Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and your calendar.
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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.
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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
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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
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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:- Ships Free
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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