Casual Dresses

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.

  • Steal The Scene Halter Mini Dress

    This is what "best dressed" looks like. With a ruched bodice and breezy A-line fit, this halter mini is perfect for date nights, vacays, or twirling at parties.

    Fit & Features

    • Slinky knit stretchy lined fabric
    • Halter V-neckline, tie closure
    • Ruched bodice
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000275

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daydream Drama Polka Dot Satin Mini Dress

    A flirty mix of sweet and sultry, this satin mini brings the playful allure. The lace trim and open lace-up back make it a total show-stealer—perfect for brunch dates, parties, or spontaneous plans that somehow turn into the best stories.

    Fit & Features

    • Polka dot print, silky satin fabric, chiffon lining, no stretch
    • Lace trim V-neckline
    • Spaghetti straps
    • Lace-up open back, hidden lower back zipper with hook-eye closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000507

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • High Drama Abstract Mesh Maxi Dress

    The kind of dress that makes an entrance before you even say hello. With an abstract print, sultry cutout back, and daring front slit, it’s made for statement moments only.

    Fit & Features

    • Abstract print, airy mesh fabric, partial knit lining
    • Strapless tube neckline
    • Cutout back
    • Front slit
    • Curve-hugging, maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000320

    Category Name: Casual Dresses

    Price: $10.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Fierce And Refined Leopard Cowl Maxi Dress

    Fierce meets refined with this leopard maxi dress made to command attention. Designed with a plunge cowl neckline and a daring high slit, it turns every step into a moment- finished with an open back and sleek hoop that makes it unforgettable from every angle.

    Fit & Features

    • Leopard print, mesh-lined fabric, moderate stretch
    • Plunge cowl neckline, tie closure
    • Open back with hoop insert
    • High front slit
    • Curve-hugging silhouette, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000319

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Darling Off-Shoulder Skater Dress

    This chiffon mini dress features an off-the-shoulder ruffle neckline with delicate lace trim and a flirty skater skirt, creating a dreamy silhouette perfect for family brunches, bridal events, and dressy occasions.

    Fit & Features

    • Chiffon-lined fabric
    • Ruffle trim off-the-shoulder neckline, tie-front
    • Corset-seamed bodice
    • Skater silhouette, drop waist seam
    • Lace trim mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000684

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soft Stunner Off-The-Shoulder Mini Dress

    A little cozy, a little glam—this off-the-shoulder knit mini brings that effortless “I just threw this on” sparkle. The foldover neckline and body-hugging fit keep things soft, sleek, and low-key irresistible.

    Fit & Features

    • Rib knit stretchy fabric with shimmer
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000197

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Caught In The Wild Leopard Mini Dress

    Go wild with it. This leopard mesh mini dress serves flirty movement and fierce energy with its ruched bodice, tiered skirt, and curve-hugging fit that’s made to stand out.

    Fit & Features

    • Sheer leopard mesh fabric with stretch lining
    • V-neckline
    • Spaghetti straps
    • Fitted bodice with ruched detailing
    • Tiered ruffle skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000318

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Exit Backless Midi Dress

    For the girl who loves leaving them speechless. This open-back midi dress brings the drama without saying a word. Bonus points if you don’t look back.

    Fit & Features

    • Rib knit stretchy fabric, double-lined
    • Fitted long sleeves
    • Crew neck
    • Cutout back
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000317

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boldly Chic Abstract Cowl Neck Maxi Dress

    Bold, body-hugging, and ready to break hearts—this halter maxi dress brings the drama with an abstract print and deep cowl neckline, perfect for sunset dinners and cocktails!

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Cowl halter neckline, tie closure
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000315

    Category Name: Casual Dresses

    Price: $7.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Ocean Bloom Halter Mini Dress

    Meet your next weekend obsession. This floral halter mini dress brings vacation energy anywhere you wear it, with its draped halter cowl neckline, open tie back, and flowy fit. Perfect for rooftop brunches, date nights, or celebrations.

    Fit & Features

    • Floral print, colored rhinestone embellishments
    • Chiffon fabric lined with chiffon
    • Cowl halter neckline
    • Dual open tie-back design
    • Side zipper and hook-eye closure
    • A-line fit, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000316

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Dot to Trot Polka Dot Mini Dress

    Playful yet polished, this polka dot mini dress hugs in all the right places. With its sweetheart neckline and curve-hugging fit, it’s a flirty staple for last-minute plans or casual brunches!

    Fit & Features

    • Polka dot print, mesh-lined fabric
    • Sweetheart neckline
    • Spaghetti straps
    • Curve-hugging fit
    • Flowy mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000437

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Flirty Frills Lace Romper

    Flirt mode: on. This strapless lace romper is the perfect mix of sweet and sultry, finished with a ruffled hem that’s made for twirling through fall nights or layering under a blazer for date night.

    Fit & Features

    • Lace fabric, knit shorts lining
    • Strapless neckline with bow
    • Form-hugging bodice
    • Layered ruffled skirt overlay
    • Runs true to size

    Style Number/Barcode: 06503-000165

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sweet Plans Plaid Romper

    Sweet, flirty, and made for your next “what should I wear?” moment. This strapless plaid romper brings easy charm with its ruched bodice, ruffle skirt detail, and bow accent that seals the deal.

    Fit & Features

    • Plaid print, stretchy knit fabric
    • Strapless neckline with front bow detail
    • Ruched, fitted bodice
    • Tiered ruffle mini-length hem, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000164

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ocean Eyes Halter Maxi Dress

    Serving sultry mermaid vibes, this maxi dress is pure liquid allure. With its daring plunge, bold hardware detail, and sleek fit, it’s the statement dress that makes every entrance unforgettable. 

    Fit & Features

    • Abstract tie-dye print, mesh-lined stretchy fabric
    • Plunge halter cowl neckline with hardware insert
    • Open back with tie closure
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000674

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt Frequency Ruffle Dress

    She’s got depth and a little drama. This abstract mesh mini dress features a plunging V-neckline, ruched bodice, and tiered ruffle hem that moves with every step—aka, the perfect mix of flirty and effortless.

    Fit & Features

    • Abstract print, mesh-lined stretch fabric
    • Plunge V-neckline
    • Twisted shoulder straps
    • Open back detail
    • Form-hugging fit
    • Tiered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000313

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lover’s Lane Lace Mini Dress

    Soft romance meets modern elegance. This long sleeve mini dress stuns with a floral-pattern lace overlay, flirty tiered ruffle skirt, and open tie-back detail that feels effortlessly chic from every angle. Perfect for bridal celebrations, brunch, or dressy parties.

    Fit & Features

    • Floral pattern lace overlay, stretchy knit lining
    • Boat neckline
    • Sheer fitted long sleeves
    • Open tie-back design
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000311

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In the Moment Bodycon Midi Dress

    Sleek, sultry, and ready to steal the spotlight—this bodycon midi dress hugs in all the right places. The twist bust detail and V-neckline keep it flirty while the long sleeves add chic flair.

    Fit & Features

    • Smooth, double-lined knit stretch fabric
    • Fitted long sleeves
    • V-neckline with a twist bust
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000307

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Catch My Glow Mesh Bodycon Mini Dress

    Flirty, fun, and fitted—this abstract mini dress flaunts your gorgeous curves on a sophisticated sleeveless silhouette made for sultry entrances into art galas and cocktail parties.

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Mock neck
    • Ruched bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000302

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dangerously Divine Long Sleeve Bodycon Dress

    Bring the heat—this long sleeve bodycon dress is bold, fitted, and ready to steal the night. The sleek ruching and daring neckline make it perfect for dressy events and date nights.

    Fit & Features

    • Smooth knit stretch fabric
    • V-neckline
    • Fitted long sleeves
    • Ruched detail
    • Bodycon fit, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000308

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Allure Long Sleeve Slit Midi Dress

    Your new go-to for looking polished without even trying. This hacci rib knit midi dress serves up a body-skimming fit, cozy texture, and a side slit for just the right amount of edge. Perfect for everything from PSL runs to dinners downtown.

    Fit & Features

    • Soft hacci rib knit stretch fabric
    • Sweetheart neckline
    • Fitted long sleeves
    • Side slit accent
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000301

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Daydream Date Bow-Front Skater Dress

    Giving total daydream vibes with a flirty twist. The bow-front detail and breezy skater silhouette make this short dress perfect for brunch, strolls, or spontaneous golden-hour photo ops.

    Fit & Features

    • Satin woven fabric, scenic print
    • Sleeveless V-neckline, bow-front detail
    • Adjustable spaghetti straps, smocked back
    • High-rise waist
    • Short skater silhouette, striped hem
    • Runs true to size

    Style Number/Barcode: 05102-000306

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out Of Office Abstract Maxi Dress

    Booked, busy, and dressed for it. This abstract mesh strapless tube maxi dress hugs your curves with a sleek fit and side slit that brings just enough drama for vacations and sunset dinners with a view.

    Fit & Features

    • Abstract print, knit fabric
    • Strapless neckline
    • High side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000305

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet But Sassy Ruffle Tube Dress

    Sweet meets spicy in this ruched tube dress with a tiered ruffle skirt—basically, your flirty girl era into fall!

    Fit & Features

    • Knit fabric
    • Strapless tube neckline
    • Form-hugging bodice
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000299

    Category Name: Casual Dresses

    Price: $9.97 $50.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Deep Drama Long Sleeve Bodycon Dress

    Bold meets sleek—this bodycon mini dress serves up long-sleeve polish with a curve-hugging ruched fit. Perfect for brunch, date nights, or any occasion when you want to look unforgettable!

    Fit & Features

    • Smooth knit stretch fabric
    • Fitted long sleeves
    • Plunge V-neckline
    • Ruched bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000295

    Category Name: Casual Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free