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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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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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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Rainbow Wave Maxi Dress
You love color, so embrace the rainbow! All eyes will be on you in this vibrantly chic maxi dress, which features a multi-hued stripe pattern, spaghetti straps, scoop neck, pockets at either hip, and plenty of stretch. Don't forget to pair it with the matching head wrap!
Style Number/Barcode: 05102-0244
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Daring In Denim Mini Dress
We dare you to be bold in this hot denim mini! The dress features a sleeveless strapless square neckline, double vertical seam detailing down the front and back, and a short, raw hem. The dress is composed of a jean fabric that offers moderate stretch and a curve hugging fit.
Model is 5'9" with a 33" bust, 24" waist and 35.5 hips. She is wearing a size small.
Style Number/Barcode: 05102-0162
Category Name: Casual Dresses
Price: $14.97 $36.90
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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Stylish And Sultry Mini Dress
You're a stylish girl who likes her look to be a little sultry too! This ribbed knit mini dress features long fitted sleeves, a wired sweetheart neckline with padded cups and a small front cut out, and a short, form hugging fit. The dress offers plenty of stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0103
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Memorable Moments Skater Dress
Create more memorable moments in this navy blue skater dress! It features a high round neckline, narrow shoulder straps that lead to a sheer lace back panel and a gold zipper, a fitted bodice with a high waist seam, and a short flowy skirt. Dress is composed of an unlined crepe fabric with a moderate stretch.
Style Number/Barcode: 05101-8465
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flowy Floral Mini Dress
This flowy floral dress is the perfect piece to transition into fall! It features a wrap front V neckline, a hidden back zipper and hook and eye closure, long sleeves with smocked cuffs, a faux button down front, a high waist seam, ruched detailing, and a flirty ruffle hem. The printed dress is composed of a sheer chiffon fabric with a stretchy knit lining.Style Number/Barcode: 05102-0303
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Live It Up In Linen Midi Dress
Live it up in this absolutely adorable ditsy floral printed midi! The dress features a sleeveless bodice, tie shoulder spaghetti straps, a sweetheart neckline with pleated detailing and a tie front, and a hidden back zipper and hook and eye closure. The dress is composed of a linen fabric with a shorter woven lining and has no stretch.Style Number/Barcode: 05102-0305
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Courtside Style Cutout Pleated Skater Dress
Look cute courtside in this stylish tennis-inspired skater dress! Featuring a trendy cutout back and a flattering skater silhouette, this pleated dress combines playful charm with modern flair.
Fit & Features
- Attached panty lining
- Scoop neckline, tank shoulder straps
- Double-lined soft knit bodice
- Cutout back design
- Woven pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000055
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Life's A Beach Mesh Dress
Hit the pool, bask by the beach, or prep to party in this colorful mesh maxi! Dress features a vibrant tropical print in turquoise, blue, and rust, a strapless neckline, dramatic ruffle trim running from bust to hem, a high front slit, and built-in briefs. Dress bodice is semi-sheer and does not include a top. Maxi is made from a mesh blend material with moderate stretch.Style Number/Barcode: 05102-0286
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Beauty Mini Dress
Girl, you're such a beauty, and this classically chic mini dress will make for the perfect 'fit. It features a sleeveless bodice, a V-neckline with a tie ruched bust detail, adjustable spaghetti straps, a square back with a hidden zipper and hook and eye closure, a trendy waist front cutout with a tie ruched detail, and a flowy skirt with an adorable ruffled mini-length hem. The short dress is composed of a woven fabric with minimal stretch. Style with a cute pair of mules.
Fit & Features
- Sleeveless bodice, V-neckline, tie ruched bust
- Adjustable spaghetti straps
- Square back, hidden zipper, hook and eye closure
- Waist front cutout, tie ruched detail
- Flowy skirt, ruffled mini-length hem
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-0263
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On Knit Mini Dress
You're always on it when it comes to style, and this basic knit mini will make for such a cute 'fit. The dress features a sleeveless bodice, tank-like shoulder straps, a square neck and back, and a short, form hugging fit. The dress is composed of a soft knit that offers plenty of stretch.Style Number/Barcode: 05102-0095
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mod Mini Belted Dress
Get retro glam in this sunny, striking mini! Dress has a body con cut and features thick, tank-style straps, a square neckline, seam detail at bust, an attached fabric belt with oversize buckle, and a pencil skirt. Dress is lined, slips on, and is made from a woven crepe material with a fair amount of stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0171
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wild Child Bodycon Mini Dress
Stay fierce in a dress as wild as you! This bodycon features elasticized spaghetti straps and a square neckline. Cut to a flirty mini length, this piece is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Dress also includes a knit lining.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0152
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Key Velvet Bodycon
The key to a fab holiday look? This black velvet bodycon dress! It has a mock neckline, long fitted sleeves, a keyhole cut out on the front and back, cross straps at the front, and a body-hugging fit. Dress is composed of an unlined, velvet knit fabric with plenty of stretch.
Style Number/Barcode: 05101-8068
Category Name: Casual Dresses
Price: $14.44 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Florals And Lace Skater Dress
Make it a lacy affair in this must have floral mini dress! It features a sleeveless bodice, a V neckline, princess seams and spaghetti straps. The back features an unlined floral lace back that leads to a lower back keyhole. The slim fit bodice leads to a curve hugging mini length silhouette. Dress is composed of a lined crepe fabric that offers a moderate stretch.Style Number/Barcode: 05101-0079
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Walk The Mock Neck Mini Dress
Talk the talk and walk the walk in this must have mini dress! It features a sleek, form hugging silhouette with a mock neck, long sleeves with thumb-hole slits, and a mini length. Brushed knit offers plenty of stretch.
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small
Style Number/Barcode: 05102-0123
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendsetter In Tie Dye Mini Dress
Be a total trendsetter in this fun tie dye mini dress! It features a sleeveless bodice, tank-like shoulder straps, a scoop neckline, a tie front accent, and a short, curve hugging fit. The dress is composed of a stretchy knit fabric.
Style Number/Barcode: 05102-0227
Category Name: Casual Dresses
Price: $11.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Babe Button Down Midi Dress
Yes babe, you'll totally work it in this chic button down midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a square neck and back, lined and padded cups, flattering horizontal seam detailing along the bust, a hidden back zipper closure, a high rise paper bag waist with a tie front belt, faux button detailing, and a mid-length skirt that offers a form hugging fit. The top is composed of a ribbed linen fabric and the skirt is made from a stretchy knit.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0245
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Unforgettably Sweet Floral Bodycon Ruffle Mini Dress
Create an alluring look in this floral mini dress in a bodycon fit with a flirty ruffled hem. Perfect for shower celebrations and graduations!
Fit & Features
- Floral print, lace-lined fabric
- Strapless neckline
- Bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5985
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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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