Casual Dresses

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STYLE SPOTLIGHT

Cute Work Dresses

Floral Print Dresses

Effortlessly Chic Casual Dresses for Spring and Summer

Refresh your warm-weather wardrobe with stylish and easygoing casual dresses from Windsor. Whether you're heading to brunch, running errands, or meeting friends for a relaxed day out, our collection offers effortless styles that keep you looking put-together with minimal effort.

This season, embrace breezy silhouettes and lightweight fabrics designed for comfort and movement. Choose from flowy midi and maxi dresses in fresh floral prints, playful minis in vibrant hues, and sleek knit dresses perfect for everyday wear. Stay on-trend with tunic and t-shirt dresses featuring stylish necklines, cutouts, and ruching details that elevate your casual looks.

Looking for a dress that easily transitions from day to night? A flattering midi dress in a soft, breathable fabric is your go-to for a chic yet comfortable outfit. Style it with white sneakers for a casual afternoon or swap them for strappy sandals to take your look into the evening.

Long casual dresses are a must-have for those easy summer days. Opt for flowy maxi styles in soft pastels or classic neutrals for an effortlessly polished vibe. Go for classic black for an ultra-versatile look. Pair your casual maxi with a denim jacket and trendy slides for a stylish yet relaxed ensemble.

If you love cozy yet chic styles, these styles are polished yet cozy, perfect for a casual yet refined outfit during transitional weather. Pair it with ankle booties for an effortless spring-to-summer transition.

No matter your plans, finding a versatile dress that fits your personal style has never been easier. From relaxed weekend outings to spontaneous getaways, our selection of everyday dresses is designed to keep up with your plans while keeping you stylish and comfortable. Explore our casual dresses online, in-app, or in-store today!

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!

  • Gorgeous Aura Strapless Floral Tie-Dye Maxi Dress

    Shine bright and serve a gorgeous aura in this strapless floral tie-dye maxi dress perfect for summertime soirees! The strapless neckline and lace-up back design exude effortless elegance, while the form-hugging fit accentuates your curves. The ruffled maxi-length hem adds a playful touch to this stunning dress. Complete the look with a ring set and sandals.

    Fit & Features

    • Floral tie-dye print, smooth knit fabric, moderate stretch
    • Strapless neckline
    • Lace-up back design
    • Form-hugging fit
    • Ruffled maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3277

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flawless Puff Sleeve Corset Midi Dress

    A flawless midi dress with femme details from the corset bodice to the puff short sleeves and flattering A-line silhouette - you'll feel like a dream in this dress! Complete the look with strappy sandals.

    Fit & Features

    • Lined woven fabric, dainty sheer lace trim, minimal stretch
    • Sweetheart neckline, ruched bust, keyhole cutout, bow-front detail
    • Corset bodice, bust underwire, flexible boning
    • Short puff sleeves, elastic cinched hems
    • Smocked lace-up back, hidden zipper with hook-eye closure
    • V-shaped drop waist
    • Midi-length A-line silhouette, front slit
    • Runs true to size

    Style Number/Barcode: 05101-3573

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Knit Off-The-Shoulder A-Line Mini Dress

    Channel that cute and cozy vibe in this adorable soft ribbed knit mini dress featuring an off-the-shoulder straight neckline with a fold-over design, long fitted sleeves, and a short A-line silhouette. Style with knee-high boots for a fall date!

    Fit & Features

    • Soft ribbed knit fabric
    • Off-the-shoulder straight neckline, fold-over design
    • Long fitted sleeves
    • Mini-length A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5892

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: HEATHERGRAY

    Available Size: XS, S, M, L

  • Smooth Talker Lace Bow Pleated Ponte Mini Dress

    Smooth ponte knit fabric shapes this sleeveless mini dress featuring a lace bow trim square neckline, spaghetti straps, and a fitted silhouette that leads to a pleated flare mini-length hem.

    Fit & Features

    • Smooth pointe knit fabric, minimal stretch
    • Lace bow trim square neckline
    • Spaghetti straps
    • Fitted silhouette
    • Pleated flare mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3661

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Fab Drop Waist Halter Skater Dress

    Look and feel fabulous in this sleeveless skater dress boasting a flirty halter V-neckline and a trendy mineral wash on the stretchy rib knit cotton fabric. Complete the look with hoop earrings.

    Fit & Features

    • Ribbed cotton-blend fabric, moderate stretch
    • Mineral wash
    • Sleeveless halter V-neckline
    • Partially open back
    • Drop waist 
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5857

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Element Turtleneck Long Sleeve Mini Dress

    Soft and lightweight ribbed knit fabric crafts this trendy mini dress perfect for styling day to night! The mini-length dress features fitted long sleeves, a folded turtleneck, and a flattering bodycon silhouette on double-lined ribbed knit fabric. Complete the look in an oversized blazer and boots for brunch downtown or date night!

    Fit & Features

    • Double-lined ribbed knit fabric, moderate stretch
    • Fitted long sleeves
    • Folded turtleneck
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5245

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: S

    Product Badge:
    • Sale
  • Cool Staple Ribbed Knit Long Sleeve Midi Dress

    This ribbed knit midi dress is designed with a cotton-blend fabric with a cool mineral wash offering plenty of stretch. The dress features a scoop neckline, long fitted sleeves, and a midi-length bodycon silhouette to show off your curves.

    Fit & Features

    • Cotton-blend ribbed knit fabric, plenty of stretch
    • Mineral wash
    • Scoop neckline
    • Long fitted sleeves
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5829

    Category Name: Casual Dresses

    Price: $11.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Silhouette Abstract Print Mesh Midi Dress

    Showcase a sultry silhouette in this sheer mesh midi dress designed with a multi-colored abstract print for a bold vibe. It features a mock neckline with long fitted sleeves, a bodycon silhouette to hug your curves, and a full-length knit lining with a scoop neckline and spaghetti straps.

    Fit & Features

    • Abstract printed sheer mesh fabric, plenty of stretch
    • Mock neckline
    • Long fitted sleeves
    • Midi-length bodycon fit
    • Full-length knit lining, scoop neckline, adjustable spaghetti straps
    • Runs true to size

    Style Number/Barcode: 05102-5879

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

  • So Iconic Abstract Print Ruched Mini Dress

    Step out like the icon you are in a mini dress that features a plunging cowl neckline with halter neck ties for a secure fit, an abstract floral print, and ruching throughout to enhance curves. Style with clear heels. 

    Fit & Features

    • Fitted mesh fabrication, moderate stretch
    • Cowl neckline
    • Open back, halter neck ties
    • Abstract floral print
    • Mini length hem
    • Ruching
    • Runs true to size

    Style Number/Barcode: 05102-5786

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ray Of Romance A-Line Lace Mini Dress

    Radiate a ray of romance in this sleeveless lace mini dress featuring a V-neckline accented with a dainty lace and ribbon bow trim and a flattering A-line silhouette. Style with heels for a date.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • V-neckline with lace and ribbon bow trim
    • Spaghetti straps
    • Mini-length A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3626

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Beauty Sleeveless A-Line Mini Dress

    This sleeveless mini dress features a crew neckline, a flattering A-line silhouette, and a front slit accent. The soft rib knit fabric offers plenty of stretch and comfort.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Crew neckline
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5631

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous One Shoulder Bodycon Mini Dress

    Look like a gorgeous dream in this sleeveless mini dress for showers, brunch, or parties! The one shoulder neckline adds a chic look, while the side ruched seams enhance your curves. The bodycon fit hugs your figure in all the right places along the mini-length hem. Complete the look with statement earrings.

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • One shoulder neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3478

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever Sweet Long Sleeve Drop Waist Skater Dress

    Stay forever sweet in this skater dress featuring a sleek square neckline and ruching that flatters your figure. Pair with heels.

    Fit & Features

    • Stretchy smooth knit fabric
    • Square neckline
    • Long fitted sleeves
    • Ruching
    • Drop waist
    • Mini-length tiered skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3745

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Showstopper Abstract Print Mesh Maxi Dress

    Serve chic vibes in this airy-lined mesh maxi dress designed with a multi-colored abstract print for a bold allure. It features a strapless straight-across neckline, a high-cut side slit, and a long bodycon silhouette to showcase your stunning curves.

    Fit & Features

    • Abstract printed sheer mesh fabric with knit lining, plenty of stretch
    • Strapless straight neckline
    • High side slit
    • Maxi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5982

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Vibes Tropical Print Asymmetric Midi Dress

    Channel those island vibes on your summer vacay in this tropical print asymmetric midi dress! The stretchy slinky knit fabric is accented with an abstract tropical pattern, an iconic look for your getaway. The mid-length dress features a sleeveless cowl neckline with chic draped detailing, tie-back halter straps, an alluring open back, an asymmetric high-cut hem, and a bodycon silhouette to hug your gorgeous curves. Style with sleek hoops for a sunset happy hour.

    Fit & Features

    • Abstract tropical print
    • Stretchy knit fabric, knit bust lining
    • Cowl neckline, tie-back halter straps
    • Open back
    • Asymmetric hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5810

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

  • Picturesque Cutie Corset Lace-Up A-Line Midi Dress

    Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette.

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Sweetheart neckline, tie-front detail
    • Thin adjustable straps
    • Corset bodice, lace-up back
    • High waist seam
    • Midi-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4059

    Category Name: Casual Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

  • Flirty Babe Drop Waist Bubble Hem Skater Dress

    You'll be a total flirty babe in this adorable short dress featuring a sleeveless square neckline with spaghetti straps, a V-shaped drop waist design, and a pleated skater silhouette with the cutest bubble hem. Style with hoop earrings and mules for date night!

    Fit & Features

    • Ribbed knit bodice, poplin woven skirt with knit lining, moderate stretch
    • Square neckline
    • Spaghetti straps
    • V-shaped drop waist
    • Short pleated skater silhouette with bubble hem
    • Runs true to size

    Style Number/Barcode: 05102-5907

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sheer Exellence Mock Neck Bodycon Mesh Midi Dress

    Experience sheer excellence in this stunning mesh midi dress perfect for dinners downtown or concerts. The sheer short sleeves and mock neckline add a touch of chic, while the bodycon silhouette flatters your figure. The sheer mesh fabric and smooth knit slip provide a luxurious feel, and adjustable spaghetti straps ensure a perfect fit. Complete the look with this midi dress in block heels and a hair clip for a fashion-forward style!

    Fit & Features

    • Sheer mesh fabric
    • Includes a smooth knit slip, adjustable spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5540

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

  • Weekend Feeling Sleeveless Bubble Hem Mini Dress

    A sleeveless knit dress features a classic crew neckline, a form-hugging fit, and a trending drop waist seam with a bubble mini-length hem. Style with a denim jacket for casual plans.

    Fit & Features

    • Knit fabric, moderate stretch
    • Crew neckline
    • Form-hugging fit
    • Drop waist seam, bubble mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5873

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Awaken Beauty A-Line Lace Short Dress

    Transform into a vision of beauty in this lace short dress at every party! This stunning dress boasts a sleeveless square neckline with a tie, enhancing your feminine charm. The A-line silhouette and short-length hem flatter your figure, while the intricate lace fabric adds a touch of elegance. Complete the look in stiletto mules and a purse!

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Square neckline with tie
    • Wide shoulder straps
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5552

    Category Name: Casual Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L, XXS

  • Cute In The City V-Neck Knit Midi Dress

    You'll be looking cute in the city in this casual midi dress perfect for a dinner date! It features bell long sleeves, a front and back V-neckline, and a flattering bodycon silhouette on rib knit fabric with a sewn-in knit lining. Complete the look with a chic crossbody bag.

    Fit & Features

    • Rib knit fabric, sewn-in knit lining
    • Moderate stretch
    • Bell long sleeves
    • Front and back V-neckline
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5192

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

  • Flouncin' Around Strapless Ruffle Mini Dress

    Show off your fun and flirty side in this strapless mini dress at parties and on dates! Featuring a figure-hugging bodycon fit, side ruched seams, and a playful ruffled mini-length hem, this dress is perfect for any occasion. Complete the look with block heels.

    Fit & Features

    • Double-lined smooth knit stretchy fabric
    • Strapless neckline
    • Bodycon fit
    • Ruffled 
    • Runs true to size

    Style Number/Barcode: 05102-5771

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Love Of Details V-Neck Lace-Up Skater Dress

    Fall in love with every chic detail of this lace skater dress sure to romance every room you walk into! With adjustable spaghetti straps and a flattering V-neckline, our dress features a lace-up mesh bodice and a playful skater silhouette. The asymmetrical ruffled trim adds a touch of flirty sophistication, making it the perfect for brides, birthday girls, or party guests! Complete the look with dainty earrings and heels.

    Fit & Features

    • Lace fabric line with stretchy knit
    • Adjustable spaghetti straps, V-neckline
    • Back zipper and hook-eye closure
    • Mesh lace-up bodice
    • Asymmetrical ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3436

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swoon Over You Strapless Lace Mini Dress

    This stunning strapless lace mini dress will make everyone swoon over your beauty at summer parties! Crafted with an airy sheer lace fabric with a knit lining for coverage, this mini-length dress is the charming style you need for the season. It features a strapless straight-across neckline with a dainty trim, a ruched seam to accentuate your curves leading to an adjustable drawstring and side slit, a ruffled hem for a flirty vibe, and a bodycon fit to flaunt your figure. Complete your look with hoop earrings and espadrille sandals.

    Fit & Features

    • Sheer lace fabric with knit lining, moderate stretch
    • Strapless straight neckline
    • Ruched seam, adjustable drawstring
    • Side slit
    • Ruffled hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3405

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: L