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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Feline Good Leopard Print Mesh Mini Dress
Whether you are out on a date night, or out with the gals you'll be feelin' good in this feline inspired leopard print mesh mini dress! Dress up with heels and hoops, or dress down with booties and a leather jacket!
Fit & Features
- Spaghetti straps
- Square neck and back
- Ruched side detailing
- Short, curve hugging fit
- Sheer mesh leopard printed fabric
- Knit lining | Plenty of stretch
- Leopard print pattern
Style Number/Barcode: 05102-0402
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ditsy Floral Daze Mini Dress
Ditsy florals are the trendy print of the season! This floral printed dress features a sleeveless square neckline with ruffle spaghetti straps, ruched detailing down the side, and a mini-length, curve-hugging silhouette. Pair this adorable dress with some cute strappy sandals for the perf daytime 'fit!
Fit & Features
- Ruffle spaghetti straps
- Square neck and back
- Ruched side detailing, adjustable drawstring at hem
- Short, form-hugging fit
- Ditsy floral print
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-0524
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Puff Sleeve Leopard Print Mini Dress
Puff sleeves and leopard print - this mini dress couldn't get any trendier!
Fit & Features
- Off the shoulder neckline
- Short puff sleeves
- High waist seam
- Short, form hugging fit
- Leopard print
- Knit fabric | Plenty of stretch
- Form hugging fit
Style Number/Barcode: 05102-0521
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Puff It Up Crepe Mini Dress
Pump up the jams and get your night going in this LBD with statement puff sleeves!
Fits & Features
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Puff Shoulder Short Sleeves
- Plunging V Neckline I Padded Bust
- Square Back I Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0624
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Puff Shoulder Short Sleeves
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As Good As Knit Gets Mini Dress
This chic white knit mini dress is as good as it gets! Paired with some glam earrings and strappy heels, you'll be lookin' fine bb!
Fit & Features
- Spaghetti straps
- Wrap front V neckline
- Ruched side detailing
- Short envelope hem
- Ribbed knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0620
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Fleur Love Scuba Mini Dress
Wrap yourself up in florals with this oh-so-lovely and charming mini dress! Easily dress your look up or down by pairing it with some sneakers or heels.
Fits & Features
- Spaghetti Straps
- Square Neckline
- Mini Length Silhouette I Front Slit
- Scuba Knit Fabric
- Form Hugging Fit I Plenty Of Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0626
Category Name: Casual Dresses
Price: $11.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flow With The Floral Skater Dress
Go with the flow of this pretty floral skater dress! Pair with some everyday sandals for an effortless, spring ready vibe.
Fit & Features
- Off the shoulder elastic banded neckline
- Three quarter length flowy sleeves
- High waist seam
- Skater skirt
- Sheer chiffon fabric | Knit lining
- Rose print
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0410
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Summer-Coded Crochet Halter Mini Dress
Serve all the summer vibes in this crochet knit mini dress designed with a halter V-neck with a beaded trim on the straps. Style with espadrille wedges for sunset happy hour.
Fit & Features
- Sheer crochet knit fabric with knit lining, moderate stretch
- Sleeveless V-neckline
- Tie-back halter straps, beaded trim
- Partially open back
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6114
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Burnout Floral Mock Neck Mini Dress
We can't get enough of these burnout floral dresses! This mini version is complete with a trendy mock neck and a short, curve hugging fit.
Fit & Features
- Mock neckline
- Back zipper closure
- Long sheer fitted sleeves
- Sheer insets at the neckline
- Sheer back
- Mesh burnout floral sheer fabric | Knit lining
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0597
Category Name: Casual Dresses
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ready Or Not Ruched Mini Dress
Ready or not, you're showing up to slay in this ruched mini dress!
Fit & Features
- Long billowy sleeves | Elastic banded cuffs
- Square neckline
- Complete stretchy smocked back
- Front ruched detailing | Dual drawstrings at hem
- Short, curve hugging fit
- Smooth woven fabric
Pink: Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Black: Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0627
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Own The Moment Tube Floral Maxi Dress
Ready to shut down the vacation pics? This strapless floral maxi dress brings effortless chic with a curve-hugging fit and leg-baring side slit.
Fit & Features
- Floral print, mesh-lined fabric, moderate stretch
- Strapless tube neckline
- High side slit
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000237
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Puff Sleeve Floral Mini Dress
Puff sleeves are so of the moment. Pair that with spring time florals and you've got yourself an adorably trendy fit! Pair this mini dress with some cute clear mules and wear either off the shoulder or on.
Fit & Features
- Short puff sleeves | Merrow edge trim
- Square neckline | Faux tie front detail
- High elastic banded waist
- Ruched side detailing
- Short, form hugging fit
- Small floral print
- Brushed knit fabric | Plenty of stretch
Model is 5'6.5" with 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0420
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dreamy In Denim Button Front Mini Dress
Look ever so dreamy in denim in this spring ready mini dress! Pair with some wedges and trendy sunnies and you'll be ready to go!
Fit & Features
- Long sleeves | Single buttons to cuff | Puff shoulders
- Sweetheart neckline | Bust seam detailing
- Partial stretchy smocked back
- Button down front
- Slanted front pockets
- Short, form-fitting style
- Jean fabric | Moderate stretch
Style Number/Barcode: 05102-0653
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Curves Ahead Bodycon Dress
Showcase your curves in this bodycon and flaut a confident look with statement heels!
Fit & Features
- Wired Sweetheart Neckline
- Adjustable Spaghetti Straps
- Lined Jersey Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0633
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vacay Vibes Skater Dress
Escape on vacay in this gorg tropical printed skater dress! Pair with some heels and accessorize with a cute woven bag and live it up!
Fit & Features
- Off the shoulder square neckline | Ruffle trim
- Long sleeves | Elastic banded hems
- High rise elastic banded waist
- Tie front belt
- Flowy skater skirt | Woven lining
- All over colorful palm print
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0603
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off The Shoulder Button Front Midi Dress
The perf midi dress that has major spring time vibes! With its short puff sleeves, button front detailing, and flowy feel, this dress is a must for your wardobe.
Fit & Features
- Off the shoulder sweetheart neckline
- Short puff sleeves
- Faux button down front
- Stretchy smocked back
- Front slit | Ruffle hem
- Flowy fit
- Woven fabric | Short knit lining
Style Number/Barcode: 05102-0637
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adore Me Floral Mini Dress
Walk right into any room and everyone will be falling head over heels for this floral look!
Fits & Features
- Spaghetti Straps
- V Neckline
- Mini Length Silhouette
- Woven Fabric I Floral Print Throughout
- Curve Hugging Fit I Ample Stretch
- Zipper Not Featured
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0399
Category Name: Casual Dresses
Price: $9.97 $23.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Asymmetric Ruched Midi Dress
Add some flower power to your look with this bold and beautiful midi dress! Goes amazing with some strappy heels
Fits & Features
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Adjustable Spaghetti Straps That Cross At The Back
- V Neckline | Lined At The Bust
- Midi Length Asymmetric Hemline
- Side Ruching
- Woven Fabric With Floral Prints
- Plenty Of Stretch | Form Hugging Fit
- Zipper Not Featured
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0333
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adjustable Spaghetti Straps That Cross At The Back
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Floral Dreaming Satin Midi Dress
We're dreaming of romance in this floral beauty! This midi dress perfectly pairs with stilettos and clutch for the perfect date night look!
Fit & Features
- V-Neckline
- Adjustable Spaghetti Straps | Cross-Back
- Floral Print
- Lined Satin Fabric
- Midi Length Silhouette
- Front Slit
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05101-0367
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fleur Paradise Chiffon Smocked Mini Dress
Slip-on this pretty mini dress and enchant them all with the bold and beautiful floral prints!
Fits & Features
- Ruffle-Trim At Square Neckline, Cuffs & Hem
- Sheer, Roomy Chiffon Long Sleeves I Elastic Cuffs
- Smocked Bodice & Mini Length Silhouette
- Curve Hugging Fit
- Ample Stretch
Style Number/Barcode: 05101-0509
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Garden Parties Pleated Midi Dress
Get ready for garden parties, backyard brunches, bridal showers, and spring weddings with this spring staple! Pair with wrap heels, or strappy mules!
Fit & Features
- Tie halter neckline
- Pleated bodice with keyhole cut out
- Smocked stretchy waist line
- Pleated flowy skirt
- Mid-length hemline
- Lightweight sheen polyester material
- Unlined | Moderate stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0724
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Heatwave Floral Halter Mini Dress
Cause a major heatwave in this sultry mini dress designed with a large floral print on smooth, stretchy knit fabric. The plunging halter V-neck and short, curve-hugging silhouette are alluring details you'll love.
Fit & Features
- Lined knit fabric, high stretch
- Large floral print
- Sleeveless plunging V-neckline
- Halter strap, partially open back
- Ruching
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000639
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: ORANGE-2
Available Size: XS, S, M, L
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Boho Breeze Tiered Mini Dress
Breeze on by like the boho babe you are in this spring ready mini dress! Paired with some strappy sandals, you'll have the best 'fit.
Fit & Features
- Tank-like shoulder straps
- Square neck and back
- Parital button down front
- Hidden back zipper | Hook and eye closure
- Stretchy smocked waist
- Tiered flowy skirt
- Lightweight woven fabric | Woven skirt lining
Style Number/Barcode: 05102-0626
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kiernan Glittering Mesh Party Dress
Get ready for a night that you will never forget, when you start the party in our glittering Kiernan skater dress that is fit for a princess!
Fit & Features
- V-neckline
- Adjustable spaghetti straps
- Square back | Zipper closure
- Fully lined with double layered glitter overlay
- Banded high waist line
- Pleated bodice
- Flowy mini hemline | Lightweight feel | Minimal stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0305
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale