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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Spring Fling Floral Chiffon Ruffle Dress
Embrace the florals and ruffles in this romantic mini dress! It features peasant long sleeves, a plunge v-neckline, and a babydoll style silhouette with flirty ruffle trim on floral chiffon-lined fabric. Complete the look in a boho ring set.
Fits & Features
- Plunging V Neckline
- Sheer Roomy Long Sleeves I Elastic Cuffs
- Back Zipper With Hook & Eye Closure
- Dual Buton Detail At Nape Of Neck I Cut Out At Back
- Mini Length Hemline
- Lined Chiffon Fabric With Floral Print I Ruffle-Trim Detail
- Minimal Stretch
Style Number/Barcode: 05102-0470
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Tiered Ruffle Midi Dress
Add a little floral to your wardobe with this gorg tiered ruffle midi dress! Paired with some wedges and sunnies, you'll be ready for brunch with the girls!
Fit & Features
- Adjustable spaghetti straps
- Ruffled square neckline
- Tiered ruffled seams
- Ruffled mid-length hem
- Stretchy smocked body
- Curve hugging fit
Style Number/Barcode: 05102-0634
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Always Sunny Strapless Ruffle Eyelet Mini Dress
This eyelet mini dress is perfect for any sunny day and will be a favorite for shower celebrations, brunch, or graduations! The dress boasts a stretchy smocked bodice that hugs your figure while the ruffled mini-length hem adds a flirty allure.
Fit & Features
- Eyelet woven-lined fabric
- Strapless neckline
- Stretchy smocked bodice
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4019
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Persuasion Sweetheart Midi Dress
We think we are in love with florals! Fall for this sweet trend in this charming midi dress! Pair with clear heels for a brunch-ready outfit!
Fit & Features
- Sweetheart Neckline | Padded Cups
- Spaghetti Straps
- Floral Print
- Lined Scuba Knit Fabric
- Midi Length Silhouette
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05101-0066
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Go Get 'Em Tiger Print Cowl Neck Mini Dress
Girl, go get em' in tiger print! We will always love our classic leopard print but have been gradually leaning into tiger to change it up and stand out a lil'! Pair with a leather jacket and boots, or black heels!
Fit & Features
- Cowl neckline
- Spaghetti straps that cross in the back
- Mini hemline
- Form fitting silhouette
- Side slit detail
- Lined at the bust | Lots of stretch
- Tiger print pattern
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 05102-0518
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Chiffon Long Sleeve Skater Dress
We're falling for this floral look! It's the perf dress for that special outing you got lined up

Fits & Features
- Surplice V Neckline
- Cuffed & Unlined, Sheer Long Sleeves
- Zipper At Back
- Mini Length | Flowy Skater Skirt
- Lined, Chiffon Fabric
- Minimal Stretch
Style Number/Barcode: 05101-0192
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 With The Program Crepe Mini Dress
Give them a little attitude when you step out in a mini dress with a little sass! Pair with your go to heels, and a pair of door knocker earrings, and stun in 2020's color of the year!
Fit & Features
- Square neckline
- Bungee spaghetti straps
- Vertical flattering seams
- Mini side slit
- Form fitting silhouette
- Fully lined
- Crepe | 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: 05102-0533
Category Name: Casual Dresses
Price: $11.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Beauty In Floral Skater Dress
Beauty, this floral skater dress was made for you! It features a sleeveless bodice, adjustable spaghetti straps, a deep V neckline, a back zipper and hook and eye closure, a tie front belt, and has a flowy skater skirt. The ivory dress is composed of a crepe fabric with a full knit lining and showcases an adorable floral print.Style Number/Barcode: 05102-0278
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Thinkin' Bout It Floral Cowl Neck Mini Dress
Thinkin' bout those sunny days out at brunch with the galzzz in a cute mini? Well we have the perf dress, the rest is up to you! Pair with a panama hat and booties for that girl-next-door finish!
Fit & Features
- Cowl neckline
- Spaghetti straps
- Form fitting silhouette
- Mini hemline
- Floral ditsy pattern
- Nylon | Stretchy
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0534
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty In Florals Mini Dress
Charm them all in this flirty mini dress! Throw on an oversized denim jacket and some cute heels and you got yourself a lewk
Fits & Features
- Plunging V Neckline & Back
- Short Sleeves
- Mini Length Silhouette
- Knit Fabric With Floral Print
- Form Hugging
- Plenty Of Stretch
Style Number/Barcode: 05102-0373
Category Name: Casual Dresses
Price: $19.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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What's The Ruche Midi Dress
A look we honestly can't get enough of! Slip into this form-hugging midi dress and show off those never-ending curves!
Fits & Features
- Spaghetti Straps
- Square Neckline
- Midi Length Silhouette
- Woven Fabric I Fully Lined
- Ruching Throughout
- Form Hugging Fit I Curve Hugging Fit
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0463
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Button Down Knit Midi Dress
For the modest yet trendy babe! This midi is a closet staple, whether it's work wear or a casual date night, just throw on some heels and you are lookin' gooood bb!
Fit & Features
- V- neckline | Long sleeves
- Oil slick buttons down the center
- Mid-length hemline
- Ribbed knit material
- Moderate stretch
- Form fitting silhouette
Style Number/Barcode: 06005-0516
Category Name: Casual Dresses
Price: $20.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Fever Midi Dress
Get into that floral fever with this adorable ditsy floral printed midi dress, perf for spring!
Fit & Features
- Ruffle spaghetti straps
- Ruffle square neckline
- High waist seam
- Front slit
- Mid-length, flowy fit
- All over ditsy floral print
- Knit fabric | Moderate stretch
Style Number/Barcode: 05102-0455
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bring On The Floral Mini Dress
Bring on the bold floral with this absolutely adorable mini! The dress has a cute ruffle hem for major flirty vibes.
Fit & Features
- Tie shoulder straps
- Slight sweetheart neckline
- Parital stretchy smocked back
- Hidden zipper | Hook and eye closure
- High waist | Flowy short skirt | Ruffle hem
- Woven fabric | Woven lining | No stretch
- All over floral print
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0607
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Forever In Love Floral Dress
Be forever in love with florals in this beyond gorg printed dress! Its flowy feel adds a major flirty vibe.
Fit & Features
- Long loose sleeves with single buttons to cuff
- Wrap front V neckline
- Back zipper | Hook and eye closure
- High waist | Tie back detail
- Wrap front tiered skirt
- Sheer floral printed chiffon fabric | Knit lining
Model is 5'9" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0527
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sprung On You Floral Ruched Mini Dress
Have them sprung on you this spring doll! Not only to we love a sweet mini dress because it's cute and flirty, but let's get real, it's an easy effortless outfit! Simply throw on some heels and booties and ur good 2 go!
Fit & Features
- V-neckline
- 3/4 Sleeve length
- Ruched detailing down the sleeves + center
- Ruched detailing lower back to hemline
- Mini skirt lining + Frontal lining at the bust
- Ruffled mini hemline
- Chiffon | Stretch offered at ruched areas
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0606
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Passion Scuba Skater Dress
Get passionate about florals this season bby! This twirl-worthy dress is what dreams are made of!
Fit & Features
- V-Neckline
- Spaghetti Straps
- Floral Print
- Double Layered Skater Skirt
- Lined Scuba Fabric
- Relaxed Fit
- Moderate Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0155
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Serving Ruffles Mini Tube Dress
Serving ruffles and bold girl confidence—this tube mini dress does the most. With a curve-hugging fit and layers of mesh ruffles, it's your plus-one for rooftop parties, flirty photo ops, and every standout moment in between.
Fit & Features
- Knit fabric with knit lining, high stretch
- Mesh ruffled design
- Strapless tube neckline, no-slip strip
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000224
Category Name: Casual Dresses
Price: $14.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Classy and Chic Asymmetrical Dress
Tie yourself to a classy and chic look in this stunning mini dress! Pair this beauty with fab pumps and a trendy crossbody to complete the look!
Fit & Features
- Square Neckline
- Spaghetti Straps
- Tie Waist Accent
- Asymmetrical Hem
- Lined Crepe Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0460
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Full Bloom Satin Cowl Mini Dress
Spring is just around the corner! Can you believe it? We are ready, satin dresses all season, it's a trend that isn't going away any time soon!
Fit & Features
- Spaghetti straps that cross and tie at the back
- Cowl neckline
- Mini hemline
- Composed of satin | Minimal stretch
- Printed floral design
- Low back
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0458
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sprung On Florals Chiffon Midi Dress
Get sprung over florals this spring! This midi dress is the perfect all occasion piece, whether your going to a shower, a bbq, or brunch, this dress is perf!
Fit & Features
- Scoop drawstring neckline
- Adjustable spaghetti straps
- Milkmaid style bodice
- Fully lined
- Chiffon | Minimal stretch
- Ditsy floral print
- Bust tie detailing | Hidden zipper closure at side
- Mini length
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0467
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Feeling Chiffon Off Shoulder Mini Dress
Bloom, baby! Look absolutely stunning in this floral mini dress!
Fits & Features
- Adjustable Shoulder Straps
- Off Shoulder Neckline & Sleeves
- Layered Ruffles Along Neckline & Hem
- Mini Length Silhouette
- Chiffon Fabric I Lining
- Form Hugging Fit I Minimal Stretch
Style Number/Barcode: 05101-0434
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Dream Corduroy Mini Dress
Keep it dreamy and charming with a pretty floral print! The corduroy fabric on this mini keep this mini feeling luxe and fab!
Fit & Features
- Square Neckline
- Short Sleeves
- Key Hole
- Cross Straps At Back
- Floral Print
- Corduroy Fabric
- Relaxed Fit
Style Number/Barcode: 05102-0481
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Classic Ribbed Midi Dress
Look like an instant classic with this curve-hugging sweater dress! The ribbed fabric creates an instant hour-glass illusion!
Fit & Features
- Off The Shoulder Neckline
- Long Sleeves
- Ribbed Knit Fabric
- Midi Silhouette
- Form Hugging Fit
- Moderate Stretch
Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06005-0417
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance