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.

  • Casually Cool Slit Maxi Dress

    Stroll outside looking casually cool and cute in this basic maxi dress design with a sleeveless scoop neck with bungee spaghetti straps, a form-hugging silhouette, and a high-cut side slit. Complete the look in a crop denim jacket and sneakers.

    Fit & Features

    • Sleeveless scoop neck
    • Bungee spaghetti straps
    • Form-hugging
    • High-cut side slit
    • Maxi-length hem
    • Rib-knit fabric, lined, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4883

    Category Name: Casual Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • True Staple Short Skater Dress

    A true staple for daytime soirees and celebrations! This short skater dress features a classic sleeveless square neck, adjustable spaghetti straps, a tie-front bust, flexible boning inserts along the bodice, and is composed of smooth woven fabric with a stretchy knit lining. Complete the look with a bracelet and heels.

    Fit & Features

    • Sleeveless square neck, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Tie-front bust, flexible boning inserts
    • Skater silhouette
    • Short-length hem
    • Woven fabric stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2016

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Babe Cutout Sweater Dress

    You'll be such a trendy babe in this adorable cutout sweater dress! Featuring a sleeveless high neckline with a racerback design, a front keyhole cutout at the bust, alluring side cutouts at the waist, a midi-length hem, and a curve-hugging silhouette, this dress is a perfect pick for a night out with the girls. Style with platform heels and a chic handbag.

    Fit & Features

    • Sleeveless high neckline, racerback design
    • Front keyhole cutout at the bust
    • Dual side cutouts at the waist
    • Midi-length hem, curve-hugging fit
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1633

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chain Effect Midi Dress With Belt

    You'll make a chain reaction by stepping out in this rib knit tank midi dress featuring a sleeveless square neck, tank shoulder straps, a detachable chain belt with lobster clasp closure, and a form-hugging silhouette. Complete the look in a chic blazer for happy hour!

    Fit & Features

    • Sleeveless square neck
    • Tank shoulder straps
    • Detachable chain belt with lobster clasp closure
    • Form-hugging silhouette
    • Midi-length hem
    • Double-lined rib knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4882

    Category Name: Casual Dresses

    Price: $19.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Moves Eyelet Lace Mini Dress

    The perfect sundress for bridal showers or outdoor parties! It features adorable puff short sleeves, a square neck, side ruched seams along the bodice, and a bodycon silhouette with a mini-length hem. Complete the look in trendy espadrille wedges.

    Fit & Features

    • Puff short sleeves
    • Square neck
    • Side ruched seams on bodice
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4874

    Category Name: Casual Dresses

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bae Breeze Cotton A-Line Short Dress

    Enter looking like bae just breezed in! Capture cuteness in this cotton short dress featuring short puff sleeves, a square neck, an open lace-up back, and an A-line silhouette. Style with a trendy crossbody bag and heels.

    Fit & Features

    • Short puff sleeves
    • Square neck
    • Open lace-up back, zipper and hook-eye closure
    • A-line silhouette
    • Short-length hem
    • Cotton fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4876

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Play The Game Checker Mini Dress

    Play the game of style with this checkered mini dress and you'll definitely get a checkmate! The sleeveless dress features a square neck, tank-style straps, flexible boning inserts, a bodycon silhouette, and a mini-length hem. Complete the look in a crop denim jacket for a casual daytime outing.

    Fit & Features

    • Sleeveless, square neck, tank-style straps
    • Flexible boning inserts
    • Back zipper and hook-eye closure
    • Bodycon fit, short-length hem
    • Checkered pattern
    • Rib-knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4877

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Loving Is Easy Eyelet Lace Tie Mini Dress

    Loving this eyelet lace mini dress is easy! Perfect for lunch with friends or bridal showers. The dress features a sleeveless square neck, spaghetti straps, a ruched bust tie, and a bodycon silhouette. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Ruched bust tie
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4873

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Silhouette High Slit Maxi Dress

    Show off your stunning silhouette in this curve-hugging high-slit maxi dress! It features a sleeveless square neckline, tank shoulder straps, a partially open back with a twist-back design and a lower back cutout, a maxi-length hem with a trendy thigh-high side slit, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch and has a sewn-in knit lining. Style with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • Partially open back, twist-back design, lower back cutout
    • Maxi-length hem, thigh-high side slit
    • Bodycon silhouette
    • Ribbed knit fabric, sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4875

    Category Name: Casual Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Go Crew Neck Slit Midi Dress

    The perfect casual midi dress to look stylish while on the go! It features cap short sleeves, a crew neck, a bodycon silhouette, a side ruched drawstring, and a flirty slit along the hem. The dress is composed of a super soft brushed knit fabric with plenty of stretch. Style with cute slide sandals and a tote bag! 

    Fit & Features

    • Cap short sleeves
    • Crew neck
    • Bodycon silhouette
    • Side ruched drawstring, slit accent
    • Midi-length hem
    • Soft brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4872

    Category Name: Casual Dresses

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Stunner Chain Strap Midi Dress

    Embrace the warmer months and showcase a stunning summertime style in this ribbed knit midi dress. It features a sleeveless square neckline, adjustable spaghetti straps with multi-colored front beaded and chain accents, a hip-hugging fit that will show off your natural curves, and a midi-length hem with a thigh-high front slit for a sassy detail. The ribbed knit fabric offers plenty of stretch. Complete the look with espadrille wedges for a playful summer vibe.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps, multi-colored front beaded and chain accents
    • Hip-hugging fit
    • Midi-length hem, high front slit
    • Ribbed knit fabric, lined bust
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4871

    Category Name: Casual Dresses

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swirls Of Style Satin Midi Dress

    Stylish marble swirls capture all the attention on this satin midi dress featuring a sleeveless v-neck, adjustable spaghetti straps, flexible boning inserts along the bodice, and a curve-hugging silhouette with a front slit accent. Complete the look in a casual crop jacket.

    Fit & Features

    • Sleeveless v-neck, adjustable spaghetti straps
    • Flexible boning inserts
    • Back zipper and hook-eye closure
    • Front slit, curve-hugging, midi-length hem
    • Marble print
    • Satin fabric, knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4867

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Charm Tie-Front Midi Dress

    Make them all fall for your stylish charm in this adorable midi dress! It features a sleeveless V-neckline with a cute tie-front detail, spaghetti straps, a midi-length hem with a high front slit for a subtle sultry vibe, and a slim-fit silhouette. The lightweight knit fabric has plenty of stretch. Pair with hoop earrings and block heels for a date night.

    Fit & Features

    • Sleeveless V-neckline, tie-front detail
    • Spaghetti straps
    • Midi-length hem, high front slit
    • Slim-fit silhouette
    • Lightweight knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4864

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual-Chic Style Muse High Slit Maxi Dress

    Show off your elevated casual-chic style in this high slit maxi dress. Featuring a sleeveless crew neckline with tank shoulder straps, trendy side cutouts at the waist, a maxi-length hem, and a thigh-high side slit, this dress will get you major compliments. The ribbed knit fabric offers plenty of stretch. Complete the look with sleek hoops and strappy heels.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Dual side cutouts at the waist
    • Maxi-length hem
    • High side slit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4866

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Frolic In Floral Tie Midi Dress

    Frolic all over town in this floral midi dress perfect for an afternoon tea with the girls! It features a sleeveless V-neck, spaghetti straps, a knot tie bust, a curve-hugging silhouette, and a flirty front slit. The dress is designed with a ditsy floral bud print on stretchy knit fabric. Complete the look in trendy wedge sandals.

    Fit & Features

    • Sleeveless V-neck
    • Spaghetti straps
    • Knot tie bust
    • Curve-hugging silhouette
    • Front slit, midi-length hem
    • Ditsy floral bud print, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4865

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Hour Floral Ruffled Skater Dress

    Snap a dreamy pic for golden hour in this floral skater dress and watch the likes come through! It features an off-the-shoulder, sweetheart neckline with ruffle trim, peasant long sleeves, a smocked bodice with a front adjustable drawstring, a cutout waist, and a flowy tiered ruffled short-length hem. Complete the look in chic clear strap mules.

    Fit & Features

    • Off-the-shoulder, sweetheart neck, ruffle trim
    • Peasant long sleeves
    • Smocked bodice, front adjustable drawstring
    • Cutout waist, skater silhouette
    • Tiered ruffle short hem
    • Watercolor floral print, non-stretch woven fabric
    • Runs true to size

    Style Number/Barcode: 05101-1987

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Alluring Marble Mesh Bodycon Dress

    This alluring marble mesh bodycon dress will draw all the attention your way! It features a square neckline, sheer long fitted sleeves, a short, curve-hugging silhouette, and an all-over marble swirl pattern. The partially lined mesh fabric offers plenty of stretch. Style with platform heels.

    Fit & Features

    • Square neckline
    • Sheer long fitted sleeves
    • Mini-length hem
    • Fitted bodycon silhouette
    • Marble swirl pattern
    • Sheer mesh fabric, partial knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4863

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sent You A Text Square Neck Mini Dress

    You might want to reply back to your new favorite casual mini dress for weekend outings or day dates! It features a sleeveless square neck, tank-style straps, and a bodycon silhouette, and is composed of a textured fabric with a stretch knit lining. Style with a denim jacket and sandals.

    Fit & Features

    • Sleeveless square neck
    • Tank-style straps
    • Bodycon silhouette
    • Mini-length hem
    • Textured fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4860

    Category Name: Casual Dresses

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Good Turtleneck Maxi Dress

    Look and feel good in this rib knit maxi dress perfect for everyday styling! It features long sleeves, a turtleneck, a form-hugging silhouette, and a side-slit accent. Complete the look in mules for a dinner date.

    Fit & Features

    • Long fitted sleeves
    • Turtleneck
    • Form-hugging silhouette
    • Side slit
    • Maxi-length hem
    • Rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4861

    Category Name: Casual Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Stroll Ditsy Floral Midi Dress

    Take a springtime stroll in this adorable ditsy floral midi dress! Featuring a square neckline, short puff sleeves, a midi-length hem with a front slit, and a flowy A-line silhouette, this dress is perfect for weekend plans. The ditsy floral printed woven fabric includes a short knit lining. Style with sandals for a date with your special someone.

    Fit & Features

    • Square neckline
    • Short puff sleeves, elastic cinched hems
    • Smocked back panel, hidden side zipper
    • Midi-length hem, front slit, A-line silhouette
    • Ditsy floral print
    • Woven fabric, short knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1985

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Live Or Ride Graphic Short Dress

    Live life comfortably or on the edge! Showcase your wild lifestyle in this graphic short dress featuring short sleeves, a crew neck, a front script that reads, "Live Or Ride Legend" and a bustier-style bodice with mesh inserts and a fitted hem. Complete the look in combat boots.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Graphic front with a script, "Live Or Ride Legend"
    • Bustier-style bodice with mesh inserts
    • Fitted, short-length hem
    • Smooth and stretchy cotton fabric
    • Fits true to size

    Style Number/Barcode: 06002-1449

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On A Roll Turtleneck Midi Dress

    The styling possibilities are endless with this turtleneck midi dress! It features long sleeves, a bodycon silhouette, and a sultry side slit on stretchy rib-knit fabric. Complete the look in suede booties for the perf autumn outfit!

    Fit & Features

    • Long sleeves
    • Turtleneck
    • Bodycon silhouette
    • Side slit
    • Midi-length 
    • Rib-knit, lined, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4855

    Category Name: Casual Dresses

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Charm Ditsy Floral Skater Dress

    Show off your cute charm in this adorable ditsy floral skater dress! It features a square neckline with a ruffled trim, a ruched bust with a tie-front detail, short puff sleeves, a fitted high waist seam, and a short flared-out skater skirt with a flowy silhouette. The lightweight woven fabric features a dainty ditsy floral print pattern. Style with espadrille sandals for a picnic date.

    Fit & Features

    • Square neckline, ruffled trim
    • Ruched bust, tie-front detail
    • Short puff sleeves, elastic cinched hems
    • Back zipper, hook and eye closure
    • High waist seam, short skater skirt, fit and flare silhouette
    • Ditsy floral print, woven fabric, bust knit lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4854

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Midi Long Sleeve Slit Dress

    You can't be disturbed cause you'll be busy admiring yourself in this rib knit midi dress featuring long sleeves, a sweetheart neckline, bust seam detail, and a form-hugging silhouette with a sultry side slit. Complete your cute look in faux suede booties for a Friendsgiving! 

    Fit & Features

    • Long sleeves
    • Sweetheart neck
    • Bust seam detail
    • Form-hugging silhouette
    • Midi-length hem, side slit
    • Ribbed knit fabric, partial lining, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4853

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale