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.

  • So Iconic Abstract Print Ruched Mini Dress

    Step out like the icon you are in a mini dress that features a plunging cowl neckline with halter neck ties for a secure fit, an abstract floral print, and ruching throughout to enhance curves. Style with clear heels. 

    Fit & Features

    • Fitted mesh fabrication, moderate stretch
    • Cowl neckline
    • Open back, halter neck ties
    • Abstract floral print
    • Mini length hem
    • Ruching
    • Runs true to size

    Style Number/Barcode: 05102-5786

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Looking Cute Strapless Tie-Dye Bodycon Mini Dress

    Looking cute is easy with this tie-dye mini dress for summer! This mini-length dress will effortlessly enhance your curves and flatter your figure featuring a trendy strapless neckline and bodycon silhouette. Complete the look with earrings and heels for a party!

    Fit & Features

    • Tie-dye print, mesh fabric lined with stretchy knit
    • Strapless neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5782

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Life's A Picnic Sweetheart Lace Gingham Mini Dress

    Life's a picnic when you look oh-so-cute in this gingham mini dress at summer carnivals and day dates! The adjustable spaghetti straps provide a perfect fit while the lace trim sweetheart neckline adds adorable vibes. The high waist seam and slim fit create a flattering silhouette, while the lace trim mini-length hem adds a playful touch. Complete the look in platform sneakers.

    Fit & Features

    • Gingham print, cotton woven fabric, no stretch
    • Adjustable spaghetti straps
    • Lace trim sweetheart neckline
    • Lace trim high waist seam
    • Slim fit
    • Lace trim mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5781

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Set To Amaze Mock Neck Abstract Mini Dress

    Everyone will admire your amazing self in this abstract mini dress all over town! Made with a unique abstract print on airy lined mesh fabric, this dress is sure to turn heads. The sleeveless design and mock neckline add a chic touch, while the ruched side seams, bodycon fit, and mini-length hem show off your curves. Complete the look with earrings.

    Fit & Features

    • Abstract print
    • Sheer mesh fabric with knit lining, plenty of stretch
    • Mock neckline
    • Ruching
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5783

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Beachy Babe Tie-Back Crochet Mini Dress

    Channel a beachy babe vibe in this trendy crochet mini dress! Designed with a sheer crochet fabric with a boho-inspired woven design, the short dress includes a stretchy knit lining for coverage. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, an adorable tie-back design, a flirty lower back cutout that peaks out on both sides, and a form-hugging fit to flaunt your figure. Style with espadrille sandals.

    Fit & Features

    • Crochet fabric with woven design, stretchy knit lining
    • Square neckline
    • Adjustable spaghetti straps
    • Tie back straps, back cutout
    • Hidden side zipper with hook and eye closure
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5780

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Lovely Look Cold Shoulder Bodycon Lace Mini Dress

    Nothing can compare to your lovely look in this lace mini dress as a stunning bride-to-be or birthday girlie! Featuring a trendy cold shoulder V-neckline, feminine flutter short sleeve cuffs, and delicate spaghetti straps, this dress hugs your curves for a bodycon fit that will turn heads. Complete the look with earrings and clutch.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Cold shoulder V-neckline
    • Flutter short sleeve cuffs, spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3423

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Love Of Details V-Neck Lace-Up Skater Dress

    Fall in love with every chic detail of this lace skater dress sure to romance every room you walk into! With adjustable spaghetti straps and a flattering V-neckline, our dress features a lace-up mesh bodice and a playful skater silhouette. The asymmetrical ruffled trim adds a touch of flirty sophistication, making it the perfect for brides, birthday girls, or party guests! Complete the look with dainty earrings and heels.

    Fit & Features

    • Lace fabric line with stretchy knit
    • Adjustable spaghetti straps, V-neckline
    • Back zipper and hook-eye closure
    • Mesh lace-up bodice
    • Asymmetrical ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3436

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Vibes High Slit Striped Knit Maxi Dress

    This casual-chic striped knit maxi dress is perfect for your laid-back weekend vibes! Designed with stretchy ribbed knit with a thin striped pattern, it features a sleeveless scoop neckline with spaghetti straps, high-cut side slits on each side for added movement, and a form-hugging slim fit on the maxi-length silhouette. Style this long dress with strappy sandals.

    Fit & Features

    • Striped ribbed knit fabric, short knit lining, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • High side slits
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5778

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Persona Strapless A-Line Mini Dress

    Turn on the charm in this strapless mini dress out on the town or at a party! The side ruched seam accentuates your curves while the A-line silhouette provides a flattering fit along the playful mini-length hem. Complete the look with heeled sandals.

    Fit & Features

    • Smooth knit fabric, moderate stretch
    • Strapless neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5642

    Category Name: Casual Dresses

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Dreams Halter V-Neck Boho Chiffon Maxi Dress

    Summer dreams are made of this boho chiffon maxi dress perfect for your vacation or weekend getaway! The halter V-neckline and spaghetti strap tassel ties provide an effortlessly chic touch, while the stretchy smocked bodice and hidden side pockets offer convenience. The flowy ruffled silhouette adds a touch of romance! Complete the look in sandals and a bracelet.

    Fit & Features

    • Bohemian print, chiffon fabric with woven lining, no stretch
    • Halter V-neckline
    • Spaghetti strap tassel ties
    • Stretchy smocked bodice
    • Hidden side pockets
    • Flowy ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5777

    Category Name: Casual Dresses

    Price: $6.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning One Halter V-Neck Ruffle Floral Maxi Dress

    You'll take every vacation or summer party by storm when you have this floral maxi dress! This stunning maxi dress features a halter V-neckline with spaghetti strap tassel ties, a stretchy smocked bodice accentuating your figure, and hidden side pockets for added convenience. The flowy ruffled silhouette and floor-length hem add a stylish finish. Complete the look in sandals and sunglasses!

    Fit & Features

    • Floral print, woven fabric with lining, no stretch
    • Halter V-neckline
    • Spaghetti strap tassel ties
    • Stretchy smocked bodice
    • Flowy ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5776

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vibrant Strapless Butterfly Print Mini Dress

    Set hearts aflutter in this vibrant butterfly print mini dress at parties or concerts! This dress is designed with a retro butterfly print on mesh fabric and boasts a strapless neckline and flattering bodycon fit. The short ruffled hem has a satin bow for added charm to your look! Style with platform shoes.

    Fit & Features

    • Butterfly print, mesh fabric lined with stretchy knit
    • Bodycon fit
    • Ruffled mini-length hem with satin bow
    • Runs short, size up if desired

    Style Number/Barcode: 05102-5775

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Watch Me Bloom Off-The-Shoulder Floral Midi Dress

    Be the talk of any garden party in this floral midi dress! The off-the-shoulder neckline exudes femininity, while the cutout waist shows some skin. The flowy midi-length silhouette and front slit offer a trendy allure. Complete the look in lace-up heels and earrings.

    Fit & Features

    • Floral print, woven fabric with lining, no stretch
    • Off-the-shoulder neckline
    • Cutout waist
    • Front slit
    • Flowy midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3414

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fit To Bloom Scoop Neck Ditsy Floral Midi Dress

    Sweet summer events are calling and this ditsy floral midi dress is here to make you look cute! Adjustable spaghetti straps and a drawstring scoop neckline provide versatile style, while the form-hugging fit and side slit add a touch of sass. Complete the look in high heels.

    Fit & Features

    • Ditsy floral print, bust lining, knit fabric, moderate stretch
    • Spaghetti straps
    • Drawstring adjustable scoop neckline, bust tie
    • Form-hugging fit
    • Side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5774

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Back Strapless Strappy Mini Dress

    Make everyone look back at you in this sassy rib knit mini dress! Perfect for summer BBQs or pool parties, this dress boasts a flattering strapless neckline and bust cutout, a strappy back design, and a bodycon fit. Complete the look in sandals and sunnies!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Strappy back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5767

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soiree Hour Lace-Up Ruffled Floral Midi Dress

    When the cocktails are poured and the music starts playing it's time to unveil this floral chiffon midi dress! Perfect for daytime soirees or showers, this midi dress features a flattering scoop neckline adorned with adjustable spaghetti straps. The lace-up back and flowy ruffled silhouette offer a touch of trendiness to this midi-length dress! Complete the look with earrings and wedges.

    Fit & Features

    • Floral print, chiffon fabric lined with woven fabric
    • Scoop neckline
    • Adjustable spaghetti straps
    • Lace-up back, zipper and hook-eye closure
    • Flowy ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3411

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flouncin' Around Strapless Ruffle Mini Dress

    Show off your fun and flirty side in this strapless mini dress at parties and on dates! Featuring a figure-hugging bodycon fit, side ruched seams, and a playful ruffled mini-length hem, this dress is perfect for any occasion. Complete the look with block heels.

    Fit & Features

    • Double-lined smooth knit stretchy fabric
    • Strapless neckline
    • Bodycon fit
    • Ruffled 
    • Runs true to size

    Style Number/Barcode: 05102-5771

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flattering Look A-Line Ruffled Mini Dress

    This A-line mini dress gives you a flattering look for every social event on your calendar! The V-neckline adds a touch of elegance to this fun, versatile piece. Perfect for a variety of occasions, this dress will keep you looking stylish. Complete the look with dainty earrings.

    Fit & Features

    • Soft model-blend knit fabric, lined, moderate stretch
    • V-neckline
    • A-Line silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5769

    Category Name: Casual Dresses

    Price: $7.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Sweetie Open Back Bow Skater Dress

    Arrive like the stunning sweetie you are in this short skater dress as the bride-to-be, graduate, or birthday girlie! This dress features a square neckline and shoulder straps, with an attention-grabbing open back and statement bow detail. The drop waist skater silhouette is flattering, and the short-length hem is perfect for showing off your legs. Complete the look in block heels.

    Fit & Features

    • Woven fabric, tulle and stretchy knit lining
    • Square neckline, shoulder straps
    • Open back, statement bow
    • Back zipper and hook-eye closure
    • Drop waist seam, skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3410

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Never A Dull Moment Strapless Cutout Maxi Dress

    Bring a stunning look in this strapless maxi dress for your look-back-it moment! The strapless neckline and cutout bust add a touch of allure, while the strappy back and form-hugging fit emphasize your figure. With a center-back slit, you'll be able to move in style. Complete the look with earrings and a clutch!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Cutout bust, strappy back
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5766

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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:
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  • Trendy Style Leopard And Floral Print Mini Dress

    Create a weekend look exuding trendy style with this multi-print mini dress! The stretchy sheer mesh fabric is detailed with a leopard and rose print for a sweet and sassy vibe. The short dress features a sleeveless V-neckline accented with a dainty sheer lace trim, spaghetti straps, and a flowy A-line silhouette with a mini-length hem. Style with cowgirl boots!

    Fit & Features

    • Leopard and rose-print
    • Stretchy sheer mesh fabric with knit lining
    • V-neckline with sheer lace trim
    • Spaghetti straps
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5764

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Baby Got Open Back Poplin Woven Mini Dress

    Get ready to turn heads in this open back poplin woven mini dress! This bodycon mini dress features a square neckline, spaghetti tie straps, and a spaghetti tie back strap for a playful twist along the sultry open back. Made with a lightweight poplin woven fabric, this dress is perfect for hot days and even hotter nights! Complete the look in heeled sandals and a purse.

    Fit & Features

    • Poplin woven fabric lined with stretchy knit
    • Spagehtti tie straps and back strap
    • Open back
    • Hidden side zipper and hook-eye closure
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5760

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Upgrading V-Neck Lace Up Bodycon Mini Dress

    Upgrade your style with this sleeveless mini dress for weekend plans! The sleek V-neckline and spaghetti straps accentuate your feminine figure, while the front lace-up and slit add a touch of allure to the mini-length hem. Complete the look with a sleek layered necklace.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Spaghetti straps
    • V-neckline
    • Lace-up front and slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-2004

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale