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.

  • Chic Moment Off-The-Shoulder Bell Sleeve Mini Dress

    An off-the-shoulder mini dress that'll give you many chic moments! The crepe dress is designed with long fitted bell sleeves with flirty tie accents and a front slit for movement. Complete the look with a necklace.

    Fit & Features

    • Viscose crepe knit fabric with knit lining, moderate stretch
    • Off-the-shoulder sweetheart neckline, can be worn on the shoulder
    • Long fitted bell sleeves, tie accents
    • Front slit
    • Mini-length hem
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5881

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casual Muse Scoop Neck Mini Dress

    A casual mini dress that's sure to become your fashion muse! The mini-length dress features fitted long sleeves, a scoop neckline, a built-in shelf bra for extra support, and a flattering bodycon silhouette on stretchy rib knit fabric. Complete the look in a moto jacket and boots for day or evening plans!

    Fit & Features

    • Fitted long sleeves
    • Scoop neckline
    • Built-in shelf bra
    • Bodycon silhouette, mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5244

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Standout Staple Crew Neck Cutout Midi Dress

    This midi dress may just become that special staple piece in your lineup! It features fitted long sleeves, a crew neck with a button-back closure and keyhole accent, a flattering bodycon silhouette and front slit, and a flirty cutout back design. Complete the look with statement earrings for a cocktail hour.

    Fit & Features

    • Fitted long sleeves
    • Crew neck, back button closure, keyhole
    • Bodycon silhouette, front slit
    • Cutout back design
    • Soft knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5335

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sleek Silhouette Ribbed Knit Off-The-Shoulder Midi Dress

    Showcase a sleek silhouette in this ribbed knit midi dress featuring an off-the-shoulder neckline with a fold-over design and a mermaid silhouette to highlight your curves. Style with knee-high boots for a chic look.

    Fit & Features

    • Ribbed knit fabric, plenty of stretch
    • Off-the-shoulder neckline
    • Fold-over design, short sleeves
    • Midi-length mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5896

    Category Name: Casual Dresses

    Price: $14.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Endlessly Effortless Crew Neck Abstract Midi Dress

    You'll always look and feel perfect in this sleeveless midi dress for parties or going out! Crafted from an abstract print mesh fabric, this dress boasts a crew neckline, a flattering bodycon silhouette, and a midi-length hem. Complete the look in stiletto heels and a purse!

    Fit & Features

    • Abstract print, mesh fabric, soft knit lining
    • Crew neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5819

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Expression Sleeveless Plaid Mini Dress

    A sleeveless plaid mini dress features a flattering square neckline with a satin bow, shoulder straps, and a bodycon silhouette. Perfect for back-to-school styling.

    Fit & Features

    • Plaid woven fabric, bust lining, minimal stretch
    • Square neckline with satin bow
    • Shoulder straps
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5825

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Lost In Love Strappy Back A-Line Mini Dress

    Everyone will be lost in love once they catch sight of you in this strappy A-line mini dress! Perfect for any occasion, this dress will have you feeling fabulous. This playful A-line mini features a flattering sweetheart neckline, shoulder straps for added support, and a strappy back for flirty fun. Complete the look in block heels.

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Sweetheart neckline
    • Shoulder straps
    • Strappy back
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5544

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chicly Femme Bodycon Abstract Mesh Midi Dress

    A sleeveless midi dress features a square neckline and a bodycon silhouette that flaunts your curves. The abstract print mesh fabric offers an artsy look. Perfect for styling with stilettos.

    Fit & Features

    • Abstract print, mesh fabric
    • Square neckline
    • Spaghetti straps
    • Bodycon midi-length fit
    • Runs true to size

    Style Number/Barcode: 05102-5580

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Sweetie Open Back Bow Skater Dress

    Arrive like the stunning sweetie you are in this short skater dress as the bride-to-be, graduate, or birthday girlie! This dress features a square neckline and shoulder straps, with an attention-grabbing open back and statement bow detail. The drop waist skater silhouette is flattering, and the short-length hem is perfect for showing off your legs. Complete the look in block heels.

    Fit & Features

    • Woven fabric, tulle and stretchy knit lining
    • Square neckline, shoulder straps
    • Open back, statement bow
    • Back zipper and hook-eye closure
    • Drop waist seam, skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3410

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Colorful Essence Sleeveless Marble Print Mini Dress

    You'll be the most colorful babe on the scene in this marble print mini dress! Perfect for art gallery openings and date nights, this sleeveless dress boasts a square neckline, adjustable spaghetti straps for a custom fit, and side ruched seams and a bodycon fit to accentuate your curves. Complete the look with a clutch and stiletto heels.

    Fit & Features

    • Marble print, mesh fabric, sewn-in knit lining, moderate stretch
    • Square neckline
    • Adjustable spaghetti straps
    • Ruched side seams
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5691

    Category Name: Casual Dresses

    Price: $42.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Easy Bliss Turtleneck Striped Mini Dress

    This sleeveless knit mini dress boasts a turtle neckline and a bodycon silhouette with a trendy striped pattern. Style with simple hoop earrings for any casual plans.

    Fit & Features

    • Striped pattern, stretchy knit fabric
    • Turtle neckline
    • Bodycon mini-length fit
    • Runs true to size

    Style Number/Barcode: 06005-2045

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Silhouette Long Sleeve Ruched Mini Dress

    Embrace your curves in this must-have mini dress! The short dress features fitted long sleeves and a scoop neckline for a flattering look, while the side ruched seams and bodycon silhouette accentuate your curves. Crafted from a double-lined buttery soft fabric that fits like a glove with plenty of stretch. Layer with a jacket and a trendy shoulder bag to complete the look!

    Fit & Features

    • Fitted long sleeves
    • Scoop neckline
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Double-lined buttery soft knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5519

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Luxe Long Sleeve Ribbed Knit Mini Dress

    Part casual, part luxe, this long-sleeved mini dress is perfect for your next date night! The ribbed knit dress features a square neckline, long sleeves, and a mini-length hem. Complete look with knee-high boots! 

    Fit & Features

    • Ribbed knit fabric with knit lining, plenty of stretch
    • Square neckline
    • Long fitted sleeves
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5899

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Carefree Chic Long Sleeve Ribbed Knit Midi Dress

    An off-the-shoulder midi dress perfect for those carefree days! It features fitted long sleeves and a bodycon fit that shows off your curves. Pair with sneakers.

    Fit & Features

    • Ribbed knit fabrication, stretchy knit lining
    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5924

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Flirt Drop Waist Ruffled Hem Mini Dress

    Show off your stunning figure in this smooth knit mini dress featuring a boat neckline, long fitted sleeves, a cute scoop back, a drop waist design, and a short tiered ruffled hem with an A-line fit for that flirty flair. Style with strappy mules!

    Fit & Features

    • Smooth nylon knit fabric, plenty of stretch
    • Boat neckline
    • Long fitted sleeves
    • Scoop back
    • Drop waist
    • Tiered ruffled mini-length hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5938

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Serving Chic Long Bell Sleeve A-Line Mini Dress

    Serve chic looks in this A-line mini dress featuring a halter V-neckline with flirty cutouts and long fitted bell sleeves to give coverage. Style with earrings.

    Fit & Features

    • Smooth knit fabric with partial lining, plenty of stretch
    • Halter V-neckline, tie-back spaghetti straps
    • Cutout shoulder design
    • Long fitted bell sleeves, slit accents
    • Lower back cutout
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3657

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Raise The Bar Ribbed Knit High Slit Midi Dress

    Raise the bar in this knit high slit midi dress boasting a sultry off-the-shoulder neckline and a form-hugging fit. Pair with boots.

    Fit & Features

    • Ribbed knit fabric, plenty of stretch
    • Off-the-shoulder neckline
    • Fold over accent at bust
    • High side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-2081

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Allure Abstract Print Mesh Midi Dress

    Show up and stun in this airy mesh midi dress accented with a trendy abstract print for a bold allure. The dress features a crew neckline, short cap sleeves, and a form-hugging silhouette to highlight your curves.

    Fit & Features

    • Abstract printed sheer mesh fabric with partial knit lining, plenty of stretch
    • Lettuce edge hems
    • Crew neckline
    • Short cap sleeves
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5628

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Adorable Drop Waist Bubble Hem Skater Dress

    Adorable and trendy will be your vibe in this soft knit skater dress featuring a mock neckline, tank shoulder straps, ruched side seams to accentuate your curves, and a short ruched bubble hem. Style with platform heels for a cute party look!

    Fit & Features

    • Double-lined brushed knit fabric, plenty of stretch
    • Mock neckline, tank shoulder straps
    • Ruching
    • Drop waist seam
    • Short skater silhouette
    • Ruched bubble hem
    • Runs true to size

    Style Number/Barcode: 05102-5902

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Moment Faux Suede Lattice Cutout Mini Dress

    Fit & Features

    • Faux suede fabric with knit lining, moderate stretch
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Back zipper with hook-eye closure
    • Dual lattice side cutouts at bodice and waist
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5782

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Marvelous Blooms Lace-Up Corset Floral Skater Dress

    Stay stunning all night in this floral skater dress at prom, birthdays, or dressy events! With adjustable spaghetti straps and a drawstring sweetheart neckline, this dress offers a perfect fit every time. The underwire bust, flexible boning, and a lace-up back provide support and a flattering silhouette, while the mini-length hem adds a playful touch. Complete the look in chic block heels.

    Fit & Features

    • Floral print, woven fabric, woven lining, no stretch
    • Adjustable spaghetti straps
    • Drawstring sweetheart neckline
    • Side zipper and hook-eye closure
    • Underwire bust
    • Flexible boning, lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3550

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sealed With Charm Ponte Mini Dress

    Seal your style with this charming ponte mini dress featuring an adorable strapless sweetheart neckline with a bow and a bodycon fit. Style with earrings.

    Fit & Features

    • Ponte knit fabric, plenty of stretch
    • Strapless sweetheart neckline
    • Bow tie front accent 
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5897

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romance Dreamer Sweetheart A-Line Lace Mini Dress

    Embrace your romantic side in this lace mini dress to add a whimsical allure to parties, birthdays, and dates! The sweetheart neckline and adjustable spaghetti straps flatter and give you a perfect fit, while the corset-trim fitted bodice and A-line silhouette provide a lovely silhouette along the ruffled mini-length hem. Complete the look with platform heels and a purse.

    Fit & Features

    • Delicate lace fabric line with stretchy knit
    • Adjustable spagehtti straps
    • Corset trim fitted bodice
    • Ruffled mini-length hem
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3302

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy Chicness Lace Trim Plaid Bodycon Dress

    This plaid mini dress features a lace rose trim square neckline, spaghetti strap ties, and a flattering bodycon silhouette perfect for casual plans. 

    Fit & Features

    • Plaid print, knit fabric with minimal stretch
    • Lace rose trim square neckline
    • Spaghetti strap ties
    • Back zipper closure
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5836

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale