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.

  • Casual Vibes Tie-Dye Knit Mini Dress

    Bring the casual vibes this season with this trendy tie-dye knit mini dress. It features a crew neckline, short sleeves, side ruching, and a mini-length, curve-hugging silhouette with side ties at the hem. Complete the look with cute sneakers for the perf everyday outfit.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Side ruching
    • Side ties at the hem
    • Short, form-hugging fit
    • Knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-1588

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casual Stunner Crepe Mini Dress

    Create a casual stunning look with this adorable crepe mini dress that is perf for every day. It features a sleeveless bodice, spaghetti straps, a square neckline, a cute tie-back detail, and a mini-length, curve-hugging silhouette. Style the dress with the tie in the front for a night out. Complete the outfit with a layered necklace and new mules.

    Fit & Features

    • Spaghetti straps
    • Square neckline
    • Tie-back detail
    • Short, form-hugging fit
    • Crepe fabric
    • Runs true to size

    Style Number/Barcode: 05102-0527

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Charming Ditsy Floral Smocked Mini Dress

    Level up the charm with this adorable ditsy floral printed mini dress! It features tie shoulder spaghetti straps, a square neckline with a ruffle trim, a tie-front at the bust, a high waist seam, and a smocked body with a mini-length, curve-hugging silhouette. Complete the look with hoop earrings and strappy sandals.

    Fit & Features

    • Tie shoulder spaghetti straps
    • Square neckline, ruffle trim
    • Tie-front at the bust
    • High waist seam
    • Smocked body
    • Short, form-hugging fit
    • Woven fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-1109

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sweetest Style Floral Mini Dress

    Showcase the sweetest style this summer season in this floral mini dress! It features a sleeveless bodice, spaghetti straps, a sweetheart neckline with a tie-front at the bust, and a mini-length, curve-hugging silhouette. The knit fabric has an all-over adorable ditsy floral print that will pair perfectly with a denim jacket and sandals.

    Fit & Features

    • Spaghetti straps
    • Sweetheart neckline
    • Tie-front at the bust
    • Short, form-hugging fit
    • Knit fabric, moderate stretch
    • Ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-1431

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Fab And Retro Tie-Dye High Slit Maxi Dress

    Keep it fab with a dress that channels a retro feel! The maxi dress features a sleeveless scoop neckline, spaghetti straps, a tie-dye print, a high side slit, and a maxi length silhouette. The dress is composed of a ribbed kit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti strap
    • Tie-dye print
    • High side slit
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1122

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Bohemian Chic Ruffled A-Line Mini Dress

    Channel your bohemian side with a pretty mini dress that channels those lowkey vibes. The dress features a sleeveless square neckline, tie-up shoulder straps, tiered ruffles, and a mini-length A-line silhouette. Complete look with cork wedges

    Fit & Features

    • Sleeveless square neck 
    • Tie-up shoulder straps
    • Tiered ruffles
    • Mini length 
    • A-line silhouette
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1046

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shrug It Off One-Shoulder Bodycon Mini Dress

    This is the perfect sleeveless mini dress for parties and cocktail hour! It features a sassy one-shoulder neckline and a sexy bodycon silhouette. Pair with boots.

    Fit & Features

    • Rib knit fabric, stretchy knit lining
    • One-shoulder neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5900

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Drawn To You Ruched Mini Dress

    Get drawn into this fab mini dress that is perf for your next date night with bae! The dress features a sleeveless sweetheart neckline, a small keyhole with a ruched drawstring, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless sweetheart neckline
    • Keyhole
    • Ruched drawstring
    • Mini length silhouette
    • Knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0664

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Stunner Ruched Mini Dress

    Bring stylish and stunning looks this season in this on-trend mini dress. It features a crew neckline, short sleeves, a front waist cutout with a cross-strap design, ruching, and a mini-length silhouette with ties at the hem. Pair this dress with heeled mules and a chic crossbody purse.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Front waist cutout, cross-strap design
    • Ruching
    • Short, form-hugging fit
    • Ties at the hem
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-2029

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Such A Babe Denim Bodycon Mini Dress

    You'll be such a babe in this denim bodycon mini dress that is a summer must-have! It features short puff sleeves, a square neckline with a corset-designed bodice, a back zipper closure, and a mini-length, curve-hugging silhouette. Complete the look with heeled mules and a pair of chic sunglasses.

    Fit & Features

    • Short puff sleeves
    • Square neckline
    • Corset-designed bodice
    • Back zipper closure
    • Short, form-hugging fit
    • Denim fabric
    • Runs true to size

    Style Number/Barcode: 05102-2356

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Flirty Vibes Off The Shoulder Floral Mini Dress

    Channel those flirty vibes with a pretty mini dress! The vibrant dress features an off-the-shoulder neckline with short puff sleeves, a mini tie-front, a ditsy floral print, a smocked back, and a mini-length silhouette. The dress is composed of a crepe fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Off the shoulder neckline, short puff sleeves
    • Mini tie-front smocked back
    • Ditsy floral print
    • Mini length silhouette 
    • Crinkle-crepe fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0573

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirtatious Vibes Floral Mini Dress

    Bring the flirty vibes in this adorable floral mini dress perf for summer! It features an off-the-shoulder sweetheart neckline with a ruffle trim, a tie-front detail, short puff sleeves, an all-over ditsy floral print, and a mini-length, curve-hugging silhouette. Complete the look with cute wedges for a weekend brunch.

    Fit & Features

    • Off-the-shoulder sweetheart neckline, ruffle trim
    • Tie-front detail
    • Short puff sleeves
    • Ditsy floral print
    • Brushed knit fabric, moderate stretch
    • Short, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-1430

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Bloom Mesh Mini Dress

    Soft meets fierce in this mesh dress—floral, animal print, and all eyes on you. The open back and flared sleeves bring that extra touch for plans that need a little drama.

    Fit & Features

    • Floral, leopard print, mesh fabric, stretchy knit lining
    • Boat neckline
    • Long flared sleeves
    • Open back with adjustable tie closure
    • Form-hugging silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000217

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • So Glam Tie Dye Ruched Mini Dress

    Keep it so glam with a tie-dye dress that gives your look a retro feel! The dress features a sleeveless square neckline, bungee spaghetti straps, a tie-dye print, a ruched side seam, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look in new top-rated shoes

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Tie-dye print
    • Ruched side seam
    • Mini length silhouette 
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-1083

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Babe Sleeveless Colorblock Mini Dress

    Channel a retro moment with a mini dress that makes a stylish statement. The dress features a sleeveless crew neckline, a colorblock design accented with exposed seams, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless crew neckline
    • Colorblock pattern with exposed seams
    • Mini length silhouette
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2064

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutout Cutie Ruched Mini Dress

    Create a chic look with a mini dress that showcases your stunning style! The mini dress features a sleeveless crew neckline, a waist cutout that creates an O-ring design, a ruched drawstring, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. 

    Fit & Features

    • Sleeveless crew neckline
    • Waist cutout 
    • Ruched drawstring 
    • Mini length silhouette 
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1968

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Butterfly Charm Ruched Mini Dress

    Bring the charm with a butterfly print dress that springs you into the season. The mini dress features a sleeveless square neckline, spaghetti straps, a butterfly print, a ruched body, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with butterfly earrings and wedges

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Butterfly print
    • Ruched body
    • Mini-length silhouette, form-hugging fit
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1454

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Dreamy Ditsy Floral Mini Dress

    Keep it dreamy with a floral mini dress that brings the romance. The dress features a sleeveless V-neckline with a ruched center, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a lined ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.

    Fit & Features

    • Sleeveless V-neckline with ruched center
    • Spaghetti straps
    • Ditsy floral print
    • Mini-length silhouette 
    • Lined ribbed knit fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2047

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summertime Stunner Mini Dress

    Show off your stunning style this summer in this gorg mini dress! It features a sleeveless sweetheart neckline with a ruffled trim, spaghetti straps, center ruching with a drawstring at the hem, and a mini-length, curve-hugging silhouette. Complete the outfit with cute wedges for the perfect graduation look.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Ruffled trim
    • Spaghetti straps
    • Center ruching, drawstring at hem
    • Short, form-hugging fit
    • Eyelet knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1205

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Stunning Floral Chiffon Skater Dress

    Style up this adorable floral chiffon dress for a simply stunning look. It features a sleeveless V neckline, adjustable spaghetti straps, front buttons, a fitted bodice, and a flirty skater skirt silhouette. Complete the outfit with hoop earrings and a straw tote.

    Fit & Features

    • Sleeveless V neckline
    • Adjustable spaghetti straps
    • Front buttons
    • Fitted bodice, smocked back
    • Back zipper closure
    • Skater skirt silhouette
    • Floral chiffon fabric
    • Runs true to size

    Style Number/Barcode: 05102-0545

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Style Tie-Front Maxi Dress

    Showcase a chic effortless style this season with this adorable maxi dress! It features a sleeveless V neckline, adjustable spaghetti straps, a tie-front detail with a small cutout, center button accents, and a flowy fit with a center slit. Pair this ribbed knit dress with a straw tote and strappy sandals.

    Fit & Features

    • Sleeveless V neckline
    • Adjustable spaghetti straps
    • Tie-front, small cutout
    • Fitted bodice
    • Center button details
    • Flowy silhouette, center slit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1174

    Category Name: Casual Dresses

    Price: $21.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Impressions Sleeveless Midi Cutout Dress

    Make a bold impression with a midi dress that cuts a sultry look! The midi dress features a plunging V-neckline, spaghetti straps, sexy cutouts at the waist, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual cutouts at the waist
    • Midi-length silhouette
    • Sheer ribbed knit fabric, knit lining
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1967

    Category Name: Casual Dresses

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Darling Strapless Bodycon Mini Dress

    A denim bodycon mini dress for a darling look paired with your fave boots at concerts and festivals!

    Fit & Features

    • Denim fabric, sewn-in knit lining, minimal stretch
    • Strapless neckline
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5901

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flowy Floral Woven Halter Dress

    Perfect for the warmer months, this flowy floral woven dress is a must-have for weekend brunches and picnic dates! It features a sleeveless square neckline, halter tie straps, a back bar strap design, a fitted stretchy smocked bodice, and a flowy skirt with an A-line silhouette. Pair this ditsy floral printed dress with cute wedges and a trendy straw tote.

    Fit & Features

    • Square neckline
    • Halter tie straps
    • Back bar strap design
    • Fitted stretchy smocked bodice
    • Flowy skirt, A-line silhouette
    • Ditsy floral print
    • Woven fabric, knit lining
    • Runs true to size

    Style Number/Barcode: 05101-1001

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free