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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Sweet & Smocked Ditsy Ruffle Midi Dress
Get into the spring vibe with this midi dress on! Easily style it up or down by switching out your white sneakers to heels!
Fits & Features
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Adjustable Spaghetti Straps
- Square Neckline
- Tiered Ruffle Detail
- Midi Length Silhouette
- Ditsy Woven Print
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05101-0501
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adjustable Spaghetti Straps
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Tortoise O-Ring Ribbed Knit Midi Dress
Casual and cute, you'll be loving the O-ring belt around this chic midi dress! We love to see you rockin' this with some white sneakers and a faux leather jacket!
Fits & Features
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Spaghetti Straps
- Scoop Neckline I Square Back
- Tortoise O-Ring Waist Belt
- Midi Length Silhouette
- Ribbed Knit Fabric I Fully Lined
- Form Hugging Fit I Plenty Of Stretch
- Zipper Not Featured
Style Number/Barcode: 05102-0673
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spaghetti Straps
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Button Up In Denim Frayed Dress
Button up in this denim dress to make a fun statement bby!
Fit & Features
- Collared Neckline
- Small Chest Pockets | Button Down Front
- Short Sleeves
- Zipper Front Closure | Side Pockets
- Frayed Hem
- Medium Wash Denim
- Relaxed Fit | Slight Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0436
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Petals Tie Waist Skater Dress
Hey doll! Showcase your pretty self in this adorable floral printed skater dress! Paired with some wedges, you'll be ready for a perf spring day.
Fit & Features
- Adjustable spaghetti straps
- Wrap front V neckline
- High rise elastic banded waist
- Tie front detail
- Flowy skater skirt
- Lightweight floral printed woven fabric
- Stretchy knit lining
Style Number/Barcode: 05102-0494
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All Eyes On The Floral Maxi Dress
All eyes on the floral. This strapless maxi dress turns up the heat with a bold bloom moment and a high side slit that knows how to make an entrance at parties and on vacay!
Fit & Features
- Statement floral print
- Mesh fabric lined with stretchy knit
- Strapless tube neckline
- High side slit
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000083
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Fun Tie Back Skater Dress
Look absolutely sweet and chic in this floral skater dress! It's the perfect attire for brunch with your girls or the upcoming baby and bridal showers!
Fits & Features
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Spaghetti Straps
- Square Neckline
- Tie Back I Low Open Back
- Mini Length Hem I Skater Style Silhouette
- Knit Fabric I Fully Lined I Floral Print
- Moderate Stretch
Style Number/Barcode: 05101-0408
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spaghetti Straps
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Fresh Start Floral Off Shoulder Dress
Spring is here and it's time for a fresh start on that wardrobe! Wear this gorgeous chiffon dress out for all those sunny affairs!
Fits & Features
- Off Shoulder Elastic Neckline & Long Sleeves
- Elastic Cuffs
- Mini Length Silhouette
- Chiffon Fabric | Full Knit Lining
- Floral Print Design
- Moderate Stretch
Style Number/Barcode: 05102-0450
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spot Me Woven Ruffle Mini Dress
Get spotted in this chic & stylish woven LBD, perf paired with some strappy sandals and a denim jacket.
Fit & Features
- Short sheer sleeves
- Wrap front V neckline
- Sheer back | Hidden zipper closure
- High waist
- Front ruched detailing | Faux drawstring
- Short, ruffle hem
- Sheer swiss dot woven fabric | Stretchy knit lining
Style Number/Barcode: 05101-0775
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get A Move On Crepe Midi Dress
You need to get a move on with making those GNO plans with your girlfriends! Make sure you pick up this party-ready dress and elevate your style with some bold earrings!
Fits & Features
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Spaghetti Straps
- Scoop Neckline
- Midi Length Silhouette I Front Slit
- Crepe Fabric
- Form Hugging Fit I Plenty Of Stretch
- Zipper Not Featured
Style Number/Barcode: 05103-0851
Category Name: Casual Dresses
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spaghetti Straps
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Falling For Charm Strappy Open Back Floral Mini Dress
Fall for the charm of this flirty floral mini dress with a head-turning strappy open back and A-line fit perfect for showing off at brunch or a spring date!
Fit & Features
- Floral print, stretchy knit fabric
- Halter V-neckline, spaghetti strap tie
- Open back, strappy spaghetti strap ties
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6042
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flower Power Puff Sleeve Mini Dress
Take on the floral trend with this gorg puff sleeve printed mini! Pair the dress with some espadrille platform sandals and a cute woven bag!
Fit & Features
- Short puff sleeves | Elastic banded cuffs
- Sweetheart neckline
- Back zipper | Hook and eye closure
- Front center ruched detailing
- Short ruffle hem
- Sheer floral printed woven fabric
- Knit lining
Style Number/Barcode: 05101-0756
Category Name: Casual Dresses
Price: $17.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plaid Moment Ruffled Mini Dress
Have a major plaid moment in this trendy little mini dress! The ruffle detailing gives off a fun & flirty vibe.
Fit & Features
- Adjustable spaghetti straps
- V neckline
- Square back
- Stretchy smocked body
- Short, tiered ruffled hem
- All over plaid print
Style Number/Barcode: 05102-0728
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Turn On The Charm Square Neck Midi Dress
Slip into this midi dress and watch that confidence skyrocket! Pair this dress with some fab heels and layer on the dainty deets.
Fits & Features
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Bungee Spaghetti Straps
- Square Neckline
- Midi Length Hemline
- Smooth, Double-Layered Jersey Knit Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0561
Category Name: Casual Dresses
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bungee Spaghetti Straps
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Sweet Love Chiffon Ruffle Strap Maxi Dress
Romance is in the air! Take everyone's breath away with this charming maxi dress!
Fits & Features
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Ruffle-Trim Shoulder Straps
- Surplice V Neckline I Smocked Back
- Adjustable Waist Tie
- Maxi Length Silhouette I Partial, Mini Length Knit Lining
- Wrap Skirt Reveals Front Slit
- Chiffon Fabric
- Moderate Stretch
Style Number/Barcode: 05101-0781
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruffle-Trim Shoulder Straps
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Floral Flaunt Chiffon Skater Dress
Show off those beautiful florals in this enchanting mini dress!
Fits & Features
- Adjustable Spaghetti Straps
- Surplice V Neckline
- Self Ties At Back With Keyhole Opening
- Mini Length I Skater Silhouette
- Lined, Chiffon Fabric I Floral Prints Throughout
- Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-0317
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Flirt Ruffle Hem Mini Dress
You'll be a major flirt in this absolutely adorable ruffle hem mini! The dress is perf paired with some wedges for a spring day out!
Fit & Features
- Short sleeves
- Wrap front | V neckline
- High rise elastic banded waist
- Wrap front skirt | Ruched detailing
- Ruffle hem
- Stretchy knit fabric
Style Number/Barcode: 05102-0651
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flowy In Floral Tie Waist Mini Dress
Charm them all with this pretty mini dress! It's perf for those upcoming warm and sunny days.
Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Smocked Back
- Waist Tie Design
- Mini Length Silhouette I Wrap Skirt Design
- Crinkle, Gauze Lined Fabric I Floral Prints
- Moderate Stretch
Style Number/Barcode: 05102-0514
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
- Adjustable Spaghetti Straps
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Center Of Attention Ruched Mini Dress
Be the center of attention in this sultry mini dress! Pair with some booties or heels for a chic look!
Fits & Features
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V Neckline
- Roomy Sheer Long Sleeves
- Elastic Shoulder & Cuffs
- Adjustable Drawstring Center Front
- Mini Length Silhouette
- Mesh Lined Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0696
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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V Neckline
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All About It Ribbed Knit Mini Dress
We're all about our basic essentials and this mini dress is a must! Pair it with some white sneakers for a daytime look or throw on a faux leather jacket and some thigh-high boots for a PM 'fit!
Fits & Features
- Scoop Neckline & Back
- Mini Length Silhouette
- Double Layered Ribbed Knit
- Form Hugging Fit
- Plenty Of Stretch
Style Number/Barcode: 05102-0668
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Livin' It Up Ruched Mini Dress
You're out here livin' your best life, and babe we're here for it! Pair this sexy ruched mini dress with some strappy heels for a fun night out.
Fit & Features
- Spaghetti straps
- Square neck and back
- Ruched sides with drawstrings at hem
- Short, curve hugging fit
- Stretchy knit fabric
Style Number/Barcode: 05102-0612
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Always Sweet Ruffled Eyelet Lace Mini Dress
Make your sweet impression in this eyelet lace mini dress detailed with ruffled straps and an adorable ruched neckline. The form-hugging fit will highlight your stunning curves.
Fit & Features
- Eyelet lace fabric lined with stretchy knit
- Sweetheart neckline, ruching
- Ruffled straps
- Mini-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-6002
Category Name: Casual Dresses
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fab In Floral Brushed Knit Maxi Dress
Walk right in like you own the place! This maxi dress features romantic florals throughout and a flowy, trailing skirt. Wear some bold earrings and block heels for a perfect 'fit!
Fits & Features
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Spaghetti Straps
- Square Neckline | Elastic Back
- Maxi Length Silhouette | Dual Front Slit
- Brushed Knit Fabric
- Form Hugging Fit | Plenty Of Stretch
- 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: 05101-0409
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spaghetti Straps
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Chiffon Tropical Floral Maxi Dress
You are bronzed and ready for vacay in this goddess-like tropical maxi dress!
Fit & Features
- V-neckline
- Spaghetti straps
- Drop shoulder detailing
- Long maxi hemline
- Chiffon material | Minimal stretch
- Tropical floral pattern
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0036
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Playful Petals Floral Chiffon Off Shoulder Mini Dress
Let your feminity show and flow in this darling mini dress!
Fits & Features
- Off Shoulder, Foldover Neckline
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette I Detachable Waist Tie I Wrap Skirt
- Chiffon Lined Fabric
- Moderate Stretch
Style Number/Barcode: 05101-0464
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance