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.

  • All Eyes On The Floral Maxi Dress

    All eyes on the floral. This strapless maxi dress turns up the heat with a bold bloom moment and a high side slit that knows how to make an entrance at parties and on vacay!

    Fit & Features

    • Statement floral print
    • Mesh fabric lined with stretchy knit
    • Strapless tube neckline
    • High side slit
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000083

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Flirt On Arrival Denim Skater Dress

    Made for flings, flirts, and feelin’ yourself. This trendy halter skater dress hugs you in all the right places with a playful bust cutout and a twirl-worthy drop waist—aka your weekend wardrobe’s new fave.

    Fit & Features

    • Denim fabric
    • Sleeveless cross-front halter neckline, tie-back straps
    • Bust cutout, metal heart accent
    • Partially open back, hidden lower back zipper closure
    • Drop waist
    • Short pleated skater silhouette
    • Runs small, size up recommended

    Style Number/Barcode: 05102-000084

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Glow Getter Strapless Cutout Mini Dress

    Catch flights and compliments. This strapless mini hugs you in all the right places with a ruched bust ring detail and cheeky cutout that turns the charm up. Brunch, beach, or bae date—it’s a serve every time.

    Fit & Features

    • Rib knit stretchy fabric
    • Strapless sweetheart tube neckline with hardware trim
    • Cutout accent
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000033

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Island It Girl One-Shoulder Cutout Maxi Dress

    Giving tropical baddie with a side of luxury, this one-shoulder maxi brings the heat with a bold leaf print, cutout waist, and gold hardware that says, "I didn’t come to play." It's made for vacation slays, beach weddings, or poolside parties!

    Fit & Features

    • Tropical leaf print, smooth stretchy knit fabric, short lining
    • One-shoulder neckline with hardware trim
    • Side cutout bodice
    • High side slit
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000082

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Abstract Effect Strapless Bodycon Mini Dress

    Every head will turn towards you in this abstract mini dress designed in a flattering bodycon silhouette that hugs your curves just right!

    Fit & Features

    • Abstract print, mesh-lined stretchy fabric
    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000078

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Meet Your Match Striped Lace-Up Midi Dress

    Your new stylish striped midi dress for casual soirees! Featuring a cutout bodice accented with sleek hardware trim, this dress offers a bold, modern edge. The lace-up open back adds a touch of allure, while the side slit offers effortless movement.

    Fit & Features

    • Striped pattern, texture knit fabric, stretchy knit lining
    • High halter neckline, spaghetti strap tie
    • Lace-up open back, lower zipper and hook-eye closure
    • Cutout bodice with hardware trim
    • Side slit
    • Form-hugging silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000081

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Floral Fantasy Strapless Cutout Maxi Dress

    Easy to wear, impossible to forget! Make your entrance in this floral maxi dress designed with a flirty cutout and form-hugging fit that accentuates your figure.

    Fit & Features

    • Floral print, mesh-lined fabric
    • Strapless neckline
    • Cutout bodice
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000079

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sea Salt Vibes Halter Crochet Midi Dress

    Your next vacay is calling, and this crochet midi dress will set the vibes! Embrace the sand and sun in this stylish dress designed with a flattering high neckline and form-hugging fit.

    Fit & Features

    • Crochet knit fabric, stretchy knit lining
    • High halter neckline, spaghetti strap ties
    • Form-hugging fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000028

    Category Name: Casual Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Charming Look Puff Sleeve Ruffled Skater Dress

    Create a charming look for weekend brunch in this eyelet knit skater dress with the cutest puff sleeves and ruffled mini-length silhouette!

    Fit & Features

    • Eyelet knit fabric, stretchy knit lining
    • Square neckline
    • Short puff sleeves, ruffled hems
    • Drop waist
    • Tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000075

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • East Coast Girlie Button Linen Skater Dress

    Pack for the perfect East Coast summer with this chic linen skater dress! Adorned with faux button accents and a ruffled mini-length hem, this dress will make you stand out in style.

    Fit & Features

    • Linen-blend woven fabric, woven lining, shorts lining
    • Boat neckline
    • Back zipper and hook-eye closure
    • Faux button accents
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000073

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Best For Last Halter A-Line Denim Mini Dress

    Be the talk of the town in this flirty denim mini dress perfect for festivals, concerts, or country bars! The plunging halter neckline shows some skin while the flattering A-line silhouette cinches your waist and flows into a flirty flared mini hem.

    Fit & Features

    • Denim fabric, moderate stretch
    • Plunge halter V-neckline, tie straps
    • A-line silhouette
    • Flared mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000070

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Paradise Halter Open Back Slit Midi Dress

    Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look.

    Fit & Features

    • Slinky knit fabric, smooth stretchy knit lining
    • Halter cowl neckline, beaded spaghetti strap tie
    • Open back with spaghetti strap tie
    • Bodycon silhouette
    • Slit accent, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000283

    Category Name: Casual Dresses

    Price: $32.00 $45.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED, BROWN

    Available Size: XS

    Product Badge:
    • Sale
  • Take Me Away Tube Midi Dress

    Effortless but still a serve. This strapless knit midi hugs your curves with a twist-front neckline and scalloped hem—perfect for brunches, beach dates, or packing for your next getaway!

    Fit & Features

    • Texture knit cotton-blend fabric, moderate stretch
    • Sweetheart strapless tube neckline
    • Twist bust
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000018

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cutest Picnic Gingham A-Line Eyelet Mini Dress

    From BBQs, picnics, to summer parties, this gingham mini dress will make the cutest impression! The faux button accents add a touch of vintage charm, while the A-line silhouette and eyelet ruffled trim create a flattering and playful look.

    Fit & Features

    • Gingham print, cotton-blend woven fabric, woven lining
    • Sweetheart neckline, eyelet trim
    • Adjustable spaghetti straps
    • Stretchy smocked back panel
    • Faux button accents
    • A-Line fit, eyelet ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000067

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Stylish Staple Ribbed Knit Bodycon Midi Dress

    A stylish staple like this bodycon midi dress needs to be in your closet. The ribbed knit fabric offers plenty of stretch, while the form-hugging fit flaunts your curves.

    Fit & Features

    • Lined ribbed knit fabric, high stretch
    • Sleeveless square neck and back design
    • Spaghetti straps
    • High side slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000066

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cutout Crush Hour Midi Dress

    Warning: This midi dress is sure to cause double takes. From the front-tie detail to the high leg slit, it’s giving effortless bombshell, perfect for pool parties or a cute brunch!

    Fit & Features

    • Sweater knit stretchy fabric
    • V-neckline with tie bust design
    • Adjustable spaghetti straps
    • Underbust cutout accent
    • Front slit
    • Bodycon fit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000014

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet And Off-The-Shoulder Sweater Skater Dress

    Look sweet on chilly days in this darling sweater mini dress featuring a cute folded, off-the-shoulder neckline and forever flattering skater silhouette. 

    Fit & Features

    • Rib knit stretchy fabric
    • Folded off-the-shoulder neckline
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000013

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Favorite Staple Striped Cutout Mini Dress

    Slip into this striped mini dress with a flirty cutout and bodycon fit - it'll be your favorite staple all season long!

    Fit & Features

    • Striped pattern, stretchy rib knit fabric
    • Strapless neckline
    • Cutout accent
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000015

    Category Name: Casual Dresses

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
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  • Flirty And Flowy Ribbed Knit Strapless Skater Dress

    Ready before the group chat even replies. This ribbed knit strapless skater dress hugs through the bodice with a flirty drop waist and flowy skirt that moves with you from brunch plans to last-minute invites.

    Fit & Features

    • Ribbed knit fabric, high stretch
      Strapless straight-across neckline
    • Drop waist design
    • Godet detailing
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000008

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paisley and Playful Halter Skater Dress

    Flirty, floaty, and made for dancing under the sun. With a smocked bust and ruffled skater fit, this halter mini dress is your go-to for festivals, vacays, or just looking way too good for no reason.

    Fit & Features

    • Paisley print, woven fabric, bust lining
    • Halter V-neckline, spaghetti strap tie
    • Stretchy smocked bust
    • Open tie-back detail
    • Flowy skater silhouette
    • Ruffled trim short hem
    • Runs true to size

    Style Number/Barcode: 05102-000065

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Laced Up And Lovely Floral Corset Dress

    Giving a fairytale with a flirty twist. This corset mini dress brings the drama with lace trim, a lace-up back, and a twirl-worthy skater skirt perfect for celebrations or garden soirees!

    Fit & Features

    • Floral print, woven fabric, woven lace trim lining
    • Sweetheart lace trim neckline, bust tie, underwire bust
    • Lace trim, adjustable shoulder straps
    • Corset lace and pleated trim bodice, flexible boning
    • Back zipper and hook-eye closure, lace-up back detail
    • Drop waist seam, voluminous skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000067

    Category Name: Casual Dresses

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Heartbreaker Hourglass Midi Dress

    Soft, sleek, and serving curves. This bodycon midi dress is your go-to when you want to keep it simple but still shut it down—with flattering bust detail and a bodycon fit perfect for showing off on date night or a chic party.

    Fit & Features

    • Soft modal fabric, smooth knit lining, moderate stretch
    • Sweetheart neckline, bust detail
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000064

    Category Name: Casual Dresses

    Price: $18.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Definitely Darling Tie Back Babydoll Mini Dress

    Fall in love with this darling eyelet mini dress!. Featuring an open tie-back design and a charming babydoll silhouette, this dress is perfect for brunch, shower celebrations, or graduations.

    Fit & Features

    • Eyelet fabric, stretchy knit lining
    • Short puff sleeves
    • Square neckline
    • Open tie-back design
    • Babydoll silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000061

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Major Heatwave Floral Halter Mini Dress

    Cause a major heatwave in this sultry mini dress designed with a large floral print on smooth, stretchy knit fabric. The plunging halter V-neck and short, curve-hugging silhouette are alluring details you'll love.

    Fit & Features

    • Lined knit fabric, high stretch
    • Large floral print
    • Sleeveless plunging V-neckline
    • Halter strap, partially open back
    • Ruching
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000063

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free