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.

  • Blissful Cutie Halter Cutout Skater Dress

    Get swept off your feet in this cute skater dress for any casual occasion! With its halter neckline and cutout bodice, this dress is designed to show off your figure, while the ruffled mini-length hem adds a flirty touch.

    Fit & Features

    • Gauze woven fabric, woven lining
    • Halter neckline with spaghetti strap ties
    • Stretchy smocked bust
    • Cutout bodice
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6017

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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  • Playful And Pretty Corset Lace-Up Midi Dress

    Playful and pretty, this corset midi dress has a timeless silhouette. It has a unique lace-up back, a flattering A-line fit, and convenient side pockets that warm your hands.

    Fit & Features

    • Woven poplin lined fabric lined with stretchy knit
    • Sweetheart neckline with bust tie
    • Adjustable shoulder straps
    • Lace-up back, side zipper and hook-eye closure
    • A-line silhouette, front slit, side pockets
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3968

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

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  • Steal The Show Strapless Lace Maxi Dress

    Steal the show in this strapless lace maxi dress designed in a semi-sheer style and a flattering form-hugging fit with a flared hem. Pair with earrings and heels.

    Fit & Features

    • Semi-sheer lace fabric with knit lining
    • Strapless neckline
    • Form-hugging fit
    • Flared maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3965

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

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  • Here To Be Loved V-Neck Eyelet Skater Mini Dress

    Layered or worn solo, this stunning skater dress features a forever flattering mini-length silhouette and an adorable eyelet pattern for the perfect femme finish.

    Fit & Features

    • Eyelet woven fabric, stretchy knit lining
    • V-neckline, bust tie
    • Adjustable spaghetti straps
    • Stretchy smocked bodice
    • Skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3950

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Game Set Slay Sweater Dress

    She’s giving preppy with a playful twist. This sleeveless sweater dress hugs in all the right places with contrast trim and a flared mini-length hem that makes it a serve for every season!

    Fit & Features

    • Rib knit stretchy fabric
    • Square neckline and tank shoulder straps, contrast trim
    • Skater silhouette
    • Pleated, flare mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2219

    Category Name: Casual Dresses

    Price: $21.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sleek Vibes Long Sleeve Ruched Midi Dress

    Channel sleek vibes in a midi dress that features a boat neckline, fitted long sleeves with thumb holes, and ruching that enhances curves. Complete look with strappy heels to take you from the office to happy hour! 

    Fit & Features

    • Smooth knit fabrication, double-lined
    • Boat neckline
    • Long sleeves with thumb holes
    • Ruching
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3954

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fun In Floral Lace Mini Dress

    So fun in floral print, this lace dress is featured in a form-hugging A-line silhouette and playful mini-length hem. Pair with cute wedge sandals for a cute summer look!

    Fit & Features

    • Floral print, lace fabric, stretchy knit lining
    • Square neck with bust tie
    • Adjustable spaghetti straps
    • Form-hugging A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6015

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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  • Casual Glam Ribbed Knit Long Sleeve Mini Dress

    The ribbed knit dress features a mock neck, long sleeves accented with thumb holes, and a mini-length hem. For a casually glam vibe, complete the look with ankle booties.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Mock neckline
    • Long fitted sleeves with thumb hole accents
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6014

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Sweet Eyelet Knit Tiered Skater Dress

    You'll look extra sweet for your next weekend brunch in this adorable eyelet knit skater dress. The strapless neckline, ruched side seams, drop waist, and short tiered design are all flirty details you'll adore.

    Fit & Features

    • Sheer eyelet knit fabric with full-length knit lining, moderate stretch
    • Strapless straight neckline
    • Ruched side seams
    • Drop waist
    • Short tiered design, skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6012

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

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  • Adorable Looks Tie Front Bodycon Midi Dress

    All of your adorable looks this season will include this eyelet midi dress with a flirty tie front and bodycon silhouette. This dress is perfect for shower celebrations or graduations!

    Fit & Features

    • Eyelet fabric
    • Tie front sweetheart neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6008

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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  • Life Is Sweet Eyelet Bodycon Ruffle Mini Dress

    The sweetest eyelet mini dress for shower celebrations, graduations, or brunch! It boasts flirty tie shoulder straps, a flattering bodycon silhouette, and a ruffled hem for cute flair.

    Fit & Features

    • Eyelet fabric
    • Square neckline, tie shoulder straps
    • Bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6006

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Always Sweet Ruffled Eyelet Lace Mini Dress

    Make your sweet impression in this eyelet lace mini dress detailed with ruffled straps and an adorable ruched neckline. The form-hugging fit will highlight your stunning curves.

    Fit & Features

    • Eyelet lace fabric lined with stretchy knit
    • Sweetheart neckline, ruching
    • Ruffled straps
    • Mini-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6002

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Twist Off-The-Shoulder Soft Knit Mini Dress

    The cashmere-like soft knit mini dress features an off-the-shoulder neckline, a popover accent with twist detail, long bell sleeves, faux wrap ties at the waist, and a fitted short-length hem. Complete a cozy stylish outfit with clear heels or ankle booties. 

    Fit & Features

    • Soft cashmere-like knit fabrication
    • Off-the-shoulder neckline
    • Popover accent with twist detail
    • Long bell sleeves
    • Faux wrap ties at the waist
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-6003

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Charming Flair Ditsy Floral Mini Dress

    Show off a charming flair in this adorable ditsy floral mini dress designed with eyelet knit fabric. The sweet vibes of the print are the perfect pairing with the sassy short bodycon silhouette.

    Fit & Features

    • Sheer eyelet knit fabric with knit lining, high stretch
    • Ditsy floral print
    • Sleeveless square neckline, dainty rosette detail, eyelet trim
    • Adjustable spaghetti straps
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5999

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Simply Sunny Eyelet Knit Mini Skater Dress

    This adorable mini skater dress is perfect for sunny weekend plans. Made with a breezy eyelet knit fabric, you'll love the flirty tie-back detail and fit-and-flare ruffled silhouette.

    Fit & Features

    • Eyelet knit fabric, sewn-in knit lining
    • Scoop neckline
    • Adjustable spaghetti straps
    • Tie-back detail, lower open back
    • Short skater silhouette, tiered ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-6000

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sweet Look Eyelet Knit Skater Dress

    Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette.

    Fit & Features

    • Eyelet knit fabric with knit lining
    • Sleeveless square neckline, underbust seam
    • Adjustable spaghetti straps
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6001

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Tea Time Corset Lace-Up Floral Skater Dress

    It's time to spill the tea at the garden party in this chic floral skater dress with a pretty corset bodice that snatches your waist and a lace-up back that turns heads!

    Fit & Features

    • Floral print, poplin woven lined lace trim fabric
    • Square neckline, lace trim, underwire bust, wide shoulder straps
    • Corset bodice, flexible boning, lace trim, lace-up back
    • Drop waist seam
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3923

    Category Name: Casual Dresses

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Lovely In Eyelet A-Line Mini Dress

    Make a lovely impression in this eyelet A-line mini dress at bridal showers or brunch with the girls! 

    Fit & Features

    • Eyelet lace fabric, stretchy knit lining
    • Strapless neckline
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5997

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Spring Fling V-Neck Paisley Skater Dress

    Swing into spring in this paisley skater dress for an adorable look all season! With a flirty halter V-neck and a flowy mini-length hem, this dress is ready for brunch or day dates.

    Fit & Features

    • Paisley print, chiffon fabric, woven lining
    • Halter V-neck
    • Spaghetti strap ties with tassels
    • Stretchy smocked bodice
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5994

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Preppy Edit Pinstripe Mini Dress

    The perfect dress for fall—this strapless pinstripe mini dress blends polished structure with playful pleats. Toss on a blazer or knee-high boots for seasonal chic.

    Fit & Features

    • Pinstripe pattern, woven fabric
    • Strapless collared neckline
    • Button front
    • Fitted bodice
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5993

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Flirt Lace Trim Scoop Neck Knit Mini Dress

    Fit & Features

    • Soft rib knit fabric, moderate stretch
    • Lace trim scoop neckline with bow tie
    • Fitted long sleeves
    • Bodycon silhouette
    • Mini-length hem, dual slit accents
    • Runs true to size

    Style Number/Barcode: 06005-2199

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destination Paradise V-Neck Floral Maxi Dress

    The perfect floral maxi dress for your next getaway! Designed in a sleeveless silhouette, this dress features a flattering V-neckline, sleek spaghetti straps, and a form-hugging fit with a flowy floor-length hem. Complete the look with earrings.

    Fit & Features

    • Floral print, mesh lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging fit
    • Flowy floor-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3915

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Buckled Beauty Off-The-Shoulder Knit Mini Dress

    An off-the-shoulder mini dress perfect for everyday slays. It features long sleeves and a foldover neckline with trendy buckled accents and a bodycon silhouette. Complete the look with boots.

    Fit & Features

    • Stretchy rib knit fabric
    • Off-the-shoulder neckline, folded with buckled accents
    • Long sleeves
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5992

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Darling Vibe Ditsy Floral A-Line Midi Dress

    Look oh-so-darling at weekend brunch in this ditsy floral A-line midi dress! The sleeveless sweetheart neckline is detailed with a dainty lace trim and tie-front design.

    Fit & Features

    • Woven fabric
    • Ditsy floral print
    • Sleeveless sweetheart neckline, dainty lace trim, lace trim spaghetti straps
    • Tie-front detail, underbust seam
    • Midi-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5989

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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