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.

  • 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

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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

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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

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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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  • Destination Vacay Tropical Floral Mini Dress

    Jet set to your destination vacay in this tropical floral print mini dress, perfect for sunset happy hour. Designed with a square neck, adjustable spaghetti straps, and a short fitted silhouette, style with gold hoops and slide-on sandals.

    Fit & Features

    • Scuba knit fabric, stretchy knit lining
    • Tropical floral print
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Back zipper closure
    • Mini-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6077

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Lovely Day Eyelet A-Line Midi Dress

    It'll be love at first wear in this strapless midi dress, perfect for shower celebrations, brunch, or parties! The intricate eyelet detailing adds a touch of romance while the flattering A-line silhouette accentuates your figure.

    Fit & Features

    • Eyelet woven fabric, woven lining
    • Strapless stretchy smocked neckline
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6078

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sweet Flirt Floral Mini Tube Dress

    Bring the sweet flirty vibes to your weekend plans in this cute mini tube dress with a dainty floral print on lined chiffon fabric. The strapless smocked bodice leads to a V-shaped waist, tiered ruffled design, and flowy skater silhouette.

    Fit & Features

    • Woven chiffon fabric with stretchy knit lining, dainty floral print
    • Strapless straight-across neckline
    • Stretchy smocked bodice
    • V-shaped waist
    • Tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4077

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • On Vacay V-Neck Floral Maxi Dress

    Look a daydream come true in this floral maxi dress while on vacay! Designed with a bold floral print on a sultry form-hugging silhouette.

    Fit & Features

    • Floral print, mesh-lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4076

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Ready To Bloom Strapless Lace-Up Floral Maxi Dress

    With the warmer months ahead it's time to bloom in this floral maxi dress perf for vacations and weekend getaways! The dress boasts an eye-catching lace-up back and a mermaid silhouette that accentuates your natural curves.

    Fit & Features

    • Floral print, knit fabric lined with stretchy knit
    • Lace-up back
    • Mermaid silhouette
    • Ruffled maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4080

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Paradise Beauty Floral Mesh Maxi Dress

    A beautiful floral mesh maxi dress for your escape to paradise! The dress boasts a flattering V-neckline and a form-hugging fit that flares into a flowy maxi-length hem. Pair with earrings and a bracelet.

    Fit & Features

    • Floral print, mesh lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging fit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4075

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Major Energy Strapless Floral Mesh Maxi Dress

    Bring major energy in this strapless floral mesh maxi dress design to flaunt your figure in a bodycon fit and show some skin with a high-side slit. Pair with mules.

    Fit & Features

    • Floral print, mesh fabric, soft and stretchy knit lining
    • Strapless neckline
    • High-side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-001515

    Category Name: Casual Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PLUM-2

    Available Size: S, L, XL

    Product Badge:
    • Sale
  • Showstopper Cutout Ruffle Slit Maxi Dress

    Serve major allure in this sleeveless maxi dress while on vacay or weekend getaway! The maxi dress delivers a sultry design with a twist plunge V-neckline, cutout bodice, and a high front slit with a ruffled trim.

    Fit & Features

    • Slinky knit fabric, short knit lining
    • Plunge twist V-neckline
    • Shoulder straps, one metal accent piece
    • Cutout bodice
    • High front slit with ruffle trim
    • Bodycon maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4070

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Breath Of Fresh Air Smocked Maxi Tube Dress

    Step out looking like a breath of fresh air in this maxi tube dress on vacay or weekend plans! The strapless, stretchy, smocked bodice ensures a perfect and comfortable fit that flatters your figure while the flowy, maxi-length hem creates an effortless look.

    Fit & Features

    • Woven fabric, bust knit lining
    • Strapless V-wired neckline
    • Stretchy smocked bodice
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6076

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Trend Moment Lace-Up Bodycon Midi Dress

    Have your trending moment in this midi dress! It's designed to hug your curves in a bodycon silhouette while the front lace-up adds a playful touch to your day or night look.

    Fit & Features

    • Knit fabric with moderate stretch
    • Square neckline
    • Lace-up front bust
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6072

    Category Name: Casual Dresses

    Price: $9.97

    Availability: Out of Stock

    Product Badge:
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  • Sunset Beauty Tropical Print Maxi Dress

    Show off your beauty at sunset happy hour in this tropical print maxi dress designed with sheer mesh fabric and a mini-length lining. The high-cut side slit adds an alluring detail to turn heads.

    Fit & Features

    • Sheer knit fabric with mini-length knit lining, high stretch
    • Tropical print
    • Sleeveless cowl neckline
    • Spaghetti straps, cross-back design
    • High side slit
    • Maxi-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6074

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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