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.

  • Looking Like A Daydream Eyelet Lace Dress

    Look like a daydream in this adorable eyelet lace mini dress for your next date. Designed with short puff sleeves and a bodycon silhouette with a ruffled hem, you'll bring flirty vibes.

    Fit & Features

    • Eyelet lace fabric with knit lining, moderate stretch
    • Sweetheart neckline, ruched bust
    • Short puff sleeves, ruffle trim
    • Bodycon silhouette
    • Mini-length tiered ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-6059

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Escape Halter Bodycon Crochet Midi Dress

    Escape on vacay in this must-have halter crochet midi dress perfect for enjoying a sunset dinner and drinks!

    Fit & Features

    • Crochet fabric, stretchy knit lining
    • Halter neckline, tie-back
    • Front bust tie with keyhole accent
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6060

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lively Elegance Smocked Floral Babydoll Dress

    You'll fall in love with this breezy floral babydoll dress, so adorable for weekend parties and graduations! With its stretchy smocked bodice and adjustable straps, you'll get the perfect fit. The chiffon fabric and pretty floral print add a touch of elegance to the playful babydoll silhouette and ruffled short-length hem.

    Fit & Features

    • Floral printed chiffon fabric, stretchy knit lining
    • Square neckline
    • Stretchy smocked bodice
    • Adjustable spaghetti straps
    • Babydoll silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6062

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cutest Icon Bow A-Line Mini Dress

    Draw everyone in with your posh and pretty aesthetic in this bow A-line mini dress! Perfect for shower celebrations or brunch.

    Fit & Features

    • Woven fabric, sewn-in woven lining
    • Square neckline, padded bra cups
    • Front bow
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000010

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Remarkable Allure Long Sleeve Mini Dress

    You'll look all kinds of alluring in this long sleeve mini dress in a sultry bodycon fit perfect for dressing up or down.

    Fit & Features

    • Stretchy knit fabric
    • Fitted long sleeves
    • Square neckline
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6063

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breeze By Strapless Striped A-Line Midi Dress

    Breeze by like a breath of fresh air in this striped midi dress! It's adorned with hidden side pockets to keep your hands warm and has a flattering A-line silhouette.

    Fit & Features

    • Striped print, woven fabric, woven lining
    • Strapless neckline
    • Stretchy smocked bodice
    • Hidden side pockets
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6069

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Fling Corset Tie A-Line Midi Dress

    Unleash your inner romantic in this midi dress at showers, graduations, or brunch! The tie bust corset bodice and lace-up back create a flattering silhouette, while the midi-length hem and textured fabric add a touch of playfulness.

    Fit & Features

    • Texture woven fabric, woven lining
    • Sweetheart neckline, wide shoulder straps
    • Dual tie front corset bodice, lace-up back
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6068

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Look Ruffle Skater Dress

    You'll love the effortlessly pretty look this flowy skater dress brings to your summer plans. It features a V-neckline, an open cross-back design, and a babydoll skater silhouette with a short ruffled hem.

    Fit & Features

    • Gauze woven fabric, woven lining
    • Sleeveless V-neckline
    • Spaghetti straps
    • Open cross-back design, tie closure, lower back cutout
    • Short ruffled hem
    • Babydoll skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6071

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ocean View Tropical Floral Satin Mini Dress

    Enjoy a dinner with an ocean view in this tropical floral satin mini dress! With a flattering strapless neckline and flowy A-line silhouette, this dress will have you feeling vibrant and luxe.

    Fit & Features

    • Tropical floral print, satin fabric, stretchy knit lining
    • Strapless neckline
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6075

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breath Of Fresh Air Smocked Maxi Tube Dress

    Step out looking like a breath of fresh air in this maxi tube dress on vacay or weekend plans! The strapless, stretchy, smocked bodice ensures a perfect and comfortable fit that flatters your figure while the flowy, maxi-length hem creates an effortless look.

    Fit & Features

    • Woven fabric, bust knit lining
    • Strapless V-wired neckline
    • Stretchy smocked bodice
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6076

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lovely Day Eyelet A-Line Midi Dress

    It'll be love at first wear in this strapless midi dress, perfect for shower celebrations, brunch, or parties! The intricate eyelet detailing adds a touch of romance while the flattering A-line silhouette accentuates your figure.

    Fit & Features

    • Eyelet woven fabric, woven lining
    • Strapless stretchy smocked neckline
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000604

    Category Name: Casual Dresses

    Price: $29.97 $64.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: M, L

    Product Badge:
    • Sale
  • In The Cards Halter Skater Mini Dress

    No matter the plans, this halter skater mini dress will have you looking fabulous! 

    Fit & Features

    • Stretchy rib knit fabric
    • Halter neckline
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2265

    Category Name: Casual Dresses

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destination Vacay Tropical Floral Mini Dress

    Jet set to your destination vacay in this tropical floral print mini dress, perfect for sunset happy hour. Designed with a square neck, adjustable spaghetti straps, and a short fitted silhouette, style with gold hoops and slide-on sandals.

    Fit & Features

    • Scuba knit fabric, stretchy knit lining
    • Tropical floral print
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Back zipper closure
    • Mini-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6077

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strolls In The Sand Halter Bodycon Mini Dress

    Stroll the beach in this halter mini dress while on vacation or enjoying the warm weather! The dress is designed in a unique texture knit that hugs your curves in a bodycon silhouette.

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Halter V-neckline, button closures
    • O-ring metal insert
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6080

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destination Cutie Tropical Cutout Slit Maxi Dress

    Get ready for your sunny destination with this stylish tropical maxi dress! Featuring a sweetheart neckline with a square insert, a flirty cutout bodice, and a high side slit, this dress is perfect for showing off your tropical vibes.

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Sweetheart neckline, square insert
    • Spaghetti straps
    • Cutout bodice, high side slit
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6081

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Mode Buckle Cutout Slit Maxi Dress

    A must-have maxi dress for any fashion-forward traveler! Featuring a sweetheart neckline with a trendy buckle accent, a sultry cutout bodice, and a high side slit, this dress will hug your curves and make you feel stylish on your vacation.

    Fit & Features

    • Texture knit fabric, smooth knit stretchy lining
    • Sweetheart neckline with buckle accent
    • Spaghetti straps
    • Cutout bodice
    • High side slit
    • Form-hugging fit, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6082

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dance To My Rhythm Abstract Tube Maxi Dress

    Perfect for any occasion when you want to stand out, this abstract maxi dress will have every eye on you! This sleek tube design hugs your curves in all the right places while the bold abstract pattern demands attention while the daring high side slit shows some leg.

    Fit & Features

    • Abstract print, mesh fabric, stretchy knit lining
    • Tube strapless neckline
    • High side slit
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6086

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Breeze Tropical Slit Midi Dress

    Turn heads on vacay in this tropical midi dress perfect for sunset cocktails and dinner! Featuring a strapless neckline with insert, this form-hugging dress will flatter your curves and keep you cool with a side slit and midi hem.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, short knit lining
    • Strapless neckline with insert
    • Form-hugging fit
    • Side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6088

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Love Eyelet Knit Mini Dress

    You'll love the effortless summer vibes of this floral eyelet knit mini dress! The short form-hugging fit will highlight your stunning curves.

    Fit & Features

    • Floral eyelet knit fabric with knit lining, high stretch
    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6090

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Style One-Shoulder Slit Tropical Maxi Dress

    Get that tropical feeling when you're in this one-shoulder maxi dress, whether you're on vacay or having some weekend fun! The curve-hugging silhouette offers a show of skin with a side cutout and high slit.

    Fit & Features

    • Tropical print, stretchy knit fabric, short knit lining
    • One-shoulder neckline
    • Side cutout
    • High side slit
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6089

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Brunch Plans Cherry Halter Skater Dress

    Turn heads effortlessly in this adorable cherry mini dress for brunch or celebrations! Its flattering halter neckline and playful skater silhouette create a perfect balance of flirty and fun for your summer wardrobe.

    Fit & Features

    • Cherry embroidered pattern
    • Gauze cotton fabric, multiple woven and tulle linings
    • Plunge halter neckline, tie closure
    • Back zipper and hook-eye closure
    • Drop waist seam
    • Skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000175

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Just Like A Dream Strappy Back Ruffled Maxi Dress

    Make a jaw-dropping entrance in this gorgeous ruffled maxi dress at shower celebrations or on vacation! The flattering V-neckline draws the eye, while the intricate strappy back adorned with beaded insets creates an unforgettable exit view.

    Fit & Features

    • Airy woven gauze fabric, woven lining
    • V-neckline
    • Dual spaghetti straps
    • Strappy back with beaded insets
    • Cascading ruffles, flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000653

    Category Name: Casual Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: RED, BROWN

    Available Size: XS, S, M, L, XL

  • Tropical Beauty V-Neck Slit Midi Dress

    Jet set on your next tropical getaway or weekend escape in this perfect slit midi dress! Featuring a bold metal insert and a flattering bodycon fit, this dress is perfect for any occasion. 

    Fit & Features

    • Palm leaf tropical print, stretchy knit fabric, soft knit lining
    • V-neckline with metal insert
    • Spaghetti straps
    • Side slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6095

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pleat The Way Scoop Neck Mini Dress

    Make way for setting the trends in this sleeveless mini dress with trendy spaghetti strap ties and a layered pleated mini-length hem. Pair with sneakers.

    Fit & Features

    • Smooth twill woven fabric, stretchy knit lining
    • Spaghetti strap ties
    • Side zipper and hook-eye closure
    • Scoop neckline
    • Form-hugging fit
    • Layered pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6096

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free