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.

  • Rare Sight Basic Crew Midi Dress

    What a rare sight you'll be in this figure-flaunting basic midi dress featuring sleek, short sleeves, a crew neck, and a bodycon silhouette on stretchy, ribbed knit fabric. Complete the look in a trendy denim jacket and sneakers.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Bodycon silhouette
    • Midi-length hem
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4352

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flower Power Skater Dress

    Elevate your spring style with this pretty floral printed skater dress. It features a subtle sweetheart neckline with ruching at the bust, short puff sleeves, a high waist, and a fit and flare silhouette with a short skater skirt with a ruffled hem. Style this lightweight chiffon dress with cute mules.

    Fit & Features

    • Sweetheart neckline, ruching at the bust
    • Short puff sleeves, elasticized hems
    • Back zipper, hook and eye closure
    • High waist seam, fit and flare silhouette
    • Short skater skirt, ruffled hem
    • Floral print
    • Sheer chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1406

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chasing Sunsets Floral Maxi Dress

    This floral maxi dress is perfect for sunset dinners while on vacay! It features sleeveless, v-neck, sleek spaghetti straps, and a slim-fit silhouette with a front side slit to showcase some skin. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless, V-neck, sleek spaghetti straps
    • Slim-fit silhouette
    • Front side slit
    • Maxi-length hem
    • Floral pattern
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1393

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Charmed One-Shoulder Ruched Dress

    This mini dress is pleased to make your acquaintance! It features a one-shoulder neckline with a tank strap, bodycon silhouette, and dual side ruching with ties so you can customize the length. Complete the look with a sleek handbag.

    Fit & Features

    • Sleeveless, one-shoulder neckline
    • Tank strap
    • Bodycon silhouette
    • Dual side ruching with ties
    • Mini-length hem
    • Ribbed knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4355

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Best Of Me V-Neck Cutout Midi Dress

    Impress the room by showing up in this sultry midi dress perfect for cocktail hour! Featuring a sleeveless, v-neck, adjustable spaghetti straps, and a flirty knot accent with dual waist cutouts that lead to the bodycon silhouette. Complete the look in chic lucite mules.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Back zipper closure
    • Front knot accent, dual waist cutouts
    • Bodycon silhouette
    • Midi-length hem
    • Slinky knit fabric, inner knit lining, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4357

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Places To Go One Shoulder Midi Dress

    You've got places to go and this one-shoulder midi dress will have you looking stylish! It features a spaghetti strap, bodycon silhouette, and an asymmetrical midi-length hem with a high side slit to showcase some legs. Composed of stretchy texture knit fabric. Finish the look in platform heels.

    Fit & Features

    • Sleeveless, one-shoulder, spaghetti strap
    • Bodycon silhouette
    • Asymmetrical midi-length hem
    • High side slit
    • Texture knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4358

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Prepped For Anything Cutout Mini Dress

    With this mini dress, you'll be ready for whatever plans come up! It features long sleeves, a collared neck, button-down closures, a sultry cutout bodice on a bodycon silhouette. Composed of stretchy rib-knit fabric. Style with mules.

    Fit & Features

    • Long sleeves, collared neck
    • Button-down closures
    • Cutout bodice
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4354

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Fit Square Neck Mini

    Flaunt it! This square neck mini offers the perfect fit featuring sleek, bungee spaghetti straps, all-over ruching detail on a bodycon silhouette. Complete the look in a fab pair of heels. 

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • All-over ruching
    • Bodycon silhouette
    • Mini hem
    • Fits true to size

    Style Number/Barcode: 05102-4353

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Retreat Chiffon Sweetheart Midi Dress

    Ready for a floral retreat? Feel the sunshine on your shoulders in this floral chiffon midi dress featuring dainty spaghetti straps, a sweetheart neckline with a bust tie, a fitted bodice, and a side slit accent. Complete the look in simple heels.

    Fit & Features

    • Sleeveless sweetheart neckline, bust tie accent
    • Spaghetti straps
    • Fitted bodice, back zipper, hook and eye closure
    • Midi-length hem, side slit
    • Ditsy floral pattern
    • Sheer chiffon fabric, knit lining
    • A-line silhouette, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4356

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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