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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Day Dates Long Sleeve Button Down Dress
This bodycon mini dress is totally date-worthy! It features long sleeves, a collared neckline, button-down closure with ruching, and a bodycon silhouette. The dress is composed of a soft knit fabric with a moderate stretch. Complete the look with booties and statement jewelry.
Fit & Features
- Long sleeves, collared neckline
- Button-down with ruching
- Bodycon silhouette
- Short length hem
- Soft knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4262
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Freedom Vibes Graphic Tunic
Show up and stun with this edgy distressed graphic tunic. It features a crew neckline, long fitted sleeves, a center eagle and flames graphic with the scripts "Freedom Vibes" and "Wild and Free," slashed detailing down the front, and a short, form-hugging fit. Style this tunic with combat booties.
Fit & Features
- Crew neckline, long sleeves
- Eagle and flames graphic
- Scripts that read "Freedom Vibes" and "Wild and Free"
- Slashed detailing
- Mini-length, form-hugging fit
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 06002-1119
Category Name: Casual Dresses
Price: $11.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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That Edgy Look Slash Corset Hoodie Tunic
Edge up your everyday look in this cool tunic featuring long cuffed sleeves, a drawstring hoodie neckline, a corset-style bodice, and slash accents throughout. Composed of a soft knit fabric with plenty of stretch. Style with knee-high boots.
Fit & Features
- Long cuffed sleeves
- Drawstring hoodie neckline
- Corset-style bodice
- Slash accents throughout
- Soft knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1110
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plaid Perfect Sleeveless Mini Dress
Plaid will forever be a timeless and perfect print! This mini dress features a sleeveless, square neckline with spaghetti straps and a bodycon fit on a short-length hem. Composed of a soft knit fabric with a moderate stretch. Style with a cute cardigan for a casual day out.
Fit & Features
- Square neckline
- Sleeveless, spaghetti straps
- Plaid pattern
- Bodycon fit, mini hem
- Soft knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4310
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Chic Satin V-Neck Slip Dress
Keep it chic this weekend in this satin slip dress for a classy night out! It features a sleeveless V-neckline, adjustable spaghetti straps, and a short-length hem. Complete the look in the matching tunic.
Shop Matching Tunic: Weekend Chic Satin Button-Front Tunic
Fit & Features
- Sleeveless
- V-neckline
- Adjustable spaghetti straps
- Short-length hem
- Satin knit fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1612
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In A Snap Long Sleeve Ribbed Dress
Look stylish in a snap with this long sleeve dress as your base for creating fire styles! It features a v-neckline with snap-button closures, a bodycon silhouette, and a mini-length hem. Composed of a rib-knit fabric with a moderate stretch. Complete the look with booties and a cropped jacket.
Fit & Features
- Long sleeves
- V-neckline, snap-button closure
- Bodycon silhouette
- Mini-length hem
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1034
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Showstopper Mini Dress
You'll be such a showstopper in this sassy-chic mini dress. It features an on-trend mock neckline, long sleeves, side ruched detailing with an adjustable tie, and a short, curve-hugging fit. The lightweight stretchy knit fabric showcases a fab all-over snake print. Style this dress with black thigh-high boots.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Side ruching, adjustable drawstring at the hem
- Mini-length, form-fitting silhouette
- Stretchy knit fabric, snake print
- Runs true to size
Style Number/Barcode: 05102-4215
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Chic Ruched Mini Dress
This cute ruched mini dress will give you that everyday chic vibe! It features a trendy square neckline, long fitted sleeves, front ruched detailing, two drawstrings at the hem, and a short, form-hugging silhouette. Style this dress with sneakers to keep it casual or mules for a more elevated look.
Fit & Features
- Square neckline
- Long fitted sleeves
- Front ruched detailing
- Two adjustable drawstrings at the hem
- Mini-length, form-fitting silhouette
- Ribbed cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4236
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stun In Snake Print Button-Down Dress
Make a stunning appearance in this snake print dress! It features long sleeves, a collared v-neck, a button-down front with ruching to flaunt your figure, and a fitted hem. Complete your look with a boater hat and heels.
Fit & Features
- Long sleeves, collared v-neck
- Snake print
- Button-down with ruching
- Short, fitted hem
- Smooth knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4216
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Trendy Ribbed Midi Dress
Keep it trendy with a midi dress that can be dressed up for your night date night with bae. The dress features a crew neckline, long sleeves, a ruched drawstring, a high side slit, and a midi-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 a plaid scarf.
Fit & Features
- Crew neckline
- Long sleeves
- Ruched drawstring
- High side slit
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4311
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simply Stylish Mock Neck Mini Dress
Simply stylish, this basic mini dress is a must-have you can dress up or down! It features a mock neckline, long fitted sleeves, and a short, form-hugging fit. The lightweight cotton fabric offers a moderate stretch. Layer on a faux leather shacket and complete the look with ankle booties.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Mini-length, form-fitting silhouette
- Cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4200
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elevated Chic Ruched Mini Dress
Elevate your everyday look with this trendy-chic mini dress. It features a wide boat neckline, long fitted sleeves, a partially open back with a V-design, back ruched detailing, and a short, curve-hugging silhouette. Complete the outfit with over-the-knee boots.
Fit & Features
- Wide boat neckline
- Long fitted sleeves
- Open back, V-design
- Ruched detailing down the back
- Mini-length, bodycon silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4134
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Basic Long Sleeve Mini Dress
This ribbed cotton mini dress is a chic basic you need in your closet! It features a crew neckline, long fitted sleeves, and a short, curve-hugging silhouette. Style this dress with cute booties.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Mini-length, form-fitting silhouette
- Ribbed cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4208
Category Name: Casual Dresses
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Sophisticated Collared Midi Dress
Keep your look sleek and sophisticated in a midi dress that's a major staple! The dress features a collared neckline, long sleeves, a side slit, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a plaid coat and ankle booties.
Fit & Features
- Collared neckline
- Long sleeves
- Side slit
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4197
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Twirl Season One-Shoulder Skater Mini Dress
A little flirty, a little playful. This dress boasts a flattering skater silhouette and an off-shoulder neckline, making it made for cute date nights and celebrations!
Fit & Features
- Sweater knit fabric, moderate stretch
- Asymmetrical one-shoulder neckline
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000079
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Major Moment High Slit Knit Midi Dress
Create a major style moment with a midi dress that wows! The dress features a square neckline, long sleeves, a high side slit, and a midi-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with ankle booties and a cabby hat.
Fit & Features
- Square neckline
- Long fitted sleeves
- High side slit
- Midi-length silhouette
- Knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4287
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The Next Level Midi Dress
Take your look to the next level with a midi dress that demands drama! The dress features a crew neckline, long sleeves, a high side slit, and a midi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with ankle booties.
Fit & Features
- Crew neckline
- Long fitted sleeves
- High side slit
- Midi-length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4138
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hawt V-Neck Ribbed Sweater Dress
The temps may be dropping but you'll raise them in this sweater dress! It features a sleeveless, spaghetti strap design, v-neck, and a fitted, mini-length hem. Complete the look with the matching top.
Shop The Matching Top: Hawt Crop Ribbed Sweater Top
Fit & Features
- Sleeveless, spaghetti straps
- V-neck
- fitted, mini-length hem
- Rib-knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1042
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cozy And Cute Cable Knit Mini Dress
Get a cozy and cute look this season in this adorable cable knit mini dress! It features a wrap front and back design with a deep V-neckline, long loose sleeves with tapered hems, a tie-front waist, and a short, curve-hugging fit. Pair this dress with thigh-high boots for a date night.
Fit & Features
- Wrap front and back
- V-neckline
- Long sleeves
- Tie-front waist
- Mini-length silhouette, form-hugging fit
- Cable knit fabric with moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4251
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Falling For Chic Mock Neck Dress
You'll be falling for the chicness of this mock neck dress! It features long sleeves, a midi-length hem, and a bodycon silhouette. The rib-knit fabric offers a moderate stretch. Complete your look with a boater hat and booties.
Fit & Features
- Long sleeves
- Mock neckline
- Midi length hem
- Bodycon silhouette
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4302
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Silhouette Marble Mesh Midi Dress
The silhouette of this trendy mesh midi dress will hug your curves! It features a sleeveless square neckline, spaghetti straps, ruched detailing down the sides, and a mid-length hem. The sheer mesh fabric includes a full knit lining and an eye-catching marble print. Style this dress with clear mules.
Fit & Features
- Sleeveless square neckline, elastic band
- Bungee spaghetti straps
- Ruching down the sides
- Mid-length, form-hugging silhouette
- Sheer mesh fabric, knit lining, moderate stretch
- Marble print
- Runs true to size
Style Number/Barcode: 05102-4330
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty In Plaid Mini Dress
Look and feel like a total babe wearing this plaid mini dress! It features a sleeveless, square neckline with spaghetti straps on a form-hugging fit offering a moderate stretch. Complete your daytime look with a cropped jacket.
Fit & Features
- Sleeveless, square neckline
- Spaghetti straps
- Plaid print
- Form-hugging fit
- Polyester fabric with moderate stretch
- Mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-4258
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dose Of Style Knit Mini Dress
Serve up major style with a mini dress that is perf for a chic layered outfit. The dress features a mock neck, long sleeves, a ruched drawstring, 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 a trench coat and boots.
Fit & Features
- Mock neck
- Long sleeves
- Ruched drawstring
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4199
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruched Babe Long Sleeve Mini Dress
Flaunt your figure in this crowd-pleasing mini dress featuring side ruching with ties on a form-hugging silhouette. The smooth knit fabric offers a moderate stretch. Perfect for styling with heels and a clutch.
Fit & Features
- Crew neck
- Long sleeves
- Side ruching with ties
- Form-hugging silhouette
- Mini-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4259
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale