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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Twist Of Fate Strapless Ruffled Maxi Dress
Because you didn’t plan to look this good... it just happened. Make your way in this breezy maxi dress designed with effortless, dreamy details from the twisted strapless bust to strappy open back and flowy ruffled silhouette.
Fit & Features
- Satin woven fabric, woven lining
- Strapless sweetheart neckline
- Twisted bust, keyhole cutout accent
- Strappy open back
- Ruffled silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000168
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The One For You Mini Sweater Dress
This chic knit mini sweater dress is def the one for you! Pair with some statement earrings and strappy mules and werk it bb!
Fit & Features
- One shoulder neckline
- Single long fitted sleeve
- Short, curve hugging fit
- Ribbed knit fabric
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06005-0540
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleeveless Ruched Midi Dress
Yessssss girl! She's classy and curvy. Up your midi game with this form-hugging dress! Pair it with your fav block heels.
Fits & Features
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Crew Neckline
- Dual Button Closure At Nape I Keyhole Opening
- Midi Length Silhouette
- Ruching Throughout
- Smooth Jersey Knit Fabric I Fully LIned
- Form Hugging Fit I Moderate Stretch
- Zipper Not Featured
Style Number/Barcode: 05102-0699
Category Name: Casual Dresses
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Crew Neckline
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Too Dot To Handle Polka Dot Midi Dress
Bb girl, you're sizzling in this dress! Add a pair of cute booties and a faux leather jacket to complement this 'fit!
Fits & Features
- Adjustable Spaghetti Straps
- Surplice V Neckline
- Side Zipper WIth Hook & Eye Closure
- Midi Length Silhouette With Front Slit
- Textured Knit Fabric I Polka Dot Design I Unlined
- Relax Fit I Minimal Stretch
- Zipper Not Featured
Style Number/Barcode: 05101-0761
Category Name: Casual Dresses
Price: $14.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get Groovin' Tie Dye Scoop Neck Mini Dress
Get to movin' bb girl! This fab and fun mini dress features a splash of tie-dye print and goes perfect with white booties or sneakers!
Fits & Features
- Tank Shoulder Straps
- Scoop Neckline
- Mini Length Hemline
- Smooth Brush Knit Fabric | Tie Dye Print
- Form Hugging Fit | Plenty Of Stretch
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0523
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Swing Into It Ruffle Mini Dress
Get into the swing of spring by refreshing that wardrobe with this cute mini dress! Slip into some block heels and add a rattan bag for a gorge look!
Fits & Features
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Adjustable Spaghetti Straps
- Surplice V Neckline With Snap Button Closure
- Button Closure At Back I Keyhole Opening I Back Zipper
- Ruched Drawstring At The Front
- Mini Length Silhouette I Tiered Ruffle-Trim Hem
- Woven Fabric I Full Knit Lining
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05102-0718
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Adjustable Spaghetti Straps
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Curve Appeal Crepe Mini Dress
Showcase your curves in this mini dress that says it all! This must-have piece perfectly pairs with pumps and chunky jewelry accents for a bold statement!
Fit & Features
- V-Neckline | Spaghetti Straps
- Vertical Princess Seams
- Mini Side Slit
- Lined Crepe Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0526
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Groovy Baby Tie Dye Mesh Mini Dress
Show them how you groove in this tie-dye mini! We'd love to see you step out in this with a white pair of booties bb girl!
Fits & Features
- Spaghetti Straps Cross & Tie At Back
- V Neckline
- Mini Length Silhouette
- Fully Lined Mesh Fabric I Tie Dye Print
- Ruching Throughout
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0466
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Groovy Gal Tie Dye Mini Dress
Give your wardrobe a splash of color with this groovy mini dress! Amp up your look by pairing this with a mini backpack and some platform sneakers!
Fits & Features
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Spaghetti Straps
- Scoop Neckline I Square, Elastic Back
- Mini Length Silhouette
- Brush Knit Fabric I Tie Dye Design
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0495
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spaghetti Straps
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Wild In Lace Leopard Dress
Unlock your wild side in this fierce mini dress! Pair this bold print with sleek hoops and stilettos for stand out lewk!
Fit & Features
- V-Neckline | Lace Trim
- Spaghetti Straps
- Side Slit | Lace Trim
- Leopard Print
- Lined Smooth Knit Fabric
- Relaxed Fit
- Moderate Stretch
Style Number/Barcode: 05102-0710
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Blissful In Lace Maxi Dress
This gorge lace maxi dress will have you looking and feeling blissful! Don't forget to pair this dress with a fab mini purse and block heels!
Fits & Features
- Crew Neckline I Button Nape & Keyhole Opening At Back
- Sheer Fitted Long Sleeves I Smocked Cuffs
- Sheer Partially Lined Bodice
- Maxi Length Hem
- Lace Fabric I Mini-Length Lining
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05101-0760
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
- Crew Neckline I Button Nape & Keyhole Opening At Back
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Simply Chic Wrap Front Romper
Simple & chic is your go-to style. This wrap front romper is perf for a daytime look paired with some gold hoops and cute wedges.
Fit & Features
- Short sleeves
- Hidden back zipper | Hook and eye closure
- Wrap front V neckline
- Button closure
- Wrap overlay
- Flowy shorts
- Woven fabric with a short lining | No stretch
Style Number/Barcode: 06303-0068
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet But Sassy Ruffle Tube Dress
Sweet meets spicy in this ruched tube dress with a tiered ruffle skirt—basically, your flirty girl era into fall!
Fit & Features
- Knit fabric
- Strapless tube neckline
- Form-hugging bodice
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000299
Category Name: Casual Dresses
Price: $9.97 $50.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Nothin' But A Sweet Thing Floral Mini Dress
Honey you ain't nothin' but a sweet thannng when you step out in this floral mini ruched dress. We are already dreaming of that spring wardrobe!
Fit & Features
- Modest v-neckline
- Lace up bust detailing
- Tank straps | Off- shoulder straps
- Form fitting silhouette | Mini hemline
- Brushed knit material
- Ruched down the center
- Floral pattern | Slight stretch
Style Number/Barcode: 05102-0431
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bold In Blooms Deep V Midi Dress
Girl, you are so fab in florals! You'll love sauntering around in the Bold In Blooms mini dress!
Fits & Features
- Dual Spaghetti Straps | Cross At Back
- Plunging V Neckline | Padded Bust
- Back Zipper With Hook & Eye Closue
- Midi Length Silhouette | Slit At Center Back
- Smooth Scuba Fabric | Floral Prints Throughout
- Curve Hugging Fit
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0193
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flirty Vibes Skater Dress
Give off major flirty vibes and capture some hearts in this adorable double layered skater dress! Keep it casual with some white sneakers or dress it up with some wedges!
Fit & Features
- Adjustable spaghetti straps
- Square neckline
- Open back | Tie closure
- High waistband
- Double layered skater skirt
- Flowy fit
- Woven fabric
Style Number/Barcode: 05101-0747
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Denim Doll Puff Sleeve Mini Dress
Spring is right around the corner and you'll want to bust out those wedges and sandals to complement this cute denim dress!
Fits & Features
- Puff Shoulder Short Sleeves I Elastic Cuffs
- Sweetheart Neckline
- Square Back I Zipper Closure
- Mini Length Silhouette
- Denim Fabric
- Curve Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0426
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get Drawn In Mini Dress
Get drawn into this must-have dress! Pair this mini dress with wedges and hoops for a head-turning look!
Fit & Features
- V-Neckline
- Spaghetti Straps
- Ruched Drawstring Center
- Lined Ribbed Fabric
- Form Hugging Fit
- Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0598
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Into The Ruched Mini Dress
Get into this ruched trend girl! Pair this curve-hugging mini dress with glitzy pumps and a statement clutch!
Fit & Features
- Plunging Wrap V-Neckline
- Spaghetti Straps
- Ruched Drawstring Seam
- Lined Smooth Knit Fabric
- Curve Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0593
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Falling For Florals Mini Dress
Fall for this pretty print this season as you charm them all! Pair this beauty with fab pumps and butterfly accessories for an unforgettable look!
Fit & Features
- Sweetheart Neckline with Built-In Boning
- Lace-Up Bodice
- Adjustable Spaghetti Straps
- Floral Print
- Lined Lightweight Woven Fabric
- Mini Skirt Length Knit Lining
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05102-0700
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dreamy Meadow Chiffon Ruffle Maxi Dress
Look like a dreamy meadow in this flowy and sweet midi dress! Slip into some block heels and you'll be ready for your spring soiree!
Fits & Features
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Adjustable Spaghetti Straps
- Surplice V Neckline I V Back
- Back Zipper
- Maxi Length Silhouette I Ruffle-Trim Hem I Partial Lining
- Adjustable Drawstring & Ruching At Front Side
- Chiffon Fabric I Floral & Botanical Prints
- Minimal Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0769
Category Name: Casual Dresses
Price: $21.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Adjustable Spaghetti Straps
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Be Amazed Ruched Off Shoulder Mini Dress
Not your typical LBD. They're going to be amazed once they see you strutting in with this mini dress! Dust your neckline with some sparkling rhinestone accents to go for that extra glow!
Fits & Features
- Off Shoulder Neckline I Elastic Interior Band
- Fitted Long Sleeves
- Drawstring Bust
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette I Mesh Lined Fabric
- Ruching Throughout I Ruffle Trim Neckline & Hem
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0767
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flirty In Floral Skater Dress
Create an efforteless flirty look in pretty florals! This skater dress' flowy feel has a flattering figure.
Fit & Features
- Adjustable spaghett straps
- Wrap front V neckline
- Square back | Zipper and hook and eye closure
- High waist seam
- Flowy layered skater skirt | Knit lining
- All over floral print
- Sheer chiffon fabric | No stretch
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-0114
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Burst Ruffle Mini Dress
Burst into the season with fab florals bby! Pair this charming print with fab wedges and pop of color to complete a brunch-ready look!
Fit & Features
- Sweetheart Neckline | Drawstring
- Short Puff Sleeves
- Mid-Drift Cut Out
- Ruched Side Seam | Drawstring
- Floral Print
- Lined Chiffon
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05102-0676
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free