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!

  • Paisley Babe V-Neck Midi Dress

    Look like a babe in this paisley midi dress to bring those retro vibes! It features a sleeveless V-neck, adjustable spaghetti straps, a bodycon silhouette, and an asymmetrical midi-hem with a trendy ruched seam. Complete the look in block heels for happy hour.

    Fit & Features

    • Sleeveless V-neck, adjustable spaghetti straps
    • Bodycon silhouette
    • Ruched side seam
    • Asymmetrical midi-length hem
    • Paisley pattern
    • Stretchy and soft knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4380

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spotted In Floral Mesh Ruffle Hem Dress

    Spotted in floral for spring! Refresh your closet with this flirty mini dress featuring a ruffle trim v-neck, adjustable spaghetti straps, a bodycon silhouette, ruffled hem, and a trendy front drawstring so you can customize the length. Composed of mesh-lined fabric with a moderate stretch. Finish the look in mules for a day date.

    Fit & Features

    • Sleeveless, ruffle trim v-neck
    • Adjustable spaghetti straps
    • Side ruched seams, front drawstring
    • Bodycon silhouette
    • Mini-length ruffled hem
    • Floral pattern, mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1453

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flower Power Skater Dress

    Elevate your spring style with this pretty floral printed skater dress. It features a subtle sweetheart neckline with ruching at the bust, short puff sleeves, a high waist, and a fit and flare silhouette with a short skater skirt with a ruffled hem. Style this lightweight chiffon dress with cute mules.

    Fit & Features

    • Sweetheart neckline, ruching at the bust
    • Short puff sleeves, elasticized hems
    • Back zipper, hook and eye closure
    • High waist seam, fit and flare silhouette
    • Short skater skirt, ruffled hem
    • Floral print
    • Sheer chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1406

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetie Puff Sleeve Mini Dress

    You'll look so sweet in this mini dress for a cute brunch fit. It features adorable short puff sleeves along the sweetheart neck with a cutout bust tie. The side ruched seams accentuate your curves on slinky knit-lined fabric with a moderate stretch. Complete the look in PVC mules.

    Fit & Features

    • Short puff sleeves, elastic cinched hems
    • Sweetheart neck, cutout bust tie
    • Side ruched seams, bodycon fit
    • Mini-length hem
    • Slinky knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4361

    Category Name: Casual Dresses

    Price: $5.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Retreat Chiffon Sweetheart Midi Dress

    Ready for a floral retreat? Feel the sunshine on your shoulders in this floral chiffon midi dress featuring dainty spaghetti straps, a sweetheart neckline with a bust tie, a fitted bodice, and a side slit accent. Complete the look in simple heels.

    Fit & Features

    • Sleeveless sweetheart neckline, bust tie accent
    • Spaghetti straps
    • Fitted bodice, back zipper, hook and eye closure
    • Midi-length hem, side slit
    • Ditsy floral pattern
    • Sheer chiffon fabric, knit lining
    • A-line silhouette, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4356

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral State Scoop Neck Mini Dress

    Got a floral state of mind? Then this mini dress is just what you need! It features a sleeveless, scoop neck, spaghetti straps, and ruched bust seam that leads to a bodycon silhouette. Complete the look in chic wedges for a cute picnic date.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Ruched bust seam
    • Bodycon silhouette
    • Mini-length hem
    • Floral print
    • Stretchy rib-knit fabric, lined
    • Fits true to size

    Style Number/Barcode: 05102-4601

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dinner Downtown Sleeveless Ruched Midi Dress

    The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch.

    Fit & Features

    • Smooth knit fabric, stretchy knit lining
    • Sleeveless crew neck
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000111

    Category Name: Casual Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S

  • Sway With Me Floral Chiffon Dress

    Sashay and sway in this adorable floral chiffon dress featuring a sleeveless, scoop neck, adjustable spaghetti straps, smocked back panel, and a flowy, ruffled tiered short hem. Complete the look in trendy sandals for your next getaway.

    Fit & Features

    • Sleeveless, scoop neck, adjustable spaghetti straps
    • Smocked back panel
    • Flowy, tiered short hem
    • Floral pattern
    • Chiffon-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4495

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Coastal Chic Striped Mesh Tunic

    Create chic beachside looks with this on-trend mesh tunic. It features a V-neckline, long fitted sleeves with flared hems, center ruched detailing, and a short, curve-hugging fit. Style this striped tunic as a cover-up over your fave bikini.

    Fit & Features

    • V-neckline
    • Long fitted sleeves, flared hems
    • Center ruching, adjustable drawstring
    • Mini-length, form-fitting silhouette
    • Striped pattern
    • Semi-sheer mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4195

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish Stunner Striped Halter Short Dress

    Keep it stylish in a short sweater dress that wows and keeps it effortless. The dress features a halter neck with an adjustable neck tie, a striped pattern, and a short-length hem. The dress is composed of an unlined knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with wedges.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Halter neck 
    • Adjustable neck ties
    • Striped pattern
    • Short-length hem 
    • Knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1231

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Splash Of Style Twist Mini Dress

    Your summer closet could use this stylish swirl print mini dress perfect for adding in brighter hues! It features a sleeveless, v-neck atop a twisted bust, spaghetti straps, bodycon silhouette, and side ruched seams to accentuate your natural curves. Complete the look in stiletto heels for a dinner with friends.

    Fit & Features

    • Sleeveless, v-neck, twisted bust, spaghetti straps
    • Bodycon silhouette
    • Side ruched seams
    • Mini-length hem
    • Swirl print
    • Stretchy soft knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4596

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Too Sweet Floral Ruffled Skater Dress

    These florals are too sweet not to fall for! Twirl all day in this chiffon skater dress featuring a sleeveless, v-neck, ruffled trim straps, waist tie, open-back design with tie closure, and a tiered ruffled skirt. Complete the look in statement earrings.

    Fit & Features

    • Sleeveless, v-neck, ruffled trim straps
    • Open-back with tie closure
    • Tie waist, tiered ruffled skirt
    • Skater silhouette
    • Floral pattern, back zipper closure
    • Chiffon fabric, inner knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1481

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Trendsetter Ruched Mini Dress

    Keep your look sweet and trendy with this adorable bodycon mini dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruched side detailing, a short, curve-hugging fit, and an all-over butterfly print. Style this dress with a pair of cute mules for an outing with the girls.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruched side detailing
    • Mini-length, form-fitting silhouette
    • Butterfly print
    • Brushed knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4370

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Puff Love Square Neck Skater Dress

    There's a lot to love about this puff sleeve skater dress! Features a square neck, smocked bodice, a trendy waist cutout, and a tiered short skirt. Composed of linen woven fabric with an inner lining. Finish the look in floral earrings for a cute spring fit.

    Fit & Features

    • Short puff sleeves, square neckline
    • Smocked bodice, waist cutout
    • Tiered short skirt
    • Skater silhouette
    • Linen woven fabric, inner lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4343

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Breeze Linen Halter Skater Dress

    Feel the breeze this spring! This linen skater dress is perfect for your next daytime soiree featuring a sleeveless halter V-neckline, open-back design, dual tie-back closure, and a flowy, A-line skater silhouette. Composed of linen fabric with an inner knit lining with minimal stretch. Style with strappy heels.

    Fit & Features

    • Sleeveless, halter V-neck
    • Open-back design, dual tie-back closure, lower back elasticized waistband
    • Flowy, A-line skater silhouette
    • Above-the-knee length hem
    • Linen fabric, inner knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4414

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eye On The Eyelet Lace Mini Dress

    Keep your eye on this prize! Bring the flirty allure in this eyelet lace mini dress featuring short puff sleeves, a ruffle sweetheart neck with tie, and a babydoll-style bodice on a form-fitting silhouette. Complete the look in lace-up sandals for a cute picnic look.

    Fit & Features

    • Short puff sleeves
    • Ruffle sweetheart neck with tie
    • Babydoll-style bodice
    • Form-fitting silhouette
    • Mini-length hem
    • Eyelet lace knit lined fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 05102-4429

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Knits Halter Midi Dress

    The cooler spring days call for your best knits! Set the tone in this halter midi sweater dress featuring a sleeveless high neck, adjustable spaghetti straps, space-dye knit pattern, bodycon silhouette, and a side slit accent to showcase some leg. Complete the look in cute mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless high neck, halter design
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Side slit, midi-length hem
    • Space-dye knit pattern
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1257

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild Vibes Sleeveless Short Dress

    Channel those wild vibes with a short dress that showcases your free-spirited side! The dress features a trendy zebra print, a sleeveless square neckline, bungee spaghetti straps, and a short-length hem. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a moto jacket for a night-out look.  

    Fit & Features

    • Zebra print
    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Short length hem
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4572

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Earn Your Stripes Sweater Midi Dress

    Earn your stripes in style rocking this sweater midi dress for all-day slays! It features a sleeveless square neck, adjustable spaghetti straps, a striped pattern, and a bodycon silhouette. Composed of a rib-knit fabric with a moderate stretch. Style with chic booties.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Striped pattern
    • Bodycon midi-length hem
    • Rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1240

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutest Look Floral Mini Dress

    Get the cutest look for the spring season with this adorable floral mini dress! It features a sleeveless sweetheart neckline with shirring at the bust, spaghetti straps, a short, curve-hugging fit, and an all-over dainty floral print pattern. Style this dress with a cropped denim jacket and strappy sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Shirring at the bust
    • Spaghetti straps
    • Mini-length, form-fitting silhouette
    • Floral print
    • Brushed knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4612

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Easy Breezy Eyelet Skater Dress

    Easy, breezy, and flirty! This eyelet skater dress is perfect for your next spring fling. It features a sleeveless, square neck, spaghetti straps, high waist seam, and a trendy open-back with twist detail on the flared short silhouette. The dress is composed of a lined lightweight woven knit fabric that offers a flattering form hugging fit with a moderate stretch. Complete the look in espadrille sandals.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • High waist seam
    • Open-back with twist detail
    • Flared short silhouette
    • Eyelet pattern
    • Lined lightweight woven knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4415

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Talker Strapless Bodycon Midi Dress

    Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000179

    Category Name: Casual Dresses

    Price: $33.90

    Availability: In Stock

    Available Color: LIGHT, BLUE, MOCHA

    Available Size: XS, M, L, S

  • Beachside Brunch Swim Coverup Dress

    Strut down the pier looking so fab in this maxi coverup dress featuring a sleeveless V-neckline, tank straps, and a form-fitting silhouette with a sultry front slit. The coverup dress is composed of an unlined semi-sheer knit fabric that offers a form-hugging fit. Perf for layering over your bikinis, complete the look in sandals.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline, tank straps
    • Surplice accent
    • Form-fitting silhouette
    • Front slit
    • Maxi-length hem
    • Unlined, semi-sheer sweater-knit fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06005-1250

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunday Girl Eyelet Lace-Up Skater Dress

    This eyelet skater dress is perfect for Sunday brunch! It features adorable short puff sleeves, a square neck, an elasticized waist, an open-back design with lace-up closure, and a flared skirt. Composed of breathable cotton fabric with an inner lining. Finish the look in strappy sandals.

    Fit & Features

    • Short puff sleeves
    • Squareneck
    • Elasticized waist
    • Open-back design, lace-up closure
    • Flared, skater silhouette, short-length hem
    • Eyelet lace cotton fabric, inner lining
    • Fits true to size, no stretch

    Style Number/Barcode: 05102-4428

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale