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!

  • Trendy Twist Cutout Mini Dress

    Trendy with a twist...you'll totally fall for this mini dress featuring a sleeveless, v-neck, spaghetti straps, a cutout bodice, side ruched seams, on knit-lined fabric with a form-hugging fit and moderate stretch. Complete the look-in mules for a daytime event.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Twist front accent
    • Cutout bodice
    • Side ruched seams
    • Form-hugging fit
    • Knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4657

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Vacay Satin Ruched Tie-Back Dress

    Planning a weekend vacay? Don't forget to pack this adorable satin dress! It features spaghetti straps and a ruched bust, a mini-length hem, and an open back with self-tie detail. Complete the look chic mules.

    Fit & Features

    • Sleeveless, spaghetti straps
    • Ruched bust
    • Mini-length hem
    • Open back with self-tie
    • Satin fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1276

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picture Perfect Marble Print Dress

    This marble print mini dress is picture-perfect for snapping an insta-worthy shot! It features a sleeveless, square neck, spaghetti straps, side ruched seams, and a form-hugging fit on stretchy-lined knit fabric. Complete the look in sleek hoop earrings.

    Fit & Features

    • Sleeveless, square neck
    • Spaghetti straps
    • Side ruched seams
    • Form-hugging fit
    • Lined knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4611

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Feels Halter Skater Dress

    Feel flirty in floral! This adorable halter skater dress will add funky freshness to your summer lineup. It features a sleeveless smocked bodice, open-back with elasticized lattice straps, and a flowy short-length hem. Complete the look in strappy heels for a birthday brunch.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • Smocked bodice
    • Open-back, elasticized lattice straps
    • Skater silhouette
    • Flowy short-length hem
    • Floral print, non-stretch woven fabric, knit lining
    • Fits true to size

    Style Number/Barcode: 05102-4707

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Neutral Vibe Mini Dress

    Showcase a chic neutral vibe in this trendy ribbed knit mini dress. It features a sleeveless square neckline, adjustable spaghetti straps, bold waist cutouts leading to an alluring open back with a cross-back strap design, and a short, curve-hugging silhouette. Style this dress with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Waist cutouts, open back, cross-back strap design
    • Mini-length, form-fitting, bodycon silhouette
    • Double-lined ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4558

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • More To Come Tube Skater Dress

    Perfect for day or night fun, this tube mini dress features playful ruffles that add a flirty touch while the skater silhouette flatters every figure with a fun, twirl-worthy flare.

    Fit & Features

    • Mesh-lined fabric
    • Strapless tube neckline
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000220

    Category Name: Casual Dresses

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Neutral Tie-Dye Mini Dress

    You'll fall in love with the trendy neutral tones of this tie-dye mini dress! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back, lace-up design, and a short, curve-hugging fit. The soft brushed knit fabric offers plenty of stretch. Style with chic mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Cross-back, lace-up design, tie closure
    • Mini-length, form-fitting silhouette
    • Neutral tie-dye pattern
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4645

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Babe Cutout Mini Dress

    For looking and feeling like a total babe. Let your legs out in this sleeveless mini dress featuring an on-trend square neck, spaghetti straps, a cutout bodice, side ruched seams and a bodycon fit. Complete the look in strappy heels for a party.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Cutout bodice
    • Bodycon fit, side ruched seams
    • Mini-length hem
    • Textured knit-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4545

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty In Floral V-Neck Mini Dress

    Flirty in floral! Go forth and bloom for summer in this mini dress featuring a sleeveless, v-neck, sleek bungee spaghetti straps, a form-fitting silhouette, and a front slit along the hem. Complete the look in doorknocker earrings and heels.

    Fit & Features

    • Sleeveless, v-neck, bungee spaghetti straps
    • Form-fitting silhouette
    • Front slit
    • Mini-length hem
    • Ditsy floral print, stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4530

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sandy Toes Crochet Bodysuit Dress

    The perfect long dress to walk the sandy beaches! This crochet maxi features a sleeveless, V-neck, adjustable spaghetti straps, dual front hoop inserts, and a bodysuit lining with dual-snap button closure on a cheeky bottom. Complete the look in boho earrings and a bracelet.

    Fit & Features

    • Sleeveless, V-neck, adjustable spaghetti straps
    • Dual front hoop inserts
    • Bodysuit lining, dual snap-button closure, cheeky bottom
    • Form-fitting silhouette
    • Maxi-length hem
    • Sheer crochet fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4675

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Muse Asymmetrical Midi Dress

    Catch all the glances like the gorgeous muse you are in this printed midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a midi-length, asymmetrical hem, a curve-hugging silhouette, and an all-over geometric multi-print pattern. Complete the look with sleek hoop earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Midi-length, asymmetrical hem, ruching down one side
    • Form-fitting silhouette
    • Geometric multi-print pattern
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4644

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachside Beauty Floral Mini Dress

    You'll be a total beachside beauty on your summer vacay in this floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, dual front verticals seams with ruched detailing, and a short, curve-hugging silhouette. The lined mesh fabric features an all-over tropical floral print. Complete the look with espadrille sandals.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Dual front vertical seams, ruched detailing
    • Mini-length, form-fitting, bodycon silhouette
    • Tropical floral print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4609

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gimme Love Texture Knit Mini Dress

    Make em' fall for you in this curve-hugging mini dress featuring a sleek, sleeveless square neck, and bungee spaghetti straps, and is composed of texture-knit fabric with plenty of stretch. Complete the look in strappy mules.

    Fit & Features

    • Sleeveless, square neck, bungee spaghetti straps
    • Curve-hugging silhouette
    • Mini-length hem
    • Texture-knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4507

    Category Name: Casual Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Darling Chiffon Ruffle Mini Dress

    Serving darling vibes on repeat. This floral mini dress is your go-to for twirling through summer plans, from picnics to shower celebrations—basically, anytime you wanna feel effortlessly pretty.

    Fit & Features

    • Floral print, chiffon lined fabric
    • V-neckline, ruffle trim
    • Adjustable spaghetti straps
    • Side zipper and hook-eye closure
    • Ruffled trim throughout
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000592

    Category Name: Casual Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

  • Jungle Queen Leopard Satin Slip Dress

    Clearly, you're the queen of the jungle in this leopard satin mini! It features sleek, adjustable spaghetti straps, a v-neckline, and a slightly flared hem with a slit accent. Composed of a luxe satin-lined fabric with no stretch. Style with chic block heels.

    Fit & Features

    • Sleeveless, V-neckline
    • Sleek adjustable spaghetti straps
    • Slit accent, Back zipper closure
    • Slightly flared hem
    • Leopard pattern
    • Luxe satin-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1461

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take A Bow Ruffled Short Dress

    Flaunt your flirty self and bow in this short dress featuring a sleeveless, square neck, adjustable spaghetti straps, a partial open-back with bow-tie closure, and a tiered ruffle hem. Complete the look in a choker necklace and mules. 

    Fit & Features

    • Sleeveless, square neck
    • Adjustable spaghetti straps
    • Partial open-back, bow-tie closure
    • Tiered ruffles
    • Short-length hem
    • Fits true to size

    Style Number/Barcode: 05102-4457

    Category Name: Casual Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Disco Diva Square Neck Mini Dress

    Get down at the disco looking like a diva in this fab retro mini dress featuring a sleeveless, square neck, bungee spaghetti straps, side ruched seams, on a knit-lined fabric with a form-hugging fit. Complete the look in platform heels for a dance party.

    Fit & Features

    • Sleeveless, square neck
    • Bungee spaghetti straps
    • Side ruched seams
    • Form-hugging fit
    • Mini-length hem
    • Retro print, knit-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4529

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Under The Palms Halter Skater Dress

    Get ready to relax under the palms in this adorable printed skater dress. It features a sleeveless V-neckline with halter straps, side cutouts leading to a strappy banded back design, a smocked high waist, and a flowy skater skirt silhouette. The lightweight gauze fabric features an all-over tropical palm leaf print. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Halter spaghetti straps, tie at the back of the neck
    • Side cutouts, strappy banded back design, tie closure
    • Smocked high waist, flowy skater skirt
    • Tropical palm leaf print
    • Gauze fabric, knit skirt lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4499

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Palisades Ruched V-Neck Midi Dress

    Let the sun kiss your shoulders in this flowy midi dress! It features a sleeveless ruched v-neck and spaghetti straps that lead to the sultry open-back with a lace-up closure. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless, ruched v-neck, spaghetti straps
    • Flowy midi-length silhouette
    • Open-back, lace-up closure
    • Gauze woven fabric
    • Inner lining
    • Fits true to size

    Style Number/Barcode: 05102-4456

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Express Yourself O-Ring Bandeau Midi Dress

    Express your stylishly bold self in this midi dress! It features a strapless, bandeau top with a string tie o-ring, cutout bodice, and midi bodycon skirt with a sultry side slit. Composed of ribbed knit fabric with a moderate stretch. Finish the look in oversized sunglasses.

    Fit & Features

    • Strapless bandeau top
    • String tie o-ring, cutout bodice
    • Midi bodycon skirt
    • Side slit 
    • Ribbed knit fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 06005-1263

    Category Name: Casual Dresses

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Retro Muse Satin Slip Dress

    You'll be a total retro muse in this sleek satin slip dress! It features a sleeveless V-neckline with a tie-front bodice, adjustable spaghetti straps, a short, A-line silhouette, and an all-over multi-colored swirl print pattern. Style this dress with hoop earrings and clear mules.

    Fit & Features

    • Sleeveless V-neckline, tie-front detail, small cutout
    • Adjustable spaghetti straps
    • Mini-length, A-line silhouette
    • All-over multi-colored swirl print
    • Woven satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4665

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chain Reaction Rib Knit Dress

    This rib knit dress may cause a chain reaction of followers! It features a sleeveless square neckline, edgy chain-link straps, and a bodycon mini-length hem. Complete the look in platform heels for girl's night.

    Fit & Features

    • Sleeveless square neckline
    • Chain-link shoulder straps
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed knit fabric, sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4480

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Miami Nights Bodycon Mini Dress

    Take on the night scene with your squad in this stunning printed mini dress. It features a sleeveless V-neckline, spaghetti straps, a dual twist-front design with waist cutouts for an alluring vibe, and a short, curve-hugging, bodycon silhouette. The stretchy knit fabric features an all-over geometric floral pattern. Complete your look with strappy stilettos.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual twist-front design, waist cutouts
    • Mini-length, form-fitting silhouette
    • Geometric floral pattern
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4498

    Category Name: Casual Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boogie On Down Lace-Up Mini Dress

    Boogie all over town in this retro mini dress featuring a sleeveless, square neck, spaghetti straps, a trendy lace-up on the back, bodycon silhouette, on swirl marble print knit fabric with a moderate stretch. Complete your groovy fit with strappy stiletto heels.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Lace-up back
    • Bodycon silhouette
    • Mini-length hem
    • Swirl marble print
    • Knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4688

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free