Casual Dresses

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STYLE SPOTLIGHT

Cute Sweater 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!

  • Picnic Date Eyelet Lace V-Neck Dress

    The cutest picnic date dress ever! Make an adorable impression in this eyelet lace dress featuring a sleeveless V-neck, ruffled straps, and a pencil silhouette on a short hem. Complete the look in wedges.

    Fit & Features

    • Sleeveless, V-neck, ruffled straps
    • Pencil silhouette
    • Short-length hem
    • Back zipper, hook and eye closure
    • Eyelet lace fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4386

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feel The Sun Halter Sweetheart Skater Dress

    Bare your shoulders in this cute skater dress on a sunny day! Its easy, breezy design features a halter sweetheart neck, tie-back closure, a ruched bust, and a flowy silhouette and back zipper closure. Composed of seersucker woven fabric with an inner knit lining. Finish the look in lace-up sandals.

    Fit & Features

    • Sleeveless, halter sweetheart neck, tie-back closure
    • Ruched bust
    • Flowy skater silhouette
    • Above the knee length
    • Back zipper closure
    • Seersucker woven fabric, no stretch, inner knit lining
    • Runs true to size

    Style Number/Barcode: 05101-1537

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropic Beauty Strappy Midi Dress

    Unveil your beauty on your tropical getaway in this figure-flattering midi dress featuring a square neckline, spaghetti straps, an open strappy back design, and a bodycon silhouette on an asymmetrical midi-length hem. Complete the look in lace-up stilettos.

    Fit & Features

    • Square neckline
    • Spaghetti straps
    • Open strappy back design
    • Bodycon silhouette
    • Asymmetrical midi-length hem
    • Tropical print fabric
    • Fits true to size

    Style Number/Barcode: 05102-4389

    Category Name: Casual Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lotus Floral Mesh Bodycon Dress

    Look lovely in this floral mesh bodycon dress for a trendy afternoon tea look! Features a sleeveless, cowl neckline, adjustable spaghetti straps, on a mini-length hem. Complete the look in cute heels and a straw hat.

    Fit & Features

    • Sleeveless, cowl neckline, adjustable spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Floral mesh-lined fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4363

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bora Bora Floral Chiffon Maxi Dress

    Got vacay on the mind? This floral chiffon maxi dress is perfect for a trip to Bora Bora! Features a sleeveless, halter neck with tie-closure, ruched bust, and a cutout bodice atop a flowy, tiered maxi skirt. Complete the look in wedges and chic sunglasses. 

    Fit & Features

    • Sleeveless, halter neck, tie-closure
    • Ruched bust
    • Cutout bodice
    • Flowy, tiered maxi skirt
    • Floral print
    • Airy chiffon fabric, inner lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4391

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Walk Floral Midi Dress

    Take a stroll at sunset on your relaxing vacay in this chic floral midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, an asymmetrical midi-length hem creating an alluring side slit, and a curve-hugging silhouette. The all-over tropical floral print pairs perfectly with strappy sandals. Complete the look with hoop earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, cross-back design
    • Asymmetrical midi-length hem, ruching, side slit
    • Form-fitting silhouette
    • Tropical floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4374

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Getaway Floral Midi Dress

    Pack this adorable floral printed midi dress in your carry-on for your next weekend getaway! It features a sleeveless square neckline, spaghetti straps, ruched detailing down one side leading to a slit, and a midi-length, curve-hugging fit. Style this dress with your fave oversized shades and espadrille wedges.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down one side leading to a slit, adjustable drawstring
    • Midi-length, form-fitting silhouette
    • All-over floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4383

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Charmer Floral Mini Dress

    You'll be such a sweet charmer in this adorable floral mini dress! It features a scoop neckline with a bust tie, short puff sleeves, ruching down the sides, and a short, form-hugging fit. The brushed knit fabric features an all-over ditsy floral print pattern. Style this dress with espadrille sandals for weekend brunch!

    Fit & Features

    • Scoop neckline, bust tie
    • Short puff sleeves, cinched hems
    • Ruching down the sides
    • Mini-length, form-fitting silhouette
    • Ditsy floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4341

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Airy Floral Skater Dress

    Chic and airy, this floral printed skater dress is ready for all your fun weekend festivities! It features a sleeveless V-neckline, adjustable spaghetti straps, an open back with an adorable tie-back design, and a high waist leading to a short skater skirt with a flirty fit and flare silhouette. Style this dress with strappy mules.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Open back, tie closure
    • High waist seam, short skater skirt, fit and flare silhouette
    • Ditsy floral print
    • Sheer woven fabric, full knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4384

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rulebreaker Graphic Cutout Short Dress

    Break the rules in a mini dress that shows off your bold side! The mini dress features a crew neckline, short sleeves, a graphic that reads: "Breaking The Rules", an image of an eagle with checkered flags and motorcycles, cutout at the back, and a short-length hem. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a moto jacket

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Graphic: "Breaking The Rules"
    • Image of eagle, motorcycle, checkered flags
    • Short length hem, cutout at the back 
    • Cotton knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06002-1204

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Socialite Linen Babydoll Dress

    The perfect linen babydoll dress for all of your social occasions is here! Featuring a sleeveless square neckline, adjustable spaghetti straps, a fitted bust, and a flared skater silhouette on a short-length hem. Complete the look in cute sandals and a straw bag.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Fitted bust, stretchy smocked back
    • Flared skater silhouette
    • Short-length hem
    • Linen woven fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1536

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twirl-Worthy Moment Skater Dress

    Get ready to have a total twirl-worthy moment in this adorable skater dress. It features a sleeveless square neckline, spaghetti straps that lead to a lace-up back design, a high waist seam, and a short skater skirt with a flirty fit and flare silhouette. Style this dress with your fave platform heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Cross-back, lace-up design, tie closure
    • High waist
    • Short skater skirt, fit and flare silhouette
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4578

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Tropic Strappy Back Midi Dress

    Flaunt your figure on vacay girl! This floral tropic midi dress is perfect for a dinner with a view. Featuring a sleeveless V-neckline, spaghetti straps, a strappy open-back, a bodycon silhouette, and an asymmetrical hem. Complete the look in chic wedges.

    Fit & Features

    • Sleeveless, V-neck, spaghetti straps
    • Strappy open-back, tie closure
    • Bodycon silhouette
    • Asymmetrical midi-length hem
    • Floral tropic print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4376

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Set the Bar Linen Cutout Mini Dress

    This flare mini dress sets the bar high! Showcase your daring side in this sleeveless dress featuring a plunge v-neck on the front and back, a smocked bodice, and side elasticized bar cutouts that lead to a flirty mini-length hem. Complete the look in wedges and dainty earrings.

    Fit & Features

    • Sleeveless, dual plunge v-neck
    • Smocked bodice
    • Side elasticized bar cutouts
    • Flare mini-length hem
    • Linen gauze fabric
    • Runs true to size

    Style Number/Barcode: 05102-4831

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Sweet A-Line Mini Dress

    Proof that effortless can still be everything. This scoop neck mini dress hugs your curves with a sleek A-line fit—perfect for date night, birthday dinners, or dressy occasions!

    Fit & Features

    • Structured woven fabric, bust lining
    • Scoop neckline, padded bra cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • A-Line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000104

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: WHITE, RED

    Available Size: S, M, L

  • Eyes On You Eyelet Tie Back Dress

    All eyes on you in this eyelet lace mini dress! It features puff sleeves, a square neck, a ruched bust, an open back with a tie closure, and a bodycon silhouette. Complete the look in lace-up sandals for a picnic date.

    Fit & Features

    • Short puff sleeves, cinched hems
    • Square neckline, ruched bust
    • Open back, tie closure
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4438

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Style Moves Midi Dress

    Make effortless style moves in this adorably-chic midi dress. It features a sleeveless square neckline with a ruffled trim, thin ruffled shoulder straps, a stretchy smocked bodice, a high waist, and a flowy, midi-length, A-line silhouette with a front slit. Complete the look with espadrille sandals.

    Fit & Features

    • Sleeveless square neckline, ruffled trim
    • Thin ruffled shoulder straps
    • Stretchy smocked bodice
    • High waist seam, flowy A-line silhouette
    • Midi-length hem, front slit
    • Lightweight linen fabric, woven skirt lining
    • Runs true to size

    Style Number/Barcode: 05102-4347

    Category Name: Casual Dresses

    Price: $12.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Make Way Square Neck Skater Dress

    Make way people, you're coming through in this flirty skater dress perfect for graduation! It features adorable short puff sleeves, a square neckline, and a high waist seam that leads to a flowy short-length hem on eyelet knit fabric. Complete the look in cute wedges.

    Fit & Features

    • Short puff sleeves, elastic ruffled hems
    • Square neckline
    • High waist seam
    • Flowy short-length hem
    • Skater silhouette
    • Eyelet knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4446

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Playful Floral Mesh Mini Dress

    Feeling playful? Brighten up your closet in this floral mesh mini dress perfect for brunch with the girls! It features a sleeveless, v-neck, adjustable spaghetti straps, a bodycon silhouette, center, and sides ruched seams to highlight your curves. Complete the look in lucite heels.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Center and side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Floral pattern, back zipper closure
    • Mesh-lined fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4461

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Farmer's Market Gingham Plaid Dress

    Head to the farmer's market looking so cute in this gingham plaid mini dress featuring a sleeveless, v-neck, sleek bungee spaghetti straps, and a bodycon silhouette with a front slit accent. Complete the look in a crop sweater and booties.

    Fit & Features

    • Sleeveless, v-neck, bungee spaghetti straps
    • Bodycon silhouette
    • Front slit accent
    • Mini-length hem
    • Gingham plaid pattern
    • Stretchy soft knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4452

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute As A Button V-Neck Midi Dress

    You're cute as can be in this v-neck midi dress perfect for a day date! It features long sleeves, a button-down front, midi length hem on a form-fitting silhouette. The rib-knit fabric offers a moderate stretch. Style with chic heels.

    Fit & Features

    • Long sleeves, v-neckline
    • Button-down front
    • Midi length hem
    • Form-fitting silhouette
    • Rib knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4257

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On Trend Marble Ruched Short Dress

    Stay on trend with a short dress that creates a head-turning moment! The dress features a fab marble print, a sleeveless square neckline, spaghetti straps, ruching, 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 wedges and a cropped denim jacket. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Marble print
    • Ruching down the sides
    • Mini-length hem 
    • Lined smooth knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4455

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruffle Realness Denim Cutout Maxi Dress

    Sweet from the front, spicy from the back. With bold cutout accents, a hoop insert, and ruffled tiered flow, this maxi is bringing the drama in the cutest way possible.

    Fit & Features

    • Denim fabric, sewn-in knit lining
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Cutout bodice design, hoop insert
    • Stretchy smocked back panel, cutout accent, lower zipper and hook-eye closure
    • Ruffled tiered maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000131

    Category Name: Casual Dresses

    Price: $30.97 $68.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty In Floral Chiffon Babydoll Dress

    It may start out as flirty but this floral babydoll dress is in for the long haul. It features a sleeveless, ruffle-trim V-neckline, adjustable spaghetti straps, open-back with cross straps, and a fitted bodice atop a tiered, flowy mini skirt. This dress is composed of airy chiffon fabric with an inner lining. Complete the look in chic sandals.

    Fit & Features

    • Sleeveless, ruffle-trim V-neck, adjustable spaghetti straps
    • Open-back, cross straps, fitted bodice
    • Hidden back zipper and hook and eye closure
    • Tiered flowy mini skirt
    • Floral pattern
    • Chiffon fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1474

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale