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.

  • Soft Serve Marble Print Mini Dress

    Look sweet enough to eat in this marble print mini dress featuring a sleeveless, square neck, bungee spaghetti straps, a form-fitting silhouette, and a fitted hem. Complete the look in lace-up heels for a date night.

    Fit & Features

    • Sleeveless, square neck, bungee spaghetti straps
    • Form-fitting silhouette
    • Mini fitted hem
    • Marble print 
    • Fits true to size

    Style Number/Barcode: 05102-4662

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Sultry Cutout Bodycon Midi Dress

    This curve-hugging bodycon midi dress is simply sultry and perf for a night out with your girls. It features a sleeveless square neckline, spaghetti straps, alluring waist cutouts at the front and back, ruching down the side seams leading to a midi-length hem, and an all-over bodycon silhouette to show off your figure. The sheer mesh fabric includes a soft knit lining and has plenty of stretch. Style with a layered chain necklace for a hint of glam!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Front and back waist cutouts
    • Ruched side seams
    • Midi-length hem, bodycon silhouette
    • Sheer mesh fabric, sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4648

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In Knots Faux Wrap Mini Dress

    You'll get tied up in knots for this elevated basic mini! It features a sleeveless, scoop neck, spaghetti straps, a bodycon silhouette, and an asymmetrical faux-wrap skirt with a knot accent. Complete the look in trendy sandals for a coffee date.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Bodycon silhouette
    • Asymmetrical faux-wrap skirt
    • Knot accent
    • Mini-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4661

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Call of The Wild Midi Slit Dress

    Answer the call in a fierce midi dress! Showcase your unique style in this geometric crepe midi dress featuring a sleeveless, V-neck, sleek spaghetti straps, and a slim-fit silhouette with a front slit accent. Complete the look in lattice booties.

    Fit & Features

    • Sleeveless, V-neck, spaghetti straps
    • Slim-fit silhouette
    • Front slit accent
    • Midi-length hem
    • Geometric print
    • Crepe knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4649

    Category Name: Casual Dresses

    Price: $4.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Swirls V-Neck Mini Dress

    Perfectly swirled and smoothed to perfection! Showcase a head-turning look in this sleeveless mini dress featuring a v-neck, bungee spaghetti straps, bodycon silhouette, slit accent, and a marble print on brushed knit fabric. Complete the look in lace-up heels for a summer party. 

    Fit & Features

    • Sleeveless, v-neck, bungee spaghetti straps
    • Bodycon silhouette
    • Slit accent
    • Mini-length hem
    • Marble print
    • Brushed knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4660

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Twist Cutout Mini Dress

    Trendy with a twist...you'll totally fall for this mini dress featuring a sleeveless, v-neck, spaghetti straps, a cutout bodice, side ruched seams, on knit-lined fabric with a form-hugging fit and moderate stretch. Complete the look-in mules for a daytime event.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Twist front accent
    • Cutout bodice
    • Side ruched seams
    • Form-hugging fit
    • Knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4657

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paisley Queen Ruched Mini Dress

    Enchant them all in your love for all things paisley! This square neck mini dress features a sleeveless bodice, spaghetti straps, a bodycon silhouette, and a front ruched seam on stretchy knit fabric. Complete the look in espadrille wedges.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Front ruched seam
    • Mini-length hem
    • Paisley print knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4650

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Options Open O-Ring Midi Dress

    Keep your options open and wear this dress for your weekend plans! It features a sleeveless, v-neck, spaghetti straps, an open-back with an o-ring insert, a bodycon silhouette, and a midi hem on stretchy rib-knit fabric. Complete the look with chic heels.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Open-back, o-ring insert
    • Bodycon silhouette
    • Midi hem
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4659

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ahead Of The Pack V-Neck Mini Dress

    Set the trend before anyone else in this cow print mini dress! Features a classic sleeveless, v-neck, bungee spaghetti straps, a bodycon silhouette, and a flirty front slit accent. Complete the look in lace-up heels for a brunch fit.

    Fit & Features

    • Sleeveless, v-neck, bungee spaghetti straps
    • Bodycon silhouette
    • Front slit accent
    • Mini-length hem
    • Cow print
    • Crepe fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4653

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Scoop Neck Mini Dress

    This mini dress requires zero gardening! It features a sleeveless, scoop neck, thin spaghetti straps, a ruched bust, floral print, and a bodycon silhouette. Complete the look with a cute mini tote.

    Fit & Features

    • Sleeveless, scoop neck, thin spaghetti straps
    • Ruched bust
    • Floral print
    • Bodycon silhouette
    • Mini-length hem
    • Crepe fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4654

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fall For Surplice Sweater Dress

    This autumn, you'll fall for this surplice sweater dress that's cozy and stylish! The mini dress features long sleeves, a plunge v-neckline, a bodycon silhouette, and a side ruched seam leading to the asymmetrical wrap hem. Complete the look in tall boots and a coat for a perf fall vibe.

    Fit & Features

    • Long sleeves
    • Plunge v-neckline
    • Surplice bodice
    • Side ruched seam, bodycon fit
    • Asymmetrical wrap mini hem
    • Smooth knit nylon-blend fabric
    • Runs true to size

    Style Number/Barcode: 06005-1473

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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