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.

  • Effortless Choice Halter Midi Dress

    This casual-chic midi dress will make styling so effortless. It features a sleeveless crew neckline with halter straps, an open back with a cross-back strap design, a midi-length, curve-hugging silhouette, and an alluring high side slit. Complete the look with a classic pair of hoops.

    Fit & Features

    • Sleeveless crew neckline
    • Halter straps
    • Open back, cross-back strap design 
    • Bodycon silhouette, side slit accent
    • Midi-length hem
    • Ribbed knit fabric, lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4588

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry Mood Snake Print Mini Dress

    This sultry mini dress was made for nights out with the squad! It features an asymmetrical one-shoulder neckline, a tank shoulder strap, ruching down the side seams, and a short, curve-hugging, bodycon silhouette. The mesh fabric features an all-over snake print pattern. Complete the look with sleek hoop earrings.

    Fit & Features

    • Sleeveless asymmetrical one-shoulder neckline
    • Single tank shoulder strap
    • Ruching down the side seams
    • Mini-length hem, fitted bodycon silhouette
    • Mesh fabric, moderate stretch
    • Snake print
    • Runs true to size

    Style Number/Barcode: 05102-4590

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Cutest Denim V-Neck Mini Dress

    Show off your cute figure in this stylish denim mini-dress! It features a sleeveless sweetheart neck, wide shoulder straps, a front exposed zipper closure, and a bodycon silhouette. Complete the look in lace-up heels for a birthday party!

    Fit & Features

    • Sleeveless sweetheart neck
    • Wide shoulder straps
    • Front exposed zipper closure
    • Bodycon silhouette
    • Mini-length hem
    • Denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05102-4591

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Reap The Rewards Cutout Mini Dress

    You'll be reaping the rewards of this rib mini dress all season long! It features long fitted sleeves and a crew neckline, a twist accent bust with a cutout waist, side ruched ties that let you customize the length, and a bodycon silhouette. Complete the look in booties.

    Fit & Features

    • Long fitted sleeves
    • Crew neckline
    • Twist accent bust, cutout waist
    • Side ruched ties to customize the length
    • Bodycon mini silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4583

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Muse Chiffon Skater Dress

    Showcase your effortless beauty in this airy chiffon skater dress. It features a sweetheart neckline with ruffled trim and a pleated bust, long bishop sleeves, a fitted high waistband, and a tiered skater skirt with a short hem and a fit and flare silhouette. Style this skater dress with your fave mules.

    Fit & Features

    • Sweetheart neckline, ruffled trim, pleated bust
    • Long sheer bishop sleeves, cinched hems
    • Smocked back design, fitted high waistband
    • Fit and flare silhouette
    • Tiered skater short-length skirt
    • Chiffon fabric fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1650

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild Blooms Floral Short Dress

    Tame your wild side and showcase this flirtatious floral short dress perfect for a casual picnic date! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a cutout back accent. Complete the look in wedges.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Bodycon silhouette
    • Cutout back accent
    • Short-length hem
    • Floral print knit fabric, knit lining at the bust, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4579

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twirl-Worthy Moment Skater Dress

    Get ready to have a total twirl-worthy moment in this adorable skater dress. It features a sleeveless square neckline, spaghetti straps that lead to a lace-up back design, a high waist seam, and a short skater skirt with a flirty fit and flare silhouette. Style this dress with your fave platform heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Cross-back, lace-up design, tie closure
    • High waist
    • Short skater skirt, fit and flare silhouette
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4578

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Days Square Neck Mini Dress

    Give your jeans a break but keep the denim spirit! You'll find yourself reaching for this denim mini dress of those days spent with friends or exploring the city. It features a sleeveless, square neck, adjustable spaghetti straps, princess seam detailing on the bodycon silhouette, and a back zipper closure. Complete the look in simple earrings and sneakers.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Back zipper closure
    • Princess seam detailing
    • Bodycon silhouette
    • Mini-length hem
    • Denim fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4571

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's Trendy Tie-Dye Mini Dress

    Showcase your trendy style in this tie-dye printed mini dress. It features a sleeveless square neckline, adjustable spaghetti straps, ruching down one side leading to an adjustable drawstring at the hem, and a short, curve-hugging silhouette. Complete your cool-girl look with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • High waist seam, ruching down one side, adjustable drawstring
    • Mini-length, form-fitting silhouette
    • Tie-dye print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4573

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Vibes Sleeveless Short Dress

    Channel those wild vibes with a short dress that showcases your free-spirited side! The dress features a trendy zebra print, a sleeveless square neckline, bungee spaghetti straps, 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 a moto jacket for a night-out look.  

    Fit & Features

    • Zebra print
    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Short length hem
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4572

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Mood Geo Print Mini Dress

    In the mood for some newness? Add this retro mini dress to your lineup this new season! It features a sleek, sleeveless, square neck, bungee spaghetti straps, and a geo print design on soft knit-lined fabric that offers a form-hugging fit. Complete the look in statement earrings for a yacht party.

    Fit & Features

    • Sleeveless, square neck, bungee spaghetti straps
    • Geo print design
    • Form-hugging fit
    • Mini-length hem
    • Soft knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4569

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet For You Marble Mesh Mini Dress

    This mesh mini dress will look so good and so sweet in your lineup! It features a sleeveless square neckline, adjustable spaghetti straps, a short, curve-hugging, bodycon silhouette, and an all-over marble print on a lined mesh fabric. Complete your cool summer look with strappy heels.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Mini-length, form-fitting, bodycon silhouette
    • Marble print
    • Sheer mesh fabric, knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4568

    Category Name: Casual Dresses

    Price: $6.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fine Details Twist V-Neck Dress

    Turn heads in the sultry details of this mini dress featuring long sleeves, a v-neck, twisted bust, and side ruched seams that flaunt your curves along the bodycon silhouette. Complete the look in knee-high boots for apple picking!

    Fit & Features

    • Long sleeves, v-neck
    • Twisted bust
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4562

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Alluring Strapless Midi Dress

    This curve-hugging strapless midi dress is simply alluring! It features a strapless straight across neckline, bold cutouts down each side at the waist, a midi-length bodycon silhouette, and a chic high slit. Style with strappy stilettos.

    Fit & Features

    • Strapless straight across neckline, elasticized band
    • Side cutouts at the waist
    • Midi-length bodycon silhouette, form-hugging fit
    • High front slit
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4561

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy Trendsetter Knit Mini Dress

    Keep up your trendsetter status in this preppy-casual knit mini dress! It features a collared V-neckline, short fitted sleeves, and a short, form-hugging fit. Style with ankle booties and a cute shacket.

    Fit & Features

    • Collared V-neckline
    • Short sleeves
    • Mini-length hem, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4566

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Neutral Vibe Mini Dress

    Showcase a chic neutral vibe in this trendy ribbed knit mini dress. It features a sleeveless square neckline, adjustable spaghetti straps, bold waist cutouts leading to an alluring open back with a cross-back strap design, and a short, curve-hugging silhouette. Style this dress with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Waist cutouts, open back, cross-back strap design
    • Mini-length, form-fitting, bodycon silhouette
    • Double-lined ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4558

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knot Gonna Lie Crew Neck Dress

    Not gonna lie, you'll be reaching for the crew neck dress on the daily! It features cap sleeves, a crew neck, a front knot accent with cutout, a bodycon silhouette, and a mini-length hem. Complete the look in cute sandals for strolling downtown.

    Fit & Features

    • Cap sleeves
    • Crew neck
    • Front knot accent and cutout
    • Bodycon silhouette
    • Mini-length hem
    • Brushed knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4555

    Category Name: Casual Dresses

    Price: $9.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set The Tone Rib Sweater Dress

    Set the tone for the new season in this fresh two-tone sweater dress for all the autumn vibes! It features long sleeves, a mock neck, a bodycon silhouette, and a mini-length hem on stretchy ribbed knit fabric. Complete the look in dainty linear earrings.

    Fit & Features 

    • Long fitted sleeves
    • Mock neck
    • Bodycon silhouette
    • Two-tone pattern
    • Mini-length hem
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1432

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bae-cation Palm Print Mini Dress

    Look and feel like a total bae on vacay! This tropical mini dress is essential for exploring the island in style. It features a sleeveless, square neck, adjustable spaghetti straps, side ruched seams, and a brushed knit fabric offering a form-hugging fit and moderate stretch. Complete the look in espadrille wedges and earrings.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Side ruched seams
    • Form-hugging fit
    • Mini-length hem
    • Palm print, brushed knit-lined fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4557

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Muse Bodycon Mini Dress

    Show off an alluring style in this sultry-chic mini dress. It features a sleeveless mock neckline, an asymmetrical cutout above the bust, a keyhole cutout at the back, and a short, curve-hugging, bodycon silhouette. Complete the look with clear mules.

    Fit & Features

    • Sleeveless mock neckline
    • Asymmetrical cutout above the bust
    • Back button closure, keyhole cutout
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4556

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Basic Bodycon Mini Dress

    Simple and sleek, this bodycon mini dress is a trendy basic! It features a sleeveless scoop neckline, tank shoulder straps, and a short, curve-hugging silhouette. Style with strappy mules and a faux leather clutch.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4551

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vineyard Floral Slit Maxi Dress

    Wine tasting anyone? This floral maxi is perfect for sipping on your fav red or white! It features a sleeveless, off-the-shoulder neckline, a form-fitting silhouette, and dual front slits for a sultry show of leg. Complete the look in wedges and a floppy hat.

    Fit & Features

    • Sleeveless, off-the-shoulder neckline
    • Flutter sleeve cuffs
    • Form-fitting silhouette
    • Dual front slits, maxi-length hem
    • Floral pattern
    • Stretch-knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4554

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Beauty Floral Bodycon Dress

    Hey beauty! Showcase your charm in this blooming floral bodycon dress. It features a sleeveless square neckline, spaghetti straps, chic ruching down the sides, and a short, curve-hugging silhouette. Style this dress with sparkly stud earrings and cute mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruched detailing down the sides
    • Mini-length, form-fitting, bodycon silhouette
    • Floral print
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4549

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Choice Bodycon Mini Dress

    This simple and stylish mini dress is an effortless choice for every day! It features a sleeveless one-shoulder neckline, a thin tank strap, and a short, curve-hugging, bodycon silhouette. The lightweight ribbed knit fabric offers plenty of stretch. Complete the look with heeled mules and a crossbody purse.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Single thin tank strap
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4550

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale