Casual Dresses

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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!

  • Call of The Wild Midi Slit Dress

    Answer the call in a fierce midi dress! Showcase your unique style in this geometric crepe midi dress featuring a sleeveless, V-neck, sleek spaghetti straps, and a slim-fit silhouette with a front slit accent. Complete the look in lattice booties.

    Fit & Features

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

    Style Number/Barcode: 05102-4649

    Category Name: Casual Dresses

    Price: $4.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Life's A Breeze Floral Cutout Midi Dress

    This floral cutout midi dress makes getting ready a breeze! It features short puff sleeves and a ruched sweetheart bodice with a flirty waist cutout that leads to a flowy, midi-length silhouette with a slit accent. Composed of a chiffon-lined fabric with no stretch. Style with a trendy mini tote.

    Fit & Features

    • Short puff sleeves
    • Ruched sweetheart bust
    • Waist cutout, smocked back
    • Midi-length silhouette with slit accent
    • Floral pattern
    • Chiffon fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1551

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Meet Me in the Meadow Chiffon Floral Maxi Dress

    Easy, breezy, and made for photoshoots and parties. This strapless chiffon maxi dress with a smocked bodice and floral print gives off-carefree weekend energy with a soft, boho vibe.

    Fit & Features

    • Floral print, chiffon fabric, short woven lining
    • Strapless smocked bodice
    • Flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000107

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, L

  • Island Views Tropical Cowl Mini Dress

    You may be in paradise but you'll be the main view in this tropical mini dress! Features a sleeveless, cowl neck, sleek spaghetti straps, bodycon silhouette, and an asymmetrical mini-length hem with a side ruched tie. Complete the look in hoop earrings and heels.

    Fit & Features

    • Sleeveless, cowl neck, spaghetti straps
    • Bodycon silhouette
    • Asymmetrical mini-length hem
    • Side ruched tie
    • Tropical pattern
    • Texture knit fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4366

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paradise Calls Tropical Midi Dress

    Vacation on the mind? You're going to need this tropical midi dress with paradise written all over it! Features a sleeveless, v-neck, adjustable spaghetti straps, a form-fitting silhouette, and a side ruched seam on an asymmetrical midi hem. Complete the look in lace-up sandals for a dinner with a view.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Form-fitting silhouette
    • Side ruched seams
    • Asymmetrical midi hem
    • Tropical pattern
    • Texture knit fabric, moderate stretch. fits true to size

    Style Number/Barcode: 05102-4367

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrapped In Chic Style Midi Sweater Dress

    Get wrapped up in chic style in this ribbed knit sweater dress. It features a sleeveless V-neckline, tank shoulder straps, a trendy knot-front design with a small center keyhole cutout, and a mid-length, curve-hugging fit. Complete the look with strappy mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline
    • Tank shoulder straps
    • Knot-front design, center keyhole cutout
    • Midi-length, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1256

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Beauty Floral Bodycon Dress

    Hey beauty! Showcase your charm in this blooming floral bodycon dress. It features a sleeveless square neckline, spaghetti straps, chic ruching down the sides, and a short, curve-hugging silhouette. Style this dress with sparkly stud earrings and cute mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruched detailing down the sides
    • Mini-length, form-fitting, bodycon silhouette
    • Floral print
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4549

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cold Brew Collared Mini Dress

    For coffee dates and everything else, you'll adore this collared v-neck mini dress designed to flatter your figure on a bodycon silhouette with a faux button-down accent and all-over ruching. Composed of sleek knit fabric with a moderate stretch. Finish the look in cute booties.

    Fit & Features

    • Sleeveless, collared v-neck
    • Faux button-down placket
    • All-over ruching
    • Bodycon silhouette
    • Mini-length hem
    • Sleek knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4482

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Glam Lattice Short Dress

    Bring it back to basics to make a glam impression in a short sweater dress that stuns! This must-have dress features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a lace-up back design, and a short-length hem. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross back 
    • Lace-up back 
    • Short-length hem 
    • Ribbed knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size 

    Style Number/Barcode: 06005-1332

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Soiree Puff Sleeve Mini Dress

    Heading to an afternoon soiree? This floral mini dress is perfect! It features adorable short puff sleeves, a sweetheart neckline, a front bust tie with a keyhole accent, and a bodycon silhouette. Complete the look with a crossbody bag.

    Fit & Features

    • Short puff sleeves, elasticized hems
    • Sweetheart neckline
    • Front bust tie, keyhole accent
    • Bodycon silhouette
    • Mini-length hem
    • Floral pattern
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4608

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy-Chic Style Halter Midi Dress

    Showcase your trendy-chic status in this of-the-moment midi dress! It features a sleeveless halter neckline, spaghetti straps that lead to a cross-back lace-up strappy design, a sleek front O-ring accent, a midi-length, curve-hugging silhouette, and an all-over geometric striped pattern. Style this dress with heeled mules.

    Fit & Features

    • Sleeveless halter neckline, spaghetti straps
    • Open back, strappy cross-back lace-up design, tie closure
    • Front O-ring detail
    • Midi-length, form-fitting silhouette
    • Geometric striped pattern
    • Knit fabric, partial front knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4411

    Category Name: Casual Dresses

    Price: $4.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chasing Sunsets Floral Maxi Dress

    This floral maxi dress is perfect for sunset dinners while on vacay! It features sleeveless, v-neck, sleek spaghetti straps, and a slim-fit silhouette with a front side slit to showcase some skin. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless, V-neck, sleek spaghetti straps
    • Slim-fit silhouette
    • Front side slit
    • Maxi-length hem
    • Floral pattern
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1393

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Poised And Chic Sweater Dress

    Keep it poised and chic with a sweater dress that is perf for every day! The dress features a sleeveless collared neckline, a button-down front, and a bodycon fit through the hip and thigh. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules and hair clips.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features 

    • Sleeveless collared neckline
    • Button-down front 
    • Bodycon fit
    • Short-length hem 
    • Ribbed knit fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size  

    Style Number/Barcode: 06005-1451

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Destination Dinner Paisley Halter Mini Dress

    Dinner plans? You're gonna need this perfect halter mini dress! It features a sleeveless bodice on an open-back with dual tie-back closure, a front slit accent, bodycon silhouette, and a paisley pattern throughout. Complete the look in lace-up heels.

    Fit & Features

    • Sleeveless, halter neckline
    • Dual tie-back closure
    • Front slit accent
    • Bodycon silhouette
    • Mini-length hem
    • Paisley pattern
    • Knit fabric, partial front knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4410

    Category Name: Casual Dresses

    Price: $4.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Places To Go One Shoulder Midi Dress

    You've got places to go and this one-shoulder midi dress will have you looking stylish! It features a spaghetti strap, bodycon silhouette, and an asymmetrical midi-length hem with a high side slit to showcase some legs. Composed of stretchy texture knit fabric. Finish the look in platform heels.

    Fit & Features

    • Sleeveless, one-shoulder, spaghetti strap
    • Bodycon silhouette
    • Asymmetrical midi-length hem
    • High side slit
    • Texture knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4358

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Nothing Bud Fun Floral Halter Dress

    Have nothing but fun in this flirty floral halter dress perfect for a brunch date! It features a sleeveless, halter v-neck with adjustable neck tie, a babydoll style bodice leading to a flowy, ruffled short hem. Showcase some skin in the open-back with tie closure. Complete the look in lace-up sandals.

    Fit & Features

    • Sleeveless, halter v-neck, adjustable necktie
    • Babydoll style bodice
    • Flowy ruffled short hem
    • Open-back, tie closure
    • Ditsy floral print, woven-lined fabric
    • Fits true to size, no stretch

    Style Number/Barcode: 05102-4364

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Let It Flow Crochet V-Neck Skater Dress

    Flowy and flirty! Twirl all day in this crochet V-neck skater dress featuring a sleeveless bodice with adjustable spaghetti straps, an open back with tie closure, and a tiered short hem. Composed of a gauze woven fabric with an inner lining. Finish the look in trendy mules.

    Fit & Features

    • Sleeveless bodice, crochet V-necklined
    • Adjustable spaghetti straps
    • Open-back, tie closure
    • Tiered short hem
    • Skater silhouette
    • Airy gauze woven fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4397

    Category Name: Casual Dresses

    Price: $21.97 $47.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Timeless Romance Open Back Lace Romper

    Enter your forever romantic era in this lace long sleeve romper boasting a flirty open back and ruffled short-length hem.

    Fit & Features

    • Lace-lined fabric
    • Scoop neckline
    • Sheer fitted long sleeves
    • Open back
    • Form-hugging fit
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 06503-1276

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Day To Night Snap Button Midi Dress

    Go from office hours to happy hour in a snap with this classy sweater midi dress! It features long sleeves, a rounded neckline, a bodycon silhouette, and a side slit with snap button accents. Composed of a ribbed knit fabric with a moderate stretch. Style with a chic jacket and heels.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Long fitted sleeves
    • Round neckline
    • Bodycon silhouette
    • Side slit, snap button accents
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1219

    Category Name: Casual Dresses

    Price: $18.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruffle Party Chiffon V-Neck Babydoll Dress

    Make a ruffle at the party in this chiffon babydoll dress featuring a sleeveless V-neckline, adjustable spaghetti straps, criss-cross back, flowy silhouette, and a ruffled trim throughout. Composed of a chiffon woven fabric with an inner skirt lining. Perfect for styling with a mini tote bag.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Criss-cross back
    • Babydoll flowy silhouette
    • Ruffled trim throughout
    • Chiffon woven fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1465

    Category Name: Casual Dresses

    Price: $6.67 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunday Girl Floral Chiffon Skater Dress

    Look cute for Sunday brunch in this floral chiffon skater dress featuring three-quarter length puff sleeves, a square neck, and a pleated waistband on the skater silhouette. Showcase a peek of skin in the open-back design with tie closure and ruffled short-length hem. Composed of a chiffon floral lined fabric with no stretch. Perfect for styling with knee-high boots.

    Fit & Features

    • Three-quarter length puff sleeves, elastic cinched hems
    • Square neckline
    • Pleated waistband, skater silhouette
    • Ruffled short-length hem
    • Open-back, tie closure, back zipper, hook and eye closure
    • Chiffon floral lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1706

    Category Name: Casual Dresses

    Price: $25.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Prepped For Anything Cutout Mini Dress

    With this mini dress, you'll be ready for whatever plans come up! It features long sleeves, a collared neck, button-down closures, a sultry cutout bodice on a bodycon silhouette. Composed of stretchy rib-knit fabric. Style with mules.

    Fit & Features

    • Long sleeves, collared neck
    • Button-down closures
    • Cutout bodice
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4354

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fab And Wild Slip Dress

    Keep it fab with a slip dress that showcases your wild side! The dress features a snake print, a sleeveless cowl neckline, adjustable spaghetti straps that cross at the back, a tie-back accent, and a short-length hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with a minimal stretch. Complete look with wedges

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps, cross at back
    • Tie back ties
    • Snake print
    • Short length hem
    • Lined lightweight woven fabric
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4345

    Category Name: Casual Dresses

    Price: $4.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Always On Point Ruched Mini Dress

    You'll always look on point in this trendy ruched mini dress! It features a sleeveless square neckline, bungee straps, a high waist seam, side ruched detailing with adjustable drawstrings, and a short, curve-hugging fit. Style this dress with sleek hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Bungee straps
    • High waist seam
    • Side ruching, adjustable drawstrings
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4472

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale