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.

  • 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:
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  • 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
  • Smocked Stunner Mini Dress

    Showcase the stylish stunner you are in this adorable smocked mini dress! It features a sleeveless bodice, thick smocked shoulder straps with ruffle detailing, a sweetheart neckline, a stretchy and smocked bust, a high waist seam with a ruffle trim, and a flowy skirt with a tiered ruffle hem. The dress is composed of a lightweight woven fabric with a woven skirt lining.

    Style Number/Barcode: 05102-0230

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Get Sprung On Florals Mini Dress

    Get sprung on this too cute mini dress! It features an off the shoulder neckline with short cuffed sleeves, a trendy tie front with a keyhole cut out, seam detailing, a smocked back, and a short, form hugging fit. The dress is composed of a woven fabric with no stretch.

    Style Number/Barcode: 05102-0099

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Rainbow Wave Maxi Dress

    You love color, so embrace the rainbow! All eyes will be on you in this vibrantly chic maxi dress, which features a multi-hued stripe pattern, spaghetti straps, scoop neck, pockets at either hip, and plenty of stretch. Don't forget to pair it with the matching head wrap! 

    Style Number/Barcode: 05102-0244

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • Trendsetter In Tie Dye Mini Dress

    Be a total trendsetter in this fun tie dye mini dress! It features a sleeveless bodice, tank-like shoulder straps, a scoop neckline, a tie front accent, and a short, curve hugging fit. The dress is composed of a stretchy knit fabric.

    Style Number/Barcode: 05102-0227

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Not So Basic Mini Dress

    Sure, you probably have your share of mini dresses. Now it's time for an of-the-moment upgrade! This ultra-chic mini features an off-the-shoulder elasticized neckline, gathered bodice and sleeves, a back zip, banded waist with back smocking, and pencil skirt with gather-drape detail. Dress is made from a mid-weight woven material with little to no stretch.

    Style Number/Barcode: 05101-0165

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Floral In Love Midi Dress
    Fall in love with this romantic floral midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline created by a knot front detail, a hidden back zipper and hook and eye closure, and an A-line mid-length fit with a front slit. The dress is composed of a lightweight woven fabric.

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0209

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Catch The Bouquet Dress

    This neutral ditsy flower pattern dress has us swooning! With a floral bouquet pattern it features a square neckline, ruffled stretchy spaghetti straps, a square back with a hidden zipper and double straight hem down the middle. This mini dressed has a ruched side detailing and an inner linen lining.  

    Style Number/Barcode: 05102-0207

    Category Name: Casual Dresses

    Price: $9.97 $47.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Braid For Shade Maxi Dress
    Elegantly subdued hues and sophisticated cut lend this maxi its easy appeal. Dress features a halter neck with deep V, banded waist with cutout and two rows of braid trim, a braided clasp back, and an A-line skirt with back zip. Dress is partially lined and made from a soft, crepe-like woven material with little to no stretch.

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0181

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Life's A Beach Mesh Dress

    Hit the pool, bask by the beach, or prep to party in this colorful mesh maxi! Dress features a vibrant tropical print, a strapless neckline, dramatic ruffle trim running from bust to hem, a high front slit, and built-in briefs. Dress bodice is semi-sheer and does not include a top. Maxi is made from a mesh blend material with moderate stretch.

    Style Number/Barcode: 05102-0159

    Category Name: Casual Dresses

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Floral Chic Mini Dress

    Add some floral chic to your pretty look with this adorable mini dress! It features a sleeveless bodice, tie shoulder spaghetti straps, a sweetheart neckline with a tie front detail, a square back with a hidden zipper and hook and eye closure, a high waist seam, and a flowy A-line skirt. The dress is composed of a woven fabric with a skirt lining, and offers no stretch.

    Style Number/Barcode: 05102-0224

    Category Name: Casual Dresses

    Price: $15.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Love Bud Sweetheart Dress

    Hey sweetheart, Hey love bud , Hey little cutie ! The dress features a sweetheart neckline , tie yourself ribbon spaghetti straps, and a built in wire for a bra-like effect. The back-line of this dress is square and includes a hidden zipper. The bodice of this dress is a body con style that is form fitting and shows off those curves and has a mini slit at the hem. The dress is composed of a canvas material that offers moderate stretch. Muah!

    Style Number/Barcode: 05102-0219

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Va Va Venom Knit Dress

    You don't bite, but you're ready to pounce! Channel your wild side in this bold mini. Dress slips on, has a curve-hugging fit, and features spaghetti straps and a scoop neck. Dress is made from a ultra-soft brushed knit fabric with a fair amount of stretch. 

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

    Style Number/Barcode: 05102-0169

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Life's A Beach Mesh Dress

    Hit the pool, bask by the beach, or prep to party in this colorful mesh maxi! Dress features a vibrant tropical print, a strapless neckline, dramatic ruffle trim running from bust to hem, a high front slit, and built-in briefs. Dress bodice is semi-sheer and does not include a top. Maxi is made from a mesh blend material with moderate stretch.

    Style Number/Barcode: 05102-0158

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flow With It Maxi Dress

    Go with the flow of this pretty summer maxi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline, a stretchy smocked square back, a front crochet top with sheer insets at the waist, and a long, floor length flowy maxi skirt with a front high thigh slit. The dress is composed of a linen fabric with no stretch.

    Style Number/Barcode: 05102-0085

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruche Hour Sleeveless Mini Dress

    Subtly sophisticated, this ruched mini is equally sultry—and ready for evenings out! Dress features a mesh overlay, high neck, slim-cut sleeveless bodice, and ruching detail at the sides, back, and front beginning at the waist. Slip-on style is fully lined and made offers a fair amount of stretch.

    Style Number/Barcode: 05103-0073

    Category Name: Casual Dresses

    Price: $11.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vixen Side Stripe Mini Dress

    Channel the look of your fave '90s-era cool girls in this of-the-moment mini. Dress features spaghetti straps, a square neckline, and stripes running vertically from bust to hem at either side. Dress slips on and  is made from an ultra-soft woven material with moderate stretch.

    Style Number/Barcode: 05102-0044

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay All Day Mini Dress

    Feel like you're on a vacay all day in this fun tropical printed mini! It features a sleeveless bodice, spaghetti straps, a scoop neckline, and a short, form hugging fit. The dress is composed of a scuba knit fabric that offers moderate stretch and showcases a vibrant print.

    Style Number/Barcode: 05102-0008

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Anything But Basic Maxi Dress

    This sophisticated, streamlined maxi will more than earn its place in your closet this season. Chic and versatile, it goes pretty much anywhere you do! Dress features a square neckline, all-over rib knit detail, crisscross spaghetti straps, adjustable keyhole tie detail, back cutout, and side slit. Dress is partially lined and made from a soft, densely knit material with moderate stretch.

    Style Number/Barcode: 05102-0012

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Take The Plunge Floral Maxi Dress
    Add a hint of island-inspired chic to your wardrobe with this gauzy sleeveless maxi dress. Dress features a deep V at front and back, a shirred banded waist, and an all-over floral print. Dress is composed of a rayon fabric and has plenty of stretch in the waist and moderate stretch throughout the rest.

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

    Style Number/Barcode: 05102-4050

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Soft And Sweet Dress

    Show off your soft sweet side baby girl! This off shoulder dress is the perfect ensemble for a day in the sun. Featuring a straight off-shoulder neckline and wooden buttons down the middle, this dress has a form fitting bodice and a ribbed knit material that will offer maximum stretch as well as a soft inner lining. Show off those shoulders girl!

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

    Style Number/Barcode: 05102-4039

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • My Wavelength Skater Mini Dress

    Good vibes only in this skater dress! The mini skater dress features a deep v-neckline, spaghetti straps that offer plenty of support, back zip, a darted bust that adds structure to the bodice, a banded waist that flatters, and A-line flared skirt. Complete outfit with chic clear heels and statement earrings.

    Fit & Features

    • Sleeveless v-neckline
    • Darted seams at the bust
    • Spaghetti straps
    • Banded waist 
    • A-line skater silhouette
    • Composed of soft mid-weight woven fabric 
    • Form hugging fit

     

    Ivory and Mint Dress: Model is 5'8" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.

    Blue Dress: Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.

    Denim Dress: Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.

    Style Number/Barcode: 05101-8697

    Category Name: Casual Dresses

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Miss Midi Striped Dress

    Hey there miss midi, we see you! and we are on the same page too, filling our closet with midi dresses this season. This piece features a  v-neckline, attached dark neutral marbled buttons, and adjustable spaghetti straps that lead to a square back. This toned midi dress has a skinny stripe pattern and is composed of a soft knit material that offers maximum stretch. 

    Style Number/Barcode: 05102-3992

    Category Name: Casual Dresses

    Price: $8.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free