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.

  • Geometric Fun Cutout Mini Dress

    This mini dress requires no math skills! Features a sleeveless V-neckline, spaghetti straps, bodycon silhouette, and a flirty front cutout bodice with ruched detail. Composed of geometric print fabric. Finish the look in strappy heels.

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Bodycon silhouette
    • Front cutout, ruched detail
    • Mini-length hem
    • Adjustable drawstrings
    • Geometric print, knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4350

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Style Moves Midi Dress

    Make effortless style moves in this adorably-chic midi dress. It features a sleeveless square neckline with a ruffled trim, thin ruffled shoulder straps, a stretchy smocked bodice, a high waist, and a flowy, midi-length, A-line silhouette with a front slit. Complete the look with espadrille sandals.

    Fit & Features

    • Sleeveless square neckline, ruffled trim
    • Thin ruffled shoulder straps
    • Stretchy smocked bodice
    • High waist seam, flowy A-line silhouette
    • Midi-length hem, front slit
    • Lightweight linen fabric, woven skirt lining
    • Runs true to size

    Style Number/Barcode: 05102-4347

    Category Name: Casual Dresses

    Price: $12.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wanderer Paisley Cutout Midi Dress

    Embrace the wanderlust life! Look like a babe in this medallion paisley midi dress featuring a sleeveless, v-neck, spaghetti straps, and knot accented bust atop a sultry cutout bodice that leads to the form-fitting midi hem. Complete the look in strappy sandals for a festival.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Knot accented bust
    • Cutout bodice
    • Form-fitting midi hem
    • Medallion paisley print
    • Crepe knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4342

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fab And Wild Slip Dress

    Keep it fab with a slip dress that showcases your wild side! The dress features a snake print, a sleeveless cowl neckline, adjustable spaghetti straps that cross at the back, a tie-back accent, and a short-length hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with a minimal stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps, cross at back
    • Tie back ties
    • Snake print
    • Short length hem
    • Lined lightweight woven fabric
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4345

    Category Name: Casual Dresses

    Price: $4.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Puff Love Square Neck Skater Dress

    There's a lot to love about this puff sleeve skater dress! Features a square neck, smocked bodice, a trendy waist cutout, and a tiered short skirt. Composed of linen woven fabric with an inner lining. Finish the look in floral earrings for a cute spring fit.

    Fit & Features

    • Short puff sleeves, square neckline
    • Smocked bodice, waist cutout
    • Tiered short skirt
    • Skater silhouette
    • Linen woven fabric, inner lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4343

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Charmer Floral Mini Dress

    You'll be such a sweet charmer in this adorable floral mini dress! It features a scoop neckline with a bust tie, short puff sleeves, ruching down the sides, and a short, form-hugging fit. The brushed knit fabric features an all-over ditsy floral print pattern. Style this dress with espadrille sandals for weekend brunch!

    Fit & Features

    • Scoop neckline, bust tie
    • Short puff sleeves, cinched hems
    • Ruching down the sides
    • Mini-length, form-fitting silhouette
    • Ditsy floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4341

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Show Your Floral Smocked Chiffon Dress

    Show your florals off in this chiffon mini dress for your next girl's day! It features long peasant sleeves, a sweetheart neck with a front knot-tie and keyhole accent, and a smocked short-length hem. Complete the look in chic sunglasses and heels.

    Fit & Features

    • Long peasant sleeves
    • Sweetheart neck
    • Front knot-tie, keyhole accent
    • Floral pattern
    • Smocked mini-length hem
    • Chiffon fabric
    • Fits true to size

    Style Number/Barcode: 05101-1378

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Totally Fab Ribbed Mini Dress

    Keep your look totally fab in a mini dress that keeps it effortlessly chic! The dress features a sleeveless V-neckline, bungee spaghetti straps, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules. 

    Fit & Features

    • Sleeveless V-neckline 
    • Bungee spaghetti straps
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06002-1050

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charmed By Ruffles Short A-Line Dress

    Get charmed by pretty ruffles in this fab dress! The dress features a square neckline, short puff sleeves, a partially open back with cinching tie-back accent, and a short length with a ruffled hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules. 

    Fit & Features

    • Square neckline
    • Short puff sleeves
    • Partially open back, tie back accents
    • Short length 
    • Ruffled hem
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size 

    Style Number/Barcode: 05102-4338

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blushing Floral Sweetheart Mini Dress

    Make the room blush when they see you in this sweetheart mini dress! It features short bishop sleeves with button closures, a built-in padded bust with underwire support, floral print, and a form-fitting silhouette. Complete the look in classy heels. 

    Fit & Features

    • Short bishop sleeves, button closures
    • Built-in padded bust with underwire
    • Sweetheart neckline
    • Floral print, back zipper closure
    • Short hem, form-fitting
    • Crepe woven-lined fabric 
    • Fits true to size, no stretch

    Style Number/Barcode: 05101-1374

    Category Name: Casual Dresses

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Cutie Puff Sleeve Mini Dress

    Look cute in this mini floral dress for a picnic date or brunch with friends. It features puff short sleeves, a sweetheart neck with keyhole tie, and a short-length hem. Complete the look in trendy sandals.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neck, keyhole tie
    • Dainty floral pattern
    • Short-length fitted hem
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4337

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ditsy Floral Scoop Mini Dress

    Fall for this ditsy floral mini to revive your springtime wardrobe! It features puff short sleeves, a scoop neckline, a bodycon silhouette, and a short-length hem. Complete the look in chic mules for brunch.

    Fit & Features

    • Puff short sleeves
    • Scoop neckline
    • Bodycon silhouette
    • Short-length hem
    • DItsy floral pattern
    • Fits true to size

    Style Number/Barcode: 05102-4336

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fiercely Bold Dragon Graphic Mini Dress

    Keep it fiercely bold with a mini dress that slays! The dress features a V-neckline, slashed detailing, an image of a dragon, text that reads: "Free Soul", long sleeves, and a mini-length silhouette. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a moto jacket and booties.  

    Fit & Features

    • V-neckline
    • Slashed distressing 
    • Image of dragon 
    • "Free Soul" in black text
    • Long sleeves
    • Mini length silhouette
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06002-1048

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Silhouette Marble Mesh Midi Dress

    The silhouette of this trendy mesh midi dress will hug your curves! It features a sleeveless square neckline, spaghetti straps, ruched detailing down the sides, and a mid-length hem. The sheer mesh fabric includes a full knit lining and an eye-catching marble print. Style this dress with clear mules.

    Fit & Features

    • Sleeveless square neckline, elastic band
    • Bungee spaghetti straps
    • Ruching down the sides
    • Mid-length, form-hugging silhouette
    • Sheer mesh fabric, knit lining, moderate stretch
    • Marble print
    • Runs true to size

    Style Number/Barcode: 05102-4330

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Let It Glitz Glitter Sweetheart Mini Dress

    Let yourself glitz and gleam in this glitter mini dress for party season! It features a sleeveless sweetheart neckline with a built-in padded bust, spaghetti straps, and a curve-defining asymmetrical mini-length hem with a faux wrap silhouette. Complete the look in strappy heels.

    Fit & Features

    • Sleeveless sweetheart neckline, padded bust
    • Spaghetti straps
    • Asymmetrical mini-length hem, faux wrap silhouette
    • Bodycon fit
    • Glitter knit fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4208

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rocker Babe Slashed Mini Dress

    Rock on babe in a tee that shows off your edgy side! The mini dress features a crew neckline, short sleeves, a bold rock-inspired graphic, a slashed design at the back, and a mini-length silhouette. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with combat boots and a swag chain belt. 

    Fit & Features 

    • Crew neckline 
    • Short sleeves
    • Rock-inspired graphic 
    • Slashed design at back 
    • Mini length silhouette
    • Cotton knit fabric 
    • Form hugging fit, moderate stretch, runs true to size 

    Style Number/Barcode: 06002-1027

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Girl Next Door Slip Dress

    Show off your trendy style in this adorable cow print slip dress! It features a sleeveless V-neckline, bungee spaghetti straps, a stylish small front slit, and a short fitted silhouette. Complete the look with ankle booties.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Short front slit
    • Mini-length fitted silhouette
    • Brushed knit fabric, moderate stretch
    • Cow print
    • Runs true to size

    Style Number/Barcode: 05102-4325

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sporty Babe Hooded Mini Dress

    Achieve that trendy sporty babe look with this casual ribbed knit mini dress. It features a hoodie, a high neckline with front drawstrings, long sleeves, ruched side detailing, and a short, curve-hugging silhouette. Style this dress with cute sneakers.

    Fit & Features

    • Hoodie
    • High neckline, front adjustable drawstrings
    • Long fitted sleeves
    • Ruched sides, adjustable drawstrings
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4324

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knott Love Halter Cutout Midi Dress

    You'll fall for this halter midi dress with just one look! Featuring a sleeveless, halter neck with tie-back closure, a trendy knot cutout bodice that shapes the bodycon silhouette. Complete the look in classy nubuck heels.

    Fit & Features

    • Sleeveless, halter neck, tie-back closure
    • Knot cutout bodice
    • Bodycon silhouette
    • Midi-length hem
    • Soft and stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4322

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Street Rider Graphic Lace-Up Tee

    Show off your need for speed with a graphic tee that gives your look an edgy feel. The tee features a crew neckline, short sleeves, a graphic that reads: " The Street Riders", an image of a skull with a helmet, and a lace-up front. The tee is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with combat boots. 

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Graphic: "The Street Riders"
    • Image of a skull with helmet 
    • Lace-up front
    • Cotton knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06002-1024

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On Top Of The Trends Cutout Mini Dress

    Stay on top of the latest trends this fall with this casual yet chic mini dress! It features a sweetheart neckline with a center knot accent at the bust, dual asymmetric front cutouts at the waist, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric has a moderate stretch for comfortable wear. Style with knee-high boots for a fall festival.

    Fit & Features

    • Sweetheart neckline, center knot detail at the bust
    • Dual asymmetric front waist cutouts
    • Long fitted sleeves
    • Mini-length hem
    • Fitted bodycon silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4320

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crazy About Ruche Collared Mini Dress

    Keep on trend with a mini dress that shows off your love for ruching! The dress features a collared neckline, a multi-button down front, long sleeves, a ruched body, and a mini-length silhouette. The dress is composed of a slinky knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules. 

    Fit & Features

    • Collared neckline
    • Long sleeves
    • Multi-button down front
    • Ruched body
    • Mini length silhouette
    • Slinky knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05101-1314

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keeping Knit Trendy Ribbed Midi Dress

    Keep it trendy with a midi dress that can be dressed up for your night date night with bae. The dress features a crew neckline, long sleeves, a ruched drawstring, a high side slit, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a plaid scarf. 

    Fit & Features

    • Crew neckline
    • Long sleeves
    • Ruched drawstring 
    • High side slit
    • Midi length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4311

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Plaid Perfect Sleeveless Mini Dress

    Plaid will forever be a timeless and perfect print! This mini dress features a sleeveless, square neckline with spaghetti straps and a bodycon fit on a short-length hem. Composed of a soft knit fabric with a moderate stretch. Style with a cute cardigan for a casual day out.

    Fit & Features

    • Square neckline
    • Sleeveless, spaghetti straps
    • Plaid pattern 
    • Bodycon fit, mini hem
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4310

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale