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.

  • Lovely In Floral Cowl Mini Dress

    You'll look lovely in this floral mini dress featuring a sleeveless, cowl neck, bungee spaghetti straps, and form-fitting silhouette on woven fabric with an inner knit lining. Complete the look in sleek wedges.

    Fit & Features

    • Sleeveless, cowl neck, bungee spaghetti straps
    • Form-fitting silhouette
    • Mini-length hem
    • Floral print
    • Woven fabric, inner knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1576

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep Knit Chill Color Block Mini Dress

    Keep your look chill for a coffee run or casual hang in this color block mini dress.  Featuring short sleeves, a collared neckline, a button-down front, and a bodycon silhouette on stretchy, rib-knit fabric. Complete the look in sleek hoop earrings.

    Fit & Features

    • Short sleeves
    • Collared neckline
    • Button-down front
    • Bodycon silhouette
    • Mini-length hem
    • Color block pattern
    • Rib-knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4466

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Playful Floral Mesh Mini Dress

    Feeling playful? Brighten up your closet in this floral mesh mini dress perfect for brunch with the girls! It features a sleeveless, v-neck, adjustable spaghetti straps, a bodycon silhouette, center, and sides ruched seams to highlight your curves. Complete the look in lucite heels.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Center and side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Floral pattern, back zipper closure
    • Mesh-lined fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4461

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jungle Cat Leopard Cowl Midi Dress

    You're the queen of the jungle in this leopard midi dress featuring a sleeveless, cowl neck, spaghetti straps, slim-fit silhouette, and a sultry front slit. Complete the look in heels.

    Fit & Features

    • Sleeveless, cowl neck, spaghetti straps
    • Slim-fit silhouette
    • Midi-length hem
    • Front slit accent
    • Leopard print
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4462

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charmed And Fab Floral Skater Dress

    Bring the charm with a skater dress that creates a fab moment! The dress features a floral print, a sleeveless wrap V-neckline, adjustable spaghetti straps, and an elastic drawstring at the waist. The waist leads to a flowy skater skirt with a tiered ruffled design. Complete look with wedges and butterfly clips. 

    Fit & Features

    • Sleeveless wrap V-neckline
    • Adjustable spaghetti straps
    • Elastic drawstring at waist
    • Floral print
    • Tiered ruffles
    • Short length skater hem 
    • Relaxed fit, minimal stretch, runs true to size 

    Style Number/Barcode: 05101-1575

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Palisades Ruched V-Neck Midi Dress

    Let the sun kiss your shoulders in this flowy midi dress! It features a sleeveless ruched v-neck and spaghetti straps that lead to the sultry open-back with a lace-up closure. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless, ruched v-neck, spaghetti straps
    • Flowy midi-length silhouette
    • Open-back, lace-up closure
    • Gauze woven fabric
    • Inner lining
    • Fits true to size

    Style Number/Barcode: 05102-4456

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take A Bow Ruffled Short Dress

    Flaunt your flirty self and bow in this short dress featuring a sleeveless, square neck, adjustable spaghetti straps, a partial open-back with bow-tie closure, and a tiered ruffle hem. Complete the look in a choker necklace and mules. 

    Fit & Features

    • Sleeveless, square neck
    • Adjustable spaghetti straps
    • Partial open-back, bow-tie closure
    • Tiered ruffles
    • Short-length hem
    • Fits true to size

    Style Number/Barcode: 05102-4457

    Category Name: Casual Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mystic Swirls Square Neck Mini Dress

    Create a sultry-mystic vibe for the night in this square neck dress featuring sleek spaghetti straps and a bodycon silhouette with backside ruching that accentuates every curve on the mesh-lined fabric. Complete the look in lucite mules. 

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Ruched back detailing
    • Marble swirl pattern
    • Mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4453

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Farmer's Market Gingham Plaid Dress

    Head to the farmer's market looking so cute in this gingham plaid mini dress featuring a sleeveless, v-neck, sleek bungee spaghetti straps, and a bodycon silhouette with a front slit accent. Complete the look in a crop sweater and booties.

    Fit & Features

    • Sleeveless, v-neck, bungee spaghetti straps
    • Bodycon silhouette
    • Front slit accent
    • Mini-length hem
    • Gingham plaid pattern
    • Stretchy soft knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4452

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On Trend Marble Ruched Short Dress

    Stay on trend with a short dress that creates a head-turning moment! The dress features a fab marble print, a sleeveless square neckline, spaghetti straps, ruching, and a short-length hem. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and a cropped denim jacket. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Marble print
    • Ruching down the sides
    • Mini-length hem 
    • Lined smooth knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4455

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Knit High Slit Midi Dress

    This elevated brushed knit midi dress will be your new go-to for a casual night out. It features a sleeveless square neckline, spaghetti straps, an alluring center cutout at the waist, a midi-length, curve-hugging fit, and a thigh-high side slit. Style with strappy stilettos.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Center cutout at the waist
    • Midi-length, form-fitting silhouette
    • High side slit
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4451

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Chic Satin V-Neck Slip Dress

    Keep it chic this weekend in this satin slip dress for a classy night out! It features a sleeveless V-neckline, adjustable spaghetti straps, and a short-length hem. Complete the look in the matching tunic.

    Shop Matching Tunic: Weekend Chic Satin Button-Front Tunic 

    Fit & Features

    • Sleeveless
    • V-neckline
    • Adjustable spaghetti straps
    • Short-length hem
    • Satin knit fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1612

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Breeze Crochet Maxi Dress

    Look and feel like a daydream in this boho maxi dress designed in a breezy, silhouette featuring a sleeveless, crochet lace v-neck bodice, spaghetti straps, and a sultry open-back with a tie closure that leads to the flowy long hem. Complete the look in strappy sandals.

    Fit & Features

    • Sleeveless, crochet lace v-neck bodice, spaghetti straps
    • Open-back, tie closure
    • Flowy maxi silhouette
    • Long-length hem
    • Partially lined woven fabric
    • Fits true to size

    Style Number/Barcode: 05102-4449

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Babe Next Door Denim Mini Dress

    You'll look like a total babe next door in this adorable denim mini dress. It features a sleeveless sweetheart neckline with a padded bust, thin adjustable straps, an exposed back zipper closure, and a short, form-hugging fit. Style with hoop earrings and trendy cowgirl boots.

    Fit & Features

    • Sleeveless, sweetheart neckline, adjustable spaghetti straps
    • Built-in padded bust
    • Back zipper, hook-eye closure
    • Mini-length hem
    • Form-fitting silhouette
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4448

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Limelight Lace-Up Bandage Dress

    Look back at it. Flaunt your hourglass in this lace-up bandage dress featuring a sleeveless, boat neckline, spaghetti straps, a mini bodycon silhouette, and an open-back with an alluring lace-up design with tie-closure. Composed of a seamless bandage-knit fabric with minimal stretch. Finish the look in stiletto heels for a night out. 

    Fit & Features

    • Sleeveless, boat neckline
    • Spaghetti straps
    • Open-back, lace-up design with tie-closure
    • Mini bodycon silhouette
    • Seamless bandage-knit fabric
    • Fits true to size, minimal stretch

    Style Number/Barcode: 06005-1302

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feel The Sun Halter Sweetheart Skater Dress

    Bare your shoulders in this cute skater dress on a sunny day! Its easy, breezy design features a halter sweetheart neck, tie-back closure, a ruched bust, and a flowy silhouette and back zipper closure. Composed of seersucker woven fabric with an inner knit lining. Finish the look in lace-up sandals.

    Fit & Features

    • Sleeveless, halter sweetheart neck, tie-back closure
    • Ruched bust
    • Flowy skater silhouette
    • Above the knee length
    • Back zipper closure
    • Seersucker woven fabric, no stretch, inner knit lining
    • Runs true to size

    Style Number/Barcode: 05101-1537

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beach Beauty Halter O-Ring Dress

    You'll be a beautiful view on the beach in this halter midi dress featuring a sleeveless, sweetheart neck, a front O-ring atop the cutout bodice that leads to the form-fitting silhouette. Complete the look with a straw purse.

    Fit & Features

    • Sleeveless, sweetheart halter neck
    • Front O-ring
    • Cutout bodice
    • Form-fitting silhouette
    • Midi-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4443

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute As A Daisy Ruffle Strap Dress

    You'll look so cute in this daisy ruffle strap dress designed in a classic sleeveless, sweetheart bodice with ruffle tank straps, and a bodycon silhouette. Composed of brushed knit fabric with a moderate stretch. Perfect for styling with lace-up heels.

    Fit & Features

    • Sweetheart bodice
    • Ruffle tank straps
    • Bodycon silhouette
    • Mini length hem
    • Daisy floral pattern
    • Brushed knit fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 05102-4440

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winter Florals Ruched Bodycon Dress

    Florals for winter? Absolutely! This bodycon dress features a sleeveless, bungee spaghetti strap on a scoop neck, ruched sides, and a fitted hem. Composed of soft-knit fabric with a moderate stretch. Perfect for styling with a moto jacket.

    Fit & Features

    • Sleeveless, bungee spaghetti straps
    • Scoop neck
    • Ruched sides, fitted hem
    • Floral pattern throughout
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4445

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Views Floral Midi Dress

    Soak in those stunning vacay views in this chic floral midi dress! It features a sleeveless bodice, a wrap-front V-neckline, spaghetti straps, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some skin. The smooth and stretchy knit fabric features an all-over tropical floral print. Complete the look with strappy heels.

    Fit & Features

    • Sleeveless bodice, wrap-front V-neckline
    • Spaghetti straps
    • Fitted midi-length silhouette, asymmetrical hem
    • Form-hugging fit
    • Tropical floral print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4441

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Make Way Square Neck Skater Dress

    Make way people, you're coming through in this flirty skater dress perfect for graduation! It features adorable short puff sleeves, a square neckline, and a high waist seam that leads to a flowy short-length hem on eyelet knit fabric. Complete the look in cute wedges.

    Fit & Features

    • Short puff sleeves, elastic ruffled hems
    • Square neckline
    • High waist seam
    • Flowy short-length hem
    • Skater silhouette
    • Eyelet knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4446

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Fridays Halter Midi Dress

    Bring the heat this summer in this sultry midi dress on a Friday night out! It features an off-the-shoulder, halter neckline, a cinched bust with cutout accents, a form-fitting silhouette, and a flirty side slit. Complete the look in strappy mules.

    Fit & Features

    • Off-the-shoulder, halter neckline
    • Cinched bust, cutout accents
    • Form-fitting silhouette
    • Side slit, midi hem
    • Texture knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4444

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Life's A Breeze Floral Cutout Midi Dress

    This floral cutout midi dress makes getting ready a breeze! It features short puff sleeves and a ruched sweetheart bodice with a flirty waist cutout that leads to a flowy, midi-length silhouette with a slit accent. Composed of a chiffon-lined fabric with no stretch. Style with a trendy mini tote.

    Fit & Features

    • Short puff sleeves
    • Ruched sweetheart bust
    • Waist cutout, smocked back
    • Midi-length silhouette with slit accent
    • Floral pattern
    • Chiffon fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1551

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Socialite Linen Babydoll Dress

    The perfect linen babydoll dress for all of your social occasions is here! Featuring a sleeveless square neckline, adjustable spaghetti straps, a fitted bust, and a flared skater silhouette on a short-length hem. Complete the look in cute sandals and a straw bag.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Fitted bust, stretchy smocked back
    • Flared skater silhouette
    • Short-length hem
    • Linen woven fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1536

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale