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.

  • Cosmic Chic Tie-Dye Knit Midi Dress

    The ribbed knit dress features a scoop neckline, fitted long sleeves, a tie-dye pattern, and a midi-length hem accented with a center slit at the hem. Complete the look with ankle booties for a casually chic vibe. 

    Fit & Features

    • Ribbed knit fabrication
    • Scoop neckline
    • Long sleeves
    • Tie-dye pattern
    • Center slit at back of hem
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 06005-2132

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Adorable Stunner Strapless A-Line Mini Dress

    You'll be an adorable stunner in this mini dress designed with crepe fabric with a contrast color block outline for a chic look. It features a strapless straight-across neckline, a high waist seam, and a short A-line silhouette to add that flirty flair.

    Fit & Features

    • Crepe fabric, stretchy knit lining
    • Contrast color block outline
    • Strapless straight neckline
    • High waist seam
    • Back zipper closure
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3801

    Category Name: Casual Dresses

    Price: $14.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Contrast Tube Mini Dress

    Sophisticated yet flirty, this strapless mini dress turns heads with its fitted bodice and pleated skirt. Add heels and jewelry for lunch in the city or a chic wine bar with the girls!

    Fit & Features

    • Woven fabric, contrast design
    • Tube strapless neckline
    • Fitted bodice
    • Pleated flare mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5913

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dream Of Me Corset Lace-Up Floral Midi Dress

    Dreamy days call for this floral midi dress that makes your cottagecore romance a reality! With a gorgeous corset bodice, lace-up back, and voluminous A-silhouette, this dress is stunning for bridal showers or garden parties.

    Fit & Features

    • Delicate floral print, woven fabric, tulle and woven linings
    • V-neckline, adjustable spaghetti straps
    • Hidden side zipper and hook-eye closure
    • Corset bodice, flexible boning, lace-up back
    • Voluminous A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3795

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Attention-Worthy Camo Print Bodycon Mini Dress

    Create an attention-worthy 'fit in this camo-printed woven mini dress featuring a strapless straight-across neckline accented with dual flap pockets, a secure back zipper closure, cargo-style pockets on each side, and a bodycon silhouette to showcase your curves. Complete the look with a bomber jacket and combat boots!

    Fit & Features

    • Camouflage printed twill woven fabric
    • Strapless straight neckline, dual flap pocket accents
    • Back zipper hook-eye closure
    • Dual cargo flap pockets
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5909

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Ease Cap Sleeve Cutout Midi Dress

    This cap sleeve midi dress is ready to elevate any casual day look to a cute level! Designed in a flattering bodycon silhouette, this dress boasts a flirty cutout back and a back slit for effortless movement. 

    Fit & Features

    • Stretchy rib knit fabric
    • Cap sleeves
    • Scoop neck
    • Cutout back
    • Center back slit
    • bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5908

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blooming Beauty Floral Print Mesh Maxi Dress

    Let your beauty bloom with a mesh maxi dress that features a sleeveless sweetheart neckline with lace trim, a bodycon-fit silhouette, and a pretty floral print throughout! Complete your date night look with stiletto heels! 

    Fit & Features

    • Sheer mesh fabric with knit lining, plenty of stretch
    • Floral print
    • Sleeveless sweetheart neckline, lace trim
    • Spaghetti straps
    • Bodycon-like fit
    • Long maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001591

    Category Name: Casual Dresses

    Price: $26.96 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Beauty So Divine Floral Satin A-Line Mini Dress

    Boast a beautiful allure in this floral satin mini dress featuring a delicate lace trim and flattering A-line silhouette. Pair with heels.

    Fit & Features

    • Floral print, silky satin fabric
    • Spaghetti straps
    • Lace trim sweetheart neckline
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3778

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fab Trendsetter Leopard Print Drop Waist Mini Dress

    Fab trendsetter will be your vibe in this leopard print mini dress featuring an off-the-shoulder neckline with short sleeves, a drop waist seam, and an asymmetric tiered mini-length hem with an A-line fit. Style with knee-high boots!

    Fit & Features

    • Leopard-printed brushed knit fabric, plenty of stretch
    • Off-the-shoulder neckline, short sleeves
    • Drop waist seam
    • Asymmetric tiered mini-length hem
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5904

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Day To Night Strapless Abstract Slit Maxi Dress

    From day to night, this strapless abstract print maxi dress is an effortless style for any plans!

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Strapless neckline
    • High side slit
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5905

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Babe Drop Waist Bubble Hem Skater Dress

    You'll be a total flirty babe in this adorable short dress featuring a sleeveless square neckline with spaghetti straps, a V-shaped drop waist design, and a pleated skater silhouette with the cutest bubble hem. Style with hoop earrings and mules for date night!

    Fit & Features

    • Ribbed knit bodice, poplin woven skirt with knit lining, moderate stretch
    • Square neckline
    • Spaghetti straps
    • V-shaped drop waist
    • Short pleated skater silhouette with bubble hem
    • Runs true to size

    Style Number/Barcode: 05102-5907

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Passion Sleeveless Lace-Up Maxi Dress

    The maxi dress features a sleeveless square neckline supported with additional built-in flexible boning, an abstract floral pattern, a lace-up back design, and a bold high-side slit. Complete the look with stiletto heels for the perfect date night outfit. 

    Fit & Features

    • Mesh fabric, sewn-in knit lining
    • Sleeveless square neckline
    • Built-in-boning
    • Floral pattern
    • Lace-up back design
    • High side slit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3773

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Romance Corset Lace-Up Floral A-Line Mini Dress

    The flirty romantic allure of this floral mini dress will take you from brunch and garden party soirees! This mini dress boasts a cinched waist with a corset bodice and head-turning lace-up back design while the a-line silhouette flatters your figure. Pair with ballet flats.

    Fit & Features

    • Dainty floral print, poplin woven fabrication
    • Sweetheart neckline with bust tie, underwire bust
    • Adjustable spaghetti straps
    • Corset bodice, lace-up back, flexible boning
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3768

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Kissed By Blooms Corset Skater Floral Dress

    Blossom so cute in this skater floral dress boasting a corset bodice that flaunts your femme figure and a trendy lace-up back for added allure!

    Fit & Features

    • Floral print, woven fabric, tulle and woven linings
    • Sweetheart neckline
    • Adjustable spaghetti straps, side zipper and hook-eye closure
    • Lace-up smocked stretchy back
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3769

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunshine Bliss Ditsy Floral Lace Corset Skater Dress

    An adorable ditsy floral short dress for brunch, day dates, or celebration! The skater dress showcases a femme allure with a lace trim corset bodice designed to snatch your figure while the back bow tie and drop waist seam accentuate your figure. Pair with a ring set.

    Fit & Features

    • Ditsy floral print, woven fabric, woven lining with lace trim
    • Lace trim sweetheart neckline
    • Adjustable shoulder straps, back zipper closure
    • Corset lace trim bodice, underwire bust, flexible boning
    • Drop waist seam, skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3770

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sealed With Charm Ponte Mini Dress

    Seal your style with this charming ponte mini dress featuring an adorable strapless sweetheart neckline with a bow and a bodycon fit. Style with earrings.

    Fit & Features

    • Ponte knit fabric, plenty of stretch
    • Strapless sweetheart neckline
    • Bow tie front accent 
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5897

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Adorable Drop Waist Bubble Hem Skater Dress

    Adorable and trendy will be your vibe in this soft knit skater dress featuring a mock neckline, tank shoulder straps, ruched side seams to accentuate your curves, and a short ruched bubble hem. Style with platform heels for a cute party look!

    Fit & Features

    • Double-lined brushed knit fabric, plenty of stretch
    • Mock neckline, tank shoulder straps
    • Ruching
    • Drop waist seam
    • Short skater silhouette
    • Ruched bubble hem
    • Runs true to size

    Style Number/Barcode: 05102-5902

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Trend Striped Knit Long Sleeve Mini Dress

    This trendy striped knit mini dress features a scoop neckline, long fitted sleeves, an open lower back accent, and a short bodycon silhouette to hug your curves. Perfect for casual chic styling, pair with knee-high boots.

    Fit & Features

    • Striped ribbed knit fabric
    • Scoop neckline
    • Long fitted sleeves
    • Open lower back
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-2119

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easily Gorgeous Strapless Cable Knit Midi Dress

    Flaunt your gorgeous curves in this chic cable knit midi dress for brunch or a casual party. The dress boasts a flattering bodycon silhouette and a center back slit for movement.

    Fit & Features

    • Cable knit design, soft stretchy knit lining
    • Strapless neckline
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5898

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shrug It Off One-Shoulder Bodycon Mini Dress

    This is the perfect sleeveless mini dress for parties and cocktail hour! It features a sassy one-shoulder neckline and a sexy bodycon silhouette. Pair with boots.

    Fit & Features

    • Rib knit fabric, stretchy knit lining
    • One-shoulder neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5900

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • She's Stylish Mock Neck Cable Knit Midi Dress

    A stylish sleeveless midi dress featuring a mock neck, a flattering form-hugging fit, and a side slit for movement. Complete the look with strappy heels.

    Fit & Features

    • Cable knit fabric, stretchy knit lining
    • Mock neck
    • Side slit
    • Form-hugging fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5897

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Denim Darling Strapless Bodycon Mini Dress

    A denim bodycon mini dress for a darling look paired with your fave boots at concerts and festivals!

    Fit & Features

    • Denim fabric, sewn-in knit lining, minimal stretch
    • Strapless neckline
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5901

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Luxe Long Sleeve Ribbed Knit Mini Dress

    Part casual, part luxe, this long-sleeved mini dress is perfect for your next date night! The ribbed knit dress features a square neckline, long sleeves, and a mini-length hem. Complete look with knee-high boots! 

    Fit & Features

    • Ribbed knit fabric with knit lining, plenty of stretch
    • Square neckline
    • Long fitted sleeves
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5899

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep It Cute Ruffled Drop Waist Skater Dress

    Keep it cute every time in this strapless skater dress designed with a flirty ruffled short-length hem. Pair it with sleek heels.

    Fit & Features

    • Ponte knit fabric with partial knit lining, moderate stretch
    • Strapless straight neckline, fold-over design
    • Drop waist
    • Mini-length tiered ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3756

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale