Casual Dresses

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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!

  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0192

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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