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.

  • Charming Duo Strapless Skater Mini Dress

    A charming strapless skater dress you'll adore for brunch or family gatherings! Pair with the matching bolero for a complete look.

    Fit & Features

    • Soft rib knit stretchy fabric
    • Strapless neckline, non-slip grip lining
    • Skater silhouette
    • Flair mini-length hem
    • Runs true to size

     

    Shop The Matching Bolero: Charming Duo Long Sleeve Bolero

    Style Number/Barcode: 06005-2235

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • Flirty Instinct Flocked Floral Velvet Ruffle Romper

    Everyone will bask in your flirtatious allure in this flocked velvet floral romper designed to wow with a ruffled mini-length and a form-hugging fit. Pair with statement flats.

    Fit & Features

    • Flocked velvet floral pattern
    • Mesh fabric, stretchy knit shorts
    • Wide shoulder straps, sweetheart neckline
    • Back zipper and hook-eye closure
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 06503-1252

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Easy And Breezy Lace-Up Midi Dress With Pockets

    So effortlessly breezy for any plans, this A-line midi dress will turn heads with a lace-up bust and back detail, while the hidden side pockets are perfect for stashing your phone or lip gloss in.

    Fit & Features

    • Poplin woven fabric, woven lining
    • Sweetheart neckline, lace-up front, stretchy smocked bust
    • Spaghetti straps
    • Lace-up back, lower zipper and hook-eye closure
    • Drop waist seam, hidden side pockets
    • A-line silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6023

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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  • One Cute Day Floral Skater Mini Dress

    If you're in the mood to look undeniably cute, this floral skater mini dress is just the ticket! Perfect for bridal showers, brunch, or a day date.

    Fit & Features

    • Floral print, eyelet woven fabric lined with stretchy knit
    • Sweetheart neckline, built-in padded underwire bust
    • Adjustable spaghetti straps
    • Back stretchy smocked panel, zipper and hook-eye closure
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3994

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

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  • Breezy Like Me Sleeveless Ruffled Maxi Dress

    An effortless woven maxi dress for shower celebrations, graduations, or meet-ups with the girls! It boasts a flowy ruffled silhouette and a floor-length hem perfect for styling with cute sandals.

    Fit & Features

    • Cotton fabric, woven lining
    • Square neckline
    • Adjustable spaghetti straps
    • Flowy ruffled silhouette
    • Maxi-length floor hem
    • Runs true to size

    Style Number/Barcode: 05102-6022

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

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  • Playful Mood Strapless Ruffled Skater Dress

    Frolicking is expected in this playful ruffled skater dress at brunch, shower celebrations, or graduation parties!

    Fit & Features

    • Chiffon lined fabric
    • Strapless sweetheart neckline
    • Stretchy smocked bodice
    • Ruffled skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3999

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

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  • Beauty In The Detail Tie Back Floral Skater Dress

    There's beauty in every detail on this floral skater dress from the flirty crisscross straps and tie-back design to the ruffled mini-length hem! 

    Fit & Features

    • Floral print, woven fabric
    • Square neckline
    • Adjustable spaghetti straps
    • Crisscross, tie-back design
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3992

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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  • Chic Beauty Strappy Back Knit Midi Dress

    This chic sleeveless midi dress is designed with a jacquard patterned sweater knit fabric and features a square neckline, halter spaghetti straps, and a bold open back with cross-back straps and tie-back straps. The midi-length form-hugging silhouette is detailed with a high front slit.

    Fit & Features

    • Knit fabric with jacquard pattern, moderate stretch
    • Square neckline, halter spaghetti straps
    • Open back, cross-back straps, tie-back straps
    • Contrast seam design at the bodice
    • High front slit
    • Midi-length form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-2227

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Uptown Doll Off-The-Shoulder Abstract Maxi Dress

    Dress to impress in this abstract print maxi dress flaunting a folded off-the-shoulder neckline, sheer fitted long sleeves, and a flattering ruched bodycon silhouette. Pair with heels.

    Fit & Features

    • Abstract print, mesh partially lined fabric
    • Folded off-the-shoulder neckline
    • Sheer fitted long sleeves
    • Ruched bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6021

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Cute Soiree Sweetheart Skater Short Dress

    Keep any occasion cute in this sweetheart skater dress with adorable tie shoulder straps and a flattering drop waist seam to accentuate your figure!

    Fit & Features

    • Poplin woven fabric, multiple tulle and stretchy knit linings
    • Sweetheart neckline
    • Tie shoulder straps
    • Lace-up back, stretch smocked panel
    • Drop waist seam
    • Skater silhouette, short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3986

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Chic Charm Striped Knit Strapless Midi Dress

    Show up with that chic charm in this striped knit midi dress designed with a strapless straight neckline and a curve-hugging bodycon fit.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Striped print
    • Strapless straight neckline
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2222

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • Alluring Silhouette Off-The-Shoulder Maxi Dress

    Show off your alluring curves in this off-the-shoulder maxi dress crafted from a rib knit fabric that fits like a glove! 

    Fit & Features

    • Rib knit stretchy fabric
    • Off-the-shoulder neckline
    • Twisted strap details
    • Bodycon silhouette
    • Flared maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6020

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

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  • Western Moves Sweetheart Denim Skater Mini Dress

    Show off your Western style in this denim skater mini dress for dancing in the desert at festivals or concerts!

    Fit & Features

    • Denim fabric, stretchy knit lining
    • Sweetheart neckline, underwire bust
    • Adjustable spaghetti straps
    • Back zipper closure
    • Bodycon bodice
    • Skater chiffon lace trim mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6018

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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  • Dearest Charm Bow Print Skater Dress

    Show off your charm in this bow print skater dress boasting flirty details like puff sleeves and a short-length hem perfect for styling with sandals.

    Fit & Features

    • Bow print, woven fabric, woven lining
    • Puff short sleeves
    • Square neckline, bust tie
    • Stretchy smocked bodice
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3981

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

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  • Love Language Floral Print Mesh Maxi Dress

    This airy mesh maxi dress speaks your love language designed with a bold floral print and long fitted silhouette. Style with mules for date night.

    Fit & Features

    • Sheer mesh fabric with full-length knit lining, high stretch
    • Large floral print
    • V-neckline
    • Adjustable spaghetti straps
    • Maxi-length hem, fitted silhouette
    • Floral print placement may vary
    • Runs true to size

    Style Number/Barcode: 05101-3978

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • 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

    Product Badge:
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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

    Product Badge:
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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:
    • Sale
  • 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

    Product Badge:
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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

    Product Badge:
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