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.

  • 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

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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:
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  • 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:
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  • 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: In Stock

    Available Color: RUST

    Available Size: S

  • 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:
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  • 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, mesh-lined 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:
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  • 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
  • Flirty Bloom Floral Ruffle Skater Dress

    Serving soft-girl romance with a side of sass, this floral halter mini dress is made for twirls and double takes. Wear it when you want compliments on repeat.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch, floral print
    • Sleeveless V-neckline
    • Tie-back halter straps, partially open back
    • Ruching, drop waist
    • Tiered ruffled design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000297

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twist of Fate One Shoulder Mini Dress

    Simply stunning and ready for date night or a bridal celebration, this sleek one-shoulder mini dress is made to hug in all the right places to flaunt your sultry curves!

    Fit & Features

    • Smooth woven stretch fabric
    • One-shoulder neckline with twist strap
    • Ruched bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000298

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Bloom Mesh Maxi Dress

    Serving fierce meets floral—this mesh maxi dress is pure goddess energy. Perfect for a sunset dinner on vacay or a chic cocktail bar.

    Fit & Features

    • Leopard, floral printed mesh-lined fabric
    • V-neckline, wide shoulder straps
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000296

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Plans Ruffle A-Line Romper

    Your plans just found their outfit—this romper is all about fun with a flirty edge. The tie-back halter straps, ruffle overlay, and A-line fit make it a go-to for nights out or weekend parties.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Sleeveless V-neckline
    • Tie-back halter straps, partially open back
    • Ruching, drop waist
    • Mini-length tiered ruffle overlay, hidden fitted shorts
    • Romper in size small is 29" shoulder to hem with a 9" front rise and a 1" inseam
    • Runs true to size

    Style Number/Barcode: 06503-000155

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Untamed Nights Zebra Print Maxi Dress

    Go full wild mode in this zebra mesh dress—plunging cowl neckline, open back with tie straps, and a daring thigh-high slit. The hardware trim at the waist adds just the right amount of edge for a dress that owns every room.

    Fit & Features

    • Zebra print, mesh fabric, stretch knit lining
    • Plunge halter cowl neckline
    • Open back with ties
    • Hardware waist trim
    • High front slit
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000292

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twirl Agenda Chiffon Mini Dress

    Romantic with a little edge, this chiffon mini is made to move. The halter neckline, lace-up corset detailing, and tiered ruffles bring that flirty, fairytale energy—perfect for brunch to concerts, and daydreaming.

    Fit & Features

    • Chiffon fabric, stretchy knit lining
    • Halter V-neckline, tie closure
    • Dual front lace-up plackets
    • Corset-inspired fitted bodice
    • Drop waist seam
    • Tiered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000293

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Untamed Nights Halter Slit Maxi Dress

    Glam meets wild in this sultry halter maxi dress. With its curve-hugging fit, statement hardware, and bold slit, it’s made for spotlight entrances and after-dark drama.

    Fit & Features

    • Animal print, knit-lined fabric with stretch
    • Halter neckline, hardware insert, spaghetti strap tie
    • Bodice cutout with hardware insert
    • High front slit
    • Form-hugging silhouette, maxi hem
    • Runs true to size

    Style Number/Barcode: 05102-000294

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Own the Moment Tube Floral Slit Bodycon Maxi Dress

    This strapless bodycon maxi dress brings major drama with a bold floral print and side thigh-high slit made to steal the spotlight at a beach brunch or on vacation!

    Fit & Features

    • Statement floral print, slinky knit stretchy fabric
    • Tube neckline
    • Side slit
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000286

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lace Me Up Denim Mini Dress

    Denim but make it daring. This lace-up halter mini brings that effortlessly cool, slightly rebellious vibe—perfect for nights when you’re feeling bold and unstoppable.

    Fit & Features

    • Vintage-inspired denim fabric
    • Halter plunge neckline
    • Lace-up front bust design
    • Stretchy smocked back panel
    • Contouring seam detailing
    • Bodycon fit, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000288

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Curve Flow Bodycon Midi Dress

    Sleek, soft, and made to flatter. This mock neck midi dress hugs in all the right places with side ruching and a soft modal blend knit fabric that gives casual polish. Perfect for weekday styling and weekend looks!

    Fit & Features

    • Soft modal-blend knit fabric, knit lining, moderate stretch
    • Sleeveless mock neck
    • Side ruched seams
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000287

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Rodeo Rebel Faux Suede Mini Dress

    Cowgirl, but make it hot. This faux suede mini dress brings western vibes with curve-hugging fit, embroidery details, and a button-front that’s strictly for show.

    Fit & Features

    • Western-embroidery, faux suede fabric, sewn-in knit lining
    • Moderate stretch
    • Strapless tube neckline
    • Side zipper and hook-and-eye closure
    • Faux front buttons
    • Bodycon fit, mini hem
    • Runs true to size

    Style Number/Barcode: 05102-000148

    Category Name: Casual Dresses

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale