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.

  • Elevated Cutout Mini Sweater Dress

    This elevated mini sweater dress is a trendy staple for this fall season! It features a mock neckline, long fitted sleeves, waist cutouts that lead to the back, and a short, curve-hugging, bodycon silhouette. Style with strappy heels.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Waist cutouts that lead to the back
    • Mini-length hem
    • Fitted bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1469

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bohemian Oasis Scoop Neck Midi Dress

    Take the cutest pics in the desert in this boho-chic midi dress! Featuring a sleeveless, ruched scoop neck with front tie, spaghetti straps, and slim-fit silhouette. Complete the look in a trendy panama hat.

    Fit & Features

    • Sleeveless, ruched scoop neck, spaghetti straps
    • Front tie accent
    • Slim-fit silhouette
    • Midi-length hem
    • Geometric print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4652

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Instinct Satin Midi Dress

    Showcase your chic instinct in this satin snake midi dress featuring a classy, sleeveless, cowl neck, dual adjustable strappy design, and a flared hem. Complete the look in sleek stiletto heels for a dinner date.

    Fit & Features

    • Sleeveless, cowl neck
    • Dual adjustable strappy design
    • Flared midi hem
    • Snake pattern
    • Satin fabric, no stretch, fits true to size

    Style Number/Barcode: 05102-4655

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Neutral Tie-Dye Mini Dress

    You'll fall in love with the trendy neutral tones of this tie-dye mini dress! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back, lace-up design, and a short, curve-hugging fit. The soft brushed knit fabric offers plenty of stretch. Style with chic mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Cross-back, lace-up design, tie closure
    • Mini-length, form-fitting silhouette
    • Neutral tie-dye pattern
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4645

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Pick Floral Mini Dress

    This adorable floral mini dress is the cutest pick for the summer season! It features a sleeveless square neckline, bungee spaghetti straps, ruched detailing down the side seams, a short, form-hugging fit, and an all-over daisy print. Style with a denim jacket and sneakers.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruching down the side seams
    • Mini-length, form-fitting silhouette
    • Small daisy floral print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4641

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Sass Off The Shoulder Dress

    Subtle yet sassy, create a sultry allure in this off-the-shoulder midi dress featuring short-sleeve cuffs, twist accent bust, and a ribbed-knit fabric offering a form-hugging fit and a moderate stretch. Complete the look in lucite heels for a summer party.

    Fit & Feature

    • Off-the-shoulder neckline
    • Short-sleeve cuffs
    • Twist accent bust
    • Form-hugging fit
    • Midi-length hem
    • Ribbed knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4646

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Muse Asymmetrical Midi Dress

    Catch all the glances like the gorgeous muse you are in this printed midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a midi-length, asymmetrical hem, a curve-hugging silhouette, and an all-over geometric multi-print pattern. Complete the look with sleek hoop earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Midi-length, asymmetrical hem, ruching down one side
    • Form-fitting silhouette
    • Geometric multi-print pattern
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4644

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Perfection Knit Mini Dress

    This adorable ribbed knit mini dress is perfect for everyday styling! It features a collared V-neckline, short sleeves, center ruched detailing with an adjustable drawstring at the hem, and a short, form-hugging fit. Complete the look with heeled mules.

    Fit & Features

    • Collared V-neckline
    • Short fitted sleeves
    • Center ruching, adjustable drawstring at the hem
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4636

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring And Effortless Maxi Dress

    Alluring and effortless, this sleek maxi dress will elevate your look. It features a sleeveless V-neckline, spaghetti straps, a wrap-front design at the bodice, a curve-hugging maxi-length silhouette, and a chic thigh-high front slit. Style this dress with a dainty layered necklace and heeled mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Wrap-front design at the bodice
    • High waist seam, maxi-length silhouette, high front slit
    • Form-hugging fit
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4633

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • What A Girl Wants V-Neck Mini Dress

    What a girl wants is this casual mini dress perfect for styling up or down! The dress features a sleeveless V-neckline, wide shoulder straps, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in stunning lace-up heels for a party.

    Fit & Features

    • Sleeveless V-neckline
    • Wide shoulder straps
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5100

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made Your Mark X-Back Midi Dress

    Make your mark in this stylish basic midi dress featuring a sleeveless crew neckline, wide shoulder straps that cross along the open back, and a form-hugging fit with a side slit detail. Complete the look in pointed-toe heels for a dinner with friends!

    Fit & Features

    • Sleeveless crew neckline
    • Wide shoulder straps cross along the open back
    • Form-hugging silhouette
    • Side slit detail
    • Midi-length hem
    • Rib-knit fabric, sewn-in lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4621

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Summer Style Maxi Dress

    Summertime is all about showcasing that effortlessly chic style! This ribbed knit maxi dress features a sleeveless one-shoulder neckline with a single spaghetti strap, a fitted high waist seam with a knot twist design, and a curve-hugging maxi-length silhouette with a trendy high slit. Complete the look with strappy mules.

    Fit & Features

    • Sleeveless one-shoulder neckline, single spaghetti strap
    • High waist seam, knot twist design
    • Maxi-length silhouette, high slit
    • Form-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4625

    Category Name: Casual Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie Dye For One Shoulder Dress

    This maxi dress is totally tie-dye for your next beach day or vacay! Featuring a sleeveless, one-shoulder neck, tank-style strap, high waist seam, and a form-fitting silhouette with a side knot accent atop an asymmetrical hem. Complete the look in cute wedges and shades.

    Fit & Features

    • Sleeveless, one-shoulder neck, tank-style strap
    • High waist seam
    • Form-fitting silhouette
    • Side knot accent
    • Asymmetrical maxi-length hem
    • Tie-dye print, brushed knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4622

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Not Your Angel Mesh Mini Dress

    You're no one's angel. Make their jaw drop in this mesh mini dress featuring a sleeveless, square neck, spaghetti straps, bodycon silhouette, front ruched seams, and an angel multi-print design. Complete the look in large hoops for a party.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Front ruched seams
    • Bodycon silhouette
    • Angel multi-print 
    • Mesh-lined fabric
    • Fits true to size

    Style Number/Barcode: 05102-4617

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lily Girl A-Line Mini Dress

    A girl like you will love this floral mini dress for a sweet summer vibe! It features a sleeveless V-neck, spaghetti straps that lace up on the open-back design, a bodycon A-line silhouette, and a front slit accent. Complete the look in wedges.

    Fit & Features

    • Sleeveless, V-neck, spaghetti straps
    • Open-back with lace-up design
    • Bodycon A-line silhouette
    • Front slit accent
    • Mini-length hem
    • Floral print, knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4618

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picture Perfect Marble Print Dress

    This marble print mini dress is picture-perfect for snapping an insta-worthy shot! It features a sleeveless, square neck, spaghetti straps, side ruched seams, and a form-hugging fit on stretchy-lined knit fabric. Complete the look in sleek hoop earrings.

    Fit & Features

    • Sleeveless, square neck
    • Spaghetti straps
    • Side ruched seams
    • Form-hugging fit
    • Lined knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4611

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Striped Sensation Ruche Mini Dress

    You'll be such a sensation in this striped mini dress featuring a sleeveless square neck, spaghetti straps, and ruched side ties on ribbed knit fabric offering a form-hugging fit and a moderate stretch. Complete your casual look in a denim jacket and tennis shoes.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Ruched side ties
    • Form-hugging fit
    • Mini-length hem
    • Striped print, ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4614

    Category Name: Casual Dresses

    Price: $9.97 $23.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Moments Twist Front Midi Dress

    This midi dress deserves a moment of admiration! It features a sleeveless, v-neck, tank straps, a sultry twisted bust with cutout detail, and a bodycon silhouette on stretchy rib-knit fabric. Complete the look in strappy heels for date night.

    Fit & Features

    • Sleeveless, v-neck, tank straps
    • Sultry twisted bust, cutout detail
    • Bodycon silhouette
    • Midi-length hem
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4610

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sun's Out Halter Button Mini Dress

    Sun's out, shoulders out! This halter mini dress is perfect for a sunny day out and about. It features a sleeveless bodice, collared neckline, a partial open-back, button-down front, and a bodycon silhouette on sweater rib-knit fabric. Complete the look in a dainty ring set. 

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, halter collared neckline
    • Partial open-back
    • Button-down front
    • Bodycon silhouette
    • Mini-length hem
    • Sweater rib-knit 
    • Runs true to size

    Style Number/Barcode: 06005-1463

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Leave Em' Breathless Sweater Dress

    Leave your crush breathless when they see you in this spicy sweater mini dress! It features an off-the-shoulder neckline, long sleeves, a cutout bust, and a bodycon silhouette. Complete the look in thigh-high boots for everyday slay! 

    Shop More Sweater Styles: The Sweater Collection

    Fit & Features

    • Off-the-shoulder neckline
    • Long sleeves
    • Cutout bust
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1456

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Silhouette Midi Sweater Dress

    This curve-hugging sweater dress was made for sunset happy hour! It features a sleeveless V-neckline with a twist-front design, a center cutout under the bust, tank shoulder straps, and a midi-length, form-fitting silhouette with a chic high side slit. Style with classic hoop earrings and clear mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline, twist-front accent
    • Center cutout under the bust
    • Tank shoulder straps
    • Midi-length hem, form-fitting silhouette, high side slit
    • Ribbed sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1462

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Live Fast Graphic Halter Tunic

    A biker babe like you is in need of this graphic tunic! It features a sleeveless, halter neck with tie closure and a front lace-up cutout with graphic detail that reads, "Live Fast/Born To Ride" on a fitted, short-length hem. Complete the look in sleek booties.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • Front lace-up cutout
    • Graphic detail that reads, "Live Fast/Born To Ride"
    • Fitted, short-length hem
    • Cotton fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1294

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Soiree Puff Sleeve Mini Dress

    Heading to an afternoon soiree? This floral mini dress is perfect! It features adorable short puff sleeves, a sweetheart neckline, a front bust tie with a keyhole accent, and a bodycon silhouette. Complete the look with a crossbody bag.

    Fit & Features

    • Short puff sleeves, elasticized hems
    • Sweetheart neckline
    • Front bust tie, keyhole accent
    • Bodycon silhouette
    • Mini-length hem
    • Floral pattern
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4608

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachside Beauty Floral Mini Dress

    You'll be a total beachside beauty on your summer vacay in this floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, dual front verticals seams with ruched detailing, and a short, curve-hugging silhouette. The lined mesh fabric features an all-over tropical floral print. Complete the look with espadrille sandals.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Dual front vertical seams, ruched detailing
    • Mini-length, form-fitting, bodycon silhouette
    • Tropical floral print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4609

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale