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.

  • True Love In Floral V-Neck Corset Skater Dress

    This sleeveless mini dress features a flattering V-neckline, adjustable spaghetti straps for a customizable fit, and a corset-inspired bodice. The skater silhouette and tiered ruffle hem gives this dress the perfect look with heels.

    Fit & Features

    • Floral print mesh fabric, stretchy knit lining
    • V-neckline
    • Adjustable spaghetti straps
    • Corset-inspired bodice
    • Skater silhouette
    • Tiered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3520

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cutest Vibe Halter Drop Waist Skater Dress

    Bring a cute vibe to brunch or a party in this halter skater dress showcasing a deep V-neckline and a pleated silhouette for flirty flare. Pair with earrings.

    Fit & Features

    • Poplin woven fabric with knit lining, minimal stretch
    • Deep V-neckline, dart seams at bust
    • Tie-back halter straps, partially open back, lower back zipper with hook-eye closure
    • V-shaped drop waist
    • Pleated short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3516

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Desirable Sultry Sweetheart Bow Bodycon Mini Dress

    The heart wants what it wants and you need this bodycon mini dress! With adjustable spaghetti straps and a sweetheart neckline trimmed with delicate lace and a satin ribbon bow, this dress adds a touch of sweetness while flattering your curves in the bodycon fit. Complete the look in stiletto heels and a chic mini purse. 

    Fit & Features

    • Woven fabric, minimal stretch
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Sweetheart neckline with lace and satin ribbon trim
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5813

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Effortless Babe V-Neck Halter Lace Trim Mini Dress

    Everyone will be asking about the effortless babe in this sleeveless mini dress! Featuring a halter V-neckline and delicate lace trim, this mini dress is sure to turn heads. The bust bow tie adds a playful touch while the bodycon fit flatters your figure. Complete the look with sandals for a sunny day out.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Halter V-neckline with lace trim
    • Bust bow tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5814

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Striped Halter V-Neck Mini Dress

    This striped mini dress will easily become your perfect favorite piece this season! The halter V-neckline and open back highlight your alluring figure, while the bodycon fit and mini-length hem flatters your curves on the striped mesh-lined fabric. Complete the look with sunglasses and sandals for a day out or on vacation!

    Fit & Features

    • Striped print, mesh fabric, soft stretchy knit lining
    • Halter V-neckline
    • Open back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5811

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Island Vibes Tropical Print Asymmetric Midi Dress

    Channel those island vibes on your summer vacay in this tropical print asymmetric midi dress! The stretchy slinky knit fabric is accented with an abstract tropical pattern, an iconic look for your getaway. The mid-length dress features a sleeveless cowl neckline with chic draped detailing, tie-back halter straps, an alluring open back, an asymmetric high-cut hem, and a bodycon silhouette to hug your gorgeous curves. Style with sleek hoops for a sunset happy hour.

    Fit & Features

    • Abstract tropical print
    • Stretchy knit fabric, knit bust lining
    • Cowl neckline, tie-back halter straps
    • Open back
    • Asymmetric hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5810

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Glitzy Look Glitter Strapless Skater Dress

    Channel all the glitz and glam in this adorable glitter knit skater dress featuring a strapless straight neckline, ruched side seams, and a subtle drop waist. The pleated skater silhouette flares out to a trendy uneven mini-length hem. Style with metallic heels for a school dance or party!

    Fit & Features

    • Stretchy glitter knit fabric
    • Strapless straight neckline
    • Ruched side seams
    • Subtle drop waist
    • Pleated skater silhouette
    • Uneven mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5809

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Gorgeous One Shoulder Bodycon Mini Dress

    Look like a gorgeous dream in this sleeveless mini dress for showers, brunch, or parties! The one shoulder neckline adds a chic look, while the side ruched seams enhance your curves. The bodycon fit hugs your figure in all the right places along the mini-length hem. Complete the look with statement earrings.

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • One shoulder neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3478

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Prettiest Darling Puff Sleeve Floral Skater Dress

    A pretty floral skater dress like this is everything this season! Designed with a dainty rose floral print, this mini dress features adorable puff sleeves and a tie bust that shapes the flattering a-line silhouette. Pair with boots.

    Fit & Features

    • Dainty rose print, woven fabric lined with stretchy knit
    • Puff short sleeves
    • Sweetheart neckline with bust tie
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3471

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Charmed Success Lace Cold Shoulder A-Line Mini Dress

    When you stroll into any event, you'll be a charming hit in this chiffon mini dress! The lace cold shoulder V-neckline and delicate spaghetti straps add a touch of elegance, while the satin bow adds a feminine and playful flair. With its A-line silhouette and mini-length hem, this dress is perfect for any occasion. Complete the look in stiletto heels and a clutch!

    Fit & Features

    • Chiffon fabric lined with stretchy knit
    • Lace cold shoulder V-neckline
    • Spaghetti straps, satin bow
    • Back zipper and hook-eye closure
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3475

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun And Blooms Floral Chiffon Skater Dress

    Sunny weather is finally here to show off this floral chiffon skater dress with a flirty ruffled short-length hem! This dress is perfect for dressy occasions.

    Fit & Features

    • Floral print, chiffon fabric, stretchy knit lining
    • V-neckline, back zipper and hook-eye closure
    • Adjustable spaghetti straps
    • Skater silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3470

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Desert Princess Halter Maxi Dress With Pockets

    Experience the effortless beauty of this boho maxi dress! The sleeveless halter neckline and spaghetti strap tie create a flowy silhouette, while the hidden side pockets add functionality. The front slit and ruffled maxi-length hem in a chic bohemian print will make you feel like a true desert princess! Complete the look in sandals and sunnies.

    Fit & Features

    • Bohemian print, woven fabric, no stretch
    • Halter neckline, spaghetti strap tie
    • Hidden side pockets
    • Flowy ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5804

    Category Name: Casual Dresses

    Price: $16.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine Romance Floral Babydoll Dress

    Indulge in the romantic allure of this floral dress for dressy events! With delicate ruffled shoulder straps and a charming babydoll silhouette, this dress offers a flirty and feminine look. 

    Fit & Features

    • Floral print, chiffon fabric
    • Square neckline
    • Ruffled shoulder straps
    • Babydoll silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3467

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling Babe Floral Woven Puff Sleeve Skater Dress

    Create a darling day date look with this floral puff sleeve skater dress! Made with a lightweight woven fabric, it is detailed with a charming dainty floral print for those sweet feminine vibes. The short dress features a V-neckline with a cute tie-front detail, short puff sleeves with a ruffled trim, a high waist seam, and a skater hem with a flirty fit-and-flare silhouette. Style with a dainty charm necklace and heels.

    Fit & Features

    • Dainty floral print
    • Woven fabric
    • V-neckline, tie-front detail
    • Short puff sleeves, ruffled trims
    • Back zipper closure, high waist seam
    • Short skater skirt, fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3466

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cheerful Cutie Strapless Gingham Skater Dress

    Spread your sunshine in this gingham skater dress for the sweetest look all summer! The strapless neckline, lace trim, and stretchy smocked waist create a flirty and comfortable look. The skater silhouette and ruffled mini-length hem with lace trim add a touch of cuteness to your look. Complete the look with a crossbody purse and sandals for any casual plans!

    Fit & Features

    • Gingham print, cotton fabric with woven lining
    • Strapless lace trim neckline
    • Stretchy smocked waist
    • Skater silhouette
    • Ruffled lace trim hem
    • Runs true to size

    Style Number/Barcode: 05102-5801

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Passion V-Neck Color Block Maxi Dress

    Dress to impress in this V-neck maxi dress to make a chic impression at parties or rehearsal dinners! The flowy silhouette and color block panels give you a stunning look, while the spaghetti straps and neck tie add a trendy touch. Complete the look with a clutch and heels.

    Fit & Features

    • Woven fabric, no stretch
    • V-neck
    • Spaghetti straps, spaghetti strap neck tie
    • Color block panels, flowy silhouette
    • Maxi length
    • Runs true to size

    Style Number/Barcode: 05102-5803

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Signature Stripes Strapless A-Line Maxi Dress

    Show off your signature style in this striped maxi dress perfect for casual summer plans! Features a strapless neckline, a stretchy smocked bodice for a comfortable fit, and a flattering A-line midi silhouette with hidden side pockets to keep your hands warm. Complete the look with sunglasses and trendy sandals.

    Fit & Features

    • Striped pattern, cotton woven fabric, no stretch
    • Strapless neckline
    • Stretchy smocked bodice
    • Hidden side pockets
    • A-line midi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5802

    Category Name: Casual Dresses

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Flirt Sweetheart Lace Trim Skater Dress

    This sleeveless chiffon skater dress features a lace trim sweetheart neckline and bodice for flirty flair while the drop waist seam accentuates your curves along the mini-length skater silhouette. Perfect for a dressy brunch or party.

    Fit & Features

    • Sheer chiffon woven fabric with stretchy knit lining
    • Lace trim sweetheart neckline with bow detail, bust underwire
    • Adjustable lace trim shoulder straps
    • Partially smocked back with zipper and hook-eye closure
    • Lace trim bodice, drop waist seam
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3461

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Dreams Hanky Hem Floral Mini Dress

    Sweet and dreamy will be your vibe in this adorable floral mini dress! Designed with a stretchy sheer mesh fabric with a knit lining for coverage, the short dress showcases a blooming floral print for the prettiest look. It features a sleeveless V-neckline with dainty lace trim for a feminine touch, spaghetti straps, a trendy drop waist silhouette, and a mini-length asymmetric hanky hem with a flowy A-line fit. Style with bow hair pins and strappy mules.

    Fit & Features

    • Floral print
    • Stretchy sheer mesh fabric with knit lining
    • V-neckline with lace trim
    • Spaghetti straps
    • Drop waist silhouette
    • Asymmetric hanky hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3462

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cherry On Top Lace Trim V-Neck Mesh Mini Dress

    This mesh mini dress is the cherry on top of your perfect summer! Featuring delicate lace trim V-neckline, adjustable spaghetti straps, and a cherry print on mesh fabric, this mini-length bodycon dress will hug your curves and flaunt your style. Complete the look in platform heels.

    Fit & Features

    • Cherry print, mesh fabric, stretchy knit lining
    • Lace trim V-neckline
    • Adjustable spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5798

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Girl Halter Open Back Tropical Mini Dress

    Getaway to paradise in this tropical mini dress! Featuring a sultry cowl halter neckline and an open back with dual spaghetti strap ties, this dress will show plenty of skin on vacay while the bodycon silhouette and mini-length hem flatter your figure. Complete the look with doorknocker earrings and heels.

    Fit & Features

    • Tropical print, mesh fabric lined with stretchy knit
    • Halter cowl neckline
    • Open back with dual spaghetti strap ties
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5795

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Babe Cutout Ruffle Hem Chiffon Midi Dress

    Show up and stun at a summer party like the bold babe you are in this fab midi dress! Designed with a crinkled chiffon fabric, the mid-length dress features a smocked body for added stretch along the figure-flaunting bodycon silhouette. The sleeveless bodice is shaped with a sweetheart neckline with the cutest tie-front design at the bust, a sultry waist cutout to reveal some skin, and adjustable spaghetti straps to find your perfect fit. The layered ruffled hem adds a flirtatious allure to the iconic look. Style this midi dress with hoop earrings and espadrille sandals!

    Fit & Features

    • Crinkled chiffon fabric, knit bust lining, moderate stretch
    • Sweetheart neckline, tie-front bust
    • Waist cutout
    • Adjustable spaghetti straps
    • Smocked body, layered ruffled hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3454

    Category Name: Casual Dresses

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Perfection Scoop Neck Bow Skater Dress

    You'll look like cute perfection in this sleeveless skater dress at soirees! With adjustable spaghetti straps, a flattering scoop neckline, and three adorable bows with ruffle trim, this skater dress will have you feeling confident and stylish in its short-length hem. Complete the look in trendy sandals and a hair accessory.

    Fit & Features

    • Airy chiffon fabric, woven lining, no stretch
    • Adjustable spaghetti straps
    • Scoop neckline
    • Back zipper and hook-eye closure 
    • Three bows with ruffle trim
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3453

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picking Flowers Halter Strappy Back Daisy Skater Dress

    This daisy print skater dress will have you dreaming of sunny days picking flowers! The halter spaghetti strap neckline perfectly frames your shoulders while the cutout bodice adds a touch of allure. The strappy open back creates a stunning statement and the skater silhouette and tiered ruffled short-length hem give you a playful and fun look. Complete the look in sandals for a brunch or day date!

    Fit & Features

    • Daisy print, woven fabric with lining, no stretch
    • Spaghetti strap
    • Strappy open back
    • Ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5794

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale