Casual Dresses

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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.

  • 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
  • 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
  • Alluring Basic High Slit Midi Dress

    This alluring basic midi dress will easily become one of your staple styles. It features a sleeveless sweetheart neckline with a built-in padded bust, adjustable spaghetti straps for a customized fit, a midi-length bodycon silhouette, and a high side slit. Pair with a moto jacket and mules.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Padded bust, bust seam outline
    • Adjustable spaghetti straps
    • Midi-length hem, fitted bodycon silhouette
    • High side slit
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4722

    Category Name: Casual Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • LA Rider Graphic Seam Short Dress

    Born to ride? Cruise through the streets of LA in this graphic short dress featuring cap sleeves, a crew neck, a front script that reads, " Motorcycle/Born to Ride/LA/CA Rider Crew", exposed seam detailing, and a front slit accent along the fitted hem. Complete the look in sleek sunglasses.

    Fit & Features

    • Cap sleeves
    • Crew neck
    • Exposed seam detailing
    • Graphic script that reads, " Motorcycle/Born to Ride/LA/CA Rider Crew"
    • Front slit accent, fitted hem
    • Form-hugging fit, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1318

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Elevated Knit High Slit Midi Dress

    This elevated brushed knit midi dress will be your new go-to for a casual night out. It features a sleeveless square neckline, spaghetti straps, an alluring center cutout at the waist, a midi-length, curve-hugging fit, and a thigh-high side slit. Style with strappy stilettos.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Center cutout at the waist
    • Midi-length, form-fitting silhouette
    • High side slit
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4451

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    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
  • 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
  • Cutie In Cap Sleeve Midi Dress

    Cute has never looked so cozy! This rib-knit midi dress is designed with cap sleeves, dual v-necklines, a bodycon silhouette, and a flirty side slit along the hem. Complete the look in sandals for a day date.

    Fit & Features

    • Cap sleeves
    • Dual v-necklines
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4715

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    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
  • Take Note V-Neck Sweater Dress

    Everyone will take note of how sultry this sweater dress is on you! It features a sleeveless, v-neck, cutout bodice with wrap tie-back closure, side slit accent, and a midi, curve-hugging silhouette. Complete the look in chic strappy heels for a daytime soiree.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, v-neck, tank-style straps
    • Cutout bodice
    • Wrap tie-back closure
    • Side slit accent
    • Midi, curve-hugging silhouette
    • Sweater rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 06005-1488

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • She's A Wildflower Strappy Back Maxi Dress

    Florals, fits, and full-on main character vibes. This floral mesh maxi dress hugs you in all the right places with a flirty strappy back and a vacay allure! 

    Fit & Features

    • Floral print, mesh fabric, soft stretchy knit lining
    • V-neckline
    • Bungee strappy open back
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000097

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Style Goals Floral Mesh Midi Dress

    Showcase total style goals in this stunning floral mesh midi dress! It features a sleeveless square neckline, spaghetti straps, an open back with a strappy design, a midi-length, curve-hugging silhouette, and a thigh-high side slit. The lined mesh fabric features all-over floral embroidery for a pretty vibe. Complete the look with hoop earrings.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, horizontal strappy design
    • Midi-length hem, bodycon silhouette
    • High side slit
    • Floral embroidery
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4738

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Find Me In Floral Mini Dress

    They can find you in this floral mini dress wandering the gardens. It features an off-the-shoulder neckline, short-sleeve cuffs, a front bust tie, and a short, curve-hugging fit. Complete the look in platform heels for a day date.

    Fit & Features

    • Off-the-shoulder neckline
    • Short-sleeve cuffs
    • Front bust tie
    • Curve-hugging silhuoette
    • Mini-length hem
    • Floral print, rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4708

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • So Charmed One-Shoulder Ruched Dress

    This mini dress is pleased to make your acquaintance! It features a one-shoulder neckline with a tank strap, bodycon silhouette, and dual side ruching with ties so you can customize the length. Complete the look with a sleek handbag.

    Fit & Features

    • Sleeveless, one-shoulder neckline
    • Tank strap
    • Bodycon silhouette
    • Dual side ruching with ties
    • Mini-length hem
    • Ribbed knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4355

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek And Chic Leopard Print Mini Dress

    Elevate your everyday outfits with this sleek and chic satin mini dress. It features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, a flirty short A-line silhouette, and an all-over trendy leopard print pattern. Style with an oversized blazer and strappy mules.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • A-line silhouette
    • Mini-length hem
    • Leopard print
    • Smooth woven satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4701

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    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
  • Knott Love Halter Cutout Midi Dress

    You'll fall for this halter midi dress with just one look! Featuring a sleeveless, halter neck with tie-back closure, a trendy knot cutout bodice that shapes the bodycon silhouette. Complete the look in classy nubuck heels.

    Fit & Features

    • Sleeveless, halter neck, tie-back closure
    • Knot cutout bodice
    • Bodycon silhouette
    • Midi-length hem
    • Soft and stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4322

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Getaway Vibes Mini Sweater Dress

    This chic mini sweater dress was made for weekend getaways. It features a sleeveless V-neckline, tank shoulder straps, a square back design, a braided knit trim, and a short, form-fitting silhouette. Complete the look with sleek hoops and your fave shades.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline
    • Tank shoulder straps
    • Square back design
    • Braided knit trim
    • Mini-length, form-fitting silhouette
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1425

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Effortless Perfection Sleeveless Midi Dress

    Showcase effortless perfection in this simple yet chic midi dress. It features a sleeveless scoop neckline, spaghetti straps, an open-back design, a midi-length, curve-hugging silhouette, and a high side slit. Style this dress with heeled mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Open-back design
    • Midi-length, form-fitting, bodycon silhouette
    • Side slit
    • Lined ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4485

    Category Name: Casual Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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