Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on 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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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
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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: 05102-6078
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
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Sweet Flirt Floral Mini Tube Dress
Bring the sweet flirty vibes to your weekend plans in this cute mini tube dress with a dainty floral print on lined chiffon fabric. The strapless smocked bodice leads to a V-shaped waist, tiered ruffled design, and flowy skater silhouette.
Fit & Features
- Woven chiffon fabric with stretchy knit lining, dainty floral print
- Strapless straight-across neckline
- Stretchy smocked bodice
- V-shaped waist
- Tiered ruffled design
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-4077
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
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On Vacay V-Neck Floral Maxi Dress
Look a daydream come true in this floral maxi dress while on vacay! Designed with a bold floral print on a sultry form-hugging silhouette.
Fit & Features
- Floral print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-4076
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready To Bloom Strapless Lace-Up Floral Maxi Dress
With the warmer months ahead it's time to bloom in this floral maxi dress perf for vacations and weekend getaways! The dress boasts an eye-catching lace-up back and a mermaid silhouette that accentuates your natural curves.
Fit & Features
- Floral print, knit fabric lined with stretchy knit
- Lace-up back
- Mermaid silhouette
- Ruffled maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-4080
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Paradise Beauty Floral Mesh Maxi Dress
A beautiful floral mesh maxi dress for your escape to paradise! The dress boasts a flattering V-neckline and a form-hugging fit that flares into a flowy maxi-length hem. Pair with earrings and a bracelet.
Fit & Features
- Floral print, mesh lined fabric
- V-neckline
- Spaghetti straps
- Form-hugging fit
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-4075
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Energy Strapless Floral Mesh Maxi Dress
Bring major energy in this strapless floral mesh maxi dress design to flaunt your figure in a bodycon fit and show some skin with a high-side slit. Pair with mules.
Fit & Features
- Floral print, mesh fabric, soft and stretchy knit lining
- Strapless neckline
- High-side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-001515
Category Name: Casual Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: In Stock
Available Color: PLUM-2
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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Showstopper Cutout Ruffle Slit Maxi Dress
Serve major allure in this sleeveless maxi dress while on vacay or weekend getaway! The maxi dress delivers a sultry design with a twist plunge V-neckline, cutout bodice, and a high front slit with a ruffled trim.
Fit & Features
- Slinky knit fabric, short knit lining
- Plunge twist V-neckline
- Shoulder straps, one metal accent piece
- Cutout bodice
- High front slit with ruffle trim
- Bodycon maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-4070
Category Name: Casual Dresses
Price: $9.97 $46.90
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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Trend Moment Lace-Up Bodycon Midi Dress
Have your trending moment in this midi dress! It's designed to hug your curves in a bodycon silhouette while the front lace-up adds a playful touch to your day or night look.
Fit & Features
- Knit fabric with moderate stretch
- Square neckline
- Lace-up front bust
- Spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6072
Category Name: Casual Dresses
Price: $9.97
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Beauty Tropical Print Maxi Dress
Show off your beauty at sunset happy hour in this tropical print maxi dress designed with sheer mesh fabric and a mini-length lining. The high-cut side slit adds an alluring detail to turn heads.
Fit & Features
- Sheer knit fabric with mini-length knit lining, high stretch
- Tropical print
- Sleeveless cowl neckline
- Spaghetti straps, cross-back design
- High side slit
- Maxi-length fitted silhouette
- Runs true to size
Style Number/Barcode: 05102-6074
Category Name: Casual Dresses
Price: $9.97 $38.90
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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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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In Tulum One-Shoulder Tropical Maxi Dress
Perfect for your vacay in Tulum, this one-shoulder tropical maxi dress was made for sunset dinners and dancing!
Fit & Features
- Tropical print, smooth knit fabric with short stretchy lining
- One-shoulder neckline
- One shoulder strap with metal accents
- Front ruffled slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6073
Category Name: Casual Dresses
Price: $9.97 $44.90
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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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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Dinner Downtown Sleeveless Ruched Midi Dress
The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch.
Fit & Features
- Smooth knit fabric, stretchy knit lining
- Sleeveless crew neck
- Side ruched seams
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6066
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Girlie Bow Pleated Skirt Romper
Feel like a dream in this modern sleeveless romper with a front bow inset and pleated skirt overlay that boasts a flirty silhouette. Complete the look with boots.
Fit & Features
- Smooth knit fabric
- Square neckline, wide shoulder straps
- Front bow inset
- Pleated skirt overlay, shorts lining
- Runs true to size
Style Number/Barcode: 06503-1267
Category Name: Casual Dresses
Price: $19.97 $46.90
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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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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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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Flawless Beauty Cutout A-Line Midi Dress
Step out in this A-line midi dress for a flawless look all spring to summer! Designed with a sleek sweetheart neckline and underbust cutout, this dress makes a delightful impression.
Fit & Features
- Woven fabric
- Sweetheart neckline
- Adjustable spaghetti straps
- Underbust cutout, back zipper closure
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6064
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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 Vibe Tropical Floral Halter Maxi Dress
You'll be a total vibe on your summertime vacay in this tropical floral print maxi dress. The plunging halter neckline, ruched side seams, and curve-hugging fit are all alluring details you'll love.
Fit & Features
- Knit fabric with knit bust lining, high stretch
- Tropical floral print
- Sleeveless plunge V-neckline
- Tie-back halter straps, partially open back
- Ruched side seams
- Maxi-length hem, curve-hugging fit
- Runs true to size
Style Number/Barcode: 05102-6056
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free