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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Fine In Florals High Neck Maxi Dress
Florals are DEF your color, bb girl! Show off your curves in our Fine In Florals maxi dress!
Fits & Features
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Spaghetti Straps That Cross & Lace-Up At The Back
- High Neckline
- Maxi Length Silhouette
- Dual Side Slits
- Smooth Jersey Knit Fabric
- Form Hugging Fit I Ample Stretch
Style Number/Barcode: 05102-0277
Category Name: Casual Dresses
Price: $20.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spaghetti Straps That Cross & Lace-Up At The Back
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Smocked Sweetheart Gingham Mini Dress
Yes girl, it's the perfect daytime date dress! Perfectly pair the look with some clean white sneakers or heeled sandals!
Fits & Features
- Elastic Sweetheart Neckline & Cuffs
- Tie Design & Cut Out At The Bust
- Woven Short Sleeves I Can Be Worn Off Shoulder
- Smocking Throughout
- Mini Length Hemline With Ruffle Trim
- Gingham Print Design
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0688
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Purrfectly Fierce Smocked Mini Dress
Look purrfectly fierce in this so of the moment leopard printed mini dress! Its smocked detailing will flatter your curves.
Fit & Features
- Strapless sweetheart neckline
- Tie front detail
- Front cut out
- Stretchy smocked body
- Short, form hugging fit
- Leopard print
Style Number/Barcode: 05102-0682
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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That Girl Energy Cutout Tube Midi Dress
Steal the scene and leave them speechless. This sleek strapless midi hugs your curves with a smooth, sculpted fit perfect for date nights, parties, or whenever you’re feeling that girl energy.
Fit & Features
- Brushed knit soft fabric, knit lining, moderate stretch
- Strapless tube neckline
- Cutout back, lower ruched seam
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000176
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Staple Ribbed Knit Bodycon Midi Dress
A stylish staple like this bodycon midi dress needs to be in your closet. The ribbed knit fabric offers plenty of stretch, while the form-hugging fit flaunts your curves.
Fit & Features
- Lined ribbed knit fabric, high stretch
- Sleeveless square neck and back design
- Spaghetti straps
- High side slit
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000066
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ruched To Perfection Midi Dress
This stunning midi dress is ruched to perfection, and will look so gorgeous on you! Paired with some strappy heels, it's totally date night material.
Fit & Features
- Spaghetti straps
- Cowl neckline
- High waist
- Ruched side detailing | Drawstring at hem
- Mid-length, asymmetric hem
- Stretchy knit fabric
- Form hugging fit
Style Number/Barcode: 05101-0727
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Girly In Gingham Smocked Mini Dress
Look oh so gorgeous and girly in this gingham smocked mini dress babe! Pair with some cute wedges and you'll have a spring ready look!
Fit & Features
- Tie shoulder spaghetti straps
- Notched V neckline | Ruffle trim
- Stretchy smocked body
- Short, form hugging fit
- All over gingham print
Style Number/Barcode: 05102-0683
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Tie shoulder spaghetti straps
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Effortless Beauty Eyelet Mini Dress
You've got that effortless beauty babe! Wear this gorg eyelet mini dress and have the perfect spring time look!
Fit & Features
- Adjustable spaghetti straps
- Wrap front V neckline
- Hidden back zipper | Hook and eye closure
- Side tie detail
- Wrap front skirt
- Eyelet detail woven fabric | No stretch
Style Number/Barcode: 05102-0686
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Mesmerizing In Mesh Lace Dress
Show off a little skin in this sexy dress! The sleek inner bodysuit provides perf coverage against the mesh skirt!
Fits & Features
- Adjustable Spaghetti Straps
- Unlined, Lace & Mesh Bodice I Underwire Bust
- Elastic Waistband
- Maxi Length Silhouette I Mesh Skirt
- Built-In Bodysuit With Dual Snap Button Closure I Cheeky Coverage
- Moderate Stretch
Style Number/Barcode: 05101-0397
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pick Of The Bunch Floral Chiffon Skater Dress
It's finally spring and that means adding more floral additions to your wardrobe! Brighten up your look with these fresh prints!
Fits & Features
- Adjustable Shoulder Straps
- V Neckline I Back Zip With Hook & Eye Closure
- Mini Length Hem I Skater Style Silhouette
- Lined Chiffon Fabric I Floral Prints Throughout
- Form Hugging Fit
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0313
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Denim Dreamer Tie Front Dress
Look oh so dreamy in denim in this adorable tie front dress! Perf for a spring day out with your gal pals.
Fit & Features
- Collared | Half snap button down front
- Long sleeves | Single buttons to cuff
- Two buttoned chest pockets
- Tie front detail | Front waist cut out
- Two slanted pockets at the waist | Two back pockets
- Front button | Hidden zipper closure
- Short, form hugging fit
Style Number/Barcode: 05102-0435
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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New Love Ditsy Smocked Mini Dress
Something sweet, something new. Charm them all by slipping into the New Love mini dress! Pair with some sneakers for a girls' day and switch to some heels for date night with the boo!
Fits & Features
- Adjustable Spaghetti Straps
- Square Neckline
- Mini Length Silhouette
- Woven Fabric I All Over Smocking
- Ditsy Floral Print I Tiered Ruffle Design
- Form Hugging Fit I Ample Stretch
Style Number/Barcode: 05102-0522
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Crochet Chic High Low Dress
Keep it cute in crochet girl! This dress is giving us major boho vibes and perfectly pairs with your fav headband and wedges!
Fit & Features
- V-Neckline
- Floral Crochet Bodice
- Adjustable Spaghetti Straps
- Smocked Back
- High Low Silhouette| Mini Skirt Length Knit Lining
- Lightweight Woven Fabric
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05102-0617
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Knit Mock Neck Mini Dress
The everyday sweater dress you need in your life. Add to cart!
Fit & Features
- Mock neckline
- Long fitted sleeves
- Short, curve hugging fit
- Ribbed knit fabric | Knit lining
- Plenty of stretch
Style Number/Barcode: 06002-0329
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bring The Romance Off Shoulder Long Sleeve Skater Dress
Date night calls for a sweet and pretty look! Style with some soft curls, a cute crossbody, and sparkly finishing touches and you'll be ready for the night!
Fits & Features
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Elasticized, Off Shoulder Neckline I Tie At Center Front
- Off Shoulder Long Sleeves I Elastic Cuffs
- Crochet Waist Design
- Mini Length, Skater Style Skirt
- Brushed Knit Design I Floral Print
- Plenty Of Stretch
Style Number/Barcode: 05101-0401
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Elasticized, Off Shoulder Neckline I Tie At Center Front
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Ready For Tonight Chiffon Blouson Mini Dress
Ooh girl, you look so ready for a night out! Bring the drama with its off-shoulder neckline and fit-and-flare blouson sleeves!
Fits & Features
- Ruffle-Trim Square Neckline, Cuffs, Hem
- Sheer Blouson Sleeves With Circle Embroidery Detail
- Mini Length Silhouette With Drawstring At Center Front
- Smocking All Over
- Bodycon Fit I Ample Stretch
Style Number/Barcode: 05102-0560
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lovely In Linen Smocked Mini Dress
Look oh so lovely in linen in this perf springtime mini! The smocked detailing make it all the more flattering!
Fit & Features
- Long sleeves | Smocked cuffs
- Square neck | Eyelet trim detail
- Front tie | Keyhole cut out
- Stretchy smocked skirt
- Short, ruffle hem
- Linen fabric
Style Number/Barcode: 05102-0681
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Playful In Polka Dots Mini Dress
Get a playful look in adorable polka dots with this LBD! The short puff sleeves make it all the more trendy.
Fit & Features
- Short sheer puff sleeves
- Sweetheart neckline
- Front ruched detailing
- Short, curve hugging fit
- Sheer mesh fabric with all over polka dot print
- Knit lining
- Plenty of stretch
Style Number/Barcode: 05101-0729
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Own the Moment Tube Floral Slit Bodycon Maxi Dress
This strapless bodycon maxi dress brings major drama with a bold floral print and side thigh-high slit made to steal the spotlight at a beach brunch or on vacation!
Fit & Features
- Statement floral print, slinky knit stretchy fabric
- Tube neckline
- Side slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000286
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring It On Floral Mini Dress
Bring on the sunny, spring weather! Look fresh in florals with the Spring It On mini dress! Wear your sleeves up or soak up some vitamin C by wearing it off the shoulder!
Fits & Features
- Short Sleeves With Elastic Shoulders & Cuffs I Can Be Worn Off Shoulder
- V Neckline I Square Back
- Keyhole Opening With Adjustable Ties
- Mini Length Silhouette
- Stretchy Woven Textured Mesh I Floral Prints
- Form Hugging Fit I Moderate Stretch
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0392
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Leopard Purrfection Satin Midi Dress
Tap into your instincts with this fiercely-inspired print! This midi dress only needs a pair of booties and dainty pieces to complete the look!
Fit & Features
- V-Neckline
- Spaghetti Straps
- Leopard Print
- Side Slit
- Lined Satin Fabric
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05101-0599
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Sweetheart Mini Dress
Show off your sweet side in this must-have mini dress! Pair with block heels and layers of dainty pieces to complete your look!
Fit & Features
- Sweetheart Neckline | Padded Cups
- Short Puff Sleeves
- Double-Lined Brush Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0539
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake A Difference Side Tie Mini Dress
Move over LBD! Work your charm in this fiesty mini dress!
Fits & Features
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Spaghetti Straps
- Square Neckline
- Mini Length Silhouette
- Drawstring & Ruching At Side Hem
- Knit Fabric
- Curve Hugging Fit I Plenty Of Stretch
- Zipper Not Featured
Style Number/Barcode: 05102-0537
Category Name: Casual Dresses
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spaghetti Straps
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Own Knit Open Back Midi Dress
Own your look bb! You know how to werk it, especially in this sultry open back knit midi dress!
Fit & Features
- Mock neckline
- Long fitted sleeves
- Open back | Twist back detail | Lower back cut out
- Curve hugging fit
- Ribbed knit fabric | Plenty of stretch
Style Number/Barcode: 05102-0656
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance