Casual Dresses

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Casual Dresses Made for Everyday Fall Plans

Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.

Easy Prints, Textures & Layers for the Season

Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.

What Makes a Dress Casual?

A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.

How Do You Transition a Casual Dress From Summer to Fall?

Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.

Which Fabrics Work Best for Everyday Dresses?

Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.

How Can You Style One Casual Dress for Different Plans?

Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.

  • Stylishly Striped Knit Off-The-Shoulder Mini Dress

    This trendy striped knit mini dress is designed with a chic off-the-shoulder straight neckline with a flattering fold-over design and a bodycon silhouette to show off your curves. Pair with sneakers for a cute everyday look.

    Fit & Features

    • Striped ribbed knit fabric, plenty of stretch
    • Off-the-shoulder straight neckline, fold-over design
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5853

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple And Stunning Ruched Mini Dress

    Simple and stunning, this classic mini dress is a closet staple. It features a sleeveless cowl neckline with a draped design, tank shoulder straps, a scoop back design, ruching down the side seams, a mini-length hem, and a bodycon silhouette that will hug your curves. Style with strappy mules for a dinner date or party.

    Fit & Features

    • Sleeveless cowl neckline
    • Tank shoulder straps
    • Scoop back design
    • Ruched side seams
    • Mini-length hem, bodycon silhouette
    • Double-lined smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5028

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Most Noteworthy Ponte Pleated Mini Dress

    A classic little black dress for your most noteworthy look for date night! The short dress features a sleeveless square neckline, spaghetti straps, and a side pleated seam that leads to the form-hugging mini-length hem on lined ponte fabric. Style the mini dress with a rhinestone necklace for a glam touch!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Side pleated seam
    • Form-hugging silhouette
    • MIni-length hem
    • Lined ponte knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05103-5077

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Passion V-Neck Color Block Maxi Dress

    Dress to impress in this V-neck maxi dress to make a chic impression at parties or rehearsal dinners! The flowy silhouette and color block panels give you a stunning look, while the spaghetti straps and neck tie add a trendy touch. Complete the look with a clutch and heels.

    Fit & Features

    • Woven fabric, no stretch
    • V-neck
    • Spaghetti straps, spaghetti strap neck tie
    • Color block panels, flowy silhouette
    • Maxi length
    • Runs true to size

    Style Number/Barcode: 05102-5803

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Truly Radiant V-Neck Lace Bodycon Mini Dress

    This sleeveless lace mini dress features a flattering ruffle trim V-neckline, spaghetti straps, and a bodycon silhouette perfect for a date or brunch.

    Fit & Features

    • Lace-lined fabric
    • Ruffle trim V-neckline
    • Spaghetti straps
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3534

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Seamless Midi Sweater Dress

    Chic and seamless, this sweater dress is perf for creating a simple yet elevated look. It features a sleeveless scoop neckline, adjustable spaghetti straps, a mid-length, curve-hugging silhouette, and a sultry thigh-high side slit. Style this dress with clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Mid-length, form-fitting silhouette
    • High side slit
    • Sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1085

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Give Me Butterflies Square Neck Skater Dress

    Show up to the party in this short skater dress and give everyone a fluttery heart for you! It features three-quarter-length puff sleeves, a square neck, a smocked back, and a fit and flare silhouette. The dress is designed with delicate butterfly embroidery on twill woven fabric with a woven lining. Complete the look with lace-up sandals.

    Fit & Features

    • Three-quarter-length puff sleeves
    • Square neck
    • Smocked back
    • Fit and flare, skater silhouette
    • Short-length hem
    • Butterfly embroidery, twill woven fabric and lining
    • Runs true to size

    Style Number/Barcode: 05102-5009

    Category Name: Casual Dresses

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Allure A-Line Mini Tube Dress

    Show off a flirty allure in this adorable mini tube dress designed with a strapless straight neckline, drop waist, and a short, tiered, A-line silhouette. Style with sneakers for a cute and casual 'fit.

    Fit & Features

    • Lined knit fabric, high stretch
    • Elasticized strapless straight-across neckline
    • Ruched side seams
    • Drop waist design
    • Mini-length tiered A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000130

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Allure Strapless Ruffled Skater Dress

    Give off a flirty allure in this adorable skater dress at summer parties! Designed with a stretchy knit fabric, the short dress features a strapless straight-across neckline, ruching at the waist, and a double-layered ruffled skater silhouette for a sweet and sassy look. Style with a dainty necklace and sneakers for a casual vibe.

    Fit & Features

    • Stretchy knit fabric lined with knit
    • Strapless straight neckline
    • Ruched waist
    • Double-layered ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5758

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Express Your Style V-Neck Ruffle Bodycon Mini Dress

    Express your devotion to style in this charming sleeveless mini dress perfect for casual showers or brunch! This dress features adjustable spaghetti straps for the perfect fit, a flirty V-neckline with a bust tie for added charm, and a bodycon fit to accentuate your curves. The mini-length hem and ruffle trim throughout add a touch of romance to this head-turning dress. Complete the look with earrings.

    Fit & Features

    • Ruffle trim throughout, knit fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • V-neckline with bust tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5789

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Flirt Floral Mini Dress

    Bring the flirtatious vibes in this adorable floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. Style this dress with sneakers for a cute and casual look.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruched detailing, drawstrings at the hem
    • Short, form-hugging fit
    • Ribbed knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05102-1404

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Vibes High Slit Tropical Knit Maxi Dress

    Give off effortless vacay vibes in this high slit tropical knit maxi dress. The tropical palm leaf print on the lightweight knit fabric will have you looking like you're ready for a getaway, even if you're just grabbing drinks at a local happy hour! The dress is shaped with a sleeveless V-neckline and spaghetti straps, and features a high-cut side slit to showcase some leg on the form-hugging mid-length silhouette. Style with gold hoops and strappy wedges!

    Fit & Features

    • Stretchy knit fabric with a bust lining
    • Tropical print
    • Sleeveless V-neckline
    • Spaghetti straps
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5537

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Of All Ribbon Bow Bodycon Mini Dress

    You'll be the cutest of all in this bodycon mini dress out on dates or brunch! Crafted from a woven fabric lined with stretchy knit, this dress features a flattering square neckline and a satin ribbon bow that adds an elegant touch. The bodycon silhouette hugs your curves beautifully, while the mini-length hem gives a playful and flirty vibe. Complete the look in sandals and sunnies!

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Square neckline
    • Satin ribbon bow
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5655

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beyond Precious V-Neck Ruffle Babydoll Dress

    You'll be looking beyond precious in this babydoll dress - the perfect summer staple!  The ruffle trim shoulder straps and v-neckline create a delicate and alluring look, while the ruffled babydoll silhouette and side pockets add a touch of playful charm to the short-length hem. Complete the look in trendy sandals.

    Fit & Features

    • Woven fabric, bust lining, no stretch
    • Ruffle trim shoulder straps
    • V-neckline
    • Ruffle babydoll silhouette
    • Side pockets
    • Runs true to size

    Style Number/Barcode: 05102-5422

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Dreams Hanky Hem Floral Mini Dress

    Sweet and dreamy will be your vibe in this adorable floral mini dress! Designed with a stretchy sheer mesh fabric with a knit lining for coverage, the short dress showcases a blooming floral print for the prettiest look. It features a sleeveless V-neckline with dainty lace trim for a feminine touch, spaghetti straps, a trendy drop waist silhouette, and a mini-length asymmetric hanky hem with a flowy A-line fit. Style with bow hair pins and strappy mules.

    Fit & Features

    • Floral print
    • Stretchy sheer mesh fabric with knit lining
    • V-neckline with lace trim
    • Spaghetti straps
    • Drop waist silhouette
    • Asymmetric hanky hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3462

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cherry On Top Lace Trim V-Neck Mesh Mini Dress

    This mesh mini dress is the cherry on top of your perfect summer! Featuring delicate lace trim V-neckline, adjustable spaghetti straps, and a cherry print on mesh fabric, this mini-length bodycon dress will hug your curves and flaunt your style. Complete the look in platform heels.

    Fit & Features

    • Cherry print, mesh fabric, stretchy knit lining
    • Lace trim V-neckline
    • Adjustable spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5798

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catch A Cutie Short Sleeve Cutout Eyelet Skater Dress

    Catch yourself a cutie wearing this eyelet skater dress to day parties this season! With playful puff sleeves and a flirty cutout. The sweetheart neckline and bust drawstring add a touch of romance, while the skater silhouette and tiered ruffled hem keep it fun and flirty. Complete the look in wedge sandals.

    Fit & Features

    • Eyelet fabric lined with stretchy knit
    • Sweetheart neckline
    • Adjustable bust drawstring, cutout
    • Skater silhouette
    • Tiered ruffles
    • Runs true to size

    Style Number/Barcode: 05102-5430

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Babe Cutout Ruffle Hem Chiffon Midi Dress

    Show up and stun at a summer party like the bold babe you are in this fab midi dress! Designed with a crinkled chiffon fabric, the mid-length dress features a smocked body for added stretch along the figure-flaunting bodycon silhouette. The sleeveless bodice is shaped with a sweetheart neckline with the cutest tie-front design at the bust, a sultry waist cutout to reveal some skin, and adjustable spaghetti straps to find your perfect fit. The layered ruffled hem adds a flirtatious allure to the iconic look. Style this midi dress with hoop earrings and espadrille sandals!

    Fit & Features

    • Crinkled chiffon fabric, knit bust lining, moderate stretch
    • Sweetheart neckline, tie-front bust
    • Waist cutout
    • Adjustable spaghetti straps
    • Smocked body, layered ruffled hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3454

    Category Name: Casual Dresses

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Yours Strapless Bubble Hem Mini Dress

    A strapless mini dress boasts a flattering smocked bodice that hugs your curves and an adorable woven bubble hem skirt. Perfect for styling with heels for a party.

    Fit & Features

    • Strapless neckline
    • Stretchy knit smocked bodice
    • Woven bubble mini-length hem, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5877

    Category Name: Casual Dresses

    Price: $14.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Refreshing Charm Smocked Striped A-Line Mini Dress

    This sleeveless striped mini dress features a flattering square neckline and a smocked A-line silhouette with a trendy drop waist seam. The ruffled hem adds a flirty touch perfect for picnics or a day at the beach. 

    Fit & Features

    • Striped woven fabric
    • Square neckline
    • Adjustable spaghetti straps
    • Smocked A-line silhouette
    • Drop waist seam
    • Mini-length ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5826

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetie Status Halter Crochet Trim Babydoll Dress

    You'll look absolutely adorable in this babydoll dress at showers, birthdays, or backyard parties! The halter neckline and cutout bodice add a touch of allure, while the crochet trim and babydoll silhouette create a delicate and feminine look along the short-length hem. Complete the look in sandals and hoop earrings.

    Fit & Features

    • Gauze woven fabric, woven lining, no stretch
    • Halter neckline with spaghetti strap ties
    • Cutout bodice
    • Crochet trim
    • Babydoll silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5421

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Behind The Scenes Long Sleeve Mini Dress

    Effortless in the front, unexpected in the back—this mini dress does both. With flowy dolman sleeves, a chic boat neckline, and an open tie-back detail, it’s the perfect mix of cozy and sultry.

    Fit & Features

    • Soft knit stretchy fabric
    • Dolman long sleeves
    • Boat neckline
    • Open tie back design
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000335

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, L

  • Angelic Beauty Strapless Printed Mesh Midi Dress

    Showcase your angelic beauty in this strapless printed mesh midi dress! The stretchy sheer mesh fabric features an angel cherub multi-print pattern for a celestial vibe, and includes a knit lining for coverage. The bodice is shaped with a strapless elasticized straight neckline, leading to ruching down the back and side seams to accentuate your gorgeous curves on the bodycon silhouette. The mid-length hem is accented with a back slit for a chic detail and added movement. Style with knee-high boots for date night.

    Fit & Features

    • Stretchy sheer mesh fabric, knit lining
    • Angel cherub multi-print pattern
    • Strapless elasticized straight neckline
    • Ruched back and side seams
    • Back slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3051

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serving Vibes Cutout Geometric Mesh Maxi Dress

    Serve major vibes in this geometric mesh maxi dress out by the beach this weekend or for a getaway! The square neckline, adjustable spaghetti straps, and form-hugging fit show off your curves while the cutout sides and back add a touch of sass. Complete with a center-back slit and maxi-length hem for effortless movement. Style this sleeveless dress with earrings and sandals.

    Fit & Features

    • Geometric print, mesh fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Square neckline
    • Cutout sides and back
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5759

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale