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.

  • 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
  • Eyes On You Eyelet Tie Back Dress

    All eyes on you in this eyelet lace mini dress! It features puff sleeves, a square neck, a ruched bust, an open back with a tie closure, and a bodycon silhouette. Complete the look in lace-up sandals for a picnic date.

    Fit & Features

    • Short puff sleeves, cinched hems
    • Square neckline, ruched bust
    • Open back, tie closure
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4438

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Falling For Eyelet Mini Dress

    Fall for this eyelet mini dress for a cute vibe all summer long! It features a sleeveless, square neck, adjustable spaghetti straps, a flirty tie-front bust, and a form-fitting silhouette. Complete the look in a dainty necklace and wedges.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Tie-front along the bust
    • Form-fitting silhouette
    • Mini-length hem
    • Eyelet knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4435

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Finest Floral Tie-Back Skater Dress

    The florals on this skater dress are oh-so-fine! Create a cute spring look in this sleeveless, boat neckline, adjustable spaghetti straps, a flirty open-back with tie closure, and a ruffled skater silhouette. Complete the look in stud earrings for Easter brunch.

    Fit & Features

    • Sleeveless, boat neckline, adjustable spaghetti straps
    • Open-back, tie closure
    • Ruffled skater silhouette
    • Short hem
    • Floral chiffon-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4432

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Born To Rock Lace-Up Graphic Tunic

    Feel the rockstar vibes in this trendy graphic tunic for all of your jam sessions! It features a sleeveless mock neck, dual side lace-up detail, and a front graphic script that reads, 'Let's Make Some Noise/Born To Be A Rockstar'. Complete the look in lug booties.

    Fit & Features

    • Sleeveless, mock neck
    • Dual side lace-up detail
    • Graphic reads, 'Let's Make Some Noise/Born To Be A Rockstar'
    • Form-fitting bodice
    • Short hem
    • Cotton knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1149

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Love Eyelet Mini Dress

    You'll fall in love with the adorable details of this eyelet mini dress! It features a sweetheart neckline with a ruffled trim, a ruched bust with a tie-front, short puff sleeves, and a mini-length, form-hugging fit. The eyelet knit fabric features a lightweight lining. Style this dress with cute espadrille sandals.

    Fit & Features

    • Sweetheart neckline, ruffled trim
    • Ruched bust, tie-front detail
    • Short puff sleeves, elasticized hems
    • Short, form-fitting silhouette
    • Eyelet knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4433

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunday Girl Eyelet Lace-Up Skater Dress

    This eyelet skater dress is perfect for Sunday brunch! It features adorable short puff sleeves, a square neck, an elasticized waist, an open-back design with lace-up closure, and a flared skirt. Composed of breathable cotton fabric with an inner lining. Finish the look in strappy sandals.

    Fit & Features

    • Short puff sleeves
    • Squareneck
    • Elasticized waist
    • Open-back design, lace-up closure
    • Flared, skater silhouette, short-length hem
    • Eyelet lace cotton fabric, inner lining
    • Fits true to size, no stretch

    Style Number/Barcode: 05102-4428

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shamrock Shake Ruched Mini Dress

    Look like a treat this St. Patrick's Day! This sleeveless mini dress features an on-trend square neck, spaghetti straps, and dual side ruching with adjustable ties, a shamrock pattern, and a bodycon silhouette. Composed of a brushed knit fabric with a moderate stretch. Finish the look in strappy sandals. 

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Dual side ruching, adjustable ties
    • Shamrock pattern
    • Bodycon silhouette
    • Mini hem
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4430

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Eye On The Eyelet Lace Mini Dress

    Keep your eye on this prize! Bring the flirty allure in this eyelet lace mini dress featuring short puff sleeves, a ruffle sweetheart neck with tie, and a babydoll-style bodice on a form-fitting silhouette. Complete the look in lace-up sandals for a cute picnic look.

    Fit & Features

    • Short puff sleeves
    • Ruffle sweetheart neck with tie
    • Babydoll-style bodice
    • Form-fitting silhouette
    • Mini-length hem
    • Eyelet lace knit lined fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 05102-4429

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Breeze Linen Halter Skater Dress

    Feel the breeze this spring! This linen skater dress is perfect for your next daytime soiree featuring a sleeveless halter V-neckline, open-back design, dual tie-back closure, and a flowy, A-line skater silhouette. Composed of linen fabric with an inner knit lining with minimal stretch. Style with strappy heels.

    Fit & Features

    • Sleeveless, halter V-neck
    • Open-back design, dual tie-back closure, lower back elasticized waistband
    • Flowy, A-line skater silhouette
    • Above-the-knee length hem
    • Linen fabric, inner knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4414

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale