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!

  • Getaway Girl Floral Smocked Tube Maxi Dress

    Girl, you'll look stunning on your weekend getaway in this floral tube maxi dress! It features a strapless square neckline, a smocked bodice, and a flowy maxi-length silhouette with a ruffle bottom hem. Don't forget to add a pair of wedges and a wide brim hat to your cart as well!

    Fit & Features

    • Strapless square neckline
    • Stretchy smocked bodice 
    • Maxi-length silhouette, mini-length lining
    • Ruffle bottom hem
    • Floral printed woven fabric
    • No stretch
    • Runs true to size

    Style Number/Barcode: 05101-0033

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Diva Sleeveless Mini Dress

    Dare to impress in denim! This denim mini dress can easily dressed up with the perfect pair of pumps and animal print! 

    Fit & Features

    • Sweetheart Neckline | Padded Cups
    • Adjustable Spaghetti Straps
    • Lace Up Front | Metal Grommets
    • Contrast Stitching 
    • Denim Fabric
    • Form Hugging Fit 
    • Moderate Stretch 

     

     


    Style Number/Barcode: 05102-0437

    Category Name: Casual Dresses

    Price: $14.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Acid Wash Denim Spaghetti Strap Button Mini Dress

    Get drawn to denim dresses this season. Slip into this curve-hugging dress for your next night out with bae. Fitted with a sleeveless sweetheart neckline, adjustable spaghetti straps to avoid wardrobe malfunctions, and corset-like seams that accentuate curves. The real details can be found in the multi-button down accent at the bodice that leads to a mini length silhouette. The light-medium acid wash denim fabric offers a form hugging fit. Complete your look with fab pumps and dainty accessories.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Corset-like seams
    • Button-down accent 
    • Adjustable spaghetti straps 
    • Mini length silhouette
    • Acid wash denim fabric 
    • Form hugging fit

    Style Number/Barcode: 05102-0474

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lace Up Sweetheart Neck Denim Mini Dress

    Lace-up in classic denim to impress. This denim dress is designed with a sweetheart neckline, a corset-like bodice complemented with lace-up straps for a customized fit, and adjustable spaghetti straps. The curve-hugging mini length dress is composed of breathable medium-wash denim fabric. Pair this head-turning dress with statement earrings and bold heels to dress up this look. 

    Fit & Features

    • Sweetheart neckline
    • Corset-like seams at bodice
    • Lace-up ties at center of the bodice
    • Adjustable spaghetti straps
    • Mini length silhouette 
    • Denim fabric 

    Style Number/Barcode: 05102-0565

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fresh As A Daisy Mini Dress

    Keep your look fresh as a daisy this season with a pretty floral mini that brings the flutters! Pair this must-have mini dress with a pair of strappy heels for a head-turning look! 

    Fit & Features 

    • Square Neckline 
    • Bungee Straps 
    • Embroidered Daisy Print 
    • Lined Mesh Fabric 
    • Mini Length Silhouette 
    • Form Hugging Fit 

     

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small. 

     

     


    Style Number/Barcode: 05102-0791

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty Fleur Tie Front Mini Dress

    Show off your soft side! Pretty blooms cover this flirty dress! It's the perfect mini for a day with your gals. 

    Fits & Features

    • Spaghetti Straps
    • Square Neckline With Tie Front I Empire Waist
    • Mini Length Silhouette 
    • Knit Fabric I Floral Print 
    • Form Hugging Fit 

    Style Number/Barcode: 05101-0445

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Look at Her Denim Tunic

    You can’t go wrong with this denim tunic! Rock it as a dress or layer it over your favorite matching set.

    Fit & Features 

    • Chest Pockets | Snap Down Front
    • Long Sleeves 
    • Round Hem 
    • Medium Wash Denim

    Style Number/Barcode: 06203-0060

    Category Name: Casual Dresses

    Price: $18.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleek Ya Out Cowl Neck Midi Dress

    Girl, look at you! Everyone's eyes will be locked on you in this pretty midi! Slip into some mules and add a panama hat for a chic look! 

    Fits & Features

    • Spaghetti Straps I Strappy Back
    • Cowl Neckline 
    • Midi Length Hem 
    • Smooth, Satin-Like Fabric 
    • Relaxed Fit I Minimal Stretch 
    • Zipper Not Included 

    Style Number/Barcode: 05102-0484

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feeling Amore Tie-Back A-Line Eyelet Mini Dress

    Fall in love with this adorable eyelet mini dress perf for weekend plans. The flirty tie-back detail and ruffled A-line silhouette will get you all the compliments.

    Fit & Features

    • Eyelet knit fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Tie-back design
    • Ruffled trim
    • Short A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5434

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • For The Love of Florals Mini Dress

    Show off your love of florals in this frilly and flirty mini dress! Throw on your favorite wedges and dainty pieces for a brunch ready look!

    Fit & Features 

    • Sweetheart Neckline
    • Sheer Chiffon Long Sleeves
    • Smocked Bodice 
    • Ruched Drawstring 
    • Daisy Floral Print
    • Smocked and Chiffon Fabric 

     

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small.  

     


    Style Number/Barcode: 05101-0845

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Eyelet Breeze Sleeveless Skater Dress

    Spring into the season with this twirl-worthy skater dress! Throw on some pumps and dainty deets to complete a brunch-ready look! 

    Fit & Features 

    • V-Neckline 
    • Spaghetti Straps 
    • Floral Eyelet Design 
    • Skater Silhouette
    • Lined Lightweight Woven Fabric
    • Relaxed Fit 
    • Minimal Stretch 

     


    Style Number/Barcode: 05102-0599

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dreaming of Denim Days Dress

    We're dreaming of sunny summer days that are perfect for hanging with the squad! Throw this denim mini dress on and pair with clear pumps and dainty pieces for a look that slays!

    Fit & Features

    • Button Down Collar 
    • Two Chest Pockets
    • Short Roll Up Sleeves
    • Tie Front Waist | Waist Cut Out
    • Side Pockets
    • Single Button | Zipper Closure
    • Denim Fabric 


    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small.  

    Style Number/Barcode: 05102-0477

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just a Breeze Floral Mini Dress

    You can’t go wrong with a floral mini dress! Style it with wedges and hoops for cute and effortless summer look.

     Fit & Features

    • Off the Shoulder
    • Ditsy Floral Print
    • Mini Length

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0713

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Darling In Denim Mini Dress

    This darling denim mini is the new dress you need! It features a sleeveless, sweetheart neckline with a built-in padded bust, adjustable spaghetti straps, piping detailing down the front, and a short, curve-hugging fit. Complete the look in PVC strap mules.

    Fit & Features

    • Sleeveless, sweetheart neckline, built-in padded bust
    • Adjustable spaghetti straps
    • Back zipper closure
    • Piping detail down the front and back
    • Short, curve-hugging fit
    • Denim fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-0120

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Zip Up Chic Mini Dress

    Zip up into this chic LBD! Perf for a casual night out with the girls when you want to feel a little dressier than jeans!

    Fit & Features

    • Collared
    • Short sleeves
    • Half zip up front
    • Short, form hugging fit
    • Stretchy knit fabric

    Style Number/Barcode: 05102-0650

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Everyone's Sweetheart Puff Sleeve Mini Dress

    You are quite the sweetheart in this fun flirty mini dress! Whether ankle booties are your style, or you are a heels babe both will make this dress pop! The ruching down the center makes her perfect for all body types, and the polka dots keep her fun and lively!

    Fit & Features

    • Sweetheart neckline | Padded bust
    • Puff shoulders
    • Long sheer sleeves with polka dot detailing
    • Fully lined body with ruching down the center
    • Zipper closure center back
    • Mesh outer + Moderate stretch

    Style Number/Barcode: 05102-0619

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Double Take Ribbed Midi Dress

    Make them look twice when you step out in this sexy midi dress!

    Fits & Features

    • Lattice front detail
    • Midi Length I Sultry Side Slit 
    • Ribbed Knit 
    • Form Hugging I Plenty Of Stretch 

    Style Number/Barcode: 06005-0656

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Florals Smocked Mini Dress

    Charm them all with this sweet and enchanting mini dress! Layer some gorge jewelry and slip into your nude wedges for a fab brunch look! 

    Fits & Features

    • Sweetheart Neckline I Tie At Center Bust
    • Short Sleeves I Ruffle Trim At Cuffs I Off Shoulder Neckline 
    • Fully Smocked Back 
    • Mini Length Silhouette 
    • Woven Fabric I Unlined 
    • Form Hugging Fit I Plenty Of Stretch 

     

     

    Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0810

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Day Dreamin’ Eyelet Mini Dress

    Get ready for a sweet summer day in this eyelet dress. Pair it with wedges and a cute mini bag.

     Fits & Features

    • All Over Eyelet Pattern
    • Puff Sleeves
    • Lace Up Detailing
    • Ruffle Hem  

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0678

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Posh In Polka Dot Smocked Mini Dress

    You'll be looking oh-so-chic and posh in this pretty polka dot mini! 

    Fits & Features

    • Square Neckline & Back 
    • Organza Sleeves With Puff Shoulders & Elasticized Cuffs 
    • Smocked Bodice & Mini Length Skirt 
    • Mesh, Ruffle Trim At The Neckline & Hem 
    • Velvet Polka Dots Throughout 
    • Form Hugging Fit I Ample Stretch 
     Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0806

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Main Girl Ruffled Mini Dress

    You are our main girl in a mini dress! Whether you're searching for a bridal piece, or white is just ur color this mini dress is a sweet addition to your closet! Pair with neutral heels and simple earrings!

    Fit & Features

    • Square neckline
    • Spaghetti straps
    • Form fitting silhouette| Flattering vertical seams
    • Mini hemline with a ruffle trim
    • Stretchy woven material
    • Hidden zipper center back

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.  

    Style Number/Barcode: 05102-0621

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Shimmy In The Spotlight Cutout Fringe Mini Dress

    Bring the drama and then some—this fringe mini dress is made to move. With bold cutouts and a flirty A-line silhouette, it’s giving girls’ night energy with main character results.

    Fit & Features

    • Linen-like cotton-blend woven fabric, stretchy knit lining
    • V-neckline with tank straps
    • Back zipper and hook-eye closure
    • Fringe trim at bust and skirt
    • Waist cutouts with stitched detailing
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000146

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fall For Me Ruched Midi Dress

    People will fall for you over and over in this sultry curve hugging ruched midi dress! 

    Fit & Features

    • Spaghetti straps
    • Square neck and back
    • All over ruched detailing
    • Mid-length, form-fitting style
    • Knit fabric | Knit lining
    • Plenty of stretch

        Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

        Style Number/Barcode: 05102-0532

        Category Name: Casual Dresses

        Price: $9.97 $35.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Floral Smocked Ruffle Mini Dress

        This smocked and ruffled floral mini dress is a major yes. Add to cart and pair with some strappy heels for a nice daytime look!

        Fit & Features

        • Puff shoulders
        • Long sleeves | Smocked detail | Ruffle hems
        • Square neckline | Ruffle trim
        • Stretchy smocked bodice
        • Ruffle details
        • Short tiered ruffle hem
        • 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: 05102-0649

        Category Name: Casual Dresses

        Price: $9.97 $46.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance