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!

  • Petals with a Plot Twist Floral Maxi Dress

    Soft? Yes. Sweet? Sure. But this maxi dress is not here to behave—with a side slit that demands attention and a form-hugging fit that doesn’t miss.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Tube strapless neckline
    • High side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000381

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

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

  • Such A Charmer Ditsy Floral Skater Dress

    Create a charming look for weekend dates with this adorable floral skater dress! It features a square neckline with a ruffled hem, short puff sleeves, dual high waist seams, and a short skater skirt with a flattering fit and flare silhouette. The lightweight chiffon fabric features a ditsy floral print pattern for the cutest spring or summer vibe. Style with espadrille sandals.

    Fit & Features

    • Square neckline, ruffled hem
    • Short puff sleeves, elastic cinched hems
    • Dual high waist seams, smocked back design
    • Short skater skirt, fit and flare silhouette
    • Ditsy floral print
    • Chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4885

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine On My Mind Linen Midi Dress

    This flowy linen midi dress was made for sunny days! It features a sleeveless V-neckline with a ruffled trim, adjustable spaghetti straps, a fitted bodice with dual high waist seams, and a midi-length hem with a relaxed A-line silhouette and a tiered, ruffled design. The airy linen fabric includes a full knit lining. Style with wedges for a dreamy look.

    Fit & Features

    • Sleeveless V-neckline, ruffled trim
    • Adjustable spaghetti straps, hidden back zipper, hook and eye closure
    • Fitted bodice, dual high waist seams
    • Midi-length hem, flowy A-line silhouette
    • Tiered, ruffled design
    • Semi-sheer linen fabric, full knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5023

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Linked Together Chain Cutout Mini Dress

    You and this mini dress are the perfect links! Flaunt your curves in this sleeveless dress featuring a square neck, adjustable spaghetti straps, a side cutout with a chainlink detail, and a bodycon silhouette. The double-lined knit fabric offers a moderate stretch. Complete the look with hoop earrings for a party!

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Side cutout, chainlink detail
    • Bodycon silhouette
    • Mini-length hem
    • Double-lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5024

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cherish Me Eyelet Lace Skater Dress

    All eyes on you in this lovely eyelet lace skater dress as the bride-to-be or graduate! The dress features a sleeveless sweetheart neck with flirty ruffle trim, adjustable spaghetti straps, a front bust tie and button accents, and a tiered fit and flare silhouette with a ruffled short hem. Complete the look in platform sandals.

    Fit & Features

    • Sleeveless sweetheart neck with ruffle trim
    • Adjustable spaghetti straps
    • Front bust tie, button accents
    • Tiered, skater silhouette
    • Ruffled short-length hem
    • Eyelet lace cotton fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4907

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Styling Ribbed Knit Midi Dress

    This casual-chic ribbed knit midi dress will create effortless styling for everyday wear! It features a sleeveless scoop neckline, tank shoulder straps, a midi-length hem that hits mid-calf, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a layered charm necklace and clear mules.

    Fit & Features

    • Sleeveless scoop neckline, scoop back design
    • Tank shoulder straps
    • Midi-length hem
    • Form-hugging fit
    • Ribbed knit fabric, top lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5037

    Category Name: Casual Dresses

    Price: $19.00 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Verge Chiffon A-Line Midi Dress

    You'll be on the verge of a stylish breakthrough with the addition of this chiffon midi dress to your fashion closet! Effortless and breezy, this dress features a sleeveless v-neckline, halter spaghetti straps, a lace-up open back that lets you customize the fit, and an asymmetrical hem with a flirty slit. Complete the look with stiletto heels and a bracelet! 

    Fit & Features

    • Sleeveless v-neckline
    • Halter spaghetti straps
    • Lace-up open back
    • A-line silhouette
    • Asymmetrical midi-length hem, slit accent
    • Chiffon fabric, stretchy knit lining
    • Fits true to size

    Style Number/Barcode: 05102-4905

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Show Face Abstract Print Mini Dress

    Show your artsy-chic side in this mesh mini dress perfect for a movie date or casual plans with friends! It features a sleeveless square neck, sleek bungee spaghetti straps, side ruched seams to accentuate your curves, and a bodycon silhouette. The dress is designed with an abstract face print on mesh fabric with a stretchy knit lining. Complete the look in a trendy crop jacket and sandals.

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Abstract face print, mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5014

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet And Cute Floral Ruffle Short Dress

    Embrace your cuteness looking so sweet in this floral short dress - a perfect pick for family gatherings or parties! It features a sleeveless scoop neck, adjustable spaghetti straps, a trendy tie-back, a ruched bust, and a ruffle-layered short-length hem. Complete the look in bow heels.

    Fit & Features

    • Sleeveless scoop neck, adjustable spaghetti straps
    • Tie-back design
    • Ruched bust
    • Ruffle layered short-length hem
    • Ditsy floral print
    • Airy woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4911

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Steal The Scene Floral Corset Ruffle Mini Dress

    This floral corset mini dress serves up ruffles, romance, and just the right amount of sass. With its curve-hugging bodice and flirty layered hem, it’s basically a love letter in dress form.

    Fit & Features

    • Flocked floral pattern, mesh-lined fabric
    • Strapless sweetheart neckline
    • Corset-inspired bodice
    • Form-hugging fit
    • Tiered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000280

    Category Name: Casual Dresses

    Price: $59.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Swing My Way Eyelet Lace Midi Dress

    This eyelet lace midi dress is sure to get your crush's attention! It features a sleeveless V-neckline, adjustable spaghetti straps, button front accents, a flattering A-line silhouette, and a front slit along the hem. Complete the look in clear block heels for a daytime soiree!

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Button front accents
    • A-line silhouette
    • Front slit, midi-length hem
    • Eyelet lace fabric, partial woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4982

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Language Of Romance Lace Babydoll Dress

    This lace babydoll dress speaks your language for romance! Let this short dress sweep you off your feet for wedding showers, graduations, or birthday brunches! It features three-quarter-length puff sleeves, a square neck, a stretchy smocked back, and an empire waist seam that flares out into the flowy hem. Complete the look in new sandals and a clutch!

    Fit & Features

    • Three-quarter-length puff sleeves
    • Square neck
    • Stretchy smocked back
    • Empire waist, fit and flare silhouette
    • Flowy short-length hem
    • Lace overlay, chiffon lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4973

    Category Name: Casual Dresses

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovely In Floral Lace Trim Midi Dress

    You'll be a sight for sore eyes in this lovely floral midi dress - a flirty option for garden weddings, dressy birthdays, and day dates! The sleeveless dress features a sweetheart neckline with a romantic eyelash lace trim, adjustable spaghetti straps, a curve-hugging bodice, and a slit accent along the flowy hem. Complete the look with earrings and heels.

    Fit & Features

    • Sleeveless sweetheart neckline, padded wired bust, eyelash lace trim
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • Curve-hugging bodice
    • Slit accent, midi-length hem, A-line silhouette
    • Delicate floral print
    • Sheer woven fabric, full lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2228

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet As Me Eyelet Lace Skater Dress

    This eyelet lace dress is sure to be the sweetest style in your closet! It features puff short sleeves, a sweetheart neck with a bust tie, ruched bust, and a fit and flare skater silhouette. Complete the look with a ring set and heels.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck, bust tie
    • Ruched bust
    • Fit and flare skater silhouette
    • Short-length hem
    • Eyelet lace, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4924

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Palms Tropical One-Shoulder Dress

    This tropical mini dress will put you in vacay mode! Flaunt some skin in this sleeveless one-shoulder dress featuring a sleek bungee spaghetti strap, side ruched seams to accentuate your curves, and a bodycon fit. The dress is designed with a palm leaf print on stretchy knit-lined fabric. Complete your getaway look in platform wedges.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Bungee spaghetti strap
    • Side ruched seams
    • Bodycon fit, mini-length hem
    • Palm leaf print
    • Lined stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4956

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Oh My Darling Floral Halter Mini Dress

    Let your crush know you've entered the room in this retro-cute mini dress perfect for getting their attention at parties! It features a sleeveless sweetheart neckline with a flirty ruffle trim, halter straps with tie-back closure, an underwire bust, a bodycon silhouette, and a curved ruffle trim hem. The dress is designed with an adorable ditsy floral print on mesh-lined fabric. Complete the look in strappy mules.

    Fit & Features

    • Sleeveless sweetheart neckline, ruffle trim
    • Halter straps, tie-back closure
    • Underwire bust
    • Bodycon silhouette
    • Ruffle trim, curved mini-length hem
    • Ditsy floral print, mesh-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4892

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet But Savage Lace Floral Leopard Mini Dress

    Giving major heartbreaker energy! This flirty A-line mini dress hugs you just right with its mesh fabric and mixed prints. Pair it with heels or a chunky boot—your vibe, your rules.

    Fit & Features

    • Floral leopard print, mesh fabric, stretchy knit lining
    • Sweetheart neckline, adjustable spaghetti straps
    • Lace underwire bust with bow
    • Back zipper and hook-eye closure
    • Princess seams down the front
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000267

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

  • Feelin' Fresh Ditsy Floral Mini Dress

    Feel fresh and flirty in this floral mini-dress for your next daytime outing! It features puff short sleeves, a square neck with a bust tie, a bodycon silhouette, and a ditsy floral print on stretchy knit fabric. Style with block heels to complete the look!

    Fit & Features

    • Puff short sleeves
    • Square neck, bust tie
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy floral print
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4900

    Category Name: Casual Dresses

    Price: $36.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Forward Chiffon Puff Sleeve Skater Dress

    Spring forward and add this adorable skater dress to your wardrobe! The short dress features a square neckline with ruching at the bust, short puff sleeves, an empire waist seam, an open back with a tie-back accent, and a short skater skirt with a flirty fit and flare silhouette. The airy chiffon fabric provides a lightweight feel. Style with strappy mules.

    Fit & Features

    • Square neckline, ruched bust
    • Short puff sleeves, elastic cinched hems
    • Empire waist seam
    • Open back, tie-back accent
    • Short skater skirt, fit and flare silhouette
    • Sheer chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2024

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Happily In Love Scoop Neck Mini Dress

    You'll be happily in love with how stunning you look in this sleeveless mini dress for a graduation or birthday brunch! It features a scoop neck with a flirty bust tie, spaghetti straps, and a bodycon silhouette on rib knit fabric with a stretchy knit lining. Complete the look in trendy wedges.

    Fit & Features

    • Sleeveless scoop neck, spaghetti straps
    • Bust tie
    • Bodycon silhouette
    • Mini-length hem
    • Rib knit, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4754

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leave An Impression Halter Sweater Mini Dress

    Leave an impression in this sweater mini dress for dates or weekend getaways! The rib knit dress features a sleeveless halter neckline, a partially open back, a bodycon silhouette, and a mini-length hem with a flirty slit. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless halter neckline
    • Partially open back
    • Bodycon silhouette
    • Mini-length hem, slit accent
    • Rib-knit sweater fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1424

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • In For Romance Short Skater Dress

    You'll be in for the romantic vibes of this short skater dress perfect for bridal showers or day dates! It features three-quarter-length puff sleeves, a sweetheart neck, a tie-front, and a fit and flare silhouette. The dress is composed of a swiss dot pattern cotton fabric with a smooth woven lining. Complete the look in simple block heels.

    Fit & Features

    • Three-quarter-length puff sleeves
    • Square neck, tie-front
    • Skater silhouette
    • Short-length hem
    • Swiss dot pattern, smooth woven lining
    • No stretch
    • Runs true to size

    Style Number/Barcode: 05102-4902

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Blooms Floral Short Dress

    Tame your wild side and showcase this flirtatious floral short dress perfect for a casual picnic date! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a cutout back accent. Complete the look in wedges.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Bodycon silhouette
    • Cutout back accent
    • Short-length hem
    • Floral print knit fabric, knit lining at the bust, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4579

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt On Arrival Denim Skater Dress

    Made for flings, flirts, and feelin’ yourself. This trendy halter skater dress hugs you in all the right places with a playful bust cutout and a twirl-worthy drop waist—aka your weekend wardrobe’s new fave.

    Fit & Features

    • Denim fabric
    • Sleeveless cross-front halter neckline, tie-back straps
    • Bust cutout, metal heart accent
    • Partially open back, hidden lower back zipper closure
    • Drop waist
    • Short pleated skater silhouette
    • Runs small, size up recommended

    Style Number/Barcode: 05102-000084

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free