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!

  • Wildflower Crew Neck Mini Dress

    Wander through the flower fields in this cute mini dress featuring cap sleeves, a crew neck, and adjustable side drawstrings on rib-knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look in caged sandals for a picnic date.

    Fit & Features

    • Cap sleeves, crew neck
    • Adjustable side drawstrings
    • Form-fitting design
    • Mini-length hem
    • Ditsy floral print
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4692

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Charm Floral Mesh Mini Dress

    Showcase your stylish charm in this adorable floral mesh mini dress. It features a sleeveless sweetheart neckline, bungee spaghetti straps, all-over ruched detailing, and a short, form-fitting silhouette that will hug your curves. Complete the look with strappy mules for weekend brunch.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Bungee spaghetti straps
    • All-over ruching
    • Mini-length, form-hugging fit
    • Floral print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4541

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set The Style Marble Print Dress

    Set the style you desire! This marble print mini dress features side ruched drawstrings that let you customize the length depending on your preference, a square neck, spaghetti straps, and a form-hugging fit. Complete the look in strappy heeled mules. 

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Side ruched customizable drawstrings
    • Marble print 
    • Form-hugging fit
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4605

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Summer Style Maxi Dress

    Summertime is all about showcasing that effortlessly chic style! This ribbed knit maxi dress features a sleeveless one-shoulder neckline with a single spaghetti strap, a fitted high waist seam with a knot twist design, and a curve-hugging maxi-length silhouette with a trendy high slit. Complete the look with strappy mules.

    Fit & Features

    • Sleeveless one-shoulder neckline, single spaghetti strap
    • High waist seam, knot twist design
    • Maxi-length silhouette, high slit
    • Form-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4625

    Category Name: Casual Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Move It To The Music Mini Dress

    Move it and groove it to the music in this sassy mini dress featuring a sleek, sleeveless, v-neck, spaghetti straps, open-back with lace-up detail, form-fitting silhouette, and a swirl print woven fabric. Complete the look in platform lucite heels.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Open-back, lace-up detail
    • Form-fitting
    • Mini-length hem
    • Swirl print, woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4522

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Retreat Mesh Mini Dress

    Look like you're ready to jet-set off to an island retreat in this mesh mini dress! It features a sleeveless square neckline, spaghetti straps, ruched detailing down the side seams, and a short, curve-hugging fit. The lined mesh fabric features an all-over tropical palm leaf print. Complete your look with espadrille wedges.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down the side seams
    • Mini-length, form-fitting silhouette
    • Tropical palm leaf print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4534

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready Set Vacay Gauze Maxi Dress

    Pack this flowy lightweight maxi dress in your carry-on as you jet set off on vacay! It features a sleeveless V-neckline, halter spaghetti straps, a smocked high waist with chic cutouts leading to an open strappy back, and a floor-length maxi silhouette with a side slit and a relaxed fit. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Halter spaghetti straps, tie at the back of the neck
    • Smocked high waist, cutouts leading to open back
    • Strappy back design
    • Maxi-length silhouette, side slit
    • Woven gauze fabric, mini skirt knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4497

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropic Like It's Hot Halter Midi Dress

    It's vacay season and this halter midi dress is here for it! Featuring a sleeveless, high neckline with a tie closure, cutout bodice with a cinch accent, and a bodycon midi-length hem. Composed of a nylon-blend knit fabric with a moderate stretch. Finish the look with trendy mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, high halter neckline, tie closure
    • Cutout bodice, cinch accent
    • Bodycon silhouette
    • Midi-length hem
    • Nylon-blend knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1305

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Rose Tie-Back Ruffle Dress

    Sweet for the summer! Heads will turn when they see you in this rose print mini dress featuring a sleeveless square neck, spaghetti straps, high-waist seam, open-back with tie closure, and a surplice ruffled trim skirt. Complete the look with cork heels.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • High waist seam
    • Open-back with tie closure
    • Surplice ruffled trim
    • Short-length hem
    • Rose print, lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1609

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Sass Off The Shoulder Dress

    Subtle yet sassy, create a sultry allure in this off-the-shoulder midi dress featuring short-sleeve cuffs, twist accent bust, and a ribbed-knit fabric offering a form-hugging fit and a moderate stretch. Complete the look in lucite heels for a summer party.

    Fit & Feature

    • Off-the-shoulder neckline
    • Short-sleeve cuffs
    • Twist accent bust
    • Form-hugging fit
    • Midi-length hem
    • Ribbed knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4646

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good Marbles Lace-Up Mini Dress

    Turn your day into a fashion slay! Stay trending in this sleeveless mini dress featuring a square neck, spaghetti straps that lace up on the open back, and Venecia marble print on stretch-knit fabric that offers a form-hugging fit. Complete the look in doorknocker earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lace-up design
    • Form-hugging fit
    • Mini-length hem
    • Venecia marble print, stretch knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4607

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Heartbreaker Hourglass Midi Dress

    Soft, sleek, and serving curves. This bodycon midi dress is your go-to when you want to keep it simple but still shut it down—with flattering bust detail and a bodycon fit perfect for showing off on date night or a chic party.

    Fit & Features

    • Soft modal fabric, smooth knit lining, moderate stretch
    • Sweetheart neckline, bust detail
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000064

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

  • Everyday Basic Knit Mini Dress

    This simple yet stylish ribbed knit mini dress is a must-have for your everyday looks. It features a sleeveless crew neckline, tank shoulder straps, an alluring lower back cutout, and a short, curve-hugging fit. Style with a denim jacket for the day and dress it up with a faux leather jacket for the night!

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Lower back cutout
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4543

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Best Of Me V-Neck Cutout Midi Dress

    Impress the room by showing up in this sultry midi dress perfect for cocktail hour! Featuring a sleeveless, v-neck, adjustable spaghetti straps, and a flirty knot accent with dual waist cutouts that lead to the bodycon silhouette. Complete the look in chic lucite mules.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Back zipper closure
    • Front knot accent, dual waist cutouts
    • Bodycon silhouette
    • Midi-length hem
    • Slinky knit fabric, inner knit lining, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4357

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Fit Square Neck Mini

    Flaunt it! This square neck mini offers the perfect fit featuring sleek, bungee spaghetti straps, all-over ruching detail on a bodycon silhouette. Complete the look in a fab pair of heels. 

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • All-over ruching
    • Bodycon silhouette
    • Mini hem
    • Fits true to size

    Style Number/Barcode: 05102-4353

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Crush Floral Skater Dress

    Take your summer crush by surprise when they see you in this flirty floral skater dress! It features a sleeveless, v-neck, ruffled trim shoulder straps, a low-cut back with zipper closure, and a tiered, flowy hem with ruffles. Complete the look in sandals for a day date.

    Fit & Features

    • Sleeveless, v-neck, ruffled trim shoulder straps
    • Low-cut back, zipper closure
    • Skater silhouette
    • Tiered, flowy hem with ruffles
    • Ditsy floral print
    • Chiffon fabric, inner lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4417

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Siesta Keys Tropical Maxi Dress

    Take a vacation to Siesta Keys looking fab in this tropical maxi dress! It features a sleeveless, v-neck, spaghetti straps, and a tie-front bust atop a cutout bodice leading to the form-fitting silhouette with a sultry side slit. Complete your vacay look in a straw hat and your fave sunglasses.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Tie-front bust
    • Cutout bodice
    • Form-fitting silhouette
    • Side slit, maxi hem
    • Tropical print
    • Fits true to size

    Style Number/Barcode: 05102-4377

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • One More Moment Sweater Dress

    Make a lasting impression leaving the pool party in this chic cover-up sweater dress! It features a sleeveless, square neck, spaghetti straps that lead to an open-back with lace-up closure, a form-fitting silhouette, and a side slit atop the midi-length hem. Complete the look in sunglasses.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lace-up closure
    • Form-fitting silhouette
    • Slit midi-length hem
    • Sweater knit fabric, slightly sheer, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1317

    Category Name: Casual Dresses

    Price: $8.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Babe Of Funk Halter O-Ring Mini Dress

    Bring back the funk babe! This retro-inspired halter dress features a sleeveless plunge V-neck with an O-ring inset, a bodycon silhouette, and a mini-length hem. Complete the look in pointed-toe booties.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, plunge V-neck, halter strap
    • O-ring inset
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1292

    Category Name: Casual Dresses

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Life Made Easy Linen Halter Maxi Dress

    Look effortlessly put together in this breezy striped linen maxi dress for a Duffy boat cruise or beachside brunch! It features a sleeveless, halter v-neck with tie-closure, a partial open-back with tie, hidden side pockets, and a flowy, maxi-length silhouette with a sultry front slit. Complete the look in a straw floppy hat and sandals. 

    Fit & Features

    • Sleeveless, halter v-neck, tie-closure
    • Partial open-back with tie
    • Hidden side pockets
    • Flowy silhouette
    • Front high-cut slit
    • Maxi-length hem
    • Striped linen fabric, lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4468

    Category Name: Casual Dresses

    Price: $6.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Captivating Floral Mesh Mini Dress

    Captivate in this gorgeous floral mini dress! It features a sleeveless, scoop neckline, spaghetti straps, ruched bust and side seams, and a bodycon silhouette. Complete the look in espadrille wedges for a lunch date. 

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Lightly padded bust with ruching
    • Side ruched seams
    • Bodycon silhouette
    • Floral mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4553

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Pick Floral Mini Dress

    This adorable floral mini dress is the cutest pick for the summer season! It features a sleeveless square neckline, bungee spaghetti straps, ruched detailing down the side seams, a short, form-hugging fit, and an all-over daisy print. Style with a denim jacket and sneakers.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruching down the side seams
    • Mini-length, form-fitting silhouette
    • Small daisy floral print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4641

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Beauty Floral Maxi Dress

    Radiate your beauty in this blooming floral printed maxi dress! It features a romantic off-the-shoulder neckline, short ruffled drape sleeves, an empire waist, and a flowy floor-length silhouette with dual high front slits. Style this dress with strappy sandals.

    Fit & Features

    • Off-the-shoulder neckline
    • Short ruffled drape sleeves
    • Empire waist
    • Floor-length silhouette, flowy fit, dual front slits
    • Floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4535

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Palms Strappy Midi Dress

    Enter paradise island in this sultry midi dress perfect for a dinner with a view! It features a sleeveless, square neck, spaghetti straps, high waist seam, and a strappy open-back, bodycon silhouette, side ruched seam, and slit along the hem. Complete the look in statement fringe earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • High waist seam, strappy open-back
    • Bodycon silhouette
    • Side ruched seam and slit
    • Midi-length hem
    • Palm print, knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4508

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale