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!

  • Major Trend Crew Neck Bodycon Midi Dress

    A sleeveless midi dress that'll keep you majorly trendy! Perfect for casual plans or vacations, this midi dress is designed with a flattering crew neckline, bodycon silhouette, and front ruched seam, this dress will accentuate your figure. The front slit adds a touch of drama, while the rib knit fabric offers a sewn-in knit lining for extra coverage. Complete the look with chic sandals and sunnies!

    Fit & Features

    • Rib-knit stretchy fabric, sewn-in knit lining
    • Bodycon silhouette
    • Front ruched seam and slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5596

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Patchwork It Belted Denim Mini Dress

    Elevate your style with this patchwork denim mini dress! Featuring a flattering square neckline, spaghetti straps, and a bodycon silhouette, this dress will hug your curves in all the right places. The exposed front zipper closure and flap pockets add a modern touch, while the adjustable waist belt cinches your waist for a perfect fit. Complete the look with platform heels for a daytime party!

    Fit & Features

    • Patchwork design
    • Non-stretch denim fabric
    • Exposed front zipper closure
    • Adjustable waist belt
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5459

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Yet Classy One-Shoulder Ribbed Knit Midi Dress

    Keep casual yet classy in this must-have sleeveless midi dress perfect for your next weekend plans! This sleek and stylish dress features a trendy one-shoulder neckline and a chic cutout accent. The bodycon silhouette and side slit not only add a flirty touch but also flatter your figure on the stretchy ribbed knit fabric. Complete the look with a chic clutch and heels.

    Fit & Features

    • Stretchy ribbed knit fabric with short knit lining
    • One-shoulder neckline, tank strap
    • Cutout accent
    • Bodycon silhouette
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5591

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All About You Lace-Up Floral Mesh Mini Dress

    Everyone will take notice of you in this floral mesh mini dress at parties and dressy dinners! This floral print dress is designed with a delicate cowl neckline and spaghetti straps to create a flattering silhouette, while the lace-up back adds a flirtiness. The side ruched seams hug your curves for a bodycon fit, while the mini-length hem is perfect for showing off your legs. Complete the look in strappy sandals and a clutch!

    Fit & Features

    • Floral print, stretchy mesh fabric with sewn-in knit lining
    • Spaghetti straps
    • Lace-up
    • Side ruched seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3262

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Icon Marble Print Mesh Bodycon Mini Dress

    Show up looking stunning like the trendy icon you are in this marble print mesh mini dress! The airy lightweight sheer mesh fabric features a trendy neutral marble print to draw all the attention your way. The sleeveless crew neckline and tank shoulder straps shape the bodice of the mini-length dress, while the bodycon silhouette will flaunt your gorgeous curves. Style with lace-up stiletto heels to get drinks with the squad!

    Fit & Features

    • Stretchy sheer mesh fabric with knit lining
    • Marble print
    • Sleeveless crew neckline
    • Tank straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5563

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hint Of Chic Cowl Neck Knit Mini Dress

    You'll love the hint of chic style this cowl neck mini dress gives your look! The soft knit fabric has a double-lined design for a smooth seamless look with plenty of stretch. The short dress is shaped with a sleeveless cowl neckline and thin tank shoulder straps. The bodycon silhouette will hug your curves along the mini-length hem. Pair with a handbag and clear heels for happy hour.

    Fit & Features

    • Stretchy double-lined knit fabric
    • Sleeveless cowl neckline
    • Thin tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5557

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance Era Floral Brocade Corset Mini Dress

    You'll be in your romance era in this chic floral brocade corset mini dress! Designed with a detailed floral brocade woven fabric with a knit lining, this dress will bring the allure to your date night look. The top is shaped with a sleeveless sweetheart neckline with a padded bust and structured underwire to provide support and eliminate the need for a bra. The corset-style bodice has flexible boning to create that sultry snatched silhouette. Find your perfect fit with the adjustable spaghetti straps that lead to a back zipper closure. The form-hugging silhouette on the mini-length dress will flaunt your stunning curves. Complete your 'fit with stilettos.

    Fit & Features

    • Floral brocade woven fabric with knit lining, minimal stretch
    • Sleeveless sweetheart neckline with structured and padded bust
    • Corset bodice with flexible boning, high waist seam
    • Adjustable spaghetti straps, back zipper with hook and eye closure
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-3177

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Flair Ruffled Wrap Chiffon Mini Dress

    This adorable floral chiffon mini dress will bring the flirty flair to your spring parties! Designed with a dainty floral print on lightweight lined chiffon fabric. This mini-length dress features a sleeveless sweetheart neckline with a built-in padded bust, spaghetti straps that lead to an open back with a cross-back strappy design, and a corset-style bodice with a fitted high waist. The A-line silhouette has a faux wrap-front creating the cutest asymmetric ruffled hem. Complete your look with strappy sandals.

    Fit & Features

    • Sheer chiffon fabric with knit lining, minimal stretch, dainty floral print
    • Sleeveless sweetheart neckline, padded bust
    • Spaghetti straps
    • Open back, cross-back straps with tie closure, lower zipper, hook and eye closure
    • Corset bodice, high waist seam
    • Faux wrap-front, asymmetric ruffled hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3113

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adorably Chic Bow-Detailed Ruffled Mesh Mini Dress

    This bow-detailed ruffled mesh mini dress is so adorably chic and perfect for date nights or parties! Made with an airy sheer mesh fabric with a full-length knit lining, this dress gives those effortless breezy vibes. The sleeveless square neckline shapes the bodice, and the adjustable spaghetti straps offer a customized fit. The dress features a ruffled tiered silhouette for the cutest look, detailed with dainty bow accents. The tiers have elastic seams for stretch. The flowy A-line fit on the mini-length hem will give your 'fit a feminine touch. Style with lace-up heels.

    Fit & Features

    • Non-stretch sheer mesh fabric, stretchy knit lining
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruffled tiered silhouette with bow accents
    • Elastic seams for stretch
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5618

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • If You Pleats Sleeveless Pleated A-Line Mini Dress

    Prep up your style with this pleated mini dress for casual plans! With a flattering square neckline and delicate spaghetti straps, this a-line dress boasts an adjustable waist belt and pleated mini hem for added charm. Complete the look with a crop denim jacket.

    Fit & Features

    • Woven fabric, slight stretch
    • Spaghetti straps
    • Back zipper closure
    • A-line silhouette
    • Pleated
    • Runs true to size

    Style Number/Barcode: 05102-5590

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paisley Babe Cowl Neck Slit Maxi Dress

    Get ready to turn heads in this paisley maxi dress! This sleeveless dress features a flirty cowl neckline, delicate spaghetti straps, and a flowy silhouette that's perfect for a day out or a backyard dinner party. With a high front slit and stunning paisley print, this maxi dress is sure to become a staple in your wardrobe. Complete the look in flat sandals.

    Fit & Features

    • Paisley print, stretchy knit fabric
    • Spaghetti straps
    • High front slit
    • Flowy silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5513

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Finders Keepers V-Neck Tie Midi Dress

    Once you find this sleeveless midi dress you'll want to keep it! Perfect for semi-formal occasions, this midi dress will make you feel chic and effortless. Designed with an adjustable V-neckline with a bust tie, sleek spaghetti straps, and a flattering curve-hugging silhouette that exudes charm. Complete the look with a bolero shrug sweater and strappy stilettos!

    Fit & Features

    • Woven fabric, no stretch
    • Spaghetti straps
    • Adjustable bust tie
    • Curve-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5551

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Once Upon This Corset Skater Dress

    Whimsy in every stitch. With lace trims, corset details, and a floaty mini hem, this skater dress feels like it was made for fairy tales, flower fields, and falling in love (again).

    Fit & Features

    • Cotton-blend woven fabric
    • Multiple petticoat tulle and lace trim woven linings
    • Strapless lace trim drawstring tie square neckline
    • Hidden side zipper and hook-eye closure
    • Corset bodice, flexible boning, lace and pleated trims, back lace-up placket
    • Drop waist seam, voluminous skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000259

    Category Name: Casual Dresses

    Price: $69.90

    Availability: In Stock

    Available Color: ROSE, IVORY

    Available Size: XS, S, M, L

  • Simplest Statement Sweetheart Rib Knit Midi Dress

    Simple and statement-making! This rib knit midi dress offers any fashionista a stylish adventure. With a flattering sweetheart neckline, twisted bust, and bodycon silhouette that puts your curves on display, you'll feel confident and flirty! The midi-length hem and side slit add a touch of sultry to this simple yet stunning dress. Perfect for casual weekend plans or a date night, style this dress with chic sandals and a necklace.

    Fit & Features

    • Stretchy rib knit fabric
    • Sweetheart neckline with twisted accent
    • Spaghetti straps
    • High side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5545

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Bound Tropical Print Woven Maxi Dress

    Jet set to your gorgeous getaway in this tropical woven maxi dress! The lightweight gauze woven fabric features a bold tropical print to bring the allure to your dreamy vacay. The maxi-length dress is shaped with a strapless straight-across neckline with a ruffled fold-over design to add a flirty flair. The fitted high waist seam has an elasticized design for added stretch and a thin tie-front belt with cute tassel accents. The dress flows out to a floor-length hem with an effortless A-line silhouette. Style this maxi dress with strappy sandals.

    Fit & Features

    • Tropical printed gauze woven fabric with short knit lining, minimal stretch
    • Strapless straight neckline with no-slip strip, ruffled fold-over design
    • Fitted elasticized high waist seam
    • Tie-front belt with tassels
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5678

    Category Name: Casual Dresses

    Price: $6.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweeter Than Ever Floral Eyelet Knit Mini Dress

    Create the sweetest springtime vibe in this adorable eyelet knit mini dress! The airy sheer knit fabric is detailed with dainty floral eyelet embroidery and includes a knit lining for coverage. The dress features a sleeveless scoop neckline with a ruched bust and cute tie-front detail, spaghetti straps, and a bodycon silhouette to highlight your figure along the mini-length hem. Style this short dress with sleek hoops and heeled sandals.

    Fit & Features

    • Sheer knit fabric with floral eyelet embroidery, knit lining
    • Moderate stretch
    • Sleeveless scoop neckline
    • Ruched bust with tie-front detail
    • Spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5517

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Charm Crepe Floral Midi Dress

    Charm from day to night in this ditsy floral midi dress! Featuring a ruffle trim sweetheart neckline, spaghetti straps, and a flirty bust tie front. The form-hugging silhouette and front slit add a touch of allure, while the ditsy floral print on crepe fabric and midi-length hem keep it sweet and romantic. Complete the look in simple block heels for a dressy date or brunch!

    Fit & Features

    • Sleeveless ruffle trim sweetheart neckline
    • Spaghetti straps, bust tie front
    • Form-hugging silhouette
    • Front slit, midi-length hem
    • Ditsy floral print, crepe fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5446

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Vibes Long Sleeve Chiffon Skater Dress

    This dreamy long sleeve chiffon skater dress has a flowy silhouette to give you that effortlessly ethereal look! The short dress is crafted with an airy sheer chiffon fabric for a lightweight feel, and includes a partial knit lining for coverage. The bodice is shaped with a V-neckline with a chic pleated surplice design, and the sheer long balloon sleeves have cinched hems. The back features a partially smocked design for added stretch. The high waist seam flows out to a short skater skirt with a fit and flare silhouette and a faux wrap-front design. Complete your outfit with block heels for a bridal shower or birthday party!

    Fit & Features

    • Sheer non-stretch chiffon fabric, partial knit lining
    • V-neckline with pleated surplice design
    • Long unlined balloon sleeves, elastic cinched hems
    • Smocked back, zipper with hook and eye closure
    • High waist seam
    • Short skater silhouette, faux wrap-front design
    • Runs true to size

    Style Number/Barcode: 05101-3139

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crushing On You Strapless Denim Corset Mini Dress

    This sexy denim corset mini dress will have them all majorly crushing on you! The denim fabric features a contrasting light and dark wash design for a trendy vibe. The strapless sweetheart neckline shapes the top, leading to a corset-style bodice with angled seams for a snatched look. The bodycon fit along the mini-length silhouette will flaunt your gorgeous curves. Complete the look with cowboy boots for a country concert or festival.

    Fit & Features

    • Denim fabric with contrast wash design, moderate stretch
    • Strapless sweetheart neckline
    • Corset bodice, angled seams
    • Back zipper with hook and eye closure
    • Bodycon fit
    • Style runs small

    Style Number/Barcode: 05102-5659

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweeten Me Up Square Neck Cutout A-Line Midi Dress

    Sweeten your style in this breezy A-line midi dress perfect for bridal showers, day dates, or brunch! With a sleeveless square neckline and adjustable spaghetti straps, this cotton midi dress offers a flattering fit while the stretchy smocked bust with lace-up detail adds a touch of sweetness. The cutout back with elasticized straps adds a hint of daring to the fitted bodice and A-line silhouette. Complete the look in strappy sandals for a chic allure.

    Fit & Features

    • Lightweight cotton woven fabric with lining
    • Adjustable spaghetti straps
    • Smocked lace-up bust
    • Cutout back
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5611

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Vibes Collared Striped Woven Skater Dress

    Sweet and stylish, this striped woven skater dress is spring-time perfection! The lightweight woven fabric features a chic vertical striped pattern for a polished look. The short dress has a collared V-neckline for that touch of sophistication, leading to a partial button-down front. The short puff sleeves add an adorable detail. The high waist is accented with a tie-back design, and flows out to a fit-and-flare skater silhouette. Pair this short dress with wedges for weekend brunch!

    Fit & Features

    • Non-stretch cotton-blend woven fabric, woven skirt lining
    • Vertical striped pattern
    • Collared V-neckline, button-down front
    • Short puff sleeves with elastic cinched hems
    • High waist with back elastic band, tie-back design
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5657

    Category Name: Casual Dresses

    Price: $6.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Getaway Tropical Print Flowy Maxi Dress

    This tropical print flowy maxi dress is giving major weekend getaway energy! The breezy lightweight woven fabric is detailed with a tropical leaf-outlined print, perf for your next vacay. The maxi-length dress features a sleeveless square neckline and adjustable spaghetti straps for a customized fit. The high waist leads to a cute tie-back design, followed by a lower back cutout for a hint of skin. The dress flows out in an A-line silhouette with a stylish tiered design. Complete your look with gold hoops and strappy sandals.

    Fit & Features

    • Tropical printed woven fabric
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • High waist with tie-back design, lower back cutout
    • Flowy A-line fit with a tiered design
    • Runs true to size

    Style Number/Barcode: 05102-5609

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Attention Getter Strapless Newspaper Print Mini Dress

    Capture attention with all eyes on you in this fab newspaper print mini dress! The textured lined woven fabric features a newspaper print with rose print accents for that trendy-girl vibe. The strapless straight-across neckline is detailed with an eyelet lace and thin velvet ribbon trim, tying at the center. The bodice features a bust seam outline with ruching to accentuate your figure. The flexible side boning adds structure, while the hidden back zipper offers effortless styling. The form-hugging fit on the mini-length hem will flaunt your stunning curves. Style with a layered choker necklace.

    Fit & Features

    • Non-stretch textured lined woven fabric, rose newspaper print
    • Strapless straight neckline with no-slip strip
    • Eyelet lace and velvet ribbon trim, tie-front, bust seam outline with ruching
    • Flexible side boning, hidden back zipper with hook and eye closure
    • Form-hugging fit
    • Strapless or sticky bra recommended
    • Runs true to size 

    Style Number/Barcode: 05102-5644

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect And Stylish Scoop Neck Ribbed Knit Midi Dress

    Perfect and stylish for everyday occasions, this basic ribbed knit midi dress is just what you need for coffee dates, shopping downtown, or grabbing dinner with friends! This stunning dress features classic short sleeves, a flattering scoop neckline, and a bodycon silhouette for a sleek curve-flaunting appeal. The side slit offers movement along the mid-length hem, while the soft and stretchy ribbed knit fabric ensures all-day comfort. Style this midi dress with a casual jacket, sandals, and a crossbody bag to complete the look!

    Fit & Features

    • Soft, stretchy ribbed knit fabric
    • Side slit
    • Bodycon silhouette
    • Midi-length 
    • Runs true to size

    Style Number/Barcode: 05102-5554

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale