

    Model is 5'9" with a 34" bust,  24" waist and 35.5" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0476

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready To Ruche Mini Dress

    Get ready to style it up in this adorable ruched mini dress! It features spaghetti straps with a flattering square neckline, front ruched detailing with a tie at the hem, and a mini-length, curve-hugging fit. Pair this dress with some clear slide-on mules and a chic clutch for the perf night-out look.

    Fit & Features

    • Spaghetti straps, square neckline
    • Dart seam detailing
    • Back zipper closure
    • High waist seam
    • Side ruched detailing with tie at the hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-3951

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Belted Sophistication Sleeveless Mini Dress

    Keep it chic in a belted dress that elevates you to a sophisticated and polished look. The dress features a sleeveless square neckline, spaghetti straps, side slit, and a belted waist with a rectangular buckle. Complete look with clear heels

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Belted waist with rectangular buckle
    • Mini length silhouette
    • Side slit
    • Ribbed knit fabric

     

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06005-0684

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty In Plaid Sleeveless Knit Mini Dress

    Look and feel pretty in this plaid mini dress, which boasts a flirty V-neckline and bodycon silhouette that shows your curves! Pair with a leather jacket and flats.

    Fit & Features

    • Woven knit fabrication
    • Sleeveless v-neckline
    • Spaghetti straps
    • Plaid print 
    • Side slit
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-5930

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Call of The Wild Leopard Ruched Mini Dress

    Channel your instincts in a mini dress that brings the fierce factor! The dress features a sleeveless square neckline, sleek spaghetti straps, and ruched side seams to give curves that cinched effect. Complete your look with sleek hoops and heels

    Fit & Features

    • Sleeveless square neckline
    • Sleek spaghetti straps
    • Ruched drawstring side seams
    • Leopard print
    • Mini length silhouette
    • Lined mesh fabric with moderate stretch
    • Form-hugging fit

    Style Number/Barcode: 05103-1734

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Button Down Beauty Maxi Dress

    Button-down in a casual maxi dress for a cute day-out outfit the next time you're picking up a must-have iced coffee! This maxi dress features a plunging sweetheart neckline with a tie-front accent, mini cutout at the bodice, and a button-down front with a high center slit. Complete your look with sleek sandals for those low-key vibes. 

    Fit & Features

    • Plunging sweetheart neckline 
    • Tie-front accent with a small cutout at the bodice
    • Adjustable spaghetti straps
    • Multi-button down front
    • High center slit
    • Maxi length silhouette
    • Ribbed knit fabric, form-hugging fit

     

    Navy Dress: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

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

    Style Number/Barcode: 05102-0746

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stripe It Down Ribbed Button Down Midi Dress

    Keep it stunning in a striped dress that wows. Step out for brunch in this midi dress that features an off the shoulder neckline with a sweetheart bust, short sleeves, a button-down front, and narrow horizontal stripes. Complete your look with strappy mules and sleek hoops

    Fit & Features

    • Off the shoulder neckline
    • Sweetheart bust
    • Short sleeves
    • Button-down front
    • Narrow horizontal stripes
    • Midi length silhouette with center front slit
    • Ribbed knit fabric, form-hugging fit


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

    Style Number/Barcode: 05102-0795

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Button Up Ribbed Mini Dress

    Button up in this classic ribbed dress to channel a cool chick vibe! Step out for a girl's night out or for a casual date night out with bae. The dress features a sleeveless bodice, a trendy square neckline, bungee straps for a secure fit, and a button-down center to create a customized look. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit and a moderate stretch. Pair this baby with your favorite heels to create a standout look and finish off with statement earrings

    Fit & Features

    • Square neckline
    • Bungee spaghetti straps 
    • Button-down center closure 
    • Lined ribbed fabric 
    • Form hugging fit 
    • Moderate stretch 

     

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

    Black Dress: Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06002-0402

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Puff Sleeve Ruched Knit Mini Dress

    Keep on trend in a puff sleeve dress. This must-have dress features a sweetheart neckline with ruched detailing, puff sleeves, and a mini length silhouette. The dress is composed of a knit fabric that offers a form hugging fit with a slight stretch. Complete look with a pair of pumps and earrings

    Fit & Features 

    • Sweetheart neckline 
    • Ruched detailing at the bust 
    • Short puff sleeves 
    • Knit fabric 
    • Form hugging fit 
    • Moderate stretch 

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

    Style Number/Barcode: 05102-0733

    Category Name: Casual Dresses

    Price: $10.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleeveless Cut Out O-Ring Ribbed Mini Dress

    Step up in a sleeveless ribbed mini dress with sexy cutout details this season. The curve-hugging ribbed dress features a flattering crew neck that leads to a chic O-Ring at the mid-drift accented with waist cut outs for a subtle hint of skin. The back reveals a matching lower back cut out to impress from all angles. The ribbed knit embraces curves while offering a moderate stretch to easily move. Complete this date-night ready look with daring hoops and strappy stilettos

    Fit & Features

    • Sleeveless
    • Crew neckline
    • O-Ring at the center, waist cut outs
    • Lower back cut out
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05102-0723

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Small Town Girl Eyelet Mini Dress

    Whether you're a small town girl, or a city babe, this sweet mini dress is a day out go-to! Slip on and head out to brunch babe!

    Fit & Features

    • Square neckline
    • Adjustable Spaghetti straps | Sleeveless
    • Mini hemline
    • Zipper closure center back
    • Eyelet linen material
    • Minimal stretch
     Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0213

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruffled Eyelet Puff Sleeve Mini Dress

    Keep it chic in an eyelet mini dress. This season-ready dress features a sweetheart neckline, a tie front accent, short puff sleeves, and ruched vertical seams that highlight and enhance curves. The relaxed waist leads to a ruffled hem. The dress is composed of a lightweight knit fabric with an eyelet pattern. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete your look with wedges and fringe earrings

    Fit & Features

    • Sweetheart neckline
    • Tie front accent 
    • Short puff sleeves
    • Vertical seams
    • Eyelet design
    • Ruffled hem 
    • Lightweight woven fabric, relaxed fit 

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

    Style Number/Barcode: 05102-0734

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feeling Floral Eyelet Mini Dress

    We’re always in the mood for a little floral print! Pair this mini dress with sandals and layered dainty jewelry.

    Fit & Features

    • All Over Eyelet Design
    • Ditsy Floral Print
    • Mini Length

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

    Style Number/Barcode: 05102-0709

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Show 'Em Off Shoulder Smocked Mini Dress

    Show off those shoulders in this cute mini dress! For a cute daytime look, pair it with your fave denim jacket and some white sneakers! 

    Fits & Features

    • Off-shoulder neckline, short sleeves
    • Keyhole opening with self-ties at front
    • Mini length silhouette 
    • Woven textured fabric, smocked back, ruffle trim detail
    • Curve hugging fit, plenty of stretch 

    Style Number/Barcode: 05102-0472

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Getaway Sleeveless Asymmetrical Ruched Midi Dress

    Head to the tropics in this midi dress that brings a tropical burst of color. This vacation-ready dress features a sleeveless bodice, a plunging V-neckline and adjustable spaghetti straps that lead to an X-back design. The relaxed fit waist leads to a midi length silhouette with a ruched side seam and an asymmetrical high slit to show off a hint of skin. The all-over tropical print features bright hues that perfectly complement the neutral background. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete your look with a pair of heels and golden hoop earrings

    Fit & Features

    • Plunging V-neckline
    • Adjustable spaghetti straps
    • X-back 
    • Midi length silhouette 
    • Tropical print
    • Asymmetrical high side slit
    • Form hugging fit

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0579

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Stunner Midi Dress

    Be a stylish stunner in this gorg floral midi dress! It features a sleeveless bodice, adjustable spaghetti straps that cross in the back, a V neckline, side ruched detailing, and an asymmetrical hem. The dress is composed of a knit fabric that offers plenty of stretch.

    Style Number/Barcode: 05102-3848

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sway With Me Fringe Mini Dress

    Add a little sway to your step in this cute mini dress! 

    Fits & Features

    • Adjustable Spaghetti Straps 
    • Back Zipper With Hook & Eye Closure 
    • Mini Length Silhouette I Ruffle Hem 
    • Subtle Fringe Detailing Along Square Neck, Bodice, & Skirt 
    • Woven Fabric With Knit Lining 
    • Minimal Stretch 

    Style Number/Barcode: 05101-0719

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ribbed Knit Ruffled Ditsy Floral Mini Dress

    Slay in a gorge ditsy floral mini dress. A ditsy floral dress is a staple piece to have for brunch or a day date with bae. This must-have features a sleeveless sweetheart neckline with a tie-front accent and ruffled trim with matching ruffled spaghetti straps. The relaxed fit waist leads to a curve-hugging mini-length silhouette. The dress is composed of ribbed knit fabric that offers a moderate stretch. Complete your floral look with cork wedges and dainty rings

    Fit & Features

    • Sleeveless sweetheart neckline
    • Tie-front bodice
    • Ruffled spaghetti straps
    • Ditsy floral print
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch

     

    Style Number/Barcode: 05102-0769

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Here Comes The Sun Strapless Ruffled Mini Dress

    Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The short tube dress features ruched sides and a ruffled hem, adding a playful touch to the bodycon silhouette.

    Fit & Features

    • Double-lined brushed knit fabric, moderate stretch
    • Strapless straight neckline
    • Ruched side seams
    • Bodycon silhouette
    • Mini-length tiered ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5784

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take a Trip Tropical Mini Dress

    You’ll be ready for date night on the beach in this tropical print mini dress. Style it with clear heels and hoops for an effortless look.

    Fits & Features

    • V-Neckline
    • Spaghetti Straps
    • Asymmetrical Hem

    Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0440

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Bloom Smocked Mini Dress

    Let your style bloom with pretty floral this spring season in this adorable mini dress! The dress keeps it fresh and flirty with a charming floral print. It features a sleeveless bodice with tie shoulder spaghetti straps, a square neckline, a stretchy smocked bust, and a high waist that flows out to a short skirt with an A-line silhouette. Complete your outfit with wedges and a trendy Panama hat for the perfect look.

    Fit & Features

    • Tie shoulder spaghetti straps
    • Square neckline
    • Smocked bust
    • High waist leading to a short skirt
    • A-line silhouette
    • Floral printed woven fabric with a stretchy knit lining
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 05102-0446

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Oh So Dainty Ruffle Trim Off Shoulder Ruched Mini Dress

    Step right into sunnier days with this charming mini dress! Opt for block heels and a cute mini purse for an eyecatching ensemble! 

    Fits & Features

    • Ruffle Trim Off Shoulder Design 
    • Tie Front 
    • Ruching Throughout
    • Mini Length Hem I Full Knit Lining
    • Form Hugging Fit I Plenty Of Stretch 

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

    Style Number/Barcode: 05102-0657

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance