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.

  • Paradise Babe Lace Up Tropical Floral Maxi Dress

    Look like a babe in paradise in this tropical floral maxi dress perfect for your next getaway or beach day! Embrace the warm, tropical vibes in this maxi-length hem dress on an airy mesh fabric bursting with a tropical floral print.  With its flowy silhouette and high slit, you'll feel like you're walking on clouds. The V-neckline and spaghetti straps add a trendy vibe while the lace-up detail adds a touch of playfulness. Complete the look in sandals and sunnies!

    Fit & Features

    • Tropical floral print
    • Mesh fabric lined with knit, moderate stretch
    • Lace-up
    • Spaghetti straps
    • High slit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3241

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sheer Desire Square Neck Bodycon Mesh Midi Dress

    Unveil a desirably chic look in this mesh midi dress at daytime parties and brunch! The adjustable spaghetti straps provide a customizable fit while the side ruching and bodycon silhouette accentuate your figure for a confident and alluring look. Elevate any occasion with this must-have dress by styling it with block heels and earrings!

    Fit & Features

    • Sheer mesh fabric lined with sewn-in knit
    • Adjustable spaghetti straps
    • Side ruching
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5506

    Category Name: Casual Dresses

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Flirtatious Floral Button Skater Dress

    With a pretty floral pattern and button accents, this skater dress exudes flirtatious romance vibes! The mini-length dress boasts a flattering V-neckline, a lace-up back that turns heads, and a twirl-worthy skater silhouette. Pair with sneakers for a casual look.

    Fit & Features

    • Burnout floral pattern, woven fabric lined with stretchy knit
    • V-neckline, adjustable spaghetti straps
    • Lace-up back
    • Faux button front accents
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3229

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sensational City Girl Strapless Cargo Mini Dress

    Hit the streets with a strapless mini dress that'll make you an instant sensational city girl! The strapless straight-across neckline and bodycon silhouette flatter any figure, while the front button closure and belt loop accents add a trendy touch. With a hidden front zipper, cargo flap pockets, and a mini-length hem, this woven dress is both fashionable and functional. Complete the look in lug boots for casual plans!

    Fit & Features

    • Cotton-blend woven fabric, minimal stretch
    • Strapless straight neckline with belt loop detailing
    • Front button closure
    • Hidden front zipper closure
    • Cargo flap pockets
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5503

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trend Right Plaid Belted A-Line Mini Dress

    Trend right in this plaid mini dress! It features a square neckline, spaghetti straps, a flattering A-line silhouette cinched with a belted waist, and a flirty pleated mini-length hem with an alluring plaid print. Complete the look with a crossbody bag.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Back zipper closure
    • A-line silhouette, belted waist
    • Pleated mini-length hem
    • Plaid print, woven fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05102-5505

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girl Power Leopard Print Strapless Midi Dress

    Show off major girl power in this sexy leopard print midi dress that was made for all eyes on you. It features a strapless straight-across neckline, ruching down the side seams, a midi-length hem, and a bodycon silhouette to put your gorgeous figure on display. The lined sheer mesh fabric features an all-over leopard print pattern to amp up the look. Style this midi dress with strappy stilettos for a nightclub!

    Fit & Features

    • Strapless straight-across neckline, no-slip strip
    • Ruched side seams, hidden side zipper, hook and eye closure
    • Midi-length hem
    • Bodycon silhouette
    • Leopard print
    • Sheer mesh fabric, mini-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-3211

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Blooms Floral Ruffle Chiffon Skater Dress

    Let this tropical floral skater dress bloom into your summer lineup! With a sweetheart neckline featuring delicate ruffle trim, adjustable spaghetti straps and padded bra cups, this skater silhouette will flatter your figure. The mini-length hem adds a flirty touch to this tropical floral printed chiffon dress. Complete the look with a crossbody purse and sandals!

    Fit & Features

    • Tropical floral print
    • Chiffon fabric with woven lining, no stretch
    • Sweetheart ruffle trim neckline
    • Padded bra cups
    • Adjustable spaghetti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3204

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crush On You Sleeveless V-Neck Skater Dress

    Everyone will end up with a crush on you in this sleeveless skater dress perfect for beach days or backyard parties! This playful dress features adjustable drawstring shoulder straps and a flattering V-neckline and back design. The fitted waist and skater silhouette create a feminine and flirty look along the short-length hem. Complete the look in heeled sandals.

    Fit & Features

    • Gauze woven fabric lined with stretchy knit
    • Adjustable drawstring shoulder straps
    • V-Neckline and back
    • Fitted waist, skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5500

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Beauty Chiffon Burnout Floral Maxi Dress

    Showcase your effortless beauty in this dreamy chiffon burnout floral maxi dress! Designed with a sheer chiffon fabric with a pretty burnout floral pattern, this airy maxi dress is perfect for romantic dates. The sleeveless bodice is shaped with a V-neckline and adjustable spaghetti straps that lead to a partially smocked back for added stretch. The button-down front leads to a high center slit for a chic detail on the flowy A-line silhouette. Style this long dress with a dainty charm necklace and stud earrings.

    Fit & Features

    • Sheer non-stretch chiffon fabric with burnout floral pattern, mini-length knit lining
    • Sleeveless V-neckline
    • Adjustable spaghetti straps, partially smocked back
    • Button-down front, center slit
    • Flowy A-line silhouette
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05101-3200

    Category Name: Casual Dresses

    Price: $7.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Sweet Look Sleeveless Ruffled Skater Dress

    A sweet skater dress for showers or brunch! With its romantic sweetheart neckline and bust tie, you'll feel so flirty. The adjustable spaghetti straps allow for a perfect fit while the ruffled skater silhouette and short-length hem add a touch of playful charm. The partially smocked back offers added stretch. Complete the look with a heart necklace and sandals.

    Fit & Features

    • Gauze woven fabric with stretchy knit lining
    • Sweetheart neckline, bust tie
    • Adjustable spaghetti straps
    • Stretchy smocked back
    • Ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5499

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All About Floral Sweetheart Crepe Skater Dress

    Sweet and sassy, this floral skater dress is a must-have for your wardrobe! Featuring a trendy sweetheart neckline and adjustable spaghetti straps, this dress is perfect for any spring or summer occasion. Its skater silhouette and short-length hem will have you twirling all day, while the playful floral print will make you stand out in style! Complete the look with hoop earrings.

    Fit & Features

    • Floral print
    • Stretchy crepe fabric, knit lining at the bust
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3196

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Day Dream Lace Up Eyelet Skater Dress

    Make your garden party daydream come true in this floral eyelet skater dress! This playful skater dress features a sweetheart neckline, spaghetti straps, and a lace-up back for a flirty touch. Its skater silhouette and short-length hem make it perfect for twirling! Complete the look with teardrop earrings and a bracelet.

    Fit & Features

    • Floral print, eyelet woven lined fabric, no stretch
    • Sweetheart neckline
    • Spaghetti straps
    • Lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3197

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Graceful Presence Sweetheart Floral Skater Dress

    Have a graceful presence in this floral skater dress at showers or graduations! A charming dress with a sweetheart neckline and tie spaghetti straps, the skater silhouette flatters your figure, while the short-length hem adds a playful touch. Complete the look in wedge sandals.

    Fit & Features

    • Floral print, woven fabric lined with stretchy knit
    • Tie spaghetti straps
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3194

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Adorable Factor Chiffon Sweetheart Midi Dress

    Raise the bar looking adorable in this chiffon midi dress perfect for upcoming dressy occasions! The midi-length dress features short puff sleeves, a sweetheart neckline, a ruched bust, and a flirty cutout waist to show some skin. The flattering A-line silhouette boasts a playful front slit and a flowy midi hem. Complete the look with cute sandals and jewelry!

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline, stretchy smocked back
    • Ruched bust, cutout waist
    • A-line silhouette, front slit
    • Midi-length hem
    • Chiffon woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-3189

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet And Chic Lace-Trim Knit Midi Dress

    So sweet and chic, this lace-trim knit midi dress is perfect for elevating your date night look! Designed with a stretchy ribbed knit fabric, this mid-length dress includes an airy mesh lining. The sleeveless V-neckline has spaghetti straps and is accented with a dainty sheer lace trim for a stylish touch, and includes an angled underbust seam to accentuate your figure. The bodycon silhouette will show off your gorgeous curves. Pair this adorable midi dress with hoop earrings and strappy mules!

    Fit & Features

    • Stretchy ribbed knit fabric, full-length mesh lining
    • Sheer lace trim
    • Sleeveless V-neckline, underbust seam
    • Spaghetti straps
    • Mid-length hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5497

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Divine Cutie Tie-Back Ruffled Skater Dress

    You'll look positively cute and divine in this short skater dress at brunch or graduations! Designed with a flattering square neckline, adjustable spaghetti straps for the perfect fit, and a tie-back design, this dress is perfect for every girlie. The skater silhouette and ruffled layer add a playful touch, while the short-length hem offers comfort and versatility. Complete the look in strappy mules.

    Fit & Features

    • Airy woven fabric, sewn-in knit lining
    • Adjustable spaghetti straps
    • Ruffled
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5733

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Radiant Vacay V-Neck Floral Chiffon Skater Dress

    Twirl your problems away on vacay in this radiant floral chiffon skater dress! The sheer peasant long sleeves, V-neckline, and corset-inspired bodice add a touch of romance, while the skater silhouette and ruffled hem bring a playful charm. Perfect for any occasion, from vacation to brunch! Complete the look in cute wedge sandals and sunnies.

    Fit & Features

    • Floral print, chiffon fabric lined with woven fabric
    • Keyhole back with button closure
    • Skater silhouette
    • Ruffled short-length hem
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05101-3186

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Has Sprung Floral Woven Skater Dress

    Let your beauty bloom in this adorable floral woven skater dress! The lightweight lined woven fabric is accented with a dainty floral print for the sweetest allure. The short dress features a sleeveless sweetheart neckline with a padded bust and structured underwire for support. The corset-style bodice will snatch your waist and highlight your bust with a tie-front detail. The thin smocked shoulder straps lead to a smocked back design for added stretch with a zipper closure. The high waist flows out to a short skater skirt with a trendy bubble hem and a fit and flare silhouette. Pair with platform heels for the cutest party look!

    Fit & Features

    • Floral woven fabric with knit lining, minimal stretch
    • Sleeveless sweetheart neckline, padded bust with underwire
    • Thin tank shoulder straps
    • Smocked back design, zipper and hook and eye closure
    • Corset bodice, tie-front detail, high waist seam
    • Short skater skirt with bubble hem, fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3187

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance Era Floral Brocade Corset Mini Dress

    You'll be in your romance era in this chic floral brocade corset mini dress! Designed with a detailed floral brocade woven fabric with a knit lining, this dress will bring the allure to your date night look. The top is shaped with a sleeveless sweetheart neckline with a padded bust and structured underwire to provide support and eliminate the need for a bra. The corset-style bodice has flexible boning to create that sultry snatched silhouette. Find your perfect fit with the adjustable spaghetti straps that lead to a back zipper closure. The form-hugging silhouette on the mini-length dress will flaunt your stunning curves. Complete your 'fit with stilettos.

    Fit & Features

    • Floral brocade woven fabric with knit lining, minimal stretch
    • Sleeveless sweetheart neckline with structured and padded bust
    • Corset bodice with flexible boning, high waist seam
    • Adjustable spaghetti straps, back zipper with hook and eye closure
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-3177

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Feelings Sleeveless Ditsy Floral Mini Dress

    Give yourself a sweet feeling in this ditsy floral mesh mini dress perfect for spring and summer soirees! With a sweetheart neckline, padded bra cups, and adjustable spaghetti straps you;ll feel confident and comfortable. The side ruched seams accentuate your curves along the bodycon fit for a playful touch. Complete the look with a choker necklace.

    Fit & Features

    • Ditsy floral print, mesh fabric, sewn-in knit lining, stretchy
    • Adjustable spaghetti straps
    • Sweetheart neckline, padded bra cups
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5550

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightful Charm Halter A-Line Midi Dress

    Step out looking delightful in this charming sleeveless midi dress for parties or showers! The halter pleated neckline and open back add a flirty touch, while the beaded tie waist cinches your waist for a flattering A-line silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Woven fabric, no stretch
    • Halter pleated neckline
    • Open back, zipper and hook-eye closure
    • Beaded tie waist
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5648

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Awaken Beauty A-Line Lace Short Dress

    Transform into a vision of beauty in this lace short dress at every party! This stunning dress boasts a sleeveless square neckline with a tie, enhancing your feminine charm. The A-line silhouette and short-length hem flatter your figure, while the intricate lace fabric adds a touch of elegance. Complete the look in stiletto mules and a purse!

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Square neckline with tie
    • Wide shoulder straps
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5552

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Intentions Sleeveless Knit Mini Dress

    Take your wardrobe to the next level in this little black dress perfect for day or night plans! This mini dress boasts a sleeveless high square neckline and spaghetti straps for a chic and modern look. The bodycon silhouette hugs your curves, while the mini-length hem adds a touch of flirtatiousness. The lightweight knit fabric offers a moderate stretch. Complete the look in a trendy crop jacket, mules, and a purse!

    Fit & Features

    • Knit fabric with moderate stretch
    • High square neckline
    • Spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1881

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Think About Me Lace-Up Floral Skater Dress

    Captivate everyone's thoughts in this floral skater dress sure to be the prettiest pick anyone has ever seen! With a square neckline and spaghetti straps, it's perfect for warmer days. The lace-up back and bow tie adds a playful touch, while the skater silhouette and mini-length hem flatter any figure. Complete the look with an adorable hair bow and sunglasses!

    Fit & Features

    • Floral print, woven fabric lined, no stretch
    • Spaghetti straps
    • Square neckline, bow tie
    • Lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5490

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale