Casual Dresses
Casual dresses that keep up with your plans—brunch, game day, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and sweater knits, these pieces prove laid-back can still look styled. Play it polished with a shirt dress or belted A-line, lean comfy-cute in a fitted bodycon, 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 outing, these casual dresses are built to move with your mood—and your calendar.
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STYLE SPOTLIGHT
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Everyday Ease: Casual Dresses for Cool-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.
Laid-Back & Versatile
Knit, ribbed, and sweater dresses bring comfort and style to crisp fall 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 burgundy 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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Breaking The Rules Plaid Mini Dress
Break the rules with a mini dress that doesn't play it safe! The dress features a plaid print, a sleeveless square neckline, spaghetti straps, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with thigh-high boots.
Fit & Features
- Plaid print
- Sleeveless square neckline
- Spaghetti straps
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4168
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Beauty A-Line Midi Dress
Bring a sweet style to your everyday look with this adorable flowy midi dress. It features a square neckline, half-length puff sleeves, a partially smocked back, a high waist, and a mid-length, A-line silhouette with a tiered hem. Complete the outfit with sleek hoop earrings and cute mules.
Fit & Features
- Square neckline
- Half-length puff sleeves, elastic cinched hems
- Partially smocked back
- High waist
- Mid-length, A-line flowy silhouette, tiered hem
- Cotton fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4243
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cutout Crush Hour Midi Dress
Warning: This midi dress is sure to cause double takes. From the front-tie detail to the high leg slit, it’s giving effortless bombshell, perfect for pool parties or a cute brunch!
Fit & Features
- Sweater knit stretchy fabric
- V-neckline with tie bust design
- Adjustable spaghetti straps
- Underbust cutout accent
- Front slit
- Bodycon fit, midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000014
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Make A Seam Ribbed Knit Mini Dress
Create a stylish scene with a dress that brings major exposure! The dress features a square neckline, long sleeves, exposed vertical seams that create an hourglass effect, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and hoops.
Fit & Features
- Square neckline
- Long sleeves
- Exposed vertical seams
- Mini length silhouette
- Ribbed knit-lined fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4214
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On That Retro Vibe Colorblock Mini Dress
Channel those retro vibes with this fab mini dress! The dress features a colorblock pattern, a crew neckline, long sleeves, a cutout at the midriff with criss-cross straps, dual ruched drawstrings at the hem, and a mini-length silhouette. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Colorblock pattern
- Crew neckline
- Long sleeves
- Cutout at midriff, criss-cross straps
- Dual ruched drawstrings
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4192
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Raising The Bar Plaid Mini Dress
Raise the bar with a mini dress that is part classy, part casual! The dress features a plaid print, a sleeveless square neckline, and a mini-length silhouette. The dress is composed of a lined knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a denim jacket.
Fit & Features
- Plaid print
- Sleeveless square neckline
- Mini length silhouette
- Lined knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4256
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pull In Closer Tie Dye Mini Dress
Pull in closer with a trendy mini dress! The dress features a tie-dye print, a crew neckline, long sleeves, ruched drawstrings, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Tie-dye print
- Crew neckline
- Long sleeves
- Ruched drawstrings
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4084
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Make It Chic Ribbed Knit Mini Dress
Make a chic impression with a mini dress that gives off those effortlessly chic vibes! The dress features a sleeveless collared neckline, a button-down front, contrasting hued trim, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules.
Fit & Features
- Sleeveless collared neckline
- Button-down front
- Contrasting hued trim
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0990
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Style Icon Denim Mini Dress
Stun like the style icon you are with a mini dress that stuns! The dress features a sleeveless sweetheart neckline, lightly padded cups, adjustable spaghetti straps, corset-like seams at the bodice, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless sweetheart neckline
- Lightly padded cups
- Adjustable spaghetti straps
- Corset-like seams at bodice
- Mini length silhouette
- Denim fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4085
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Stunner Brushed Knit Mini Dress
Stun like the major babe you are with a chic mini dress! The dress features a collared neckline, short sleeves, a zipper front closure, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and a clear clutch.
Fit & Features
- Collared neckline
- Zipper front
- Short sleeves
- Mini length silhouette
- Double-lined brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4286
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The Classic Plaid Mini Dress
Keep it classy with a plaid mini dress that channels those preppy vibes! The dress features a sleeveless square neckline, spaghetti straps, a plaid print, and a mini-length silhouette. The dress is composed of a lined brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with booties.
Fit & Features
- Sleeveless square neckline
- Spaghetti strap
- Plaid print
- Mini length silhouette
- Lined brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4232
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Fab Tie-Dye Mini Dress
Get a casually fab look in this on-trend tie-dye mini dress. It features a crew neckline, short sleeves, ruched detailing down the sides with ties at the hem, and a short, curve-hugging silhouette. Style this dress with a denim jacket and sneakers.
Fit & Features
- Crew neckline
- Short sleeves
- Ruching down the sides
- Ties at the hem
- Mini-length, form-hugging fit
- Ribbed knit fabric, plenty of stretch, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-4233
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All The Right Moves Ruched Mini Dress
Make all the right moves with a mini dress that showcases your curves! The dress features a sleeveless square neckline, bungee spaghetti straps, a ruched body, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ruched body
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4275
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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First In Class Plaid Mini Dress
Keep it classy with a plaid dress that is perf for making a stylish first impression. The dress features a sleeveless square neckline, spaghetti straps, a plaid print, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with heels.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Plaid print
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4169
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Extra Extra Newspaper Print Mini Dress
You'll be the talk of the town babe in this eye-catching mini dress! It's designed with a unique newspaper print, ruched tie sides, and thin spaghetti straps. Wear it with hoops and lace-up heels to be tomorrow's front page news!
Fit & Features
- Bodycon fit with moderate stretch
- Thin spaghetti straps
- V-neckline
- Ruched sides with ties
- Brushed knit fabric, newspaper print
- Runs true to size
Style Number/Barcode: 05102-4203
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Own That Ruched Tie Bodycon Dress
It's time to own the night, and this bodycon dress is the way to do it! It features a stunning ruched front detail, short sleeves, and a round neckline. Slip it on with lace-up heels for total babe vibes.
Fit & Features
- Short sleeves
- Round neckline
- Ruched front detail
- Bodycon fit
- Fits true to size
Style Number/Barcode: 05102-4167
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Abstract Beauty Mesh Midi Dress
Stun like the one-of-a-kind beauty you are with a midi dress that slays! The dress features a sleeveless square neckline, bungee spaghetti straps, an abstract-watercolor print, and a midi-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear heels.
Fit & Features
- Sleeveless square neckline, elastic band
- Bungee spaghetti straps
- Abstract watercolor print
- Midi-length silhouette
- Lined mesh fabric, ruched detailing
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4229
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Style In Stride V-Neck Collar Denim Mini Dress
Your best bet is this collar denim mini dress for a unique look at concerts or festivals! Set the trend in this sleeveless bodycon dress perf for styling with western boots.
Fit & Features
- Vintage-inspired denim fabric, minimal stretch
- Collar V-neckline
- Zip-up front closure
- Faux front pockets
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5914
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Preppy Trendsetter Plaid Mini Dress
Keep your everyday look on-trend in this preppy plaid mini dress! It features a collared V-neckline, short sleeves, a short, form-hugging silhouette, and is composed of a knit fabric with a moderate stretch. Style this dress with a denim jacket and sneakers for the perf cute and casual outfit.
Fit & Features
- Collared V-neckline
- Short sleeves
- Mini-length, form-hugging fit
- Plaid print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4244
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Strappy Waist Sleeveless Midi Dress
This ribbed knit midi dress is the perf option for a casual yet still sultry look! It features a sleeveless crew neckline, tank shoulder straps, a front waist cutout with a strappy design, and a mid-length, curve-hugging silhouette with a chic side slit. Style this dress with strappy heels.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Front waist cutout, strappy design
- Mid-length, form-hugging fit
- Side slit
- Lined ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4272
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Retro Mood Tie Dye Midi Dress
Channel a retro mood with a midi dress that is totally fab! The dress features a tie-dye print, a crew neckline, short sleeves, and a high side slit with a twist knot accent. The dress is composed of smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a denim jacket.
Fit & Features
- Crew neckline
- Short sleeves
- High side slit, twist knot accent
- Tie-dye pattern
- Midi length silhouette
- Cotton kbit fabric
- Form-hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4271
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Oh-So-Fab Tie-Dye Maxi Dress
Keep your look trendy and fab in this curve-hugging tie-dye maxi dress. It features a sleeveless asymmetrical one-shoulder neckline, a single spaghetti strap, a flattering high waist seam, and a form-fitting maxi-length silhouette with a sultry thigh-high side slit. Complete the outfit with clear heels.
Fit & Features
- Sleeveless asymmetrical one-shoulder neckline
- Single spaghetti strap
- High waist seam
- Maxi-length silhouette, form-hugging fit
- High side slit, ruched detailing
- Knit fabric, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-4277
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Chic Plaid Mini Dress
Oh-so-chic, this plaid mini dress is a staple you can take into the fall season! It features a trendy square neckline, spaghetti straps, and a short, curve-hugging silhouette. Style this knit dress with clear heels and a faux leather jacket.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Mini-length, form-hugging fit
- Plaid print
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-1105
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Vibes Babydoll Dress
Effortless and chic, this babydoll dress is perf for casual days where you still want to dress up. It features a V-neckline, three-quarter length sleeves, and a short, flowy silhouette with a tiered design. Style this dress with cute mules.
Fit & Features
- V-neckline
- Three-quarter length sleeves, cinched hems
- Mini-length, flowy babydoll fit
- Tiered design
- Woven crepe fabric, textured pattern
- Runs true to size
Style Number/Barcode: 05102-4294
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale