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
Discover New Skater Dress Styles
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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Trend Right Plaid Belted A-Line Mini Dress
Trend right in this plaid mini dress! It features a square neckline, spaghetti straps, a flattering A-line silhouette cinched with a belted waist, and a flirty pleated mini-length hem with an alluring plaid print. Complete the look with a crossbody bag.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Back zipper closure
- A-line silhouette, belted waist
- Pleated mini-length hem
- Plaid print, woven fabric, slight stretch
- Runs true to size
Style Number/Barcode: 05102-5505
Category Name: Casual Dresses
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Staple Tie-Front Ribbed Knit Midi Dress
This adorable tie-front midi dress is a stylish staple for an effortlessly chic look! It features a crew neckline, long fitted sleeves, a tie-front design at the waist, a mid-length hem with a high side slit, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Pair with ankle booties!
Fit & Features
- Stretchy ribbed knit fabric
- Crew neckline
- Long fitted sleeves
- Tie-front waist design
- High side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5248
Category Name: Casual Dresses
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Class Mock Neck Long Sleeve Midi Dress
Enjoy feeling like a boss in this high-class midi dress! The fitted long sleeves with thumbholes offer protection without compromising style, while the mock neckline, bodycon silhouette, and midi-length hem create a sleek and modern look. The stretchy ribbed knit fabric has a full-length lining. Complete the look with statement booties for a dinner downtown!
Fit & Features
- Fitted long sleeves with thumbholes
- Mock neckline
- Bodycon silhouette
- Midi-length hem
- Stretchy ribbed knit fabric, full-length knit lining
- Runs true to size
Style Number/Barcode: 05102-5396
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fun And Flirty Halter Neck Skater Dress
This adorable skater dress is perf for twirling and giving off those fun and flirty vibes at your next party! It features a sleeveless deep V-neckline with halter straps that lead to a tie-back design, an open back, dual high waist seams, and a short skater skirt with a fab fit and flare silhouette. The plisse woven fabric includes a full knit lining. Complete your look with a lariat necklace and platform heels.
Fit & Features
- Sleeveless deep V-neckline
- Halter straps, tie-back design
- Open back
- Dual high waist seams
- Short skater skirt, fit and flare silhouette
- Plisse woven fabric, full-length knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2908
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Winter Sweetheart Wrap-Front High Slit Midi Dress
Create an adorable winter 'fit with this wrap-front midi dress you'll want to wear all season long. It features a V-neckline with a chic surplice wrap-front design, long fitted sleeves, a midi-length hem with a high-cut side slit, and a form-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Complete your look with a moto jacket and sleek ankle boots.
Fit & Features
- V-neckline, surplice wrap-front design
- Long fitted sleeves
- Midi-length hem, high side slit
- Form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5338
Category Name: Casual Dresses
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Abstract Beauty Printed High Slit Midi Dress
You'll fall in love with the abstract beauty of this chic printed midi dress! Crafted from a sheer woven fabric with a full-length knit lining, this mid-length dress features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, a partially open back with a cross-back strap design and lower back straps, a high-cut side slit to showcase some leg, a flowy A-line silhouette, and an all-over multi-colored abstract print pattern to catch everyone's eye. Style with a layered necklace and clear heels for a gallery opening!
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Partially open back, cross-back strap design, lower back straps
- Mid-length hem, high-cut side slit, flowy A-line silhouette
- Multi-colored abstract print
- Sheer woven fabric, full-length knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5525
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Adorable Style Cable Knit Mini Dress
You'll fall in love with the adorable style of this cable knit mini dress for the cozy winter season. It features a V-neckline with a surplice design, long sleeves, a faux wrap-front creating an asymmetric mini-length hem, and a form-hugging silhouette. The cable knit fabric offers a moderate stretch. Style with a chic trench coat and knee-high boots.
Fit & Features
- V-neckline, surplice design
- Long sleeves
- Faux wrap-front design
- Asymmetric mini-length hem
- Form-hugging silhouette
- Cable knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5359
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Signature Style Collared Wrap Mini Dress
This wrap mini dress is perf for showcasing that signature chic style! It features a collared V-neckline with a pleated surplice design, long fitted sleeves, a high waist seam with ruched detailing to highlight your silhouette, a faux wrap-front design leading to an asymmetric mini-length hem, and a form-hugging fit. The knit fabric offers plenty of stretch. Complete your look with knee-high boots.
Fit & Features
- Collared V-neckline, pleated surplice design
- Long fitted sleeves
- High waist seam, ruching
- Faux wrap-front design, asymmetric mini-length hem
- Form-hugging fit
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-2948
Category Name: Casual Dresses
Price: $5.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fashionable Chic Sweater Maxi Dress
Perfect for any occasion, this fashion-forward sweater maxi dress delivers the perfect blend of comfort and style. Featuring a flattering bodycon silhouette, tank straps, and a sweetheart neckline for added appeal, this luxuriously soft sweater knit maxi dress will take your look to the next level. Layer on a faux leather jacket for an effortless and cool style!
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Bodycon silhouette
- Maxi-length hem
- Sweater ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1898
Category Name: Casual Dresses
Price: $3.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wild West Energy Denim Mini Dress
This denim mini dress comes with a lace-up front and bold embroidery and studs that bring rodeo-core to the party.
Fit & Features
- Denim fabric
- Tube neckline
- Front lace-up placket
- Studs and embroidery details
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000211
Category Name: Casual Dresses
Price: $59.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: XS, S, M, L
Product Badge: -
Retro Luxe Velvet Mock Neck Mini Dress
Embrace a luxurious and retro look in this velvet mini dress! It features fitted long sleeves, a mock neckline, a mini-length hem, and a bodycon silhouette that flatters your curves. The flocked velvet retro pattern gives it a glamorous look and brings a luxe vibe. The sheer mesh fabric features a sleeveless knit lining down the body of the dress. Complete the look in metallic heels for a party!
Fit & Features
- Fitted long sleeves
- Mock neckline, dual back button closures, keyhole cutout
- Mini-length hem
- Bodycon silhouette
- Flocked velvet design, retro pattern
- Sheer mesh fabric, sleeveless knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2856
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Downtown Chic Abstract Print Midi Dress
This alluring abstract print midi dress is a stylish pick for a dinner date downtown! It features a mock neckline, long fitted sleeves, a midi-length hem, a form-hugging silhouette, and an all-over abstract multi-print pattern. The sheer and stretchy mesh fabric includes a sleeveless full-length knit lining with adjustable spaghetti straps. Pair this trendy midi dress with gold hoops and clear heels.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Midi-length hem, form-hugging fit
- Abstract multi-print pattern
- Sheer mesh fabric, sleeveless full-length knit lining, adjustable spaghetti straps
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5491
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Twisted Up Long Sleeve Rib Knit Midi Dress
Get twisted up in this stylish midi dress! The rib knit dress features fitted long sleeves, a V-neckline, a twisted bust accent, and a bodycon silhouette with flattering side ruched seams and a midi-length hem perfect for styling with your favorite booties or heels. Complete the look in best-selling shoes to make a fabulous statement this season!
Fit & Features
- Fitted long sleeves
- V-neckline
- Twisted bust accent
- Bodycon silhouette, side ruched seams
- Midi-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5112
Category Name: Casual Dresses
Price: $5.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Winter Beauty Cable Knit Mock Neck Mini Dress
Showcase your beauty in this cozy cable knit mini dress this winter season! It features a ribbed mock neckline, long balloon-style sleeves with tapered ribbed hems, a mini-length hem, and a form-hugging fit. The classic cable knit fabric offers a moderate stretch. Style this mini dress with over-the-knee boots for a chic look.
Fit & Features
- Ribbed mock neckline
- Long balloon sleeves, tapered ribbed hems
- Mini-length hem
- Form-hugging fit
- Cable knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5358
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Find Your Style Button Down Pleated Mini Dress
Make a style statement in this woven shirt mini dress! Featuring long sleeves with button cuffs, a collar neckline, a button down front, and a flattering A-line silhouette and pleated mini-length hem for an adorable and undeniable stylish look. Complete the look in knee-high boots for brunch downtown!
Fit & Features
- Long sleeves with button cuffs
- Collar neckline
- Button down front
- A-line silhouette
- Pleated mini-length hem
- Woven poplin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-5379
Category Name: Casual Dresses
Price: $14.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Change Of Season Long Sleeve Ribbed Knit Midi Dress
Step out this season in this casual-chic long sleeve midi dress! It features a V-neckline with a button design at the bust, long fitted sleeves, a midi-length hem with dual high-cut side slits, and a form-hugging fit. The lightweight ribbed knit fabric offers plenty of stretch for comfortable wear. Style this midi dress with a moto jacket and ankle booties for an edgy elevated look.
Fit & Features
- Stretchy ribbed knit fabric
- V-neckline, two-button design
- Long fitted sleeves
- Dual side slits
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5310
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simply Fine In Floral A-Line Midi Dress
Take your look to the next level with this gorgeous floral midi dress. With its cowl neckline, adjustable spaghetti straps, A-line silhouette, and a painted floral print on woven fabric, this midi-length dress will make you feel stylish and fine! Complete the look in sleek stiletto heels for a semi-formal soiree.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- A-line silhouette
- Midi-length hem
- Painted floral print
- Lightweight woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-2920
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Charmed Mock Neck Bodycon Mini Dress
This bodycon mini dress would be charmed to make your acquaintance! A short dress that features fitted bell long sleeves and a mock neckline, and is composed of a rib knit fabric with a sewn-in knit lining. Style the mini dress with a chic crossbody bag for a day date!
Fit & Features
- Fitted bell long sleeves
- Mock neckline
- Bodycon silhouette
- Mini-length hem
- Rib knit fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5204
Category Name: Casual Dresses
Price: $5.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Destination Tropical Ruffle Maxi Dress
Arrive at your destination in this tropical maxi dress looking stunning and ready for fun! The maxi dress features a strapless neckline, non-slip grip lining, flexible boning, a form-hugging fit, and an effortless high front slit and ruffled flowy hem. Complete your vacation look with a handbag and sandals!
Fit & Features
- Strapless neckline, non-slip grip lining
- Back zipper and hook-eye closure
- Flexible boning
- Form-hugging fit
- High front slit, ruffled flowy maxi hem
- Tropical print, airy mesh fabric, partial knit lining
- Runs true to size
Style Number/Barcode: 05102-5383
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In The Cut One Shoulder Cutout Mini Dress
Let your style speak volumes with this mini dress perfect for dates or birthday brunch! The mini-length dress features a one-shoulder neckline with a puff short sleeve, a side drawstring cutout, and a flattering form-hugging silhouette on texture woven fabric. Complete the look with an envelope clutch and heels.
Fit & Features
- One-shoulder neckline, puff short sleeves
- Side drawstring cutout
- Form-hugging silhouette
- Mini-length hem
- Texture woven fabric, slight stretch
- Runs true to size
Style Number/Barcode: 05102-5401
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Can't Help It Off-The-Shoulder Sweater Dress
If chic comes naturally, this sweater maxi dress can't help but make your style shine! The maxi dress features an off-the-shoulder folded neckline, fitted long sleeves, a flattering bodycon silhouette, and a side slit on stretchy rib knit fabric. Complete the look in sleek stiletto heels for date nights or holiday parties!
Fit & Features
- Off-the-shoulder folded neckline
- Fitted long sleeves
- Bodycon silhouette, side slit
- Maxi-length hem
- Stretchy rib knit sweater fabric
- Runs true to size
Style Number/Barcode: 06005-1793
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Zip It Long Sleeve Cargo Pocket Mini Dress
This casual mini dress is perfect for the fashionista with an eye for style! Its fitted long sleeves, crew neckline, and zipper closure give a classic feel, while the bodycon silhouette, side cargo flap pockets, and mini-length hem on lined rib knit fabric create a flattering and unique style. Complete the look with booties for day or night plans!
Fit & Features
- Fitted long sleeves, crew neckline
- Front zipper closure
- Bodycon silhouette
- Side cargo flap pockets
- Mini-length hem
- Lined stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5407
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On A Vacay Strapless Tropical Slit Maxi Dress
From sunny vacations to island getaways, this tropical maxi dress is destined to go with you on your next trip!
Fit & Features
- Tropical palm print, mesh fabric lined with stretchy knit
- Strapless neckline
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6110
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In The Lineup Mock Neck High Slit Midi Dress
This alluring mock neck high slit midi dress needs to be in your winter lineup! It features a mock neckline, long fitted sleeves, a trendy ruched side seam with an adjustable drawstring, an asymmetric midi-length hem creating a high-cut side slit, and a form-hugging silhouette to flaunt your figure. The brushed knit fabric offers plenty of stretch. Style this midi dress with ankle booties!
Fit & Features
- Mock neckline
- Long fitted sleeves
- Ruched side seam, adjustable drawstring
- Asymmetric midi-length hem, high-cut side slit
- Form-hugging silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5404
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale