Casual Dresses

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STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print 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!

  • Casual Showstopper Lace-Up Midi Dress

    This midi dress is a casual showstopper! Make heads turn in this alluring dress featuring a sleeveless square neck, spaghetti straps that lace up in the back, a bodycon silhouette, and a fitted hem with a back-slit accent. Complete the look in dainty stiletto heels for a daytime celebration.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Lace-up back, lower zipper and hook-eye closure
    • Bodycon silhouette
    • Fitted midi-length hem, back slit
    • Texture knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5095

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Girl Style Turtleneck Midi Dress

    Elevate your fall wardrobe and show off a chic girl style with this bodycon midi dress! It features a sleeveless bodice, a turtleneck, a midi-length hem with a thigh-high side slit, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a layered chain necklace and ankle booties!

    Fit & Features

    • Sleeveless bodice
    • Turtleneck
    • Midi-length hem
    • High side slit
    • Bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5096

    Category Name: Casual Dresses

    Price: $17.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Basic Crew Neck Slit Midi Dress

    Forever your basic midi dress with head-turning detail! It features classic cap sleeves, a crew neckline, a flirty cutout back accent, a flattering bodycon silhouette, and a midi-length hem with a high front slit. The soft brushed knit fabric has plenty of stretch. Complete the look with a glam ring set for a family party or casual date!

    Fit & Features

    • Cap sleeves
    • Crew neckline
    • Cutout back accent
    • Bodycon silhouette
    • Midi-length hem, high front slit
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5334

    Category Name: Casual Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Let's Have Some Fun Lace Bodycon Ruffle Mini Dress

    Looking for a flirty, fun vibe? Then you'll adore this lace mini dress designed with a flattering ribbon lace trim V-neckline and a bodycon fit with a ruffled hem.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Lace ribbon trim V-neckline
    • Adjustable spaghetti straps
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000079

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Work Or Play Ruffle Strap Button Skater Dress

    Work or play, this cotton skater dress is a charming choice for a stroll downtown or a coffee date! It features a sleeveless V-neckline, adorable ruffled straps, a stretchy smocked bodice, a button-down front, and a flattering short-length hem. Complete the look in strappy heels.

    Fit & Features

    • Sleeveless V-neckline
    • Ruffled straps
    • Stretchy smocked bodice
    • Button-down front
    • Skater silhouette, short-length hem
    • Lightweight cotton fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5369

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Color Splash Tie Dye Glitter Midi Dress

    Make a splash this summer in this colorful tie-dye midi dress! It features a sleeveless square neck, adjustable spaghetti straps, side ruched seams that accentuate your curves along the bodycon silhouette, a flirty side slit, and a midi-length hem. The dress is designed with a trendy all-over tie dye print and glitter on mesh fabric with a sewn-in knit lining. Complete the look in heels for an outdoor party!

    Fit & Fetaures

    • Sleeveless square neck, adjustable spaghetti straps
    • Side ruched seams, bodycon silhouette
    • Back zipper and hook-eye closure
    • Side slit, midi-length hem
    • All-over tie-dye print, glitter
    • Mesh fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5348

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Curve Allure Mock Neck Maxi Dress

    Bring the allure to your look in this curve-flaunter maxi dress perfect for a dinner out with friends or date night! It features a sleeveless mock neck, bodycon silhouette, and side slit accent, and is crafted from smooth knit fabric with lining. Complete the look with a cute crop jacket.

    Fit & Features

    • Sleeveless mock neck
    • Bodycon silhouette
    • Side slit accent
    • Maxi-length hem
    • Smooth knit fabric, lined, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5232

    Category Name: Casual Dresses

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Divine Darling Square Neck Ruffle Mini Dress

    Breeze in looking so darling in this sleeveless mini dress for a day date or dinner party! It features a square neckline, adjustable spaghetti straps, an eye-catching tie-back closure, and a flattering wrap hem with ruffle trim. The dress is composed of an airy woven fabric with a stretchy knit lining. Complete the look with strappy block heels.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Tie-back closure
    • Wrap mini-length hem, ruffle trim
    • Airy woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2860

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Sultry Cutout Bodycon Midi Dress

    This curve-hugging bodycon midi dress is simply sultry and perf for a night out with your girls. It features a sleeveless square neckline, spaghetti straps, alluring waist cutouts at the front and back, ruching down the side seams leading to a midi-length hem, and an all-over bodycon silhouette to show off your figure. The sheer mesh fabric includes a soft knit lining and has plenty of stretch. Style with a layered chain necklace for a hint of glam!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Front and back waist cutouts
    • Ruched side seams
    • Midi-length hem, bodycon silhouette
    • Sheer mesh fabric, sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4648

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Chill Crew Neck Knit Dress

    You'll feel effortlessly chill in this basic midi dress perfect for looking cute on the go! It features short sleeves, a crew neck, a bodycon silhouette, a side slit accent, and a knee-length hem. The dress is composed of a soft hacci rib knit fabric with plenty of stretch. Style with trendy flat sandals for grabbing coffee!

    Fit & Features

    • Short sleeves
    • Crew neck
    • Bodycon silhouette
    • Side slit accent
    • Knee-length hem
    • Hacci rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5190

    Category Name: Casual Dresses

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Colorful Style Strapless Abstract Mini Dress

    Showcase a colorful style in this abstract print mini dress out and about with the girls! The dress features a strapless neckline, bodycon silhouette, and a fitted hem on mesh fabric with a stretchy knit lining. Complete the look with a sleek choker and sandals!

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Mini-length fitted hem
    • Abstract print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5275

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Loving Basics V-Neck Bodycon Tank Dress

    Every girl loves her basics and this sleeveless tank dress is perfect for day or night styling! It features a sleeveless notch V-neckline, a bodycon silhouette, and a fitted mini-length hem on stretchy rib knit fabric. Complete the look in a layered choker necklace for a backyard dinner party or casual hang!

    Fit & Features

    • Sleeveless notch V-neckline
    • Bodycon silhouette
    • Fitted mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5176

    Category Name: Casual Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Caught In The Midi Crew Neck Tank Dress

    A midi dress you wouldn't mind being spotted in! The dress features a sleeveless crew neck, a bodycon silhouette, and a fitted midi-length hem on stretchy rib knit fabric. Complete the look in a sleek layered necklace for lunch with friends!

    Fit & Features

    • Sleeveless crew neck
    • Bodycon silhouette
    • Fitted midi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5242

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Be Mine Ditsy Floral A-Line Midi Dress

    Make this ditsy floral midi dress be yours for the summer and beyond! It features a sleeveless V-neckline, adjustable spaghetti straps, a trendy tie-back cutout design, and a flattering A-line silhouette, front slit with a frayed trim, and midi-length hem. Complete the look in block heels for a dressy soiree!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back cutout design
    • Hidden side zipper closure
    • A-line silhouette, front slit, frayed trim
    • Midi-length hem
    • Ditsy floral print, airy woven fabric, short chiffon lining
    • Runs true to size

    Style Number/Barcode: 05102-5320

    Category Name: Casual Dresses

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Curve-Hugging Chic Sheer Lace Maxi Dress

    Flaunt your stunning silhouette in this casual curve-hugging sheer lace maxi dress. It features a crew neckline, short sleeves, dainty ruffled trims, a maxi-length hem with a back slit accent, and a bodycon fit. The sheer textured lace fabric offers a moderate stretch. Style with clear heels.

    Fit & Features

    • Crew neckline, short sleeves
    • Back zipper and hook-eye closure
    • Ruffled trims
    • Maxi-length hem, back slit
    • Bodycon silhouette
    • Sheer textured lace fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5228

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Striking And Chic Marble Print Midi Dress

    So striking and chic, this marble print midi dress will capture all the attention at happy hour! It features a sleeveless V-neckline, spaghetti straps, an asymmetric high-cut midi-length hem creating a thigh-high slit, and a bodycon silhouette that will flaunt your figure. The buttery smooth and stretchy knit fabric features an all-over multicolored marble print pattern. Style with clear mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Asymmetric high-cut midi-length hem, high slit
    • Bodycon silhouette
    • Multi-colored marble print
    • Smooth and stretchy knit fabric, full-length sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5231

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hit The Tropics V-Neck Midi Dress

    Ready for vacay babe? Hit the tropics in this perfect midi dress featuring a sleeveless V-neck, adjustable spaghetti straps, a side ruched seam, bodycon fit, and an asymmetrical side slit cutout. Complete the look in cute platform wedges.

    Fit & Features

    • Sleeveless V-neck
    • Adjustable spaghetti straps
    • Side ruched seam, bodycon fit
    • Asymmetrical midi hem, side slit cutout
    • Tropical print
    • Smooth knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4896

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vibrant Getaway Abstract Midi Dress

    This abstract print midi dress was made for your next getaway! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, side ruched seams, and a flirty asymmetrical side slit along the hem. Complete the look in cute sandals.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Bodycon silhouette, side ruched seams
    • Asymmetrical side slit, midi-length hem
    • Abstract print
    • Smooth knit fabric, bust lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5216

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Off-Duty Icon Mock Neck Mini Dress

    A sleek mock neck and bodycon ruched silhouette keep your fit snatched from every angle, while the abstract print brings chic energy to your next date night or rooftop dinner.

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Mock neck
    • Ruched bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000188

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Coastal Vacay Tie-Shoulder Ruffled Short Dress

    This cute and casual ruffled short dress is perfect for a coastal summer vacay! It features a sleeveless scoop neckline, tie-shoulder tank straps, hidden side pockets, a drop waist seam with a ruffled short-length hem, and a relaxed A-line silhouette. The cotton fabric has no stretch. Style with gold hoops and espadrille sandals!

    Fit & Features

    • Sleeveless scoop neckline
    • Tie-shoulder tank straps
    • Hidden side pockets
    • Drop waist seam, ruffled short-length hem
    • Relaxed A-line silhouette
    • Cotton fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5345

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leave An Impression Abstract Midi Dress

    Leave an impression everywhere you go in this abstract midi dress! It features a sleeveless square neckline, spaghetti straps, side ruched seams to accentuate your curves, and a flattering bodycon silhouette. The dress is designed with a figure-flattering abstract print on knit fabric with a stretchy lining. Complete the look in cute sandals for a lunch date.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Abstract print, smooth knit fabric, stretchy lining
    • Runs true to size

    Style Number/Barcode: 05102-5252

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually Effortless Smooth Knit Bodycon Mini Dress

    Enjoy an effortless day or night out with this casual smooth knit mini dress! Its strapless neckline and bodycon silhouette are perfect for showing off those curves, while the mini-length hem ensures you get noticed! The dress is composed of a slinky smooth knit fabric with a stretchy knit lining. Complete the look in sassy lace-up sandals.

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Slinky smooth knit fabric, stretchy knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5289

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendsetting Cutie Cable Knit Lace-Up Dress

    Step out as a trendsetting cutie in this cable knit midi dress perfect for daytime strolls! It features a sleeveless square neck, thin shoulder straps that create the lace-up back design, a tie-waist belt, a bodycon silhouette, a side slit, and a midi-length hem. Complete the look in flat sandals and sunglasses.

    Fit & Features

    • Sleeveless square neck, thin shoulder straps
    • Lace-up back design
    • Tie-waist belt
    • Bodycon silhouette
    • Side slit, midi-length hem
    • Cable knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5155

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Taking Care Of Business Collar Tank Mini Dress

    Take care of business in preppy style! This sleeveless mini dress features a trendy collared V-neckline, a bodycon silhouette, and a fitted mini-length hem on stretchy rib knit fabric. Complete the look with a dainty bracelet for a coffee shop hang!

    Fit & Features

    • Sleeveless collared V-neckline
    • Bodycon silhouette
    • Fitted mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5139

    Category Name: Casual Dresses

    Price: $13.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale