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.

  • Back To Basics Ribbed Knit Midi Dress

    Every girl needs this basic ribbed knit midi dress in her line up! The dress features a classic crew neckline and short sleeves perfect for layering with a sweater or jacket and a form-hugging fit.

    Fit & Features

    • Ribbed knit fabric with brushed knit lining, plenty of stretch
    • Crew neckline
    • Short sleeves
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5603

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

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  • Confident Cutie Sleeveless V-Neck A-Line Mini Dress

    Get ready to feel confident and cute in this basic A-line mini dress perfect for styling up or down! The soft and stretchy rib knit fabric includes a full knit lining for added coverage. This dress is perfect for any occasion with a flattering V-neckline, delicate spaghetti straps, and a stylish A-line silhouette. Complete the look in a chunky choker and sneakers!

    Fit & Features

    • Soft and stretchy rib knit fabric, full knit lining
    • V-neckline
    • Spaghetti straps
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5651

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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  • Stylish Persona Strapless A-Line Mini Dress

    Turn on the charm in this strapless mini dress out on the town or at a party! The side ruched seam accentuates your curves while the A-line silhouette provides a flattering fit along the playful mini-length hem. Complete the look with heeled sandals.

    Fit & Features

    • Smooth knit fabric, moderate stretch
    • Strapless neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5642

    Category Name: Casual Dresses

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casual Chic Ruched Ribbed Knit Maxi Dress

    Effortlessly elevate your everyday looks with this casual chic ribbed knit maxi dress. It features a sleeveless boat neckline, tank shoulder straps with a trendy twist-back design, ruched side seams at the waist to accentuate your curves, and a fitted A-line silhouette with a maxi-length hem to flaunt your figure. Style with hoop earrings and strappy mules.

    Fit & Features

    • Stretchy ribbed knit
    • Boat neckline
    • Tank shoulder straps, twist-back design
    • Side ruching at the waist
    • Fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5834

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Dream Twirl Tie Strap Pleated A-Line Mini Dress

    Twirl all day in this pleated A-line mini dress at casual parties or outings! Featuring a flattering square neckline and delicate spaghetti strap ties, this A-line silhouette dress offers a flattering style. The hidden hook and eye fasteners provide a seamless look, while the pleated mini-length hem adds a flirty touch. Complete the look in platform shoes and earrings!

    Fit & Features

    • Stretch woven fabrication
    • Spaghetti strap ties
    • Square neckline
    • Hidden front hook and eye fasteners
    • A-line pleated silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5737

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Charmed Success Lace Cold Shoulder A-Line Mini Dress

    When you stroll into any event, you'll be a charming hit in this chiffon mini dress! The lace cold shoulder V-neckline and delicate spaghetti straps add a touch of elegance, while the satin bow adds a feminine and playful flair. With its A-line silhouette and mini-length hem, this dress is perfect for any occasion. Complete the look in stiletto heels and a clutch!

    Fit & Features

    • Chiffon fabric lined with stretchy knit
    • Lace cold shoulder V-neckline
    • Spaghetti straps, satin bow
    • Back zipper and hook-eye closure
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3475

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • Trendy Era Drop Waist A-Line Mini Dress

    Enter your trendy era with this woven mini dress featuring a sleeveless square neckline and a halter strap accented with a buckle trim detail. The drop waist design leads to a short pleated A-line silhouette.

    Fit & Features

    • Woven fabric
    • Square neckline
    • Halter strap with buckle trim detail
    • Partially open back, zipper closure
    • Drop waist design
    • Mini-length pleated A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5974

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cheerful Cutie Strapless Gingham Skater Dress

    Spread your sunshine in this gingham skater dress for the sweetest look all summer! The strapless neckline, lace trim, and stretchy smocked waist create a flirty and comfortable look. The skater silhouette and ruffled mini-length hem with lace trim add a touch of cuteness to your look. Complete the look with a crossbody purse and sandals for any casual plans!

    Fit & Features

    • Gingham print, cotton fabric with woven lining
    • Strapless lace trim neckline
    • Stretchy smocked waist
    • Skater silhouette
    • Ruffled lace trim hem
    • Runs true to size

    Style Number/Barcode: 05102-5801

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Mood Scoop Neck Lace A-Line Mini Dress

    Get in the mood to romance your look with this lace A-line mini dress perfect for a dressy soiree! This fun and flirty lace A-line mini features a scoop neckline and adjustable spaghetti straps for a perfect fit while the mini-length hem adds a touch of flirty. Complete the look with the matching bolero. 

    Shop Matching Bolero: In The Mood Long Sleeve Lace Bolero

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Scoop neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3332

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Wild For Style Strapless Zebra Print Midi Dress

    Let this strapless midi dress tame your worries over having nothing to wear! It features a strapless neckline, a figure-flaunting bodycon silhouette, and a midi-length hem on zebra print knit fabric that gives you a wild style. Complete the look with earrings for any occasion!

    Fit & Features

    • Zebra print, knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5820

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Living A Dream Marble Off-The-Shoulder Midi Dress

    This dreamy mesh midi dress is ready for you to take on any event! The stylish marble mesh fabric is sure to make a dramatic statement with its off-the-shoulder neckline, ruched fitted sheer long sleeves, flattering side ruched seams, and bodycon silhouette. Complete the look in stiletto heels for a birthday dinner or date night!

    Fit & Features

    • Off-the-shoulder neckline
    • Ruched fitted sheer long sleeves
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Marble print, mesh fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5332

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sweet Escape Lace-Up Tropical Midi Dress

    Have the sweetest look in this tropical midi dress for your next vacay escape! With a flattering square neckline, delicate spaghetti straps, and a lace-up back, this bodycon dress will hug your curves down to the high-cut asymmetrical midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Tropical print, lined knit fabric, plenty of stretch
    • Square neckline
    • Spaghetti straps
    • Lace-up back
    • Asymmetric high-cut hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5564

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • True Love In Floral V-Neck Corset Skater Dress

    This sleeveless mini dress features a flattering V-neckline, adjustable spaghetti straps for a customizable fit, and a corset-inspired bodice. The skater silhouette and tiered ruffle hem gives this dress the perfect look with heels.

    Fit & Features

    • Floral print mesh fabric, stretchy knit lining
    • V-neckline
    • Adjustable spaghetti straps
    • Corset-inspired bodice
    • Skater silhouette
    • Tiered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3520

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Unforgettable Cutie Bow A-Line Ponte Mini Dress

    Bring an unforgettable cute vibe in this strapless ponte mini dress perfect for semi-formal events or brunch! Featuring a strapless neckline with a charming bow and contrast trim, this dress boasts an A-line silhouette and a mini-length hem for a flirty and flattering look. Complete the look with a necklace.

    Fit & Features

    • Ponte knit fabric, moderate stretch
    • Strapless neckline, contrast trim and bow
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3636

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good Looks Mock Neck Long Sleeve Knit Midi Dress

    This mock neck midi dress will look so good on you! The midi dress features fitted long sleeves, a flattering form-hugging fit, and a center back slit on soft and stretchy ribbed knit fabric. Complete the look with a moto jacket for day or evening plans!

    Fit & Features

    • Soft and stretchy ribbed knit fabric
    • Mock neckline
    • Fitted long sleeves
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5221

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Style Ruched Knit Halter Skater Dress

    Show off your sassy style at weekend outings in this adorable halter skater dress. Made with stretchy smooth knit fabric, it features a sleeveless V-neckline, trendy tie-back halter straps leading to a partially open back, ruched seams at the waist to accentuate your curves, a short double-layered skater skirt for a flirty vibe, and a fit-and-flare silhouette. Complete the look with a charm necklace and strappy mules!

    Fit & Features

    • Stretchy smooth knit, top knit lining
    • V-neckline, tie-back halter straps
    • Partially open back
    • Ruched seams at the waist
    • Double-layered skater skirt
    • Fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5832

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Trendy Girl Next Door Strapless Denim Mini Dress

    Create a trendy girl next door vibe in this denim cargo mini dress! Made with a stretchy cotton-blend denim fabric, this dress features a strapless straight-across neckline, a secure back zipper closure, faux chest pockets, and large cargo-style flap pockets at the waist. The form-hugging silhouette will flaunt your gorgeous figure. Style this mini-length dress with cowboy boots for a country concert!

    Fit & Features

    • Cotton-blend denim fabric, moderate stretch
    • Strapless straight neckline, front no-slip strip
    • Back zipper with hook and eye closure
    • Faux chest pockets
    • Cargo flap pockets
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5524

    Category Name: Casual Dresses

    Price: $11.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Vacay Lace-Up Tropical Maxi Dress

    Your summer vacay needs this tropical maxi dress! Made from a stretchy knit fabric adorned with a tropical print, this maxi dress features a flattering cowl neckline, spaghetti straps, and a lace-up back for head-turning allure. The form-hugging fit flaunts your figure while the high side slit offers a show of leg. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Cowl neckline
    • Spaghetti straps, lace up back
    • Form-hugging fit
    • High side slit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5743

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Destined For Love Lace-Up Short Skater Dress

    You'll be destined for love in this short skater dress perfect for dressy parties! This flirty dress features a square neckline, adjustable spaghetti straps, and a lace-up back for a perfect fit. The skater silhouette and short-length hem add a playful touch, while the burnout pattern on the mesh fabric adds a touch of intrigue. Complete the look in block heels.

    Fit & Features

    • Burnout pattern, mesh fabric, tulle and stretchy knit lining
    • Square neckline
    • Adjustable spaghetti straps
    • Lace-up, back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3319

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Preppy-Chic Belted And Pleated Skater Dress

     This preppy-chic twill skater dress features a collared neckline with a partial button-down front, short cap sleeves, and a subtle drop waist with a belted design. The mini-length pleated skater fit adds that flirty touch to the short silhouette.

    Fit & Features

    • Twill woven fabric, slight stretch
    • Collared neckline, button-down front
    • Cap sleeves
    • Belted drop waist
    • Mini-length pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5915

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Abstract Babe Ruched Mesh Midi Dress

    Let your look do the talking in this mesh midi dress! With an eye-catching abstract print and adjustable spaghetti straps, this midi dress will show off your style while the bodycon fit and side-ruched seams enhance your curves. Complete the look in trendy mules for an art show downtown!

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Side ruched seams
    • Bodycon silhouette, midi-length hem
    • Abstract print, mesh fabric, sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5508

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Artsy Scene Mock Neck Abstract Mini Dress

    Indulge in the artsy scene in this mock neck abstract mini dress for downtown art walks! This sleeveless dress boasts a figure-flattering bodycon silhouette with side ruching, while the mini-length hem adds a flirty touch. The abstract print adds a bold and unique touch to this must-have dress. Complete the look in edgy boots and a shoulder bag.

    Fit & Features

    • Abstract print
    • Mesh fabric, sewn-in knit lining, stretchy
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5630

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Bow Babe Strapless Pleated Ponte Romper

    A strapless ponte romper features a form-hugging fit and a drop waist with an adorable ribbon bow and pleated short-length hem. Perfect for styling with a crop jacket and sandals.

    Fit & Features

    • Ponte knit fabric, slight stretch
    • Strapless neckline
    • Form-hugging fit
    • Drop waist with ribbon bow trim
    • Short pleated hem
    • Runs true to size

    Style Number/Barcode: 06503-1221

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Make Hearts Flutter Short Sleeve Cutout Maxi Dress

    You'll instantly be crushing on this maxi dress perfect for weekend dinner parties or vacation! The flutter sleeves and plunging neckline create a playful vibe, while the elasticized waist and side cutouts show a hint of skin along the flowy maxi-length silhouette. Complete the look in strappy sandals.

    Fit & Features

    • Gauze woven fabric, short knit stretchy lining
    • Flutter short sleeves
    • Plunge V-neckline and V-cut back
    • Elasticized strappy waist with side cutouts
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5719

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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