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.
Now Trending
STYLE SPOTLIGHT
Discover New Skater Dress Styles
Everyday Ease: Casual Dresses for Transitional-Weather Plans
From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.
Laid-Back & Versatile
Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.
Chic from Day to Night
Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in nuetral or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.
Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.
What Makes a Dress Casual?
Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.
Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.
How Do I Style a Dress Casually?
Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.
For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!
-
Crochet In Color Dress
This cute crochet dress is perfect for a day out! It features a V neckline, padded cups, adjustable spaghetti straps that create an X back, a sheer crochet waist, and a short flared skirt with a full lining. Dress is composed of a combination lace and gauze fabric that offers a relaxed fit with minimal stretch.*Also available in Plus.
Style Number/Barcode: 05102-3959
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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