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.

  • Trip To Paradise Tropical Print Maxi Dress

    This bold and alluring tropical print maxi dress calls for a trip to paradise! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a floor-length hem with a thigh-high front slit, and a flowy silhouette. The smooth knit fabric showcases a tropical palm leaf print. Style with strappy sandals for sunset drinks.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back design
    • High waist seam
    • Floor-length hem, high front slit, flowy silhouette
    • Tropical palm leaf print
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5025

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute View Ditsy Floral Chiffon Skater Dress

    You'll be a cute view in this ditsy floral chiffon dress at casual family parties or weekend getaways! It features puff short sleeves, a sweetheart neck, a front bust ruched drawstring, a stretchy smocked back, and a skater silhouette with a short-length hem. The dress is composed of a chiffon fabric with a ditsy floral print and a stretchy knit lining. Complete the look in trendy sandals.

    Fit & Features

    • Puff short sleeves, elastic ruffled hems
    • Sweetheart neckline
    • Front bust ruched drawstring
    • Stretchy smocked back
    • Skater silhouette, short-length hem
    • Ditsy floral print, chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5022

    Category Name: Casual Dresses

    Price: $5.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Picked First Floral Lace-Up Dress

    You'll always be picked first in this floral mini dress perfect for afternoon soirees! It features a sleeveless square neck, spaghetti straps that shape the lace-up open back, a bodycon silhouette, and a mini-length hem. The dress is designed with a watercolor floral print on knit fabric with a stretch lining. Complete the look in adorable wedge sandals.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Lace-up, open-back
    • Bodycon silhouette
    • Mini-length hem
    • Watercolor floral print, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5020

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paint Me In Floral V-Neck Maxi Dress

    This floral maxi dress will fit like a dream and give off major artsy vibes! It features a sleeveless V-neckline, spaghetti straps, a hip-hugging fit, and a sultry front slit along the flowy hem. Complete the look in dainty earrings for a daytime soiree!

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Hip-hugging fit
    • Front slit, flowy maxi-length hem
    • Floral watercolor print
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5018

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • One More Moment Sweater Dress

    Make a lasting impression leaving the pool party in this chic cover-up sweater dress! It features a sleeveless square neck, spaghetti straps that lead to an open back with lace-up closure, a form-fitting silhouette, and a high side slit atop the midi-length hem. Complete the look with sandals and sunglasses.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Open back, lace-up closure
    • Form-fitting silhouette
    • Side slit, midi-length hem
    • Sweater knit fabric, slightly sheer, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1688

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Time To Escape Tropical Print Maxi Dress

    Get ready to escape on a gorgeous getaway in this sultry tropical print maxi dress! It features a sleeveless asymmetric one-shoulder neckline with a spaghetti strap, a bold and alluring asymmetric waist cutout with a trendy O-ring accent, a hip-hugging fit that will hug your natural curves, and a floor-length hem with a thigh-high side slit to showcase some leg. The all-over palm leaf print on the stretchy knit fabric captures those tropical oasis vibes. Style with strappy sandals.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Single adjustable spaghetti strap
    • Asymmetric waist cutout, O-ring accent
    • Hip-hugging fit, floor-length hem, high side slit
    • Tropical palm leaf print
    • Knit fabric, mini-length lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5016

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunset Happy Hour Ruffled Skater Dress

    This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag.

    Fit & Features

    • Sleeveless V-neckline
    • Halter tie-back straps, open back
    • Stretchy smocked high waist
    • Short skater skirt, tiered ruffled design
    • Fit and flare silhouette
    • Twill fabric, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-5531

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Notice Me Lace Ruffle Mini Dress

    Make 'em' stop and stare at you in this lace mini dress as the chic bride-to-be or gorgeous graduate! The dress features a sleeveless V-neckline, adjustable spaghetti straps that crisscross along the back, a form-hugging fit, and a flirty asymmetrical ruffle trim hem. Complete the look in block heel sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Crisscross back
    • Form-hugging fit
    • Ruffle trim mini-length hem
    • Lace fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2637

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Perfection Mock Neck Sweater Dress

    Showcase chic perfection in this classic ribbed knit sweater dress. It features a mock neckline, long fitted sleeves with puff accents at the shoulders, and a short, curve-hugging silhouette. The knit fabric offers plenty of stretch. Style with knee-high boots.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Puff shoulders
    • Mini-length hem
    • Form-hugging silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1681

    Category Name: Casual Dresses

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Give Me Butterflies Square Neck Skater Dress

    Show up to the party in this short skater dress and give everyone a fluttery heart for you! It features three-quarter-length puff sleeves, a square neck, a smocked back, and a fit and flare silhouette. The dress is designed with delicate butterfly embroidery on twill woven fabric with a woven lining. Complete the look with lace-up sandals.

    Fit & Features

    • Three-quarter-length puff sleeves
    • Square neck
    • Smocked back
    • Fit and flare, skater silhouette
    • Short-length hem
    • Butterfly embroidery, twill woven fabric and lining
    • Runs true to size

    Style Number/Barcode: 05102-5009

    Category Name: Casual Dresses

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Show Face Abstract Print Mini Dress

    Show your artsy-chic side in this mesh mini dress perfect for a movie date or casual plans with friends! It features a sleeveless square neck, sleek bungee spaghetti straps, side ruched seams to accentuate your curves, and a bodycon silhouette. The dress is designed with an abstract face print on mesh fabric with a stretchy knit lining. Complete the look in a trendy crop jacket and sandals.

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Abstract face print, mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5014

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cue The Charm Linen Off-The-Shoulder Dress

    This linen skater dress cues the charm you'll be bringing to wine tasting with the ladies or a birthday brunch! It features a cute off-the-shoulder ruffle trim neckline with elasticized short-sleeve cuffs, a tie-waist belt, and a flattering short-length tiered ruffle hem. Complete the look with a dainty tennis bracelet and sandals.

    Fit & Features

    • Off-the-shoulder ruffle trim neckline
    • Elasticized short-sleeve cuffs
    • Back zipper and hook-eye closure
    • Tie-waist belt
    • Skater silhouette, short-length tiered ruffle hem
    • Linen fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2341

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Sunshine Linen Tie-Back Midi Dress

    For the sun-soaked days ahead, this linen midi dress will make a cute companion! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back closure, and a flowy ruffled hem. Style with trendy sandals and sunglasses.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Tie-back closure
    • Flowy ruffled midi hem
    • Airy linen fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05102-5012

    Category Name: Casual Dresses

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Staple Wrap-Front Mini Dress

    Update your wardrobe with this cute and casual mini dress that is a stylish staple! It features a crew neckline, short sleeves, a trendy wrap-front design at the waist with a tie closure, a form-hugging fit, and a mini-length hem. The soft brushed knit fabric offers plenty of stretch for comfort. Complete the look with ankle booties.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Wrap-front design at the waist, tie closure
    • Form-fitting silhouette
    • Mini-length hem
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5007

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Getaway Tropical Print Midi Dress

    Get a gorgeous look for your next vacay getaway with this alluring tropical print midi dress. It features a sleeveless square neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, ruching at the waist, a midi-length hem with an asymmetric high side slit, and a curve-hugging silhouette. The all-over palm leaf pattern on the stretchy knit fabric will bring those tropical vacation vibes. Style with cute wedges.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Open back, cross-back lace-up strappy design, tie closure
    • Ruched detailing at the waist
    • Midi-length hem, asymmetric high side slit
    • Curve-hugging silhouette
    • Tropical palm leaf print, knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5008

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • That 70s Chick Retro Print Mini Dress

    Inspired by the groovy era, you'll look like a cute chick in this retro mini dress perfect for parties! It features a sleeveless square neck, spaghetti straps, side ruched seams that hug your figure, a bodycon silhouette, and a geometric-retro print design. Complete the look with bold earrings.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Geometric-retro print
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5005

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Time To Slay Bodycon Midi Dress

    It's your time to slay in this simple yet chic bodycon midi dress! It features an asymmetrical boat neckline with a partial off-the-shoulder design, long fitted sleeves with thumb hole accents, a midi-length hem, and a curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Style with strappy heels.

    Fit & Features

    • Asymmetrical boat neckline, partial off-the-shoulder design
    • Long fitted sleeves, thumb hole accents
    • Midi-length hem
    • Curve-hugging fit
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5006

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Escape With Me Tropical Mini Dress

    Escape to an island getaway with this tropical mini dress perfect for a sunset dinner by the shore! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a knotted bust accent, and a bodycon silhouette. The smooth lined knit fabric offers a moderate stretch. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Knotted bust accent
    • Bodycon silhouette, mini-length hem
    • Tropical print
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5004

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Showcase Your Charm Sheer Lace Maxi Dress

    Showcase your charm in this airy sheer lace flowy maxi dress. It features a V-neck and back with wrap designs, tie-back straps, short billowy bell sleeves with slit accents, a stretchy smocked high waist, a partial button-down design leading to a high front slit, a maxi-length silhouette with an adorable ruffled hem, and an A-line fit. The dainty sheer lace fabric includes a partial mini-length woven lining. Complete your look with espadrille wedges for a summer party.

    Fit & Features

    • V-neck and back, wrap designs, tie-back straps
    • Short bell sleeves, slit accents
    • Stretchy smocked high waist
    • Partial button-down design, high front slit
    • Maxi-length silhouette, ruffed hem, A-line fit
    • Sheer lace fabric, partial mini-length woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5003

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • True Colors Marble Print Mini Dress

    Show your true colors of style in this marble print dress perfect for casual plans! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a mini-length hem. Style with trendy heels and a denim jacket to complete the look!

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Marble print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5000

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Striking Style Marble Print Midi Dress

    Showcase a striking style and a stunning look in this curve-hugging marble print midi dress! It features a sleeveless cowl neckline, spaghetti straps, an asymmetric midi-length hem creating a sultry thigh-high side slit, a bodycon silhouette, and an all-over alluring marble print pattern. The smooth knit fabric offers plenty of stretch. Complete the look with clear mules.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Asymmetric midi-length hem, high side slit
    • Bodycon fit
    • Marble print
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5001

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catching Flights O-Ring Halter Midi Dress

    Catch flights not feelings! This halter midi dress is bringing those getaway vibes. It features a sleeveless halter neckline with a tank strap, an O-ring bust insert with a cutout accent and a form-hugging silhouette. Complete the look in cute flat sandals for a sunset cocktail hour!

    Fit & Features

    • Sleeveless halter neckline, tank strap
    • O-ring bust insert, cutout accent
    • Form-hugging silhouette
    • Midi-length hem
    • Stretchy rib knit fabric, knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5002

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Romance Tropical Print Maxi Dress

    Give off a romantic allure at your sunset dinner date in this form-hugging maxi dress! It features a sleeveless cowl neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, a floor-length hem with a sultry asymmetric high side slit to showcase some leg, ruched detailing, and an all-over tropical palm leaf print. Style with hoop earrings and espadrille wedges.

    Fit & Features

    • Sleeveless cowl neckline, spaghetti straps
    • Open back, cross-back lace-up strappy design, tie closure
    • High waist seam, floor-length hem, asymmetric high side slit
    • Form-hugging fit, ruched detailing
    • Tropical palm leaf print
    • Knit fabric. lined bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4996

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Soak Up The Sun Tropical Print Maxi Dress

    You'll be ready for those relaxing beachside strolls in this gorgeous tropical print maxi dress. It features a sleeveless V-neckline, spaghetti straps, an alluring backless design, a flowy, floor-length hem, and a thigh-high front slit. The smooth knit fabric showcases a tropical palm leaf print. Style with slip-on sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Backless design, single lattice strap
    • Flowy floor-length hem, high front slit
    • Tropical palm leaf print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4997

    Category Name: Casual Dresses

    Price: $5.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance