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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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!
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Live It Up Tie Dye Knit Mini Dress
Live it up in this majorly on-trend tie dye mini dress! Featuring a chic lace-up back and a curve-hugging fit, this dress is perf to make a stylish statement at your next brunch. Simply pair it with some clear mules for a gorgeous look.
Fit & Features
- Scoop neckline
- Spaghetti straps leading to a lace-up back
- Short, form-hugging fit
- Tie dye knit fabric
Style Number/Barcode: 05102-0884
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stylishly Ruched Ribbed Knit Mini Dress
This stylish ruched ribbed knit mini is the perf everyday dress you need in your closet! Featuring trendy ruched detailing and double ties at each side, this dress can be worn as a mini or a midi. Pair with some sleek booties for your new fave fall 'fit.
Fit & Features
- Crew neckline
- Short sleeves
- Ruched detailing
- Double ties at each side
- Ribbed knit fabric
- Form-hugging fit
Style Number/Barcode: 05102-0838
Category Name: Casual Dresses
Price: $19.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Need For Basics Ribbed Midi Dress
Get your need for basics in a dress that can be dressed up or dressed down for your next day out. The dress features a trendy square neckline, tank-like straps, and a midi length silhouette. Complete your look with clear heels and statement hoop earrings.
Fit & Features
- Sleeveless square neckline
- Tank-like straps
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0871
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Knit Ruched Mini Dress
This ribbed knit ruched mini dress will be a staple in your fall wardrobe! It features a curve-hugging silhouette with ruched detailing and side tie accents. It can be worn as a cute mini or pulled down as a midi dress. Pair with some bold door knocker earrings and clear heels for that chic vibe you can wear to date night.
Fit & Features
- High crew neckline
- Tank-like shoulder straps
- Form-hugging fit
- Ruched detailing
- Side ties at hem
- Ribbed knit fabric
Style Number/Barcode: 05102-1828
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Vibes Knit Midi Dress
Rock those basic vibes in a dress that keeps it comfortable and chic. The everyday dress features a sleeveless bodice, a v-neckline with notched detail, and a midi length silhouette. Complete your look with chunky sneakers and a chunky necklace to create a trendy streetwear look.
Fit & Features
- Sleeveless bodice
- V-neckline with notched detail
- Midi length silhouette
- Knit fabric
- Form hugging fit
- Moderate stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0924
Category Name: Casual Dresses
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keep It Rosey Slip Midi Dress
Keep it rosey in this cute slip dress that keeps your look effortlessly pretty! Step out this season in a slip dress that features a pretty floral print, a high side slit and a midi length silhouette. Complete your look with clear heels and fringe earrings.
Fit & Features
- Plunging v-neckline
- Adjustable spaghetti straps
- Floral print
- High side slit
- Midi length silhouette
- Lightweight woven fabric
- Relaxed fit
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0836
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feelin' Basic V Neck Knit Mini Dress
Sometimes it's a good thing to be basic! This knit mini dress features a deep V neckline and a short, flattering, curve-hugging fit. Keep it casual with some chunky sneakers and gold hoops for a day date with bae.
Fit & Features
- Spaghetti straps
- V neckline
- Square back
- Mini length silhouette
- Double-lined knit fabric
Style Number/Barcode: 05102-0880
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Style Vibe Striped Knit Long Sleeve Mini Dress
Lean into the cozy style vibes with this trendy striped ribbed knit mini dress featuring a mock neckline, long fitted sleeves, and a short bodycon silhouette to hug your curves. Pair with knee-high boots!
Fit & Features
- Striped ribbed knit fabric, plenty of stretch
- Mock neckline, lettuce-edge trim
- Long fitted sleeves, lettuce-edge trims
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5882
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Twist Back Ribbed Knit Midi Sweater Dress
Keep your look on point and trendy in this chic twist back knit sweater dress! Featuring a partially open back and a mid-length, curve-hugging silhouette, this dress is perfect for the fall season. Dress it up with statement earrings for a cute fall date night.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Open back with twist back detail
- Mid-length silhouette
- Form-hugging fit
- Ribbed sweater knit fabric
Style Number/Barcode: 06005-0846
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keepin' Knit Chic Midi Sweater Dress
Keep it chic and stylish in this knit midi sweater dress, a perf transitional piece into the new season! It features a curve-hugging fit and a mid-length silhouette. Pair the dress with some trendy heeled booties for that must-have fall look.
Fit & Features
- V neckline
- Tank-like shoulder straps
- Mid-length silhouette
- Form-hugging fit
- Ribbed sweater knit fabric
Style Number/Barcode: 06005-0832
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruffled Romance Off The Shoulder Maxi Dress
Spark romance in a ruffled dress that is too gorgeous! The maxi dress is perfect for your next date night with bae. The dress features an alluring off the shoulder neckline, a ruffled bodice, and a tiered ruffle maxi length silhouette. Complete your stunning date night outfit with clear heels and duster earrings.
Fit & Features
- Off the shoulder neckline
- Ruffled bodice
- Off the shoulder straps that cascade shoulders
- Tiered maxi length silhouette, partially sheer
- Mini skirt length knit lining
- Lightweight woven fabric
- Relaxed fit, minimal stretch
Style Number/Barcode: 05102-1007
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Total Babe Sultry Ruched Mini Dress
Hey babe! Get ready to werk it in this sultry ruched mini dress! Featuring a short, curve-hugging silhouette and an allover polka dot print, this little black dress is perf for a date night out. Simply add on some chic mules and you'll be gorgeous from head to toe.
Fit & Features
- Adjustable spaghetti straps
- Scoop neckline
- High waist seam under bust
- Ruched, form-hugging fit
- Dual drawstrings at hem
- Mini length silhouette
- Polka dot printed mesh fabric
Style Number/Barcode: 05102-0636
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Viper Vixen Snake Print Mini Dress
You'll be a total stylish vixen in this trendy snake print mini dress! It features a flattering square neckline and a curve-hugging fit. Keep it chic with some dazzling duster earrings and heels for a night out.
Fit & Features
- Spaghetti straps
- Square neck and back
- Short, form-hugging fit
- All over snake print
- Knit fabric
Style Number/Barcode: 05102-0837
Category Name: Casual Dresses
Price: $10.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Off The Shoulder Button Down Mini Dress
This adorable off the shoulder button down mini dress is perfect for transitioning to the cooler fall months! Featuring long fitted sleeves and a curve-hugging fit, pair this knit dress with some chunky sneakers for a trendy chic look.
Fit & Features
- Off the shoulder neckline
- Long fitted sleeves
- Button-down front
- Short, form-hugging fit
- Ribbed knit fabric
Style Number/Barcode: 05102-0828
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Dream Tie Dye Ruched Mini Dress
You'll look like such a dream in this trendy tie dye mini dress! It features ruched detailing with side ties and a form-fitting style that will hug your curves. Pair this dress with some sleek gold hoops and chunky sneakers for that perf everyday vibe.
Fit & Features
- Crew neckline
- Short sleeves
- Ruched detailing
- Side ties at hem
- Short, form-hugging fit
- Tie dye print
- Knit fabric
Style Number/Barcode: 05102-0867
Category Name: Casual Dresses
Price: $13.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep It Sweet Puff Sleeve Mini Dress
Keep your look sweet and stylish in this adorable puff sleeve mini dress! It features a tie front detail and a short, curve-hugging fit. Pair this cute dress with some strappy heels and a chic mini handbag for a brunch date with your squad.
Fit & Features
- Short puff sleeves
- Sweetheart neckline
- Tie front detail
- Back zipper closure
- Short, form-hugging fit
- Woven fabric
- Runs true to size
Style Number/Barcode: 05102-1011
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All About Knit Mock Neck Mini Dress
You'll be totally all about this chic mock neck mini dress! Featuring long fitted sleeves and a curve-hugging fit, this dress is perfect for the fall season. Pair with gold hoop earrings and chunky sneakers for that fab everyday 'fit.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Short, form-hugging fit
- Knit fabric
Style Number/Barcode: 05102-0855
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Timelessly Chic Ribbed Knit Basic Midi Dress
Keep it timelessly chic in a dress that wows! Perfect for a cocktail event or making the right first impression, this mini dress is a must! The dress features a crew neckline with a racer bust, a fitted form-hugging fit, and composed of a ribbed knit fabric. Complete your chic outfit with mules and duster earrings.
Fit & Features
- Sleeveless crew neckline
- Racer bust
- Ribbed knit fabric
- Form hugging fit
- Midi length silhouette
Style Number/Barcode: 05102-0894
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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The Every Day Knit Mini Dress
Keep it cute in a basic mini dress that is perfect to wear any day! The dress features an off the shoulder neckline with a boat neck bust, short sleeves, and composed of a flattering knit fabric. Complete your outfit with sleek stilettos and a cute crossbody.
Fit & Features
- Off the shoulder neckline
- Short sleeves
- Boat neckline
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0892
Category Name: Casual Dresses
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tied to Basics Ribbed Knit Scoop Neck Mini Dress
Get tied to basics in a ribbed mini dress that is oh too gorgeous! The dress features a scoop neckline, tie spaghetti straps, and composed of a ribbed knit fabric that hugs curves in all the right places. Complete your casually cute look with stud earrings and block heels.
Fit & Features
- Scoop neckline
- Tie spaghetti straps
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0978
Category Name: Casual Dresses
Price: $7.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Fierce Ribbed Knit Mini Dress
Keep it fab and fierce in a mini dress that keeps your look on point! The ribbed mini dress features a plunging sweetheart neckline, bust seams at the cups, adjustable spaghetti straps, and composed of a form-hugging ribbed knit fabric. Complete your look with hoop earrings and wedge heels.
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Bust seams at the cups
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0792
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Charming Ditsy Floral Ruffled Mini Dress
Charm in a floral dress that brings the gorge factor for your next brunch date. The dress features a sweetheart neckline with ruffled trim, adjustable spaghetti straps, a ditsy floral print, and a mini length silhouette with a multi-tiered ruffled detail. Complete your charming outfit with wedge heels and a sleek bracelet.
Fit & Features
- Sleeveless sweetheart neckline with ruffled trim
- Adjustable spaghetti straps
- Ditsy floral print
- Multi-tiered ruffled detail
- Mini length silhouette
- Smocked knit fabric
Model is 5'9" with 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-1009
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simply Amazing Long Bell Sleeve Mini Dress
A simply amazing little black dress you'll adore wearing on dressy occasions! It features a square neckline, long bell sleeves with trendy ruched adjustable ties and slit accents, a flattering bodycon silhouette, and a mini-length hem. The dress is composed of a double-lined soft brushed knit fabric. Complete the look with a chic mini purse and heels.
Fit & Features
- Double-lined soft brushed knit fabric
- Moderate stretch
- Square neckline
- Long bell sleeves, ruched adjustable ties, slit accents
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5318
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Feels Ruched Tie Dye Mini Dress
Throw it back in a retro dress that gives us groovy feels. The dress features a sleeveless square neckline, a tie-dye print, and mini length silhouette with ruched drawstrings to customize fit or create an asymmetrical hem. Complete your outfit with trendy block heels and fringe earrings.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Tie-Dye print
- Mini length silhouette
- Ruched drawstring
- Smooth knit fabric
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0845
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance