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.

  • Delightful Impact Corset Slit Chiffon Midi Dress

    A sleeveless chiffon midi dress boasts a sweetheart tie neckline, a corset-inspired bodice with a lace-up back, and a front slit for a stylish flair. Perfect for styling with heels for a dressy occasion.

    Fit & Features

    • Burnout pattern, chiffon fabric lined with stretchy knit
    • Sweetheart tie neckline, shoulder straps
    • Underwire bust, side zipper and hook-eye closure
    • Corset bodice, lace-up back
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3591

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Preppy Chicness Lace Trim Plaid Bodycon Dress

    This plaid mini dress features a lace rose trim square neckline, spaghetti strap ties, and a flattering bodycon silhouette perfect for casual plans. 

    Fit & Features

    • Plaid print, knit fabric with minimal stretch
    • Lace rose trim square neckline
    • Spaghetti strap ties
    • Back zipper closure
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5836

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Chic Ruched Ribbed Knit Maxi Dress

    Effortlessly elevate your everyday looks with this casual chic ribbed knit maxi dress. It features a sleeveless boat neckline, tank shoulder straps with a trendy twist-back design, ruched side seams at the waist to accentuate your curves, and a fitted A-line silhouette with a maxi-length hem to flaunt your figure. Style with hoop earrings and strappy mules.

    Fit & Features

    • Stretchy ribbed knit
    • Boat neckline
    • Tank shoulder straps, twist-back design
    • Side ruching at the waist
    • Fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5834

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Flawless Puff Sleeve Corset Midi Dress

    A flawless midi dress with femme details from the corset bodice to the puff short sleeves and flattering A-line silhouette - you'll feel like a dream in this dress! Complete the look with strappy sandals.

    Fit & Features

    • Lined woven fabric, dainty sheer lace trim, minimal stretch
    • Sweetheart neckline, ruched bust, keyhole cutout, bow-front detail
    • Corset bodice, bust underwire, flexible boning
    • Short puff sleeves, elastic cinched hems
    • Smocked lace-up back, hidden zipper with hook-eye closure
    • V-shaped drop waist
    • Midi-length A-line silhouette, front slit
    • Runs true to size

    Style Number/Barcode: 05101-3573

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Side Lace Trim Floral A-Line Mini Dress

    A floral mini dress that shows your sweet side in a flattering scoop neckline, spaghetti straps, and a lace trim with a bow accent along the A-line silhouette. The floral printed knit fabric offers stretch and comfort. 

    Fit & Features

    • Floral printed knit fabric, bust lining, moderate stretch
    • Spagehtti straps
    • Scoop neckline
    • Lace trim bow accent
    • A-Line mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5833

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Easy Bliss Turtleneck Striped Mini Dress

    This sleeveless knit mini dress boasts a turtle neckline and a bodycon silhouette with a trendy striped pattern. Style with simple hoop earrings for any casual plans.

    Fit & Features

    • Striped pattern, stretchy knit fabric
    • Turtle neckline
    • Bodycon mini-length fit
    • Runs true to size

    Style Number/Barcode: 06005-2045

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Style Ruched Knit Halter Skater Dress

    Show off your sassy style at weekend outings in this adorable halter skater dress. Made with stretchy smooth knit fabric, it features a sleeveless V-neckline, trendy tie-back halter straps leading to a partially open back, ruched seams at the waist to accentuate your curves, a short double-layered skater skirt for a flirty vibe, and a fit-and-flare silhouette. Complete the look with a charm necklace and strappy mules!

    Fit & Features

    • Stretchy smooth knit, top knit lining
    • V-neckline, tie-back halter straps
    • Partially open back
    • Ruched seams at the waist
    • Double-layered skater skirt
    • Fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5832

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Whimsical Cutie Butterfly Polka Dot Satin Maxi Dress

    Soar toward any celebration in this whimsical and cute polka dot satin maxi dress! Featuring cap sleeves and a gorgeous butterfly lace trim sweetheart neckline, this dress adds a touch of elegance. The button-down back with a cutout accent completes the maxi silhouette, making you the center of attention! Complete the look in strappy block heels and a necklace.

    Fit & Features

    • Polka dot print, satin fabric, no stretch
    • Butterfly lace trim sweetheart neckline
    • Button-down back and zipper hook-eye closures
    • Cutout back accent
    • Maxi length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3555

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picture Perfect V-Neck Smocked A-Line Midi Dress

    You'll be the picture of perfection in this adorable A-line midi dress at showers or birthday brunch! With its flattering V-neckline and stretchy smocked bodice, this dress hugs your body in all the right places. The tie spaghetti straps add a touch of delicacy, while the V-cut waist seam and A-line silhouette create a flattering look along the midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Woven fabric lined with non-stretch woven
    • Tie spaghetti straps
    • V-neckline
    • Stretchy smocked bodice
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3560

    Category Name: Casual Dresses

    Price: $11.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Style Tie-Back Bodycon Slit Zebra Midi Dress

    This sleeveless bodycon midi dress features a flattering scoop neckline and spaghetti straps that shape the tie-back design and a side slit. The stretchy knit material boasts a zebra print perfect for brunch or parties.

    Fit & Features

    • Stretchy knit material, zebra print, sewn-in knit lining
    • Scoop neckline
    • Spaghetti straps
    • Tie-back design
    • Side slit
    • Bodycon midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5830

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Marvelous Blooms Lace-Up Corset Floral Skater Dress

    Stay stunning all night in this floral skater dress at prom, birthdays, or dressy events! With adjustable spaghetti straps and a drawstring sweetheart neckline, this dress offers a perfect fit every time. The underwire bust, flexible boning, and a lace-up back provide support and a flattering silhouette, while the mini-length hem adds a playful touch. Complete the look in chic block heels.

    Fit & Features

    • Floral print, woven fabric, woven lining, no stretch
    • Adjustable spaghetti straps
    • Drawstring sweetheart neckline
    • Side zipper and hook-eye closure
    • Underwire bust
    • Flexible boning, lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3550

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cool Staple Ribbed Knit Long Sleeve Midi Dress

    This ribbed knit midi dress is designed with a cotton-blend fabric with a cool mineral wash offering plenty of stretch. The dress features a scoop neckline, long fitted sleeves, and a midi-length bodycon silhouette to show off your curves.

    Fit & Features

    • Cotton-blend ribbed knit fabric, plenty of stretch
    • Mineral wash
    • Scoop neckline
    • Long fitted sleeves
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5829

    Category Name: Casual Dresses

    Price: $11.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Style Bow Detail Polka Dot Mesh Mini Dress

    Show off the sweetest style on summer dates in this bow detail polka dot mini dress! Designed with an airy sheer mesh fabric with a knit lining for coverage, this mini-length dress is accented with an adorable polka dot pattern for the cutest vibe. It features a sleeveless V-neck and back design with a dainty eyelet trim, tank shoulder straps, a mini bow detail at the bust for a sweet touch, tie-back spaghetti straps, and a flirty flowy A-line silhouette. Pair with strappy mules.

    Fit & Features

    • Polka dot printed sheer mesh fabric with knit lining
    • Plenty of stretch
    • V-neck and back, tank shoulder straps
    • Mini bow detail, eyelet trim
    • Tie-back straps
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5828

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Refreshing Charm Smocked Striped A-Line Mini Dress

    This sleeveless striped mini dress features a flattering square neckline and a smocked A-line silhouette with a trendy drop waist seam. The ruffled hem adds a flirty touch perfect for picnics or a day at the beach. 

    Fit & Features

    • Striped woven fabric
    • Square neckline
    • Adjustable spaghetti straps
    • Smocked A-line silhouette
    • Drop waist seam
    • Mini-length ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5826

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Trending Strapless Striped Bodycon Mini Dress

    Trend right in this strapless mini dress featuring a twist sweetheart neckline with a keyhole cutout and a flattering bodycon silhouette. The striped knit material hugs your curves making it perfect for pairing with sneakers or sandals. 

    Fit & Features

    • Striped print, stretchy knit material
    • Strapless sweetheart twist neckline
    • Keyhole cutout
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5824

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Elevated Strapless Linen-Blend Dress

    Effortlessly elevated, this breezy linen-blend dress is such a summer staple. It features a strapless straight-across neckline, a secure back zipper closure, a ruched fitted high waist, hidden side pockets, and a flowy A-line mid-length silhouette for that relaxed casual-chic vibe. Style with espadrille sandals.

    Fit & Features

    • Linen-blend fabric
    • Strapless straight neckline
    • Back zipper hook-eye closure
    • Ruched high waist
    • Side pockets
    • A-line fit, mid-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5823

    Category Name: Casual Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Expression Sleeveless Plaid Mini Dress

    A sleeveless plaid mini dress features a flattering square neckline with a satin bow, shoulder straps, and a bodycon silhouette. Perfect for back-to-school styling.

    Fit & Features

    • Plaid woven fabric, bust lining, minimal stretch
    • Square neckline with satin bow
    • Shoulder straps
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5825

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Truly Radiant V-Neck Lace Bodycon Mini Dress

    This sleeveless lace mini dress features a flattering ruffle trim V-neckline, spaghetti straps, and a bodycon silhouette perfect for a date or brunch.

    Fit & Features

    • Lace-lined fabric
    • Ruffle trim V-neckline
    • Spaghetti straps
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3534

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfectly Poised Sweetheart Polka Dot A-Line Dress

    Always put your best sweet self forward in this sleeveless polka dot dress at parties or on day dates! The sweetheart neckline with bust tie and spaghetti strap shoulder ties elevate your look, while padded bra cups provide support and comfort. The A-line silhouette and mini-length hem create a flattering style. Complete the look with hoop earrings.

    Fit & Features

    • Polka dot print, lined woven fabric, no stretch
    • Spaghetti strap shoulder ties
    • Sweetheart neckline with bust tie
    • Padded bra cups
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5822

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Little Wild One-Shoulder Zebra Print Maxi Dress

    Your next night out just got a little wild in this sassy zebra print maxi dress perfect for vacation or the weekend! This form-hugging dress features a one-shoulder neckline and spaghetti strap, with a side drawstring cutout to show some skin. The high side slit and maxi-length hem add a flirty touch to this fierce and flattering piece. Complete the look with heeled sandals and earrings.

    Fit & Features

    • Zebra printed knit fabric, plenty of stretch
    • One-shoulder neckline, spaghetti strap
    • Side drawstring cutout
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5821

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Laced In Chic Lace-Up Skater Dress

    Chic and charming, this lace skater dress boasts a flirty lace-up back that'll capture all the attention at parties!

    Fit & Features

    • Lace fabric, mesh lining, stretchy knit lining
    • V-neckline
    • Spaghetti straps
    • Lace-up back
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3521

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Be My Forever Ribbon Bow Bodycon Mini Dress

    Flattery will get you everywhere in this sleeveless mini dress perfect for boasting an adorable look! The scoop neckline is adorned with delicate lace and charming bow detail, while the tank shoulder straps give a flirty touch. The bodycon silhouette and mini-length hem finish this flawless dress. Complete the look in platform high heels for a party.

    Fit & Features

    • Woven fabric with minimal stretch
    • Scoop neckline, lace and ribbon trim, bow
    • Back zipper and hook-eye closure
    • Tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5817

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endlessly Effortless Crew Neck Abstract Midi Dress

    You'll always look and feel perfect in this sleeveless midi dress for parties or going out! Crafted from an abstract print mesh fabric, this dress boasts a crew neckline, a flattering bodycon silhouette, and a midi-length hem. Complete the look in stiletto heels and a purse!

    Fit & Features

    • Abstract print, mesh fabric, soft knit lining
    • Crew neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5819

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adorable Intent Sleeveless Bow Bodycon Mini Dress

    Keep up with the adorable coquette trend in this sleeveless mini dress! Adorned with charming shoulder straps and playful bows, this dress will hug your curves in all the right places and flatter your figure with its bodycon fit and mini-length hem. Complete the look with strappy sandals.

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Shoulder straps with bows
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5818

    Category Name: Casual Dresses

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale