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.

  • Trend Right Plaid Belted A-Line Mini Dress

    Trend right in this plaid mini dress! It features a square neckline, spaghetti straps, a flattering A-line silhouette cinched with a belted waist, and a flirty pleated mini-length hem with an alluring plaid print. Complete the look with a crossbody bag.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Back zipper closure
    • A-line silhouette, belted waist
    • Pleated mini-length hem
    • Plaid print, woven fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05102-5505

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Staple Tie-Front Ribbed Knit Midi Dress

    This adorable tie-front midi dress is a stylish staple for an effortlessly chic look! It features a crew neckline, long fitted sleeves, a tie-front design at the waist, a mid-length hem with a high side slit, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Pair with ankle booties!

    Fit & Features

    • Stretchy ribbed knit fabric
    • Crew neckline
    • Long fitted sleeves
    • Tie-front waist design
    • High side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5248

    Category Name: Casual Dresses

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Class Mock Neck Long Sleeve Midi Dress

    Enjoy feeling like a boss in this high-class midi dress! The fitted long sleeves with thumbholes offer protection without compromising style, while the mock neckline, bodycon silhouette, and midi-length hem create a sleek and modern look. The stretchy ribbed knit fabric has a full-length lining. Complete the look with statement booties for a dinner downtown!

    Fit & Features

    • Fitted long sleeves with thumbholes
    • Mock neckline
    • Bodycon silhouette
    • Midi-length hem
    • Stretchy ribbed knit fabric, full-length knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5396

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fun And Flirty Halter Neck Skater Dress

    This adorable skater dress is perf for twirling and giving off those fun and flirty vibes at your next party! It features a sleeveless deep V-neckline with halter straps that lead to a tie-back design, an open back, dual high waist seams, and a short skater skirt with a fab fit and flare silhouette. The plisse woven fabric includes a full knit lining. Complete your look with a lariat necklace and platform heels.

    Fit & Features

    • Sleeveless deep V-neckline
    • Halter straps, tie-back design
    • Open back
    • Dual high waist seams
    • Short skater skirt, fit and flare silhouette
    • Plisse woven fabric, full-length knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2908

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winter Sweetheart Wrap-Front High Slit Midi Dress

    Create an adorable winter 'fit with this wrap-front midi dress you'll want to wear all season long. It features a V-neckline with a chic surplice wrap-front design, long fitted sleeves, a midi-length hem with a high-cut side slit, and a form-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Complete your look with a moto jacket and sleek ankle boots.

    Fit & Features

    • V-neckline, surplice wrap-front design
    • Long fitted sleeves
    • Midi-length hem, high side slit
    • Form-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5338

    Category Name: Casual Dresses

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Abstract Beauty Printed High Slit Midi Dress

    You'll fall in love with the abstract beauty of this chic printed midi dress! Crafted from a sheer woven fabric with a full-length knit lining, this mid-length dress features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, a partially open back with a cross-back strap design and lower back straps, a high-cut side slit to showcase some leg, a flowy A-line silhouette, and an all-over multi-colored abstract print pattern to catch everyone's eye. Style with a layered necklace and clear heels for a gallery opening!

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Partially open back, cross-back strap design, lower back straps
    • Mid-length hem, high-cut side slit, flowy A-line silhouette
    • Multi-colored abstract print
    • Sheer woven fabric, full-length knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5525

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Adorable Style Cable Knit Mini Dress

    You'll fall in love with the adorable style of this cable knit mini dress for the cozy winter season. It features a V-neckline with a surplice design, long sleeves, a faux wrap-front creating an asymmetric mini-length hem, and a form-hugging silhouette. The cable knit fabric offers a moderate stretch. Style with a chic trench coat and knee-high boots.

    Fit & Features

    • V-neckline, surplice design
    • Long sleeves
    • Faux wrap-front design
    • Asymmetric mini-length hem
    • Form-hugging silhouette
    • Cable knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5359

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Signature Style Collared Wrap Mini Dress

    This wrap mini dress is perf for showcasing that signature chic style! It features a collared V-neckline with a pleated surplice design, long fitted sleeves, a high waist seam with ruched detailing to highlight your silhouette, a faux wrap-front design leading to an asymmetric mini-length hem, and a form-hugging fit. The knit fabric offers plenty of stretch. Complete your look with knee-high boots.

    Fit & Features

    • Collared V-neckline, pleated surplice design
    • Long fitted sleeves
    • High waist seam, ruching
    • Faux wrap-front design, asymmetric mini-length hem
    • Form-hugging fit
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-2948

    Category Name: Casual Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fashionable Chic Sweater Maxi Dress

    Perfect for any occasion, this fashion-forward sweater maxi dress delivers the perfect blend of comfort and style. Featuring a flattering bodycon silhouette, tank straps, and a sweetheart neckline for added appeal, this luxuriously soft sweater knit maxi dress will take your look to the next level. Layer on a faux leather jacket for an effortless and cool style!

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Maxi-length hem
    • Sweater ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1898

    Category Name: Casual Dresses

    Price: $3.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild West Energy Denim Mini Dress

    This denim mini dress comes with a lace-up front and bold embroidery and studs that bring rodeo-core to the party.

    Fit & Features

    • Denim fabric
    • Tube neckline
    • Front lace-up placket
    • Studs and embroidery details
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000211

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Retro Luxe Velvet Mock Neck Mini Dress

    Embrace a luxurious and retro look in this velvet mini dress! It features fitted long sleeves, a mock neckline, a mini-length hem, and a bodycon silhouette that flatters your curves. The flocked velvet retro pattern gives it a glamorous look and brings a luxe vibe. The sheer mesh fabric features a sleeveless knit lining down the body of the dress. Complete the look in metallic heels for a party!

    Fit & Features

    • Fitted long sleeves
    • Mock neckline, dual back button closures, keyhole cutout
    • Mini-length hem
    • Bodycon silhouette
    • Flocked velvet design, retro pattern
    • Sheer mesh fabric, sleeveless knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2856

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Downtown Chic Abstract Print Midi Dress

    This alluring abstract print midi dress is a stylish pick for a dinner date downtown! It features a mock neckline, long fitted sleeves, a midi-length hem, a form-hugging silhouette, and an all-over abstract multi-print pattern. The sheer and stretchy mesh fabric includes a sleeveless full-length knit lining with adjustable spaghetti straps. Pair this trendy midi dress with gold hoops and clear heels.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Midi-length hem, form-hugging fit
    • Abstract multi-print pattern
    • Sheer mesh fabric, sleeveless full-length knit lining, adjustable spaghetti straps
    • Plenty of stretch
    • Runs true to size

      Style Number/Barcode: 05102-5491

      Category Name: Casual Dresses

      Price: $19.97 $38.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Twisted Up Long Sleeve Rib Knit Midi Dress

      Get twisted up in this stylish midi dress! The rib knit dress features fitted long sleeves, a V-neckline, a twisted bust accent, and a bodycon silhouette with flattering side ruched seams and a midi-length hem perfect for styling with your favorite booties or heels. Complete the look in best-selling shoes to make a fabulous statement this season! 

      Fit & Features

      • Fitted long sleeves
      • V-neckline
      • Twisted bust accent
      • Bodycon silhouette, side ruched seams
      • Midi-length hem
      • Stretchy rib knit fabric
      • Runs true to size

      Style Number/Barcode: 05102-5112

      Category Name: Casual Dresses

      Price: $5.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Winter Beauty Cable Knit Mock Neck Mini Dress

      Showcase your beauty in this cozy cable knit mini dress this winter season! It features a ribbed mock neckline, long balloon-style sleeves with tapered ribbed hems, a mini-length hem, and a form-hugging fit. The classic cable knit fabric offers a moderate stretch. Style this mini dress with over-the-knee boots for a chic look.

      Fit & Features

      • Ribbed mock neckline
      • Long balloon sleeves, tapered ribbed hems
      • Mini-length hem
      • Form-hugging fit
      • Cable knit fabric
      • Moderate stretch
      • Runs true to size

      Style Number/Barcode: 05102-5358

      Category Name: Casual Dresses

      Price: $5.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Find Your Style Button Down Pleated Mini Dress

      Make a style statement in this woven shirt mini dress! Featuring long sleeves with button cuffs, a collar neckline, a button down front, and a flattering A-line silhouette and pleated mini-length hem for an adorable and undeniable stylish look. Complete the look in knee-high boots for brunch downtown!

      Fit & Features

      • Long sleeves with button cuffs
      • Collar neckline
      • Button down front
      • A-line silhouette
      • Pleated mini-length hem
      • Woven poplin fabric, no stretch
      • Runs true to size

      Style Number/Barcode: 05102-5379

      Category Name: Casual Dresses

      Price: $14.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Change Of Season Long Sleeve Ribbed Knit Midi Dress

      Step out this season in this casual-chic long sleeve midi dress! It features a V-neckline with a button design at the bust, long fitted sleeves, a midi-length hem with dual high-cut side slits, and a form-hugging fit. The lightweight ribbed knit fabric offers plenty of stretch for comfortable wear. Style this midi dress with a moto jacket and ankle booties for an edgy elevated look.

      Fit & Features

      • Stretchy ribbed knit fabric
      • V-neckline, two-button design
      • Long fitted sleeves
      • Dual side slits
      • Form-hugging fit
      • Runs true to size

      Style Number/Barcode: 05102-5310

      Category Name: Casual Dresses

      Price: $6.97 $24.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Simply Fine In Floral A-Line Midi Dress

      Take your look to the next level with this gorgeous floral midi dress. With its cowl neckline, adjustable spaghetti straps, A-line silhouette, and a painted floral print on woven fabric, this midi-length dress will make you feel stylish and fine! Complete the look in sleek stiletto heels for a semi-formal soiree.

      Fit & Features

      • Sleeveless cowl neckline
      • Adjustable spaghetti straps
      • A-line silhouette
      • Midi-length hem
      • Painted floral print
      • Lightweight woven fabric, no stretch
      • Runs true to size

      Style Number/Barcode: 05101-2920

      Category Name: Casual Dresses

      Price: $5.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • So Charmed Mock Neck Bodycon Mini Dress

      This bodycon mini dress would be charmed to make your acquaintance! A short dress that features fitted bell long sleeves and a mock neckline, and is composed of a rib knit fabric with a sewn-in knit lining. Style the mini dress with a chic crossbody bag for a day date!

      Fit & Features

      • Fitted bell long sleeves
      • Mock neckline
      • Bodycon silhouette
      • Mini-length hem
      • Rib knit fabric, sewn-in knit lining
      • Moderate stretch
      • Runs true to size

      Style Number/Barcode: 05102-5204

      Category Name: Casual Dresses

      Price: $5.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Stunning Destination Tropical Ruffle Maxi Dress

      Arrive at your destination in this tropical maxi dress looking stunning and ready for fun! The maxi dress features a strapless neckline, non-slip grip lining, flexible boning, a form-hugging fit, and an effortless high front slit and ruffled flowy hem. Complete your vacation look with a handbag and sandals!

      Fit & Features

      • Strapless neckline, non-slip grip lining
      • Back zipper and hook-eye closure
      • Flexible boning
      • Form-hugging fit
      • High front slit, ruffled flowy maxi hem
      • Tropical print, airy mesh fabric, partial knit lining
      • Runs true to size

      Style Number/Barcode: 05102-5383

      Category Name: Casual Dresses

      Price: $22.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • In The Cut One Shoulder Cutout Mini Dress

      Let your style speak volumes with this mini dress perfect for dates or birthday brunch! The mini-length dress features a one-shoulder neckline with a puff short sleeve, a side drawstring cutout, and a flattering form-hugging silhouette on texture woven fabric. Complete the look with an envelope clutch and heels.

      Fit & Features

      • One-shoulder neckline, puff short sleeves
      • Side drawstring cutout
      • Form-hugging silhouette
      • Mini-length hem
      • Texture woven fabric, slight stretch
      • Runs true to size

      Style Number/Barcode: 05102-5401

      Category Name: Casual Dresses

      Price: $6.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Can't Help It Off-The-Shoulder Sweater Dress

      If chic comes naturally, this sweater maxi dress can't help but make your style shine! The maxi dress features an off-the-shoulder folded neckline, fitted long sleeves, a flattering bodycon silhouette, and a side slit on stretchy rib knit fabric. Complete the look in sleek stiletto heels for date nights or holiday parties!

      Fit & Features

      • Off-the-shoulder folded neckline
      • Fitted long sleeves
      • Bodycon silhouette, side slit
      • Maxi-length hem
      • Stretchy rib knit sweater fabric
      • Runs true to size

      Style Number/Barcode: 06005-1793

      Category Name: Casual Dresses

      Price: $6.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Zip It Long Sleeve Cargo Pocket Mini Dress

      This casual mini dress is perfect for the fashionista with an eye for style! Its fitted long sleeves, crew neckline, and zipper closure give a classic feel, while the bodycon silhouette, side cargo flap pockets, and mini-length hem on lined rib knit fabric create a flattering and unique style. Complete the look with booties for day or night plans!

      Fit & Features

      • Fitted long sleeves, crew neckline
      • Front zipper closure
      • Bodycon silhouette
      • Side cargo flap pockets
      • Mini-length hem
      • Lined stretchy rib knit fabric
      • Runs true to size

      Style Number/Barcode: 05102-5407

      Category Name: Casual Dresses

      Price: $6.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • On A Vacay Strapless Tropical Slit Maxi Dress

      From sunny vacations to island getaways, this tropical maxi dress is destined to go with you on your next trip! 

      Fit & Features

      • Tropical palm print, mesh fabric lined with stretchy knit
      • Strapless neckline
      • Form-hugging silhouette
      • High side slit
      • Maxi-length hem
      • Runs true to size

      Style Number/Barcode: 05102-6110

      Category Name: Casual Dresses

      Price: $9.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • In The Lineup Mock Neck High Slit Midi Dress

      This alluring mock neck high slit midi dress needs to be in your winter lineup! It features a mock neckline, long fitted sleeves, a trendy ruched side seam with an adjustable drawstring, an asymmetric midi-length hem creating a high-cut side slit, and a form-hugging silhouette to flaunt your figure. The brushed knit fabric offers plenty of stretch. Style this midi dress with ankle booties!

      Fit & Features

      • Mock neckline
      • Long fitted sleeves
      • Ruched side seam, adjustable drawstring
      • Asymmetric midi-length hem, high-cut side slit
      • Form-hugging silhouette
      • Brushed knit fabric, plenty of stretch
      • Runs true to size

      Style Number/Barcode: 05102-5404

      Category Name: Casual Dresses

      Price: $9.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale