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.

  • Flowy Floral Mini Dress
    This flowy floral dress is the perfect piece to transition into fall! It features a wrap front V neckline, a hidden back zipper and hook and eye closure, long sleeves with smocked cuffs, a faux button down front, a high waist seam, ruched detailing, and a flirty ruffle hem. The printed dress is composed of a sheer chiffon fabric with a stretchy knit lining.

    Style Number/Barcode: 05102-0303

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Such A Beauty Mini Dress

    Girl, you're such a beauty, and this classically chic mini dress will make for the perfect 'fit. It features a sleeveless bodice, a V-neckline with a tie ruched bust detail, adjustable spaghetti straps, a square back with a hidden zipper and hook and eye closure, a trendy waist front cutout with a tie ruched detail, and a flowy skirt with an adorable ruffled mini-length hem. The short dress is composed of a woven fabric with minimal stretch. Style with a cute pair of mules.

    Fit & Features

    • Sleeveless bodice, V-neckline, tie ruched bust
    • Adjustable spaghetti straps
    • Square back, hidden zipper, hook and eye closure
    • Waist front cutout, tie ruched detail
    • Flowy skirt, ruffled mini-length hem
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-0263

    Category Name: Casual Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Plaid Knit Mini Dress
    Pretty plaid is the way to go! This knit mini dress features a sleeveless bodice, spaghetti straps, a scoop neck, a square back, and a short, curve hugging fit. The dress offers plenty of stretch and includes a knit lining.

    Style Number/Barcode: 05102-0302

    Category Name: Casual Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Live It Up In Linen Midi Dress
    Live it up in this absolutely adorable ditsy floral printed midi! The dress features a sleeveless bodice, tie shoulder spaghetti straps, a sweetheart neckline with pleated detailing and a tie front, and a hidden back zipper and hook and eye closure. The dress is composed of a linen fabric with a shorter woven lining and has no stretch.

    Style Number/Barcode: 05102-0305

    Category Name: Casual Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Rock On Distressed Tunic Top
    Hey, wild child! Show off your spirited side in this distressed tunic top (or be bold and make it a mini!). Top features a crew neck, short sleeves, shredded V detail at chest and hem, and a large "Rock On" contrast graphic. Top is cut for a slim fit and made from an ultra-soft rayon knit with moderate stretch.

    Style Number/Barcode: 06002-0188

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Spot On A-Line Midi Dress

    Throw on a cozy knit sweater, add a pair of boots, and your outfit will be looking spot on! Showcasing a smudge spot print, the sleeveless bodice features adjustable shoulder straps and a v-neckline. Decorative buttons trail down the front, leading to a center split. Linen crafted, this dress features an A-line silhouette and offers little to no stretch. Zipper at center back. 

     Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0301

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Florals And Lace Skater Dress
    Make it a lacy affair in this must have floral mini dress! It features a sleeveless bodice, a V neckline, princess seams and spaghetti straps. The back features an unlined floral lace back that leads to a lower back keyhole. The slim fit bodice leads to a curve hugging mini length silhouette. Dress is composed of a lined crepe fabric that offers a moderate stretch.

    Style Number/Barcode: 05101-0079

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Katelyn Ruched Midi Dress

    Chic and fab, the Katelyn ruched midi dress is a new go-to. She features a sleeveless bodice, a Y neck with halter straps, a knot detail, and a front keyhole cut out, and a square back with a zipper closure. Her high waist band leads to a curve hugging skirt with ruched side details and a mid-length hem. The dress is composed of a stretchy knit fabric with a pretty sheen.

    Model is 5'8" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small. 

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0238

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovely Little Linen Skater Dress

    Leave a flirty impression in this lovely little linen skater dress! It features long fitted sleeves with ruffled elastic cuffs, a deep V neckline with a ruffle trim, a hidden back zipper and hook and eye closure, ruffle detail seams, and a flowy skater skirt. The dress is composed of a lightweight linen fabric with a woven lining and has no stretch.

    Style Number/Barcode: 05102-0300

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Girl Mini Dress

    Show us your sweet side with this eyelet-detailed mini dress! It features a V neckline, ruffled cap sleeves, single-button closure with keyhole at back, an empire waist, and a short A-line skirt with pockets leading to a wavy hemline. Dress is lined, made from cotton, includes a linen short underlay. 

    Style Number/Barcode: 05102-0310

    Category Name: Casual Dresses

    Price: $16.97 $47.60

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Talk Skater Dress

    This adorable skater dress will definitely sweet talk its way into your closet! It features short flowy sleeves, a plunging V neckline, an open back with a top tie closure with tassel details, a back hidden zipper and hook and eye closure, a high waist seam, a back tie detail, a faux button down front, and a flowy skater skirt. The dress is composed of a woven gauze fabric with a woven lining and has no stretch.

    Style Number/Barcode: 05102-0174

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay Vibes Crochet Knit Maxi Dress

    Channel those vacay vibes with a maxi dress that brings those resort vibes! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a lower back keyhole with tie-back straps, and a maxi length silhouette. The dress is composed of a lined gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Lower back keyhole with tie-back straps
    • Maxi length silhouette
    • Lined gauze knit fabric
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0297

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Chic Midi Dress

    Get a total casual chic vibe with this adorable daytime LBD! It features a V neckline, short sleeves, and a mid-length, curve hugging fit. The dress is composed of a ribbed knit fabric that offers plenty of stretch.

    Style Number/Barcode: 05102-0197

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Solid Stunner Ruched Tube Dress
    We'll keep it brief: this mini is made for for your next night out! Tube-style dress features a curve-hugging cut, strapless neckline, and all-over strategic ruching detail. Don't forget to pair it with the matching duster! Dress slips on and is made from a smooth, solid woven material with moderate stretch.

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0165

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Go With The Flow Maxi Dress

    Go with the flow of this gorgeous maxi dress! It features a sleeveless deep V-neckline with a lined crochet lace top, adjustable spaghetti straps, a tie-back detail with a lower back cutout, and a flowy, floor-length skirt with pleated detailing and a relaxed fit. Style this dress with new earrings and strappy sandals for your summer vacay.

    Fit & Features

    • Sleeveless deep V-neckline
    • Lined crochet lace top
    • Adjustable spaghetti straps
    • Tie-back detail, lower back cutout
    • Floor-length skirt, pleated detailing
    • Relaxed fit
    • Gauze fabric
    • Runs true to size

    Style Number/Barcode: 05102-0295

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breezy Babe Crochet Maxi Dress

    Enchant them all in this maxi dress! It's the perf vacay dress you need to pack before that trip! 

    Fits & Features

    • Adjustable Spaghetti Straps
    • V Neckline I Lined Crochet Front Design  
    • Tie Open Back 
    • Flowy Maxi Length Silhouette 
    • Textured Knit Fabric I Partial, Mini Length Knit Lining
    • Relaxed Fit I Moderate Stretch  

    Style Number/Barcode: 05102-0294

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Plus Thrill Of Knit Ribbed Dress

    Toe the perfect line between casually chic and sultry-on-trend in this off-the-shoulder mini. Dress features all-over medium-width ribbing, a scoop neck, decorative wood-like buttons and a full lining. Dress is made from a soft, heavier-weight cotton blend with a fair amount of stretch. 

    Style Number/Barcode: 15102-0035

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Buckled In Sleeveless Mini Dress

    Ready to take this sultry mini for a ride? We thought so! Dress features all-over ribbing and a sleeveless bodice with scoop neck and buckle-detailed shoulder straps. Dress is made from a soft, densely woven material with plenty of stretch.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small. 

    Style Number/Barcode: 06005-0112

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Read My Lips Tunic Top

    Make a strong style statement without saying a word in this tunic top. Pair it with skinny denim or go bold and make it a mini! Top features spaghetti straps and a large rainbow-colored graphic. Top nips slightly at waist and is made from an ultra-soft woven material with a fair amount of stretch.

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.  

    Style Number/Barcode: 06002-0131

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready For My Snap Midi Dress
    Get ready to take all the snaps in this simply stunning midi! The sweater dress features a sleeveless bodice, tank-like shoulder straps, a scoop neckline, double white striped detailing and gold faux snap buttons down each side, and a mid-length fit. The black dress is composed of a ribbed knit fabric with plenty of stretch.

    Style Number/Barcode: 06005-0096

    Category Name: Casual Dresses

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fab And Flared Midi Dress
    Keep it fab in this twirl-worthy must have! The black dress features a V neckline, spaghetti straps and a midi length silhouette with flared hem. Dress is composed of an unlined ribbed sweater knit fabric that offers a form hugging fit with a moderate stretch.

    Style Number/Barcode: 06005-0113

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • See You Soon Shirt Dress
    A classic with a twist—quite literally! This ultra-chic little white shirt dress is beyond versatile: think work, weekend, lunch, brunch, and everything in between! Dress features a collared open V front, a seamed back, long sleeves with double-button cuffs, flattering twist detail at waist, and a draped straight-line skirt.

    Style Number/Barcode: 06003-0310

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffle Ride Skater Dress

    Keep it cool in this breezy-beautiful skater dress! It features adjustable spaghetti straps, a seamed V neck bodice, tiers of ruffle trim at the bust, waist, thigh and hem, and an A-line skirt with back zip. Dress is fully lined and made from a lightweight Tencel-blend with natural crinkle-effect and little to no stretch.

    Style Number/Barcode: 05102-0329

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Such A Babe Button Down Midi Dress

    Yes babe, you'll totally work it in this chic button down midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a square neck and back, lined and padded cups, flattering horizontal seam detailing along the bust, a hidden back zipper closure, a high rise paper bag waist with a tie front belt, faux button detailing, and a mid-length skirt that offers a form hugging fit. The top is composed of a ribbed linen fabric and the skirt is made from a stretchy knit.

    Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0245

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance