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.

  • Total Sweetheart Floral High Slit Maxi Dress

    Show off your sweet side with a floral dress that brings the romance! The dress features a sleeveless V-neckline, spaghetti straps, a floral print, and a maxi length silhouette accented with a high side slit. The dress is composed of a smooth knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Floral print
    • Maxi length silhouette
    • High side slit
    • Smooth knit fabric 
    • Relaxed fit, moderate stretch 

    Style Number/Barcode: 05102-0773

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Slay In Style Ribbed Scoop Neck Midi Dress

    Slay in this midi dress that brings some major chic vibes! The dress features a scoop neckline, tank-straps, and a chic tie-waist belt to create an hourglass illusion. Complete your night-out look with a faux leather jacket.

    Fit & Features

    • Scoop neckline
    • Tank-straps
    • Tie-waist belt 
    • Ribbed sweater knit fabric
    • Midi-length silhouette
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-0929

    Category Name: Casual Dresses

    Price: $4.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ribbed Knit Ruffled Ditsy Floral Mini Dress

    Slay in a gorge ditsy floral mini dress. A ditsy floral dress is a staple piece to have for brunch or a day date with bae. This must-have features a sleeveless sweetheart neckline with a tie-front accent and ruffled trim with matching ruffled spaghetti straps. The relaxed fit waist leads to a curve-hugging mini-length silhouette. The dress is composed of ribbed knit fabric that offers a moderate stretch. Complete your floral look with cork wedges and dainty rings. 

    Fit & Features

    • Sleeveless sweetheart neckline
    • Tie-front bodice
    • Ruffled spaghetti straps
    • Ditsy floral print
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch

     

    Style Number/Barcode: 05102-0769

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All About Floral Lace Skater Dress

    Showcase your love for lace with a skater dress that says it all! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a sheer floral lace back, and a flirty and flowy skater silhouette. Complete the look with wedges.

    Fit & Features

    • Sleeveless V-neckline 
    • Adjustable spaghetti straps, sheer floral lace back
    • Hidden side zipper and hook and eye closure
    • Skater silhouette
    • Lined chiffon fabric 
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05101-0832

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Sweet Sweetheart Ditsy Floral Mini Dress

    You'll look too sweet in a floral dress that brings the charm. This pretty date-night dress features a sweetheart neckline, a tie front accent, and a ditsy floral print. Complete your look with a light wash denim jacket and wedges. 

    Fit & Features

    • Sleeveless sweetheart neckline
    • Tie front accent at the center of the bodice
    • Spaghetti straps 
    • Ditsy floral print
    • Mini length silhouette

     

    Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0767

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffle Detail Eyelet Off The Shoulder Mini Dress

    Ruffle up your gorg look with this effortless eyelet detail mini dress! Pair with some gold hoops and strappy mules for an everyday style you'll love!

    Fit & Features

    • Off the shoulder square neckline
    • Short ruffle sleeves
    • Ruffle overlay
    • Center ruffle detail
    • High waist
    • Short ruffle hem
    • Eyelet detail woven fabric

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0764

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Basic Lace-Up Denim Mini Dress

    Keep it basic with a cute denim mini dress! The dress features a sleeveless V-neckline, spaghetti straps, a lace-up back, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and door knocker earrings. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Lace-up back 
    • Mini length silhouette
    • Denim fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0765

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy And True Eyelet Mini Dress

    Keep true to your love of trendy finds in this mini dress! The dress features an off-the-shoulder neckline with a sweetheart bust, short puff sleeves, a ruched center, an eyelet design, and a mini-length silhouette. Complete look with clear mules. 

    Fit & Features

    • Off the shoulder neckline, sweetheart bust
    • Short puff sleeves
    • Ruched center
    • Eyelet pattern 
    • Mini length silhouette
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0762

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Meant To Be Ruffled Mini Dress

    You and this dress are totally meant to be! The dress features a sleeveless V-neckline, spaghetti straps, lace-up back, a mini-length silhouette with a faux-wrap overlay, and ruffles. The dress is composed of a mesh fabric that offers a form-hugging fit with a moderate stretch. Complete the look with platform wedges and a butterfly necklace. 

    Fit & Features

    • Sleeveless V-neckline
    • Lace-up back 
    • Mini length silhouette
    • Faux-wrap overlay 
    • Ruffles 
    • Lined mesh fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-0758

    Category Name: Casual Dresses

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Love At First Bloom Ditsy Floral Mini Dress

    Fall headfirst for this floral dress that showcases your sweet side. It features adjustable spaghetti straps, a ruffled sweetheart neckline with a center cutout and tie-front, a stretchy smocked back, and a short, curve-hugging fit. Complete your look with strappy sandals and a cute handbag.

    Fit & Features

    • Adjustable spaghetti straps
    • Ruffled sweetheart neckline
    • Center cutout and tie-front
    • Stretchy smocked back
    • Mini-length, form-hugging fit
    • Sheer chiffon fabric with a ditsy floral print, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-0756

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrapped In Lace Ruched Mini Dress

    Wrap yourself in an elegant lace mini dress that brings the sophistication. The dress features a sleeveless v-neckline, adjustable spaghetti straps, a ruched body, and a mini length silhouette with a ruffled hem. The dress is composed of a lined floral lace fabric that offers a form hugging fit with minimal stretch. Complete look with wedges for a pretty brunch outfit.

    Fit & Features

    • Sleeveless v-neckline
    • Adjustable spaghetti straps
    • Ruched body
    • Mini length silhouette with ruffled hem
    • Lined floral lace fabric
    • Form hugging fit
    • Minimal stretch 

    Style Number/Barcode: 05102-0750

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortlessly Stunning Crochet Waist Maxi Dress

    You'll look effortlessly stunning in this flowy maxi dress that is perfect for the warmer months. It features spaghetti straps that lead to a cross-back design, a lace top with a V neckline, a sheer crochet high waist, and a flowy floor-length gauze skirt with a side slit. Complete the look with on-trend wedges.

    Fit & Features

    • Spaghetti straps
    • Cross back design
    • Lace top, V neckline
    • Sheer crochet high waist
    • Floor-length gauze skirt, side slit
    • Flowy silhouette
    • Runs true to size

    Style Number/Barcode: 05102-0754

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Button Down Beauty Maxi Dress

    Button-down in a casual maxi dress for a cute day-out outfit the next time you're picking up a must-have iced coffee! This maxi dress features a plunging sweetheart neckline with a tie-front accent, mini cutout at the bodice, and a button-down front with a high center slit. Complete your look with sleek sandals for those low-key vibes. 

    Fit & Features

    • Plunging sweetheart neckline 
    • Tie-front accent with a small cutout at the bodice
    • Adjustable spaghetti straps
    • Multi-button down front
    • High center slit
    • Maxi length silhouette
    • Ribbed knit fabric, form-hugging fit

     

    Navy Dress: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Mustard Dress: Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0746

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Charmer Ditsy Floral Mini Dress

    You'll charm them all in this adorable ditsy floral mini dress! It features a sleeveless sweetheart neckline with a ruffle trim, a tie-front detail, adjustable spaghetti straps, and a mini-length, curve-hugging silhouette. Style this dress with a pair of strappy sandals.

    Fit & Features

    • Sleeveless sweetheart neckline, ruffle trim
    • Tie-front detail
    • Adjustable spaghetti straps
    • Partial smocked back
    • Short, form-hugging fit
    • Chiffon fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-0757

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep It Groovy Tie-Dye Maxi Dress

    Keep your summer look groovy and on-trend with this tie-dye maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a high waist seam, and a floor-length silhouette with a thigh-high side slit. Style this dress with strappy sandals for a laid-back vibe.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back design
    • High waist seam
    • Floor-length silhouette, high side slit
    • Relaxed fit
    • Brushed knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-0745

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Laid Back Glamour Crochet Knit Midi Dress

    Keep it effortlessly glam with a crochet-knit dress! The dress features a sleeveless V-neckline, a mini side slit, and a midi length silhouette. The dress is composed of a crochet knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless V-neckline
    • Mini side slit
    • Midi length silhouette
    • Crochet knit fabric 
    • Relaxed fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0674

    Category Name: Casual Dresses

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Brunch Babe Floral Mini Dress

    We know you love to get cute for brunch with the girls! Style this smocked floral mini dress with white heels and gold accessories.

    Fit & Features

    • Tie front detail
    • Front cut out
    • Stretchy smocked body
    • Short, form hugging fit
    • Ditsy Floral print
    • Adjustable Spaghetti Straps

    Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0744

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Babe Sleeveless Midi Dress

    Hey babe, show off your adorable style in this floral midi dress that is perf for spring. It features a sleeveless square neckline, thin ruffle shoulder straps, a fitted bodice, and a flowy mid-length silhouette with a thigh-high slit. Complete the look with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Thin ruffle shoulder straps
    • Fitted bodice
    • Flowy mid-length silhouette
    • High front slit
    • Ditsy floral print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-0741

    Category Name: Casual Dresses

    Price: $20.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Square Neck Denim Mini Dress

    A casually chic mini dress is a must for any wardrobe! Add a cute cross body purse and slip into some mules for the perf daytime outfit! 

    Fits & Features

    • Square Neckline With Contrast Stitching I Vertical Dart Seams
    • Short Sleeves With Elastic Cuffs
    • Back Zipper With Hook & Eye Closure
    • Mini Length Hem
    • Denim Fabric 
    • Relax Fit I Moderate Stretch 

    Style Number/Barcode: 05102-0738

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flaunt Those Florals Waist Tie Dress

    Work that springtime magic in this pretty and sweet maxi dress! Add a woven bag and wedges for a completed look! 

    Fits & Features

    • Plunging V Neckline 
    • Waist Tie Design 
    • Sleeveless Bodice
    • Maxi Length Silhouette 
    • Woven Fabric I Ditsy Floral Print Design 
    • Relax Fit I Minimal Stretch 

    Style Number/Barcode: 05102-0739

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Babe In Denim Mini Dress

    Made for a babe like you! Stow away those jeans and rock this denim mini dress. For chillier days, pair it with a long sleeve tee and some matching sneakers! 

    Fits & Features

    • Adjustable Spaghetti Straps
    • Sweetheart Neckline 
    • Linear Seams & Stitching Down Front 
    • Back Zipper With Hook & Eye Closure
    • Mini Length Silhouette
    • Denim Fabric 
    • Form Hugging Fit I Moderate Stretch 

    Style Number/Barcode: 05102-0740

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Take On The Night Chiffon Smocked Mini Dress

    We'd love to see you take on the night in this, gorgeous! Just slip into some strappy heels to really elevate your lewk! 

    Fits & Features

    • Surplice V Neckline 
    • Sheer Long Sleeves 
    • Smocking At The Cuffs & Skirt 
    • Cut Out At Back With Button Closure
    • Mini Length Silhouette I Ruffle Trim Hem 
    • Chiffon Fabric 
    • Form Hugging Fit I Moderate Stretch 

    Style Number/Barcode: 05101-0810

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pop Of Color Block Ditsy Floral Midi Dress

    Give them a pop of color this season in this flowy dress! Add a pair of block heels and cute mini purse for an OOTD! 

    Fits & Features

    • Tank Shoulder Straps
    • Plunging V Neckline & Back 
    • Back Zipper With Hook & Eye Closure
    • Midi Length I Overlapping Ruffle Trim Hem 
    • Woven Fabric With Ditsy Floral Print & Color Block Design I Partial, Mini Length Lining
    • Relax Fit I Minimal Stretch 

    Style Number/Barcode: 05101-0809

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Dream Tie Dye Satin Midi Dress

    You'll look like the perf sunset dream in this tie dye midi dess! Pair with some espadrille sandals for a stylish summer time vibe.

    Fit & Features

    • Tie shoulder spaghetti straps
    • Cowl square neckline
    • Flattering horiztonal seam under the bust
    • Back bar detail | Partial open back
    • Flowy mid-length hem
    • Tie dye satin-like fabric | Sheer woven lining

    Style Number/Barcode: 05102-0737

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free