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.

  • Paradise Calls Tropical Midi Dress

    Vacation on the mind? You're going to need this tropical midi dress with paradise written all over it! Features a sleeveless, v-neck, adjustable spaghetti straps, a form-fitting silhouette, and a side ruched seam on an asymmetrical midi hem. Complete the look in lace-up sandals for a dinner with a view.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Form-fitting silhouette
    • Side ruched seams
    • Asymmetrical midi hem
    • Tropical pattern
    • Texture knit fabric, moderate stretch. fits true to size

    Style Number/Barcode: 05102-4367

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Trendsetter Ruched Mini Dress

    Keep your look sweet and trendy with this adorable bodycon mini dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruched side detailing, a short, curve-hugging fit, and an all-over butterfly print. Style this dress with a pair of cute mules for an outing with the girls.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruched side detailing
    • Mini-length, form-fitting silhouette
    • Butterfly print
    • Brushed knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4370

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachside Brunch Swim Coverup Dress

    Strut down the pier looking so fab in this maxi coverup dress featuring a sleeveless V-neckline, tank straps, and a form-fitting silhouette with a sultry front slit. The coverup dress is composed of an unlined semi-sheer knit fabric that offers a form-hugging fit. Perf for layering over your bikinis, complete the look in sandals.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline, tank straps
    • Surplice accent
    • Form-fitting silhouette
    • Front slit
    • Maxi-length hem
    • Unlined, semi-sheer sweater-knit fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06005-1250

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bold Impressions Sleeveless Midi Cutout Dress

    Make a bold impression with a midi dress that cuts a sultry look! The midi dress features a plunging V-neckline, spaghetti straps, sexy cutouts at the waist, 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 the look with mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual cutouts at the waist
    • Midi-length silhouette
    • Sheer ribbed knit fabric, knit lining
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1967

    Category Name: Casual Dresses

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunday Girl Floral Chiffon Skater Dress

    Look cute for Sunday brunch in this floral chiffon skater dress featuring three-quarter length puff sleeves, a square neck, and a pleated waistband on the skater silhouette. Showcase a peek of skin in the open-back design with tie closure and ruffled short-length hem. Composed of a chiffon floral lined fabric with no stretch. Perfect for styling with knee-high boots.

    Fit & Features

    • Three-quarter length puff sleeves, elastic cinched hems
    • Square neckline
    • Pleated waistband, skater silhouette
    • Ruffled short-length hem
    • Open-back, tie closure, back zipper, hook and eye closure
    • Chiffon floral lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1706

    Category Name: Casual Dresses

    Price: $25.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Nothing Bud Fun Floral Halter Dress

    Have nothing but fun in this flirty floral halter dress perfect for a brunch date! It features a sleeveless, halter v-neck with adjustable neck tie, a babydoll style bodice leading to a flowy, ruffled short hem. Showcase some skin in the open-back with tie closure. Complete the look in lace-up sandals.

    Fit & Features

    • Sleeveless, halter v-neck, adjustable necktie
    • Babydoll style bodice
    • Flowy ruffled short hem
    • Open-back, tie closure
    • Ditsy floral print, woven-lined fabric
    • Fits true to size, no stretch

    Style Number/Barcode: 05102-4364

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lotus Floral Mesh Bodycon Dress

    Look lovely in this floral mesh bodycon dress for a trendy afternoon tea look! Features a sleeveless, cowl neckline, adjustable spaghetti straps, on a mini-length hem. Complete the look in cute heels and a straw hat.

    Fit & Features

    • Sleeveless, cowl neckline, adjustable spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Floral mesh-lined fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4363

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Getaway Sleeveless Maxi Dress

    Get ready for a gorgeous getaway in this alluring sleeveless maxi dress! It features a V-neckline, spaghetti straps, a cross-back strap design, a fitted high waist seam, and a floor-length silhouette with a chic high front slit. The knit fabric features an all-over tropical palm leaf print. Style this dress with strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back strap design
    • Fitted high waist seam
    • Floor-length silhouette, high front slit
    • Palm leaf print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4362

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Earn Your Stripes Sweater Midi Dress

    Earn your stripes in style rocking this sweater midi dress for all-day slays! It features a sleeveless square neck, adjustable spaghetti straps, a striped pattern, and a bodycon silhouette. Composed of a rib-knit fabric with a moderate stretch. Style with chic booties.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Striped pattern
    • Bodycon midi-length hem
    • Rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1240

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Essential Sleeveless Midi Dress

    The perfect sleeveless midi sweater dress for every occasion! It features a V-neck, tank straps, and a bodycon silhouette on ribbed knit fabric with a moderate stretch. Complete the look in sleek hoops and heels.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline, tank straps
    • Bodycon silhouette
    • Midi-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1239

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetie Puff Sleeve Mini Dress

    You'll look so sweet in this mini dress for a cute brunch fit. It features adorable short puff sleeves along the sweetheart neck with a cutout bust tie. The side ruched seams accentuate your curves on slinky knit-lined fabric with a moderate stretch. Complete the look in PVC mules.

    Fit & Features

    • Short puff sleeves, elastic cinched hems
    • Sweetheart neck, cutout bust tie
    • Side ruched seams, bodycon fit
    • Mini-length hem
    • Slinky knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4361

    Category Name: Casual Dresses

    Price: $5.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Stunner Striped Halter Short Dress

    Keep it stylish in a short sweater dress that wows and keeps it effortless. The dress features a halter neck with an adjustable neck tie, a striped pattern, and a short-length hem. The dress is composed of an unlined knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with wedges.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Halter neck 
    • Adjustable neck ties
    • Striped pattern
    • Short-length hem 
    • Knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1231

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Day To Night Snap Button Midi Dress

    Go from office hours to happy hour in a snap with this classy sweater midi dress! It features long sleeves, a rounded neckline, a bodycon silhouette, and a side slit with snap button accents. Composed of a ribbed knit fabric with a moderate stretch. Style with a chic jacket and heels.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Long fitted sleeves
    • Round neckline
    • Bodycon silhouette
    • Side slit, snap button accents
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1219

    Category Name: Casual Dresses

    Price: $18.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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