Casual Dresses

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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!

  • Cute Style Button Ruffled Striped Linen Skater Dress

    Catch everyone's attention with your cute style in this striped skater dress perfect for casual summer plans!  Made with striped linen fabric, this dress is perfect for any occasion. Featuring a scoop neckline with a bust tie and adjustable spaghetti straps, this dress is both stylish and comfortable. The button down front and ruffled trim add a fun touch, while the skater silhouette and short-length hem create a flattering look. Complete the look with hoop earrings and trendy sandals.

    Fit & Features

    • Striped print linen-blend fabric lined with woven, no stretch
    • Scoop neckline with bust tie
    • Adjustable spaghetti straps
    • Button down front and ruffle trim
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5731

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off-The-Shoulder Moments Slit Maxi Dress

    This off-the-shoulder maxi dress features ruched details that contour your shape, plus a high side slit for effortless allure. Perfect for shower celebrations, formal dinners, or anytime you want all eyes on you.

    Fit & Features

    • Smooth knit stretchy fabric
    • Folded off-the-shoulder neckline
    • Fitted long sleeves
    • High side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000344

    Category Name: Casual Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: RUST

    Available Size: XS, S, M, L, XL

    Product Badge:
    • New Arrival
  • Beauty On Vacay Cutout Abstract Maxi Dress

    From seaside dinners to dancing under the moonlight, this abstract print maxi dress will have you looking like a beauty on the island! It features delicate spaghetti straps, a sweetheart neckline with an O-ring bust insert, a cutout bodice to reveal some skin, and a flattering bodycon silhouette and maxi-length hem. Complete the look with strappy wedges.

    Fit & Features

    • Abstract print, knit fabric, short knit lining
    • Spaghetti straps
    • Sweetheart neckline
    • O-ring bust insert, cutout
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5584

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Sweetheart Smocked Gingham Cotton Skater Dress

    This short skater dress features an adorable gingham print on lightweight lined cotton fabric. The smocked waist offers added stretch, while the fit-and-flare silhouette gives that flirty touch, perfect for a day date.

    Fit & Features

    • Gingham printed cotton fabric with woven lining, no stretch
    • Scoop neckline with keyhole cutout and tie-front
    • Adjustable spaghetti straps
    • Stretchy smocked waist
    • Short tiered skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5891

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Natural Romancer Crew Neck Lace Mini Dress

    Indulge in the effortless romance of this lace mini dress perfect for bridal showers, rehearsal dinners, and parties! This stunning dress features short sleeves, a flattering crew neckline, and a bodycon silhouette that hugs your curves. The sheer lace fabric exudes romance, while the attached knit slip lining provides comfort and coverage. Complete the look with earrings and strappy sandals.

    Fit & Features

    • Sheer lace fabric with stretch
    • Attached slip knit lining
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5548

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Muse Watercolor Chiffon Flowy Midi Dress

    You'll be a dreamy muse in this gorgeous watercolor chiffon flowy midi dress! The airy lined chiffon fabric is detailed with a mesmerizing watercolor print for the perf summertime vibe. The mid-length dress features a sleeveless halter neckline with a center stone accent, tie-back spaghetti straps, a partially open back for a touch of allure, and a lower-smocked back design for added stretch. The fitted high waist flows out to a gorgeous A-line silhouette with an asymmetrical hemline for beautiful movement. Style this long dress with espadrille wedges.

    Fit & Features

    • Watercolor print
    • Sheer chiffon fabric with smooth woven lining
    • Halter neckline, stone detail, tie-back straps
    • Partial open back, lower stretchy smocked back
    • Flowy A-line silhouette
    • Asymmetrical hemline
    • Runs true to size

    Style Number/Barcode: 05101-3306

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Babe With Taste Buckle Strap Pleated Mini Dress

    Let everyone know you're a babe with taste in this pleated mini dress! Made from a twill woven fabric for structure and has a stretchy knit lining for coverage. With a square neckline and seam detailing, this dress exudes style. The adjustable buckle shoulder straps provide a customizable fit, while the fitted bodice and pleated mini-length hem flatter your figure. Complete the look with sunglasses and a purse!

    Fit & Features

    • Twill woven fabric, stretchy knit lining
    • Square neckline
    • Back zipper closure
    • Adjustable buckle shoulder straps
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5629

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Muse Tropical Floral Knit Bodycon Mini Dress

    You'll be a gorgeous vacay muse in this tropical floral mini dress! The sleek stretchy knit fabric showcases a blooming tropical floral print perfect for your summer trips. The short dress features a sleeveless square neckline, spaghetti straps, an alluring ruched waist cutout with an adjustable drawstring, and a bodycon silhouette to flaunt your figure. Style with espadrille wedges.

    Fit & Features

    • Tropical floral print
    • Stretchy knit fabric
    • Square neckline
    • Spaghetti straps
    • Ruching waist cutout, drawstring
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5614

    Category Name: Casual Dresses

    Price: $11.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Remarkable Vibe One Shoulder Printed Mesh Mini Dress

    This mini-length dress features a flattering one-shoulder neckline and a bodycon silhouette. The stretchy mesh-lined fabric boasts a multi-print design that keeps your style fresh. 

    Fit & Features

    • Multi-print, mesh-lined fabric, moderate stretch
    • One-shoulder neckline
    • Shoulder strap
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5701

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty In Paradise One-Shoulder Tropical Maxi Dress

    You'll be looking so pretty as you stroll the beach in paradise in this tropical maxi dress! The smooth stretchy knit fabric showcases a bold tropical print perfect for an island vacay. The long dress is shaped with a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap. The sultry ruched cutout at the waist features an adjustable drawstring for a customized look. Reveal some leg with the sexy high-cut side slit on the maxi-length silhouette. Style this slim-fit dress with espadrille wedges.

    Fit & Features

    • Stretchy knit fabric, knit lining at the bust
    • Tropical print
    • Asymmetric one-shoulder neckline, spaghetti strap
    • Ruched side cutout, adjustable drawstring
    • High side slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5542

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Side Lace Trim Floral A-Line Mini Dress

    A floral mini dress that shows your sweet side in a flattering scoop neckline, spaghetti straps, and a lace trim with a bow accent along the A-line silhouette. The floral printed knit fabric offers stretch and comfort. 

    Fit & Features

    • Floral printed knit fabric, bust lining, moderate stretch
    • Spagehtti straps
    • Scoop neckline
    • Lace trim bow accent
    • A-Line mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5833

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Deets Cap Sleeve Open Twist Back Midi Dress

    This crew neck midi dress may look basic from the front but the open back reveals sultry deets! Featuring classic cap sleeves and a twisted open back design to flaunt some skin, and a bodycon silhouette that hugs your curves. Complete the look with a clutch for a dinner party!

    Fit & Features

    • Brushed knit fabric lined with stretchy knit
    • Crew neckline
    • Twisted open back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5754

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Notice Me Abstract Print Bodycon Mini Dress

    This abstract print dress will get you noticed at every party! Featuring adjustable spaghetti straps and a flattering square neckline, a mini-length hem, and a bodycon fit that hugs your natural curves. Complete the look with earrings and stiletto heels.

    Fit & Features

    • Abstract print, mesh fabric, sewn-in knit lining
    • Square neckline
    • Adjustable spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5671

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Curves For Days Off-The-Shoulder Midi Dress

    Serve major curves in this off-the-shoulder midi dress at parties and dressy occasions! Featuring a flattering off-the-shoulder sweetheart neckline and a tie-front bust, this dress accentuates your figure in all the right ways. The cutout bodice adds a flirty charm, while the ruched seams and bodycon fit hug your figure for a sultry silhouette on mesh-lined fabric. Complete the look in stiletto heels.

    Fit & Features

    • Mesh fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Tie-front bust, cutout bodice
    • Side ruched seams
    • Center back slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-2623

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jungle Luxe Backless Maxi Dress

    Unapologetically bold, this maxi dress is made for making an entrance. The plunging halter neckline and curve-hugging fit keep it sleek, while the strappy lace-up back and animal print bring all the wild energy.

    Fit & Features

    • Animal multi-print design, stretchy knit fabric
    • Halter plunge neckline
    • Strappy back with hard trim insets
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000473

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L, XL

    Product Badge:
    • New Arrival
  • Stylish Striped Halter Crochet Midi Dress

    Stay stylish in this striped crochet midi dress for a sunny day by the beach or on vacation! It features a flattering halter neckline, adjustable spaghetti strap ties, and a bodycon fit that accentuates your curves along the midi-length hem. Complete the look with sunglasses and a tote bag!

    Fit & Features

    • Striped pattern, crochet fabric, short knit stretchy lining
    • Halter neckline with spaghetti strap ties
    • Bodycon fit
    • Midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2032

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Style Cowl Neck Slit Paisley Maxi Dress

    Bask in the aesthetic perfection of this paisley mesh maxi dress whether you're on vacation or having a sunset dinner with friends! This form-hugging dress features a cowl neckline and spaghetti straps, highlighting your figure in all the right ways. The high-side slit and sheer maxi-length hem add a touch of allure to this must-have dress! Complete the look with a necklace and earrings.

    Fit & Features

    • Paisley print, partially lined mesh fabric
    • Cowl neckline
    • Spaghetti straps
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5694

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dose Of Sweetness Bodycon Floral Mini Dress

    Ditsy florals add sweetness to this bodycon mini dress you'll adore for casual summer plans! Designed with a sheer eyelet knit fabric with a knit lining, this dress offers plenty of stretch for comfortable wear. It features adjustable spaghetti straps, a sleeveless square neckline with a dainty lace trim, ruching at the bust accented with a mini flower detail, and a flattering bodycon fit with a mini-length hem. Complete the look with earrings and sneakers.

    Fit & Features

    • Ditsy floral print
    • Sheer eyelet knit fabric with knit lining, plenty of stretch
    • Adjustable spaghetti straps
    • Square neckline, dainty lace trim
    • Ruched bust with mini flower detail
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5730

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Admire You Scoop Neck Layered Lace Mini Dress

    Everyone will admire you in this lace mini dress perfect for any plans. Designed with layered sheer lace fabric, this dress is a total flirt. The adjustable spaghetti straps create a perfect fit, while the delicate scoop neckline enhances the bodycon fit and mini-length hem. Complete the look with a dainty necklace.

    Fit & Features

    • Layered sheer lace fabric with plenty of stretch
    • Adjustable spaghetti straps
    • Scoop neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5750

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soiree Hour Lace-Up Ruffled Floral Midi Dress

    When the cocktails are poured and the music starts playing it's time to unveil this floral chiffon midi dress! Perfect for daytime soirees or showers, this midi dress features a flattering scoop neckline adorned with adjustable spaghetti straps. The lace-up back and flowy ruffled silhouette offer a touch of trendiness to this midi-length dress! Complete the look with earrings and wedges.

    Fit & Features

    • Floral print, chiffon fabric lined with woven fabric
    • Scoop neckline
    • Adjustable spaghetti straps
    • Lace-up back, zipper and hook-eye closure
    • Flowy ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3411

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Bound Cutout Tropical Mesh Midi Dress

    You'll be ready for your trip with this tropical mesh midi dress! This dress features a square neckline, spaghetti straps, and a bodycon fit for a flattering silhouette. The side cutout drawstring adds a touch of fun while the side slit and midi-length offer a sultry feel. Complete the look in trendy sandals.

    Fit & Features

    • Tropical palm leaf print
    • Mesh fabric, stretchy knit lining
    • Spaghetti straps
    • Square neckline
    • Side cutout drawstring
    • Bodycon fit, side slit
    • Runs true to size

    Style Number/Barcode: 05102-5710

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Never A Dull Moment Strapless Cutout Maxi Dress

    Bring a stunning look in this strapless maxi dress for your look-back-it moment! The strapless neckline and cutout bust add a touch of allure, while the strappy back and form-hugging fit emphasize your figure. With a center-back slit, you'll be able to move in style. Complete the look with earrings and a clutch!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Cutout bust, strappy back
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5766

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Amazing Strapless Tie-Dye Mini Dress

    Keep things casual and cute in this tie-dye mini dress for upcoming summer fun! Boasting a trendy tie-dye print on soft knit fabric, this dress brings an effortless boho charm featuring a strapless neckline and bodycon fit. Complete the look in sandals.

    Fit & Features

    • Tie-dye print, soft knit fabric with stretchy knit lining
    • Strapless neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5788

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smell The Garden Square Neck Floral Midi Dress

    Enter the fresh fragrance of this floral midi dress into your spring and summer lineup! With a square neckline and spaghetti straps, this dress will hug your curves in all the right places with its bodycon fit. The side ruched seams add more detail to this stylish midi-length dress. Complete the look in platform sneakers for a trendy allure.

    Fit & Features

    • Brushed knit stretchy fabric, floral print, knit lining
    • Spaghetti straps
    • Square neckline
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5562

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale