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.

  • In A Daze Strapless Cutout Striped Knit Mini Dress

    The perfect striped mini dress for summer dazes and effortless styling! Crafted from a stretchy ribbed knit fabric with a trendy striped print, this dress features a strapless straight-across neckline and cutout design at the waist for an alluring vibe. The bodycon fit on the mini-length silhouette will accentuate your gorgeous curves. Style this dress with sunglasses and sandals!

    Fit & Features

    • Striped pattern
    • Stretchy ribbed knit fabric
    • Strapless straight neckline
    • Waist cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1971

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • 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:
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  • Everyday Style Short Sleeve Ruched Mini Dress

    Level up your everyday style with this simple yet chic mini dress! The lightweight smooth nylon fabric includes a knit lining and offers plenty of stretch for ultra-comfortable wear. Shaped with a classic scoop neckline and short sleeves, the mini-length dress features ruching down the side seams to flaunt your figure on the bodycon silhouette. Pair with a denim jacket and sneakers.

    Fit & Features

    • Smooth nylon fabric with knit lining, plenty of stretch
    • Scoop neckline
    • Short sleeves
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5669

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Notice Me Abstract Print Bodycon Mini Dress

    This abstract print dress will get you noticed at every party! Featuring adjustable spaghetti straps and a flattering square neckline, a mini-length hem, and a bodycon fit that hugs your natural curves. Complete the look with earrings and stiletto heels.

    Fit & Features

    • Abstract print, mesh fabric, sewn-in knit lining
    • Square neckline
    • Adjustable spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5671

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Exceptional Bliss Lace-Up Floral Chiffon Maxi Dress

    Answer that invite in exceptional blissful style in this floral chiffon maxi dress perfect for showers, graduations, or vacations! With spaghetti straps, a lace-up back, and a flowy ruffled silhouette, this maxi dress is both comfortable and stylish. The stretchy smocked waist and maxi floor-length hem provide a flattering look for any occasion. Complete the look with dainty earrings.

    Fit & Features

    • Floral print, chiffon fabric lined with woven fabric
    • Spaghetti straps
    • Lace-up back
    • V-Neckline
    • Flowy ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3345

    Category Name: Casual Dresses

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Romance That Wows Large Blossom Floral Maxi Dress

    Make a stunning entrance in this large blossom floral maxi dress at dinner while on vacation or the weekend! Showcasing a statement blossoming floral print, this maxi dress is designed to turn heads. With a flattering V-neckline and delicate spaghetti straps, this dress hugs your curves in a bodycon silhouette and is finished with a maxi-length hem. Complete the look in strappy sandals and earrings!

    Fit & Features

    • Large blossoming floral print
    • Mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3343

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Effortless Cutie Bow Lace-Up Floral Mini Dress

    Look effortlessly cute in this floral mini dress this summer! The stretchy knit fabric is accented with a dainty floral print for a charming look. This bodycon dress features adjustable spaghetti straps and a sleeveless square neckline adorned with a ribbon bow and delicate crochet trim for a touch of elegance. The lace-up back allows for a perfect fit while the mini-length hem adds a flirty touch. Style with statement earrings.

    Fit & Features

    • Floral print, stretchy knit fabric
    • Square neckline with ribbon bow and crochet trim
    • Adjustable spaghetti straps
    • Lace-up back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5665

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Perfection Bodycon Striped Mini Dress

    With this striped mini dress and sunnies, you'll be effortlessly cute for a perfect weekend out or vacation! Featuring a square neckline with a twist and spaghetti straps, this dress is designed to hug your body and accentuate your natural curves. The mini-length hem adds a flirty touch. Complete the look with sandals and sunnies!

    Fit & Features

    • Striped pattern, texture knit fabric, moderate stretch
    • Spaghetti straps
    • Square neckline with twist
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5675

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Charm Crew Neck Bodycon Midi Dress

    The perfect basic midi dress for any occasion! It features a classic crew neck, cap sleeves, and a bodycon silhouette that flatters your curves. Pair with sleek heels and earrings.

    Fit & Features

    • Smooth jersey knit fabric, double-lined
    • Crew neck
    • Cap sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5661

    Category Name: Casual Dresses

    Price: $28.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pleasant Cutie Collared V-Neck Belted Midi Dress

    Make your look sweet and simple in this sleeveless midi dress perfect for summer plans! The collared V-neckline and button-down closures offer a classic touch, while the adjustable belted waist gives you a flattering A-line silhouette complete with a midi-length hem. Style this midi dress with wedges and earrings.

    Fit & Features

    • Woven fabric with lining, no stretch
    • Collared V-neckline
    • Button-down closures
    • Adjustable belted waist with buckle
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3347

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • What You Want Strappy Cutout Slit Midi Dress

    This sleeveless midi dress is just what you want to elevate your everyday style! Featuring a flattering square neckline, spaghetti straps, and a strappy cutout twist back, this bodycon dress will make you stand out in any crowd. The side slit adds a touch of sexiness to the midi-length hem. Complete the look in sleek stiletto heels for upcoming weekend plans!

    Fit & Features

    • Double-lined rib knit fabric, moderate stretch
    • Spaghetti straps
    • Square neckline
    • Strappy cutout twist back
    • Side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5663

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Done In One Ribbed Knit Bodycon Midi Dress

    Be ready in a flash with this done-in-one bodycon midi dress perfect for styling up or down! Made with stretchy ribbed knit fabric, it's also soft and comfortable to wear all day. It features a flattering scoop neckline and tank shoulder straps for a comfortable and stylish fit. With a bodycon silhouette and midi-length hem, this dress will hug your curves! Complete the look in a crop denim jacket and sandals.

    Fit & Features

    • Ribbed knit fabric, sewn-in knit lining, moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5666

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Admired Scoop Neck A-Line Mini Dress

    You'll always admire having this sleeveless mini dress for dressing up or down! Made from lined stretchy rib knit fabric, this dress hugs your curves in a flattering A-line silhouette. The scoop neckline and thin spaghetti straps add a flattering look. Style with a cute jacket and your favorite sneakers!

    Fit & Features

    • Stretchy rib knit fabric, full knit lining
    • Spaghetti straps
    • Curve-hugging, A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5652

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Fling High Slit Ditsy Floral Knit Midi Dress

    Embrace your flirtatious side in this adorable floral knit midi dress! The lightweight stretchy knit fabric is detailed with the cutest ditsy floral print pattern for the spring season. The mid-length dress features a crew neckline, short sleeves, a small back keyhole cutout, a large lower back cutout to add some allure, a high-cut front slit, and a bodycon silhouette to flaunt your curves. Style with hoop earrings and a charm necklace.

    Fit & Features

    • Stretchy knit fabric
    • Ditsy floral print
    • Crew neckline, short sleeves
    • Back keyhole cutout, lower back cutout
    • High front slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5653

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Strolls In The Sand V-Neck Tropical Skater Mini Dress

    Getaway in this tropical skater mini dress to the beach or on vacay! Featuring adjustable spaghetti straps and a flattering V-neckline, this dress hugs your silhouette with an elasticized waist and side cutouts. Its skater silhouette and mini-length hem make it perfect for any daytime adventure. Complete the look in cute sandals.

    Fit & Features

    • Tropical print, woven fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • V-neckline
    • Elasticized waist with side cutouts
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5656

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Vibes Collared Striped Woven Skater Dress

    Sweet and stylish, this striped woven skater dress is spring-time perfection! The lightweight woven fabric features a chic vertical striped pattern for a polished look. The short dress has a collared V-neckline for that touch of sophistication, leading to a partial button-down front. The short puff sleeves add an adorable detail. The high waist is accented with a tie-back design, and flows out to a fit-and-flare skater silhouette. Pair this short dress with wedges for weekend brunch!

    Fit & Features

    • Non-stretch cotton-blend woven fabric, woven skirt lining
    • Vertical striped pattern
    • Collared V-neckline, button-down front
    • Short puff sleeves with elastic cinched hems
    • High waist with back elastic band, tie-back design
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5657

    Category Name: Casual Dresses

    Price: $6.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crushing On You Strapless Denim Corset Mini Dress

    This sexy denim corset mini dress will have them all majorly crushing on you! The denim fabric features a contrasting light and dark wash design for a trendy vibe. The strapless sweetheart neckline shapes the top, leading to a corset-style bodice with angled seams for a snatched look. The bodycon fit along the mini-length silhouette will flaunt your gorgeous curves. Complete the look with cowboy boots for a country concert or festival.

    Fit & Features

    • Denim fabric with contrast wash design, moderate stretch
    • Strapless sweetheart neckline
    • Corset bodice, angled seams
    • Back zipper with hook and eye closure
    • Bodycon fit
    • Style runs small

    Style Number/Barcode: 05102-5659

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fall Into Fashion Crew Neck Open Back Maxi Dress

    You'll be the cutest thing around in this sleeveless maxi dress all season! With its sleek crew neckline, alluring strappy open back, and flattering form-hugging fit, this dress is both stylish and versatile. Complete with a side slit and maxi-length hem, it's the perfect piece for any occasion. Style this maxi dress with earrings and sandals.

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neckline
    • Strappy open back
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5654

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Striped Halter Crochet Midi Dress

    Stay stylish in this striped crochet midi dress for a sunny day by the beach or on vacation! It features a flattering halter neckline, adjustable spaghetti strap ties, and a bodycon fit that accentuates your curves along the midi-length hem. Complete the look with sunglasses and a tote bag!

    Fit & Features

    • Striped pattern, crochet fabric, short knit stretchy lining
    • Halter neckline with spaghetti strap ties
    • Bodycon fit
    • Midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2032

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Confident Cutie Sleeveless V-Neck A-Line Mini Dress

    Get ready to feel confident and cute in this basic A-line mini dress perfect for styling up or down! The soft and stretchy rib knit fabric includes a full knit lining for added coverage. This dress is perfect for any occasion with a flattering V-neckline, delicate spaghetti straps, and a stylish A-line silhouette. Complete the look in a chunky choker and sneakers!

    Fit & Features

    • Soft and stretchy rib knit fabric, full knit lining
    • V-neckline
    • Spaghetti straps
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5651

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Main Style Ribbed Knit Tank Mini Dress

    This adorable tank mini dress will be your new main style to create the cutest everyday looks! Designed with a stretchy ribbed knit fabric for comfortable wear, it features a sleeveless scoop neck and back, thin tank shoulder straps, and a bodycon silhouette to flaunt your figure. Pair this short dress with a denim jacket and sneakers for a coffee date with friends.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Scoop neck and back
    • Thin tank straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1975

    Category Name: Casual Dresses

    Price: $8.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Of All Ribbon Bow Bodycon Mini Dress

    You'll be the cutest of all in this bodycon mini dress out on dates or brunch! Crafted from a woven fabric lined with stretchy knit, this dress features a flattering square neckline and a satin ribbon bow that adds an elegant touch. The bodycon silhouette hugs your curves beautifully, while the mini-length hem gives a playful and flirty vibe. Complete the look in sandals and sunnies!

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Square neckline
    • Satin ribbon bow
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5655

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Day To Night Charm Lace-Up Ditsy Floral Mini Dress

    Be effortlessly charming in this ditsy floral mini dress day to night! This dress features a flattering sweetheart neckline, sleek spaghetti straps, and a mini bow along the bust to accentuate your figure. The open lace-up back and bodycon silhouette add a touch of sexiness, while the ditsy floral print on stretchy ribbed knit fabric keeps you comfortable and looking cute! Complete the look in boots to edge up your allure.

    Fit & Features

    • Stretchy ribbed knit fabric, knit lining
    • Ditsy floral print
    • Sweetheart neckline, mini bow detail
    • Spaghetti straps
    • Open lace-up back
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5650

    Category Name: Casual Dresses

    Price: $6.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love Impression Crew Neck Tie-Dye Bodycon Mini Dress

    This tie-dye mini dress will have you falling head over heels! It features classic short sleeves and a crew neckline, a bodycon fit to flaunt your curves, and a mini-length hem. Complete the look with earrings and stiletto heels for any occasion!

    Fit & Features

    • Tie-dye print, mesh fabric, partial lining
    • Crew neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5646

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free