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!
-
Stripe It Right Sweater Dress
Stripe it right with this adorable sweater dress! It features a mini mock neck, short cap sleeves, and a short, curve hugging fit. The white dress is composed of a ribbed knit fabric that offers plenty of stretch and showcases a black and red striped print.
Style Number/Barcode: 06005-6179
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Spiced Up Knit Midi Dress
Spice up your wardrobe in this season appropriate copper midi dress! This cozy sweater dress features an off the shoulder neckline, long fitted sleeves, a comfortable slim fit, and a flatter midi length. Dress is composed of a ribbed knit fabric that offers plenty of stretch.
Style Number/Barcode: 06005-5987
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Pop Of Stripes Knit Dress
Accentuate those curves with a flattering pop of stripes! This black knit mini dress features an off the shoulder neckline, short sleeves, horizontal pink and white stripes across the bust and hips, and a comfortable slim fit. Dress is composed of a casual knit fabric with plenty of stretch.Model is 5'7" with a 34" bust, a 24" waist, and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-0006
Category Name: Casual Dresses
Price: $36.90
Availability: Out of Stock
Product Badge:- Clearance
-
Rock N' Roll Vintage Tunic
Channel your inner rocker with this vintage-inspired tunic! It features a round neckline, a multi strap distressed inset, short sleeves, a contrasting guitar graphic with a block script that reads: "Rock & Rock: Live Fast Die Young" and a distressed detailing throughout. Tunic is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch.Style Number/Barcode: 06002-0004
Category Name: Casual Dresses
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Can't Relate Henley Mini Dress
Basic? Sorry can't relate. Stand out in this natural mini dress that features a sleeveless bodice, a sweetheart neckline, a multi button down front with wooden buttons, wide shoulder straps and a mini length silhouette. Dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-1279
Category Name: Casual Dresses
Price: $22.00 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Flawless Style Knit Off-The-Shoulder Long Sleeve Mini Dress
Show off your stunning curves in this form-hugging mini dress made with pointelle knit fabric with plenty of stretch. It features a chic off-the-shoulder neckline with a fold-over design, long fitted sleeves, and ruched side seams along the short bodycon silhouette.
Fit & Features
- Pointelle knit fabric with knit lining, plenty of stretch
- Off-the-shoulder neckline with fold-over design
- Unlined long fitted sleeves
- Ruched side and back seams
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5917
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Pointelle knit fabric with knit lining, plenty of stretch
-
Glow Getter Strapless Cutout Mini Dress
Catch flights and compliments. This strapless mini hugs you in all the right places with a ruched bust ring detail and cheeky cutout that turns the charm up. Brunch, beach, or bae date—it’s a serve every time.
Fit & Features
- Rib knit stretchy fabric
- Strapless sweetheart tube neckline with hardware trim
- Cutout accent
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000033
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Spotted In Style Mini Dress
Spotted! You'll be stylin' from head to toe in this fab mini dress. It features a sleeveless bodice, thin shoulder straps, a V neckline, a sultry front waist cut out with a bar accent, and a short, form hugging fit. The leopard print dress is composed of a ponte knit fabric with moderate stretch.Model is
5’6.5” with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05103-3445
Category Name: Casual Dresses
Price: $13.44 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Ruched And Ready Mini Dress
Get ready to go out with the squad in this must have LBD! The black dress features a sleeveless bodice, a square neckline, narrow shoulder straps and a mini length silhouette. The body features ruched detailing throughout to showcase curves! Dress is composed of a lined mesh fabric that offers a moderate stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 05103-0177
Category Name: Casual Dresses
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Triple Threat Rhinestone Bodycon Dress
No one can mess with this ivory triple threat dress! They won't be able to take their eyes off you with this piece's side cut outs and three sparkling rhinestone bars. Dress has a deep V neckline with a lightly padded bust, narrow cord straps, an invisible back zipper, and princess seams for a longer and leaner illusion. Garment is composed of a thick crepe fabric that offers a moderate stretch. Includes a full lining.
Style Number/Barcode: 05103-2906
Category Name: Casual Dresses
Price: $17.97 $43.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Eyes On Me Mini Dress
Demand attention in this Insta-worthy day dress! It features a flirty off-the-shoulder neckline paired with short sleeves. Dress has a round hemline and is composed of a textured knit fabric that offers plenty of stretch.Model is 5'6" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-2257
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Nautical By Nature Mini Dress
This navy blue and white mini dress is a little naughty, but still sweet! It features a white, sleeveless knit bodice with a V neckline and adjustable shoulder straps. Her A-line skirt has a high paper bag waist with a tie belt, a double row of large buttons on the front, and side pockets.Model is 5'6.5 with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-4049
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Twist In Florals Maxi Dress
Give your look a pretty twist in this navy maxi dress! It features a sleeveless bodice, a plunging V neckline, narrow shoulder straps and an open back with tie strap accent. The slim fit bodice leads to a curve hugging maxi length silhouette accented with a high side slit. The all over floral print features pink hues to contrast with the navy background. Dress is composed of a lightweight woven fabric that offers a form hugging fit with a minimal stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 05102-4015
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Full Scoop Tank Mini Dress
Get the full scoop in this casual cutie! This black knit dress features a scoop neckline, tank-style straps, white stripes running down the sides, and a mini length. Dress is pullover with plenty of stretch.Model is 5'9" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-4036
Category Name: Casual Dresses
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Buttoned And Striped Maxi Dress
Give yourself a cute and casual look with this buttoned and striped maxi dress! It features a sleeveless bodice, spaghetti straps, a scoop neckline, a faux button down front, and a front slit. The black and white dress is composed of a knit fabric with 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: 05102-4028
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Casual Cutie Linen Maxi Dress
Go for casual and cute in this taupe dress! It features a V neckline, adjustable narrow straps and a maxi length silhouette with hidden side pockets. Dress is composed of a double lined linen knit fabric that offers a relaxed fit with minimal stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-3966
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Plus Crochet In Color Dress
This cute crochet dress is perfect for a day out! It features a V neckline, adjustable spaghetti straps that create an X back, a sheer crochet waist, and a short flared skirt with a full lining.
Style Number/Barcode: 15102-0017
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Lovely Little Floral Dress
Look oh so lovely in this little floral printed mini dress! It features a sleeveless bodice, spaghetti straps, a square neckline, a lettuce edge trim, and a short, form hugging fit. The natural hued dress is composed of a smocked and stretchy linen fabric and showcases an adorable all over ditsy floral print.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-3979
Category Name: Casual Dresses
Price: $13.94 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sculpted Chic Ribbed Knit Midi Dress
The ribbed knit dress features a sweetheart neckline with a twist accent at the bust, long sleeves, and a midi-length hem. Channel a casual vibe with chunky sneakers.
Fit & Features
- Ribbed knit fabrication
- Sweetheart neckline with twist accent
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5962
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Blooming Beauty Mini Dress
Have a cute brunch with your bffs as you bloom with beauty in this floral mini dress! It features an off the shoulder neckline with an overlay, a high waist seam, and a subtle ruffled seam at the hem. The black dress is composed of an unlined lightweight, flowy linen fabric with no stretch and showcases a pretty pink floral print.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-3981
Category Name: Casual Dresses
Price: $10.00 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Groovy Gal Striped Cutout Mini Dress
When your dress is the moment, this one’s got that groovy energy! The bold bell sleeves and plunging neckline were made for concerts, bright lights, and dance floors.
Fit & Features
- Striped texture knit fabric, soft stretchy knit lining
- Plunging V-neckline with half hoop insert
- Bell long sleeve
- Side cutouts and open back
- Bodycon silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000118
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Back In Basics Mini Dress
Fall back on basics for an effortlessly trendy look! This ivory mini dress features a sleeveless strapless bodice, a square neckline, and a short, curve hugging fit. The basic dress is composed of a sheer knit fabric with a full knit lining and 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: 05102-3971
Category Name: Casual Dresses
Price: $10.00 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Fiercely Wild Mini Dress
You're fiercely wild, so you need a dress to match! This mini dress features a sleeveless bodice, spaghetti straps, a scoop neckline, and a short, flattering fit. The dress is composed of a lined knit fabric and offers plenty of stretch and a curve hugging style. Zipper not included.
Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
Style Number/Barcode: 05102-3946
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Denim For Days Mini Dress
We're living for denim this season! Slay any day in this cute denim dress that features a scoop neckline, adjustable narrow straps and a matching scoop back. The curve hugging mini length silhouette features faded accents to create a pretty contrast! Dress is composed of a double lined denim fabric that offers a moderate stretch.Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
Style Number/Barcode: 05102-3952
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free