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.

  • 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:
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  • 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:
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  • 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
  • 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:
    • Ships Free
  • 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:
    • Sale
  • 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:
    • Sale
  • 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:
    • Sale
  • 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:
    • Ships Free
  • 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:
    • Ships Free
  • 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:
    • Ships Free
  • 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:
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  • 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