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.

  • Popular Poise Mock Neck Abstract Mini Dress

    An abstract print mini dress features sheer fitted long sleeves, a mock neckline, and a flattering bodycon fit. Perfect for styling with stiletto heels.

    Fit & Features

    • Abstract print, mesh fabric, sewn-in knit lining
    • Mock neckline
    • Fitted sheer long sleeves
    • Bodycon mini-length fit
    • Runs true to size

    Style Number/Barcode: 05102-5581

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chicly Femme Bodycon Abstract Mesh Midi Dress

    A sleeveless midi dress features a square neckline and a bodycon silhouette that flaunts your curves. The abstract print mesh fabric offers an artsy look. Perfect for styling with stilettos.

    Fit & Features

    • Abstract print, mesh fabric
    • Square neckline
    • Spaghetti straps
    • Bodycon midi-length fit
    • Runs true to size

    Style Number/Barcode: 05102-5580

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Set For Cuteness Twist Back Slit Rib Knit Maxi Dress

    You and this maxi dress are set for cuteness all season long! Made with rib knit fabric, this dress is both comfortable and stylish, perfect for any occasion. Featuring a square neckline and shoulder straps, this dress offers a form-hugging fit that will accentuate your curves. The twist-back design adds a trendy touch while the high side slit and maxi-length hem provide an alluring appeal. Complete the look with sandals and sunnies!

    Fit & Features

    • Stretchy rib knit fabric
    • Square neckline
    • Shoulder straps
    • Twist back design
    • High side slit
    • Form-hugging
    • Runs true to size

    Style Number/Barcode: 05102-5577

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blissful Afternoons Corset A-Line Midi Dress

    Enjoy an afternoon of bliss looking so sweet in this A-line midi dress at showers or semi-formal weddings! The sweetheart neckline and adjustable spaghetti straps accentuate your figure while the corset bodice with built-in padded underwire bust provides support. The flowy A-line silhouette and midi-length hem add elegance to your look. Complete the look in strappy heeled sandals.

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Sweetheart neckline
    • Corset bodice, built-in padded underwire bust
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3309

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always On Point Ruched Knit Mini Dress

    This trendy ruched knit mini dress will have your everyday 'fits always on point! Made with a stretchy ribbed knit fabric for comfortable wear, this mini-length dress features a sleeveless scoop neckline with thin tank shoulder straps and ruched detailing to accentuate your curves on the bodycon silhouette. Style with a boyfriend blazer and heels for happy hour!

    Fit & Features

    • Stretchy ribbed knit fabric lined with knit
    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Ruching
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5569

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Laid Back Fave Crew Neck Tank Maxi Dress

    Your new laid-back fave tank maxi dress for styling up or down for any occasion! Crafted from rib knit fabric, this crew neck dress offers a form-hugging fit and a maxi-length hem for a flattering silhouette. Complete the look in cute sandals and sunnies!

    Fit & Features

    • Rib-knit stretchy fabric
    • Crew neck
    • Form-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5573

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Admiring Style Strapless Ruffle High Low Denim Dress

    Prepare for plenty of admiring stares when you're in this stylish denim strapless dress! This cute and casual dress features a sweetheart neckline and form-hugging fit, accentuating your curves in all the right places. The patchwork seam detailing adds a touch of unique style, while the high-low ruffled hem adds a playful and flirty element. Complete the look in platform shoes and sunnies!

    Fit & Features

    • Denim fabric, slight stretch
    • Strapless sweetheart neckline
    • Back zipper and hook-eye closure
    • Form-hugging fit
    • Ruffle high low hem
    • Runs true to size

    Style Number/Barcode: 05102-5574

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made To Amaze Strapless Marble Bodycon Midi Dress

    Everyone will admire your style in this strapless marble bodycon midi dress at the art show downtown! Made from a mesh fabric boasting a gorgeous marble print, you'll be sure to amaze. With a strapless neckline and side ruched seams, this dress hugs your curves in all the right places for a bodycon fit along the midi-length hem. Complete the look with stiletto heels.

    Fit & Features

    • Marble print, stretchy mesh fabric, sewn-in knit lining
    • Strapless neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5576

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweeter Than Pie Scoop Neck Gingham Mini Dress

    So on trend and sweeter than pie, this gingham mini dress is essential for spring-to-summer fun! This mini-length dress is made from woven fabric and features a charming gingham print that exudes effortless style.  The scoop neckline and tank shoulder straps flatter your figure, while the form-hugging fit accentuates your curves. Complete the look in cute sandals and a mini purse!

    Fit & Features

    • Gingham print, woven fabric, slight stretch
    • Back zipper closure
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5568

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Day Sleeveless Mermaid Denim Midi Dress

    Look cute and casual wherever you go in this denim midi dress! Featuring spaghetti straps, a sweetheart neckline, a flattering mermaid silhouette, and a flared midi-length hem, this dress will have you looking and feeling amazing. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Denim fabric, minimal stretch
    • Spaghetti straps
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5567

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sway With Me Halter V-Neck Paisley Skater Dress

    This breezy skater dress brings the romance with a halter neckline and swingy silhouette made to float with you. Perfect for golden hour snaps, weekend wandering, or spontaneous getaways!

    Fit & Features

    • Paisley print, woven fabric, bust lining
    • Halter V-neckline with spaghetti strap ties
    • Stretchy smocked bust
    • Tie back design
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5575

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Muse Watercolor Chiffon Flowy Midi Dress

    You'll be a dreamy muse in this gorgeous watercolor chiffon flowy midi dress! The airy lined chiffon fabric is detailed with a mesmerizing watercolor print for the perf summertime vibe. The mid-length dress features a sleeveless halter neckline with a center stone accent, tie-back spaghetti straps, a partially open back for a touch of allure, and a lower-smocked back design for added stretch. The fitted high waist flows out to a gorgeous A-line silhouette with an asymmetrical hemline for beautiful movement. Style this long dress with espadrille wedges.

    Fit & Features

    • Watercolor print
    • Sheer chiffon fabric with smooth woven lining
    • Halter neckline, stone detail, tie-back straps
    • Partial open back, lower stretchy smocked back
    • Flowy A-line silhouette
    • Asymmetrical hemline
    • Runs true to size

    Style Number/Barcode: 05101-3306

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Ditsy Floral V-Neck Mini Dress

    This ditsy floral mini dress will have you dreaming of sunshine days! Flaunt your figure with the bodycon fit of this dress showcasing a flattering V-neckline, dainty spaghetti straps, a tie-front bust for added detail, and a mini-length hem on ditsy floral print mesh fabric. Complete the look in sandals and a mini tote bag.

    Fit & Features

    • Ditsy floral print
    • Mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Slit accent
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5571

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Enchanting A-Line Floral Chiffon Midi Dress

    Have everyone under your spell in this floral chiffon midi dress as a stunning wedding guest or to attend a garden party! Featuring a square neckline with a bust tie, elasticized shoulder straps, and an A-line silhouette, this dress flatters any figure. The front slit and midi-length hem add a touch of sophistication. Complete the look in block heels and earrings!

    Fit & Features

    • Floral print, chiffon fabric, stretchy knit lining
    • Elasticized shoulder straps
    • Square neckline, bust tie
    • Back zipper and hook-eye closure
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3304

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance Dreamer Sweetheart A-Line Lace Mini Dress

    Embrace your romantic side in this lace mini dress to add a whimsical allure to parties, birthdays, and dates! The sweetheart neckline and adjustable spaghetti straps flatter and give you a perfect fit, while the corset-trim fitted bodice and A-line silhouette provide a lovely silhouette along the ruffled mini-length hem. Complete the look with platform heels and a purse.

    Fit & Features

    • Delicate lace fabric line with stretchy knit
    • Adjustable spagehtti straps
    • Corset trim fitted bodice
    • Ruffled mini-length hem
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3302

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Dream Lace-Up Ruffled Maxi Dress

    A dreamy sleeveless maxi dress perfect for styling for beach city days or coastal vacations! The scoop neckline and bust tie accentuate your figure, while adjustable spaghetti straps provide the perfect fit. The lace-up back adds a touch of charm, while the flowy ruffled silhouette and maxi-length hem exude effortless chicness! Complete the look with strappy sandals and sunglasses.

    Fit & Features

    • Woven fabric, short knit stretchy lining
    • Scoop neckline with bust tie
    • Adjustable spaghetti straps
    • Lace-up back
    • Flowy tiered ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5565

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Match Sleeveless Striped Ribbed Knit Mini Dress

    You and this striped knit mini dress are the perfect match for sunny days! With a playful scoop neckline and cutout back, this mini dress is a cute piece for any fun occasion. Its bodycon fit flatters your figure while the striped pattern adds a touch of quirkiness. The ribbed knit fabric offers a moderate stretch for comfortable wear. Complete the look with flat sandals.

    Fit & Features

    • Striped pattern
    • Ribbed knit fabric with moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Cutout back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1940

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stroll The Beach V-Neck Floral Paisley Maxi Dress

    Wherever your summer travels take you, always be in style with this casual floral paisley maxi dress! Featuring adjustable spaghetti straps and a stretchy smocked V-neckline, you'll have the perfect fit for a day in the sun. The crisscross back adds a playful touch, while the ruffled hem gives a flirty flair to the flowy silhouette. Complete the look with a cute hair accessory and sandals!

    Fit & Features

    • Floral paisley print, woven fabric, stretchy knit lining
    • Adjustable spaghetti straps, crisscross back
    • Stretchy smocked V-neckline
    • Flowy silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5566

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Staple Ribbed Knit Bodycon Mini Dress

    Comfy and chic, this knit bodycon mini dress is the simple staple you need in your closet! Made with a stretchy ribbed knit fabric, it features a sleeveless scoop neckline, spaghetti straps, and a form-hugging fit to flaunt your curves along the bodycon silhouette. Style this mini-length dress with a denim jacket and sneakers for a cute and casual vibe.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Scoop neckline
    • Spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1937

    Category Name: Casual Dresses

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Escape Lace-Up Tropical Midi Dress

    Have the sweetest look in this tropical midi dress for your next vacay escape! With a flattering square neckline, delicate spaghetti straps, and a lace-up back, this bodycon dress will hug your curves down to the high-cut asymmetrical midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Tropical print, lined knit fabric, plenty of stretch
    • Square neckline
    • Spaghetti straps
    • Lace-up back
    • Asymmetric high-cut hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5564

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smell The Garden Square Neck Floral Midi Dress

    Enter the fresh fragrance of this floral midi dress into your spring and summer lineup! With a square neckline and spaghetti straps, this dress will hug your curves in all the right places with its bodycon fit. The side ruched seams add more detail to this stylish midi-length dress. Complete the look in platform sneakers for a trendy allure.

    Fit & Features

    • Brushed knit stretchy fabric, floral print, knit lining
    • Spaghetti straps
    • Square neckline
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5562

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Icon Marble Print Mesh Bodycon Mini Dress

    Show up looking stunning like the trendy icon you are in this marble print mesh mini dress! The airy lightweight sheer mesh fabric features a trendy neutral marble print to draw all the attention your way. The sleeveless crew neckline and tank shoulder straps shape the bodice of the mini-length dress, while the bodycon silhouette will flaunt your gorgeous curves. Style with lace-up stiletto heels to get drinks with the squad!

    Fit & Features

    • Stretchy sheer mesh fabric with knit lining
    • Marble print
    • Sleeveless crew neckline
    • Tank straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5563

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tempting Allure Sweetheart A-Line Lace Mini Dress

    A lace A-line mini dress that will captivate everyone in the room! With a playful sweetheart neckline, adjustable spaghetti straps, and an underwire bust, this dress accentuates your curves, while the A-line silhouette and ruffled tie mini-length hem add a touch of whimsy. Complete the look with a clutch for a dressy evening event.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Sweetheart neckline, adjustable tie
    • Adjustable spaghetti straps
    • Underwire bust, back zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3300

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Enchanting Look V-Neck Button Down Skater Dress

    Your day just got sweeter in this sleeveless skater dress perfect for spring and summer occasions! This V-neck skater dress boasts adjustable spaghetti straps and button closures that allow for the perfect fit while the skater silhouette and short-length hem elevate your style. Complete the look with sandals and sunnies!

    Fit & Features

    • Woven fabric with lining, no stretch
    • Adjustable spaghetti straps
    • V-Neckline
    • Button down front
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5555

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale