Casual Dresses

Show filters
Sort:
Size
Color
Price
All filters
Sort
Loading...

Product Recommendations

STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

Discover New Skater Dress Styles

Everyday Ease: Casual Dresses for Cool-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.

Laid-Back & Versatile

Knit, ribbed, and sweater dresses bring comfort and style to crisp fall 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 burgundy 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!

  • Cute As A Daisy Ruffle Strap Dress

    You'll look so cute in this daisy ruffle strap dress designed in a classic sleeveless, sweetheart bodice with ruffle tank straps, and a bodycon silhouette. Composed of brushed knit fabric with a moderate stretch. Perfect for styling with lace-up heels.

    Fit & Features

    • Sweetheart bodice
    • Ruffle tank straps
    • Bodycon silhouette
    • Mini length hem
    • Daisy floral pattern
    • Brushed knit fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 05102-4440

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Budding Romance Chiffon Skater Dress

    Isn't a new romance so exciting! Enter into your new spring fling in this floral chiffon skater dress featuring a sleeveless, ruffled V-neck, adjustable spaghetti straps, an open back with cross straps, and a tiered ruffle trim skirt. Complete the look in lucite mules for the perf day date.

    Fit & Features

    • Sleeveless, ruffled V-neck, adjustable spaghetti straps
    • Open-back, cross straps, back zipper closure
    • Tiered ruffle trim skirt
    • Skater-style silhouette
    • Floral pattern
    • Chiffon fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1482

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blushing Floral Sweetheart Mini Dress

    Make the room blush when they see you in this sweetheart mini dress! It features short bishop sleeves with button closures, a built-in padded bust with underwire support, floral print, and a form-fitting silhouette. Complete the look in classy heels. 

    Fit & Features

    • Short bishop sleeves, button closures
    • Built-in padded bust with underwire
    • Sweetheart neckline
    • Floral print, back zipper closure
    • Short hem, form-fitting
    • Crepe woven-lined fabric 
    • Fits true to size, no stretch

    Style Number/Barcode: 05101-1374

    Category Name: Casual Dresses

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Denim Spirit Tie-Back Mini Dress

    Cute, casual, with the spirit of denim in a sleek bodycon mini dress! Features a sleeveless, square neck, spaghetti straps, and a tie-back closure on a sultry open-back design. Complete the look in strappy mules for a day date.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Open tie-back, zipper closure
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4248

    Category Name: Casual Dresses

    Price: $4.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Beauty Ruffled Floral Dress

    Showcase your beauty in this sweet floral chiffon dress! It features short puff sleeves, a sweetheart neckline, a high waist with a fit and flare silhouette, and a short flowy skirt with a charming ruffled hem. The sheer chiffon fabric features an all-over dainty floral print and includes a lightweight woven lining. Style this dress with cute espadrille sandals.

    Fit & Features

    • Short puff sleeves, elasticized hems
    • Sweetheart neckline, ruching at the bust, partially smocked back
    • High waist seam, fit and flare silhouette
    • Mini-length flowy skirt, ruffled hem
    • Floral print
    • Sheer chiffon fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1430

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Burst Ruffled Short Dress

    Bring a burst of florals with a short dress that will have you brunch ready! The dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, and a cutout at the midriff. The smocked waist leads to a flowy skater silhouette with tiered ruffles. The dress is composed of a lined chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with wedges

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Cutout at midriff, smocked waistband
    • Floral print
    • Skater silhouetted, tiered ruffles
    • Lined chiffon fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05101-1505

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mocktail Sleeveless Rib Knit Mini Dress

    This chic mini dress was made for cocktail hour! It features a sleeveless, mock neck, bodycon silhouette, and is composed of stretchy rib-knit lined fabric. Complete the look in a hair clip to create a stunning updo.

    Fit & Features

    • Sleeveless, mock neck
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy rib-knit lined fabric
    • Fits true to size

    Style Number/Barcode: 05102-4546

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vineyard Floral Slit Maxi Dress

    Wine tasting anyone? This floral maxi is perfect for sipping on your fav red or white! It features a sleeveless, off-the-shoulder neckline, a form-fitting silhouette, and dual front slits for a sultry show of leg. Complete the look in wedges and a floppy hat.

    Fit & Features

    • Sleeveless, off-the-shoulder neckline
    • Flutter sleeve cuffs
    • Form-fitting silhouette
    • Dual front slits, maxi-length hem
    • Floral pattern
    • Stretch-knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4554

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rare Sight Basic Crew Midi Dress

    What a rare sight you'll be in this figure-flaunting basic midi dress featuring sleek, short sleeves, a crew neck, and a bodycon silhouette on stretchy, ribbed knit fabric. Complete the look in a trendy denim jacket and sneakers.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Bodycon silhouette
    • Midi-length hem
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4352

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Endless Sun Crepe Knit Midi Dress

    Bare your shoulders in this floral midi dress for brunch with the girls! Featuring spaghetti straps, a sweetheart neckline, and a front slit accent on crepe knit fabric with a moderate stretch. Complete the look in heeled mules and hoops.

    Fit & Features

    • Sleeveless, spaghetti straps
    • Sweetheart neckline, slit accent
    • Floral print
    • Midi hem
    • Crepe knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4305

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Free The Butterfly Ruche Mini Dress

    Spread your wings butterfly babe! Look cute in this mini dress featuring a sleeveless, square neckline, adjustable spaghetti straps, and side ruched seams to accentuate your curves on the mini-length hem. Composed of a soft knit-lined fabric with a moderate stretch. Style with platform heels for a fun night out.

    Fit & Features

    • Sleeveless square neckline, adjustable spaghetti straps
    • Side ruched seams, bodycon silhouette
    • Butterfly print
    • Mini-length hem
    • Knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4385

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Geometric Fun Cutout Mini Dress

    This mini dress requires no math skills! Features a sleeveless V-neckline, spaghetti straps, bodycon silhouette, and a flirty front cutout bodice with ruched detail. Composed of geometric print fabric. Finish the look in strappy heels.

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Bodycon silhouette
    • Front cutout, ruched detail
    • Mini-length hem
    • Adjustable drawstrings
    • Geometric print, knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4350

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All About You High Neck Floral Mini Dress

    Slip into this floral mini dress and command attention wherever you go. This bodycon silhouette hugs your curves in all the right places, while the chic high neck adds a touch of sophistication.

    Fit & Features

    • Floral print, mesh-lined fabric
    • High neck
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5921

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Prowlin' Leopard Mini Slip Dress

    On the prowl and looking fierce! This leopard mini slip dress features a sleeveless V-neckline, sleek bungee spaghetti straps, a bodycon silhouette, and a front slit accent. Complete the look in classy hoop earrings.

    Fit & Features

    • Sleeveless V-neck, bungee spaghetti straps
    • Bodycon silhouette
    • Front slit accent
    • Mini-length hem
    • Leopard pattern
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4418

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charmed And Fab Floral Skater Dress

    Bring the charm with a skater dress that creates a fab moment! The dress features a floral print, a sleeveless wrap V-neckline, adjustable spaghetti straps, and an elastic drawstring at the waist. The waist leads to a flowy skater skirt with a tiered ruffled design. Complete look with wedges and butterfly clips

    Fit & Features

    • Sleeveless wrap V-neckline
    • Adjustable spaghetti straps
    • Elastic drawstring at waist
    • Floral print
    • Tiered ruffles
    • Short length skater hem 
    • Relaxed fit, minimal stretch, runs true to size 

    Style Number/Barcode: 05101-1575

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sway With Me Chiffon Dot Tiered Dress

    Sashay all day! Look adorbs in this chiffon sleeveless dress featuring a square neck, tie-straps, and a flowy tiered design on a short-length hem. Complete the look in a cute boater hat.

    Fit & Features

    • Sleeveless, square neck, tie-straps
    • Flowy tiered design
    • Short-length hem
    • Chiffon dot fabric, inner knit lining
    • Fits true to size

    Style Number/Barcode: 05101-1513

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Scene V-Neck Mini Dress

    Make a scene in this floral mini dress sure to cause compliments! Featuring a sleek, sleeveless v-neckline, bungee spaghetti straps, and a bodycon silhouette atop a mini-length hem with a flirty slit accent. Complete the look in chic sandals for a fun day out.

    Fit & Features

    • Sleeveless, v-neckline
    • Bungee spaghetti straps
    • Bodycon silhouette
    • Mini-length hem, slit accent
    • Floral pattern
    • Stretch-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4419

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Instinct Satin Midi Dress

    Showcase your chic instinct in this satin snake midi dress featuring a classy, sleeveless, cowl neck, dual adjustable strappy design, and a flared hem. Complete the look in sleek stiletto heels for a dinner date.

    Fit & Features

    • Sleeveless, cowl neck
    • Dual adjustable strappy design
    • Flared midi hem
    • Snake pattern
    • Satin fabric, no stretch, fits true to size

    Style Number/Barcode: 05102-4655

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bohemian Oasis Scoop Neck Midi Dress

    Take the cutest pics in the desert in this boho-chic midi dress! Featuring a sleeveless, ruched scoop neck with front tie, spaghetti straps, and slim-fit silhouette. Complete the look in a trendy panama hat.

    Fit & Features

    • Sleeveless, ruched scoop neck, spaghetti straps
    • Front tie accent
    • Slim-fit silhouette
    • Midi-length hem
    • Geometric print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4652

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Idyllwild Floral Bust Tie Mini Dress

    Put your curves on display in this cute floral mini dress designed in a sleeveless, sweetheart neck with a ruched bust tie, spaghetti straps, and side ruched seams. Composed of a brushed knit fabric with a moderate stretch. Finish the look in hoop earrings.

    Fit & Features

    • Sleeveless, sweetheart neck, ruched bust tie
    • Spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Floral pattern, brushed knit fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 05102-4369

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ahead Of The Pack V-Neck Mini Dress

    Set the trend before anyone else in this cow print mini dress! Features a classic sleeveless, v-neck, bungee spaghetti straps, a bodycon silhouette, and a flirty front slit accent. Complete the look in lace-up heels for a brunch fit.

    Fit & Features

    • Sleeveless, v-neck, bungee spaghetti straps
    • Bodycon silhouette
    • Front slit accent
    • Mini-length hem
    • Cow print
    • Crepe fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4653

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cool Girl Vibes Space Dye Mini Dress

    Bring the cool girl vibes in this trendy curve-hugging mini sweater dress! It features a sleeveless halter neckline with tie-back straps, a center O-ring accent at the bust, a front waist cutout, and a fitted mini-length silhouette. The sweater knit fabric features a space dye design. Style this dress with gold hoops and cute mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, halter neckline, tie-back straps
    • Center O-ring accent at the bust
    • Front waist cutout under the bust
    • Short, form-fitting silhouette
    • Sweater knit fabric, moderate stretch
    • Space dye knit design
    • Runs true to size

    Style Number/Barcode: 06005-1400

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Scoop Neck Mini Dress

    This mini dress requires zero gardening! It features a sleeveless, scoop neck, thin spaghetti straps, a ruched bust, floral print, and a bodycon silhouette. Complete the look with a cute mini tote.

    Fit & Features

    • Sleeveless, scoop neck, thin spaghetti straps
    • Ruched bust
    • Floral print
    • Bodycon silhouette
    • Mini-length hem
    • Crepe fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4654

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jungle Cat Leopard Cowl Midi Dress

    You're the queen of the jungle in this leopard midi dress featuring a sleeveless, cowl neck, spaghetti straps, slim-fit silhouette, and a sultry front slit. Complete the look in heels.

    Fit & Features

    • Sleeveless, cowl neck, spaghetti straps
    • Slim-fit silhouette
    • Midi-length hem
    • Front slit accent
    • Leopard print
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4462

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free