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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Flow With It Maxi Dress
Go with the flow of this pretty summer maxi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline, a stretchy smocked square back, a front crochet top with sheer insets at the waist, and a long, floor length flowy maxi skirt with a front high thigh slit. The dress is composed of a linen fabric with no stretch.
Style Number/Barcode: 05102-0085
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruche Hour Sleeveless Mini Dress
Subtly sophisticated, this ruched mini is equally sultry—and ready for evenings out! Dress features a mesh overlay, high neck, slim-cut sleeveless bodice, and ruching detail at the sides, back, and front beginning at the waist. Slip-on style is fully lined and made offers a fair amount of stretch.
Style Number/Barcode: 05103-0073
Category Name: Casual Dresses
Price: $11.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vixen Side Stripe Mini Dress
Channel the look of your fave '90s-era cool girls in this of-the-moment mini. Dress features spaghetti straps, a square neckline, and stripes running vertically from bust to hem at either side. Dress slips on and is made from an ultra-soft woven material with moderate stretch.
Style Number/Barcode: 05102-0044
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vacay All Day Mini Dress
Feel like you're on a vacay all day in this fun tropical printed mini! It features a sleeveless bodice, spaghetti straps, a scoop neckline, and a short, form hugging fit. The dress is composed of a scuba knit fabric that offers moderate stretch and showcases a vibrant print.
Style Number/Barcode: 05102-0008
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Anything But Basic Maxi Dress
This sophisticated, streamlined maxi will more than earn its place in your closet this season. Chic and versatile, it goes pretty much anywhere you do! Dress features a square neckline, all-over rib knit detail, crisscross spaghetti straps, adjustable keyhole tie detail, back cutout, and side slit. Dress is partially lined and made from a soft, densely knit material with moderate stretch.
Style Number/Barcode: 05102-0012
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take The Plunge Floral Maxi Dress
Add a hint of island-inspired chic to your wardrobe with this gauzy sleeveless maxi dress. Dress features a deep V at front and back, a shirred banded waist, and an all-over floral print. Dress is composed of a rayon fabric and has plenty of stretch in the waist and moderate stretch throughout the rest.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-4050
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft And Sweet Dress
Show off your soft sweet side baby girl! This off shoulder dress is the perfect ensemble for a day in the sun. Featuring a straight off-shoulder neckline and wooden buttons down the middle, this dress has a form fitting bodice and a ribbed knit material that will offer maximum stretch as well as a soft inner lining. Show off those shoulders girl!
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-4039
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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My Wavelength Skater Mini Dress
Good vibes only in this skater dress! The mini skater dress features a deep v-neckline, spaghetti straps that offer plenty of support, back zip, a darted bust that adds structure to the bodice, a banded waist that flatters, and A-line flared skirt. Complete outfit with chic clear heels and statement earrings.
Fit & Features
- Sleeveless v-neckline
- Darted seams at the bust
- Spaghetti straps
- Banded waist
- A-line skater silhouette
- Composed of soft mid-weight woven fabric
- Form hugging fit
Ivory and Mint Dress: Model is 5'8" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.
Blue Dress: Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Denim Dress: Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-8697
Category Name: Casual Dresses
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Miss Midi Striped Dress
Hey there miss midi, we see you! and we are on the same page too, filling our closet with midi dresses this season. This piece features a v-neckline, attached dark neutral marbled buttons, and adjustable spaghetti straps that lead to a square back. This toned midi dress has a skinny stripe pattern and is composed of a soft knit material that offers maximum stretch.
Style Number/Barcode: 05102-3992
Category Name: Casual Dresses
Price: $8.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stun And Snap Mini Dress
Stun in this snap-worthy LWD (Little White Dress)! The sweater dress features a sleeveless bodice, spaghetti straps, a V neckline, a gold faux snap button front, and a short, curve hugging fit. The black dress is composed of a ribbed knit fabric that offers plenty of stretch.Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06005-0175
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Miss Midi Striped Dress
Hey there miss midi, we see you! and we are on the same page too, filling our closet with midi dresses this season. This piece features a v-neckline, attached dark neutral marbled buttons, and adjustable spaghetti straps that lead to a square back. This red toned midi dress has a skinny stripe pattern and is composed of a soft knit material that offers maximum stretch.
Style Number/Barcode: 05102-3994
Category Name: Casual Dresses
Price: $9.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweetly Tied Skater Dress
Sweeten up your look with this adorable red skater dress! It features a sleeveless bodice, adjustable halter straps that lead to a button back closure with a keyhole cut out below, a back zipper and hook and eye closure, a V neckline, a cute tie front detail, and a flowy skater skirt. The dress is composed of a lightweight linen fabric with a short knit lining.
Style Number/Barcode: 05102-3826
Category Name: Casual Dresses
Price: $13.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ruffled And Rowdy Dress
Dance around and get rowdy in ruffles! This adorable mini dress features a v-neckline with a snap and hook closure. The bodice of this dress is line with a ruffled trim, thick ruffled straps that lead to a low back, with a hidden zipper and a self tie bow. The skirt is adorned with a tiered ruffle effect. The dress is composed of a chiffon style material and offers no stretch yet, a flowy fit and includes a smooth inner lining. Now take a twirl!
Style Number/Barcode: 05102-0206
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Botanical Beauty Midi Dress
This botanical print dress features a square ruffled neckline, elastic ruffle straps and a straight bodice. The backing of the dress has a hidden zipper and stretch smock detailing.This piece has a dark toned floral print and is mid-length with a smooth inner lining and a side slit.It is composed of a sheer chiffon-like material that offers a relaxed fit with minimal stretch. On a stroll through the park or a gals brunch date, this dress is bound to have heads turning!Model is 5'9" with a 32" bust, a 24" waist, and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0210
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Color Wheel Striped Mini Dress
Rendered in bright stripes, this mini makes an impact. Dress features a fitted bodice with off-the-shoulder neckline, contrast gently pleated, A-line skirt, and a gathered elasticized waist with decorative tie. Dress is made from a soft, lightweight woven material with stretch through the bodice and waist.
Style Number/Barcode: 05102-0000
Category Name: Casual Dresses
Price: $11.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Wrapped Mini Dress
Keep it simply sophisticated in this statement mini dress! The dress features a plunging wrap V neckline with pleated accents, adjustable spaghetti straps and an asymmetrical hem with ruched detailing. Dress is composed of a lined smooth knit fabric that offers a curve hugging fit with a moderate stretch. Includes a back zipper closure.
Style Number/Barcode: 05102-3948
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Classic Chic Shirt Dress
This classic chic mini shirt dress is everything you need and more. It features a collar, a plunging wrap front V neckline, long sleeves with buttons to cuff, a high waist seam, side ruched detailing, and a short fit. The dress is composed of a woven fabric with no stretch.
Model is 5'9" with a 33" bust, 24" waist and 35.5 hips. She is wearing a size small.
Style Number/Barcode: 05102-0293
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Smocked And Stylin' Mini Dress
This adorable floral printed mini is smocked and stylin'! The dress features a sleeveless bodice, tie shoulder spaghetti straps, a square neckline with a bust keyhole cut out, a square back, pleated details, and a stretchy and smocked fit. The dress is composed of a lightweight linen fabric that offers a form hugging fit.
Style Number/Barcode: 05102-0283
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Stunner Midi Dress
Be a stylish stunner in this gorg floral midi dress! It features a sleeveless bodice, adjustable spaghetti straps that cross in the back, a V neckline, side ruched detailing, and an asymmetrical hem. The dress is composed of a knit fabric that offers plenty of stretch.
Style Number/Barcode: 05102-3848
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Knotch It Up Mini Dress
This dress is a cute versatile a piece, dress it up with some strappy heels or throw on your favorite sneaks. This piece features a sleeveless bodice, with U shaped neckline, a knotch cut out at the center of the bust area. The dress has a smooth inner lining and is composed of a soft knit material that is ribbed for a casual style. The hem hits above mid thigh, and is form fitting with a moderate stretch.Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06002-0107
Category Name: Casual Dresses
Price: $8.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Steal The Scene Skater Dress
Steal the scene and turn heads in this captivating skater dress! It features a sleeveless bodice, spaghetti straps that lead to an open cross back and lattice details, vertical seams that run down the bust, a high waist seam, and a flowy high low skater skirt. The dress is composed of a crepe fabric that offers moderate stretch.Style Number/Barcode: 05101-8831
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Connection Mini Dress
Make a sweet connection in florals! This must have mini dress features a sleeveless bodice, a cowl neck, spaghetti straps and a mini length silhouette to show glowing gams! The neutral tone is complemented with pretty florals throughout! Dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch.
Style Number/Barcode: 05102-0086
Category Name: Casual Dresses
Price: $13.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fresh Blooms Side Slit Maxi Dress
It's time to refresh and reset for the szn! This spring-ready maxi will be your go-to piece for daytime events! Slip into some mules and add some layered necklaces for a pretty OOTD!
Fits & Features
- Spaghetti Straps
- Scoop Neckline
- Thigh High Side Slit
- Maxi Length Silhouette
- Form Hugging Fit
- Zipper Not Included
Model is 5'9" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0289
Category Name: Casual Dresses
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Knit Mini Dress
This mini dress is composed of a very soft knit material. It is form fitting, hugs your curves and has a maximum stretch, and the hem meets mid thigh. It features a round neckline and spaghetti straps that lead to a round back. This dress will pair well with sneakers and a jean jacket or a leather jacket and heels! Play dress up with it, it goes with everything!
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0232
Category Name: Casual Dresses
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free