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.

  • Cherry On Top Lace-Up Cutout Chiffon Skater Dress

    Nothing says wow like this chiffon skater dress that puts the cherry on top of your look at brunch, birthdays, or shower celebrations! Designed with a V-neckline, adjustable ruffled straps, and a pleated bust, this dress accentuates your curves. The cutout waist and back with lace-up detailing add a playful touch, while the skater silhouette and tiered ruffled hem give a flirty and flattering fit! Complete the look in fashionable platform sneakers.

    Fit & Features

    • Chiffon fabric lined with woven fabric
    • Adjustable ruffled straps
    • Lace-up, back zipper hook-eye closure
    • Cut out sides and back
    • Ruffled
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2947

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paint The Night Abstract Open Back Midi Dress

    It’s giving art, elegance, and effortless wow. This slinky slip dress was made to glide through gallery nights, rooftop drinks, and every “who is she?” moment in between.

    Fit & Features

    • Abstract print, woven fabric
    • V-neckline
    • Spaghetti straps
    • Open strappy back
    • Curve-hugging silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000615

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Vacation Long Sleeve V-Neck Cutout Mini Dress

    This V-neck mini dress pairs perfectly with your next vacation or pool party! This playful and stylish dress features long sleeves with flare cuffs, a V-neckline with a hoop insert, and cutout details on the bodice and back. Its bodycon fit and mini-length hem will highlight your curves while you explore exotic destinations or the resort bar! Complete the look with sunnies.

    Fit & Features

    • Texture knit fabric, sewn-in knit lining, minimal stretch
    • V-Neckline with hoop insert
    • Cutout bodice and back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5705

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Buckled Beauty Off-The-Shoulder Knit Mini Dress

    An off-the-shoulder mini dress perfect for everyday slays. It features long sleeves and a foldover neckline with trendy buckled accents and a bodycon silhouette. Complete the look with boots.

    Fit & Features

    • Stretchy rib knit fabric
    • Off-the-shoulder neckline, folded with buckled accents
    • Long sleeves
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5992

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sweet Charm Off-The-Shoulder Floral Mesh Mini Dress

    Showcase your sweet charm at spring and summer parties in this floral mesh mini dress! The airy sheer mesh fabric is accented with a dainty floral print for the prettiest vibe and includes a full-length knit lining for coverage. The off-the-shoulder sweetheart neckline gives the dress a feminine touch, and features sheer short-sleeved cuffs and a V-cut bust design with a tie-front detail. The ruching down the side seams will accentuate your gorgeous curves along the bodycon silhouette. Style this adorable mini dress with clear heels.

    Fit & Features

    • Stretchy sheer mesh fabric with knit lining
    • Floral print
    • Off-the-shoulder sweetheart neckline, short sleeve cuffs
    • V-cut bust design with tie-front detail
    • Ruched bust and side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3050

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artsy Babe Paisley Bodycon Slit Midi Dress

    Strut like an artsy babe in this paisley mesh midi dress showcasing a flattering bodycon silhouette with a flirty front slit. Complete the look with a handbag.

    Fit & Features

    • Paisley print, mesh fabric, stretchy knit lining
    • Square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5932

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Day Ruffled Ditsy Floral Skater Dress

    You'll love every moment spent in this ditsy floral skater dress! The square neckline and spaghetti tie straps add a flirty touch, while the stretchy smocked bodice ensures a comfortable fit. With a playful ruffled skater silhouette and a mini-length hem, this dress is perfect for any occasion. Complete the look in wedges.

    Fit & Features

    • Ditsy floral print, woven fabric lined with knit
    • Spaghetti tie strap
    • Square neckline
    • Ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5425

    Category Name: Casual Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adorable Looks Tie Front Bodycon Midi Dress

    All of your adorable looks this season will include this eyelet midi dress with a flirty tie front and bodycon silhouette. This dress is perfect for shower celebrations or graduations!

    Fit & Features

    • Eyelet fabric
    • Tie front sweetheart neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6008

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Breeze Tropical Cutout Slit Maxi Dress

    Feel the island breeze in this tropical maxi dress while on vacation!  With a square neckline, spaghetti straps, and a form-hugging fit, this maxi dress is perfect for a day in the sun. The cutout bodice and high front slit add a touch of playfulness to your island look. Complete the look with sandals.

    Fit & Features

    • Tropical palm print, smooth stretchy knit fabric, sewn-in knit lining
    • Square neckline
    • Spaghetti straps
    • Cutout bodice, high slit
    • Form-hugging
    • Runs true to size

    Style Number/Barcode: 05102-5670

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Breezes Halter Boho Satin Maxi Dress

    Enter the room in this chic boho satin maxi dress to make a bold impression! The sleeveless dress boasts a halter neckline and a flowy silhouette adorned with a high front slit. Style with stiletto heels.

    Fit & Features

    • Boho print, satin woven fabric. sewn-in woven lining
    • Halter neckline
    • Spaghetti strap
    • Flowy silhouette
    • High front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5865

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Picture Striped Midi Dress

    With an ice cream in hand and strappy sandals on, this striped midi dress will have you looking pretty everywhere you go! Featuring a flattering square neck and curve-hugging fit, this dress accentuates your figure down to the midi hem.

    Fit & Features

    • Striped print, stretchy knit fabric, sewn-in knit lining
    • Square neckline
    • Wide shoulder straps
    • Curve-hugging fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5860

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Lovely Floral Eyelet Mini Dress

    Oh-so-lovely, this floral eyelet knit mini dress is perfect for weekend brunch. You'll adore the short puff sleeves, sweet tie-front detail, and pretty A-line silhouette.

    Fit & Features

    • Sheer eyelet knit fabric with knit lining, plenty of stretch
    • Dainty floral print
    • Sweetheart neckline, ruched bust
    • Keyhole cutout, tie-front detail
    • Short puff sleeves, elastic cinched hems
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6050

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Preppy Edit Pinstripe Mini Dress

    The perfect dress for fall—this strapless pinstripe mini dress blends polished structure with playful pleats. Toss on a blazer or knee-high boots for seasonal chic.

    Fit & Features

    • Pinstripe pattern, woven fabric
    • Strapless collared neckline
    • Button front
    • Fitted bodice
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5993

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Silhouette Off-The-Shoulder Maxi Dress

    Show off your alluring curves in this off-the-shoulder maxi dress crafted from a rib knit fabric that fits like a glove! 

    Fit & Features

    • Rib knit stretchy fabric
    • Off-the-shoulder neckline
    • Twisted strap details
    • Bodycon silhouette
    • Flared maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6020

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Talker Strappy Back Halter Skater Mini Dress

    Sweeten any room with your vibe in this halter skater dress, which flaunts a strappy open back that turns heads with every wear! 

    Fit & Features

    • Woven fabric, stretchy knit lining
    • Halter V-neckline with spaghetti strap tie
    • Open back with tie-back detail
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6029

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Get Cutesy V-Neck Gingham Skater Dress

    Get cutesy in this gingham skater dress for a dreamy look this spring to summer! With a lace trim neckline and flattering drop waist seam that accentuates your figure, this short dress looks like a dream.

    Fit & Features

    • Gingham print, poplin woven fabric, lined
    • Laced trim V-neckline
    • Spaghetti straps
    • Button front details
    • Drop waist seam
    • Skater silhouette, short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5990

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Just For Fun Strapless Floral A-Line Mini Dress

    A floral mini dress made for fun and compliments! With a flattering strapless neckline and A-line silhouette, you'll look and feel your best.

    Fit & Features

    • Floral print, eyelet fabric lined with stretchy knit
    • Strapless neckline
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6040

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Plaid Mood Sleeveless A-Line Mini Dress

    The plaid mesh mini dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, and an A-line silhouette. Complete the look with loafers for a preppy vibe.

    Fit & Features

    • Sheer mesh fabric with knit lining, plenty of stretch
    • Plaid print
    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Mini-length hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5987

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Bliss Tie-Back Slit Maxi Dress

    Ideal for making a statement at any occasion, this artsy print maxi dress combines chic with effortless style. Featuring a flattering A-line silhouette and a stylish front slit, this dress offers a breezy look that turns heads with a tie-back design.

    Fit & Features

    • Artsy print, woven fabric, stretchy knit lining
    • V-neckline
    • Adjustable spaghetti straps
    • Tie-back design
    • A-line silhouette
    • Front slit, flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6039

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutest Spirit Short Sleeve Knot Tie Mini Dress

    This short sleeve mini dress is the cutest for casual outings! Made from soft and stretchy rib knit fabric, this dress will keep you comfy and stylish all day long. With a flattering bodycon fit and a unique front knot tie detail, this dress exudes charm. The asymmetrical mini-length hem adds a touch of playfulness, making this a must-have. Complete the look in platform sneakers.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Crew neckline
    • Bodycon fit
    • Front knot tie detail
    • Runs true to size

    Style Number/Barcode: 05102-5762

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Look Abstract Print Mesh Midi Dress

    Create a dreamy look to catch all the stares in this abstract print mesh midi dress designed with a high front slit on a curve-hugging bodycon silhouette.

    Fit & Features

    • Sheer mesh fabric with full-length brushed knit lining, high stretch
    • Abstract print
    • Sleeveless square neck and back
    • Spaghetti straps
    • Midi-length hem, high front slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5876

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Street Chic Faux Suede Mini Dress

    A little jacket inspo, a lot of city attitude. This faux suede mini dress brings structure and edge to your fall lineup. Perfect for styling with a long sleeve top and boots on crisp autumn days.

    Fit & Features

    • Soft, smooth faux suede fabric
    • Mock neckline, dual snap-button closures
    • Front zip-up closure
    • A-line fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000202

    Category Name: Casual Dresses

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easy And Breezy Lace-Up Midi Dress With Pockets

    So effortlessly breezy for any plans, this A-line midi dress will turn heads with a lace-up bust and back detail, while the hidden side pockets are perfect for stashing your phone or lip gloss in.

    Fit & Features

    • Poplin woven fabric, woven lining
    • Sweetheart neckline, lace-up front, stretchy smocked bust
    • Spaghetti straps
    • Lace-up back, lower zipper and hook-eye closure
    • Drop waist seam, hidden side pockets
    • A-line silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6023

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Many Admirers Open Back Bodycon Midi Dress

    Crafted in a smooth knit fabric that hugs every curve, this cap sleeve midi dress will leave your admirers speechless! The dress boasts a showstopping open back while the bodycon silhouette flaunts your figure along the slit midi-length hem. Pair with stiletto heels.

    Fit & Features

    • Smooth knit stretchy fabric
    • Cap sleeves
    • Scoop neckline
    • Open back
    • Bodycon silhouette
    • Midi-length hem, side slit
    • Runs true to size

    Style Number/Barcode: 05102-5984

    Category Name: Casual Dresses

    Price: $14.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free