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.

  • Tropical Beauty V-Neck Slit Midi Dress

    Jet set on your next tropical getaway or weekend escape in this perfect slit midi dress! Featuring a bold metal insert and a flattering bodycon fit, this dress is perfect for any occasion. 

    Fit & Features

    • Palm leaf tropical print, stretchy knit fabric, soft knit lining
    • V-neckline with metal insert
    • Spaghetti straps
    • Side slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6095

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

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  • Retro Vision Halter Striped Crochet Midi Dress

    The perfect blend of modern and retro! This halter striped crochet midi dress can easily be styled with sandals for the day and heels for night.

    Fit & Features

    • Striped design, crochet fabric, short stretchy knit lining
    • Halter neckline, spaghetti strap tie
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2264

    Category Name: Casual Dresses

    Price: $8.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Timeless Romance Open Back Lace Romper

    Enter your forever romantic era in this lace long sleeve romper boasting a flirty open back and ruffled short-length hem.

    Fit & Features

    • Lace-lined fabric
    • Scoop neckline
    • Sheer fitted long sleeves
    • Open back
    • Form-hugging fit
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 06503-1276

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Cool Breeze Cutout Striped Knit Mini Dress

    As the temps rise so will your style in this striped knit mini dress with a flirty cutout back and bodycon fit perfect for layering with a denim jacket on cooler nights.

    Fit & Features

    • Striped pattern, knit fabric
    • Scoop neckline
    • Wide shoulder straps
    • Cutout back
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2268

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • In The Cards Halter Skater Mini Dress

    No matter the plans, this halter skater mini dress will have you looking fabulous! 

    Fit & Features

    • Stretchy rib knit fabric
    • Halter neckline
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2265

    Category Name: Casual Dresses

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sweet Like Me Scoop Neck Skater Mini Dress

    Showcase your sweet side in this ribbed knit mini dress made to please the crowd! It features a sleek scoop neckline and a skater silhouette that flatters every figure. Style with a handbag.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Scoop neckline
    • Tank shoulder straps
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000006

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

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  • Just Like A Dream Strappy Back Ruffled Maxi Dress

    Make a jaw-dropping entrance in this gorgeous ruffled maxi dress at shower celebrations or on vacation! The flattering V-neckline draws the eye, while the intricate strappy back adorned with beaded insets creates an unforgettable exit view.

    Fit & Features

    • Airy woven gauze fabric, woven lining
    • V-neckline
    • Dual spaghetti straps
    • Strappy back with beaded insets
    • Cascading ruffles, flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000653

    Category Name: Casual Dresses

    Price: $35.96 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED, BROWN

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

    Product Badge:
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  • Sweetest Poise Button Bodycon Midi Dress

    Polished and poised, this sweet sleeveless midi dress will elevate your everyday style with chic button accents and a bodycon fit.

    Fit & Features

    • Stretchy rib knit fabric
    • Square neckline
    • Wide shoulder straps
    • Button accents, front faux pockets
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2261

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Allure Ruffle Eyelet Knit Mini Dress

    Bring the cutest allure to summer dates in this flirty eyelet knit mini dress that will get you all the compliments. The adorable dress features a plunging V-neck with a ruffled trim under the bust, ruffled spaghetti straps, and a short A-line silhouette.

    Fit & Features

    • Eyelet knit fabric, stretchy knit lining
    • Sleeveless plunging V-neckline, bar strap detail, keyhole cutout
    • Ruffled trim under the bust
    • Ruffle trim spaghetti straps, adjustable
    • Open back, tie-back strap design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6091

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Soft And Chic Ribbed Knit Off-The-Shoulder Mini Dress

    Soft and chic, this mini dress is made with ribbed knit fabric offering plenty of stretch for comfortable wear. It features an off-the-shoulder straight neckline with a long fold-over design for a trendy look and a short bodycon silhouette to highlight your curves.

    Fit & Features

    • Ribbed knit fabric
    • Off-the-shoulder straight neckline
    • Long fold-over design
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2259

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Island Style One-Shoulder Slit Tropical Maxi Dress

    Get that tropical feeling when you're in this one-shoulder maxi dress, whether you're on vacay or having some weekend fun! The curve-hugging silhouette offers a show of skin with a side cutout and high slit.

    Fit & Features

    • Tropical print, stretchy knit fabric, short knit lining
    • One-shoulder neckline
    • Side cutout
    • High side slit
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6089

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Serve Sultry Vibes Halter Cowl Neck Maxi Dress

    Serve sultry vibes only in this sleek knit maxi dress at your next rooftop party. The halter cowl neckline, alluring open back, and curve-hugging mermaid silhouette will steal all the glances.

    Fit & Features

    • Slinky knit fabric, knit lining, high stretch
    • Sleeveless cowl neckline, halter strap
    • Open back
    • Ruching
    • Maxi-length hem
    • Curve-hugging mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4110

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Flirty Girlie Lace-Up A-Line Mini Dress

    Say hello to your new favorite mini dress for celebrations to brunch! Featuring flutter sleeves for a touch of flirtiness, a lace-up back for a customizable fit, and an a-line silhouette to flatter any figure.

    Fit & Features

    • Woven fabric, lace trims, stretchy knit lining
    • Square neckline, with keyhole bust tie
    • Flutter sleeves
    • Lace-up back
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4108

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Summer Love Eyelet Knit Mini Dress

    You'll love the effortless summer vibes of this floral eyelet knit mini dress! The short form-hugging fit will highlight your stunning curves.

    Fit & Features

    • Floral eyelet knit fabric with knit lining, high stretch
    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6090

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • She's A Vision Abstract Cowl Slit Maxi Dress

    Make a statement and turn heads in this abstract maxi dress on vacation or at a chic pool party! The cowl neck, adorned with hoop trims, adds a touch of glamour, while the high side slit and maxi length hem elongate your silhouette and add a hint of allure.

    Fit & Features

    • Abstract print, stretchy knit fabric
    • Cowl neckline with hoop trims, spaghetti strap
    • Open strappy back
    • High side slit, hoop insert
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6084

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Breezy Charm Halter Babydoll Mini Dress

    A charming halter dress for dinner dates or beachside strolls. Its lightweight babydoll silhouette offers a comfortable, flowy fit, while the playful ruffle mini hem brings a flirty finish!

    Fit & Features

    • Woven gauze fabric, woven lining
    • Sweetheart halter neckline, hoop insert, spaghetti strap tie
    • Cutout keyhole accent
    • Padded bra cups
    • Flowy babydoll silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6087

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fairytale Daze Strappy Back Chiffon Skater Dress

    This stunning skater dress is the perfect blend of effortless and ethereal. It is designed with flirty ruffles and a strappy tie-back that turns heads at parties!

    Fit & Features

    • Chiffon fabric, woven lining
    • V-neckline, spaghetti straps
    • Strappy tie-back, lower zipper and hook-eye closure
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4097

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Breeze Tropical Slit Midi Dress

    Turn heads on vacay in this tropical midi dress perfect for sunset cocktails and dinner! Featuring a strapless neckline with insert, this form-hugging dress will flatter your curves and keep you cool with a side slit and midi hem.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, short knit lining
    • Strapless neckline with insert
    • Form-hugging fit
    • Side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6088

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Dance To My Rhythm Abstract Tube Maxi Dress

    Perfect for any occasion when you want to stand out, this abstract maxi dress will have every eye on you! This sleek tube design hugs your curves in all the right places while the bold abstract pattern demands attention while the daring high side slit shows some leg.

    Fit & Features

    • Abstract print, mesh fabric, stretchy knit lining
    • Tube strapless neckline
    • High side slit
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6086

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Vacay Mode Buckle Cutout Slit Maxi Dress

    A must-have maxi dress for any fashion-forward traveler! Featuring a sweetheart neckline with a trendy buckle accent, a sultry cutout bodice, and a high side slit, this dress will hug your curves and make you feel stylish on your vacation.

    Fit & Features

    • Texture knit fabric, smooth knit stretchy lining
    • Sweetheart neckline with buckle accent
    • Spaghetti straps
    • Cutout bodice
    • High side slit
    • Form-hugging fit, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6082

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Destination Cutie Tropical Cutout Slit Maxi Dress

    Get ready for your sunny destination with this stylish tropical maxi dress! Featuring a sweetheart neckline with a square insert, a flirty cutout bodice, and a high side slit, this dress is perfect for showing off your tropical vibes.

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Sweetheart neckline, square insert
    • Spaghetti straps
    • Cutout bodice, high side slit
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6081

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Flirtatious Scene Halter Lace Skater Dress

    Make it a flirty scene in this lace skater dress boasting a sultry halter V-neckline with metal accents and a flattering tiered ruffled mini-length hem. Complete the look with boots.

    Fit & Features

    • Lace-lined fabric
    • Halter V-neckline with metal accents
    • Skater silhouette
    • Tiered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4095

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Strolls In The Sand Halter Bodycon Mini Dress

    Stroll the beach in this halter mini dress while on vacation or enjoying the warm weather! The dress is designed in a unique texture knit that hugs your curves in a bodycon silhouette.

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Halter V-neckline, button closures
    • O-ring metal insert
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6080

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Days In Paradise Strapless Cutout Mini Dress

    Indulge in pure paradise in this cutout mini dress! Featuring a sweetheart neckline accented with a stunning hoop and stone insert, this bodycon dress is designed to hug your every curve. 

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Strapless sweetheart neckline with hoop and stone insert
    • Padded bra cups, back zipper and hook-eye closure
    • Cutout accent
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6079

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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