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!

  • Color Story Square Neck Short Dress

    Vibrant and bold, who doesn't want to hear the end of this story? This sleeveless tunic top features an on-trend, square neck, bungee spaghetti straps, a color block pattern, and a bodycon silhouette. Complete the look in large hoop earrings.

    Fit & Features

    • Sleeveless, square neck, bungee spaghetti straps
    • Color block pattern
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1317

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Piece Of Me Crew Cutout Mini Dress

    Show off flirty peeks of skin on this sleeveless mini dress featuring a crew neck, bodycon silhouette, and cutout accents along the waist. Complete the look in strappy sandals for happy hour.

    Fit & Features

    • Sleeveless, crew neck
    • Bodycon silhouette
    • Cutout accents along the waist
    • Mini-length hem
    • Brushed knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4735

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take Me Away Tube Midi Dress

    Effortless but still a serve. This strapless knit midi hugs your curves with a twist-front neckline and scalloped hem—perfect for brunches, beach dates, or packing for your next getaway!

    Fit & Features

    • Texture knit cotton-blend fabric, moderate stretch
    • Sweetheart strapless tube neckline
    • Twist bust
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000018

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: SAGE

    Available Size: XS, S, M, L

  • Summer Love Eyelet Mini Dress

    You'll fall in love with the adorable details of this eyelet mini dress! It features a sweetheart neckline with a ruffled trim, a ruched bust with a tie-front, short puff sleeves, and a mini-length, form-hugging fit. The eyelet knit fabric features a lightweight lining. Style this dress with cute espadrille sandals.

    Fit & Features

    • Sweetheart neckline, ruffled trim
    • Ruched bust, tie-front detail
    • Short puff sleeves, elasticized hems
    • Short, form-fitting silhouette
    • Eyelet knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4433

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Back Beauty Linen Halter Skater Dress

    They'll love to watch you leave in this gorgeous skater dress featuring a sleeveless, halter neck with tie closure, and a smocked bodice that leads to a flowy, skater short silhouette with an open back and lattice bar accents. Complete the look in sleek hoop earrings for a day date. 

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • Smocked bodice
    • Flowy skater silhouette
    • Short-length hem
    • Open-back, lattice bar accents
    • Linen fabric, lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4404

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Live Fast Graphic Halter Tunic

    A biker babe like you is in need of this graphic tunic! It features a sleeveless, halter neck with tie closure and a front lace-up cutout with graphic detail that reads, "Live Fast/Born To Ride" on a fitted, short-length hem. Complete the look in sleek booties.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • Front lace-up cutout
    • Graphic detail that reads, "Live Fast/Born To Ride"
    • Fitted, short-length hem
    • Cotton fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1294

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lovely In Floral Cowl Mini Dress

    You'll look lovely in this floral mini dress featuring a sleeveless, cowl neck, bungee spaghetti straps, and form-fitting silhouette on woven fabric with an inner knit lining. Complete the look in sleek wedges.

    Fit & Features

    • Sleeveless, cowl neck, bungee spaghetti straps
    • Form-fitting silhouette
    • Mini-length hem
    • Floral print
    • Woven fabric, inner knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1576

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Color Story Crepe Mini Dress

    Tell the trendiest color story with this fab mini dress! It features a sleeveless, square neck, spaghetti straps, bodycon silhouette, and a color block pattern. Complete the look in sleek hoop earrings for a lunch date.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Color block pattern
    • Crepe-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4704

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fine Lines Chambray Skater Dress

    Flirty and fine! Look and feel effortlessly cute in this chambray striped skater dress featuring a sleeveless, v-neck, ruffled trim, and a babydoll-style seam that leads to the flowy short-length hem. Complete the look in braid strap mules.

    Fit & Features

    • Sleeveless, v-neck, ruffled trim
    • Babydoll-style seam
    • Flowy short-length hem
    • Chambray striped fabric, lining, no stretch
    • Back keyhole accent, button closure
    • Fits true to size

    Style Number/Barcode: 05102-4602

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Scene Satin A-Line Dress

    Set the scene for drinks at sunset in this satin a-line dress featuring a sleeveless, scoop neck, spaghetti straps, tie-front bust, and a form-fitting silhouette on marble print fabric. Complete the look in lucite heels.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Tie-front bust
    • Form-fitting, a-line silhouette
    • Mini-length hem
    • Marble print, satin fabric, inner lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4705

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie Dye For One Shoulder Dress

    This maxi dress is totally tie-dye for your next beach day or vacay! Featuring a sleeveless, one-shoulder neck, tank-style strap, high waist seam, and a form-fitting silhouette with a side knot accent atop an asymmetrical hem. Complete the look in cute wedges and shades.

    Fit & Features

    • Sleeveless, one-shoulder neck, tank-style strap
    • High waist seam
    • Form-fitting silhouette
    • Side knot accent
    • Asymmetrical maxi-length hem
    • Tie-dye print, brushed knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4622

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wanderer Paisley Cutout Midi Dress

    Embrace the wanderlust life! Look like a babe in this medallion paisley midi dress featuring a sleeveless, v-neck, spaghetti straps, and knot accented bust atop a sultry cutout bodice that leads to the form-fitting midi hem. Complete the look in strappy sandals for a festival.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Knot accented bust
    • Cutout bodice
    • Form-fitting midi hem
    • Medallion paisley print
    • Crepe knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4342

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Florals Chiffon Skater Dress

    Charm them all with a floral dress that brings those sweet vibes! The dress features a sleeveless V-neckline, adjustable spaghetti straps, an open-back design with cute tie-back ties, and a skater silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with a minimal stretch. Complete look with wedges

    Fit & Features

    • Floral print
    • Sleeveless V-neckline
    • Adjustable spaghetti straps 
    • Open back, tie-back ties
    • Skater silhouette
    • Chiffon fabric
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05101-1100

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Party Paisley Knit Mini Dress

    This adorable paisley printed mini dress is perfect for all of your casual summer parties! It features a sleeveless square neckline, spaghetti straps that lead to a lace-up back design, and a short, form-hugging fit. The brushed knit fabric offers plenty of stretch. Style this dress with cute mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, lace-up back design, tie closure
    • Mini-length, form-fitting silhouette
    • All-over paisley print pattern
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4496

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Glam Ruched Short Dress

    Keep it glam on your tropical getaway with a mini dress that brings those island vibes! The dress features a tropical floral print, a sleeveless square neckline, spaghetti straps, ruching, and a short length with a rounded hem. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a straw hat

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching
    • Tropical floral print
    • Short length hem
    • Lined smooth knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4683

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Falling For Eyelet Mini Dress

    Fall for this eyelet mini dress for a cute vibe all summer long! It features a sleeveless, square neck, adjustable spaghetti straps, a flirty tie-front bust, and a form-fitting silhouette. Complete the look in a dainty necklace and wedges.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Tie-front along the bust
    • Form-fitting silhouette
    • Mini-length hem
    • Eyelet knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4435

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruffle Up And Go Tube Romper

    Short, sweet, and kinda irresistible. This tube romper flirts with every step thanks to its strapless straight neckline, drop waist design, and adorable ruffled overlay.

    Fit & Features

    • Ponte knit fabric, moderate stretch
    • Strapless straight-across neckline
    • Drop waist design
    • Tiered ruffled mini-length overlay, A-line silhouette
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000099

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Back In Stock
  • Perfect Weekend Vibes Mini Dress

    This sleek satin floral dress is perfect for your weekend outings! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back lace-up design, and a mini-length, A-line silhouette. The lightweight satin fabric features an all-over dainty floral print. Style this dress with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back lace-up design, tie closure
    • Mini-length, A-line silhouette
    • Dainty floral print
    • Smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4494

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever In Floral Mini Dress

    They can catch you forever in this floral mini dress! It features a sleeveless sweetheart neckline, spaghetti straps, and a tie-front along the bust on ribbed knit fabric that offers a form-hugging fit. Complete the look in flirty mules for a daytime occasion.

    Fit & Features

    • Sleeveless, sweetheart neck, spaghetti straps
    • Tie-front along the bust
    • Form-hugging fit
    • Mini-length hem
    • Ditsy floral print
    • Ribbed-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4668

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Views Floral Midi Dress

    Soak in those stunning vacay views in this chic floral midi dress! It features a sleeveless bodice, a wrap-front V-neckline, spaghetti straps, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some skin. The smooth and stretchy knit fabric features an all-over tropical floral print. Complete the look with strappy heels.

    Fit & Features

    • Sleeveless bodice, wrap-front V-neckline
    • Spaghetti straps
    • Fitted midi-length silhouette, asymmetrical hem
    • Form-hugging fit
    • Tropical floral print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4441

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect For Paradise Midi Dress

    This curve-hugging midi dress is perfect for your vacation in paradise, or to just look like you're on one! It features a sleeveless V-neckline, spaghetti straps, a midi-length asymmetrical hem to showcase some leg, and an all-over tropical floral print to match the vibe of a vacay. Style this dress with strappy mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length asymmetrical hem
    • Form-fitting silhouette
    • Tropical floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4474

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Babe Next Door Denim Mini Dress

    You'll look like a total babe next door in this adorable denim mini dress. It features a sleeveless sweetheart neckline with a padded bust, thin adjustable straps, an exposed back zipper closure, and a short, form-hugging fit. Style with hoop earrings and trendy cowgirl boots.

    Fit & Features

    • Sleeveless, sweetheart neckline, adjustable spaghetti straps
    • Built-in padded bust
    • Back zipper, hook-eye closure
    • Mini-length hem
    • Form-fitting silhouette
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4448

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charmed By Ruffles Short A-Line Dress

    Get charmed by pretty ruffles in this fab dress! The dress features a square neckline, short puff sleeves, a partially open back with cinching tie-back accent, and a short length with a ruffled hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules

    Fit & Features

    • Square neckline
    • Short puff sleeves
    • Partially open back, tie back accents
    • Short length 
    • Ruffled hem
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size 

    Style Number/Barcode: 05102-4338

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Preppy Collared Mini Dress

    Your current mood? Preppy and ready for anything with this cute mini dress featuring short sleeves, a collared V-neck, and a bodycon silhouette on rib-knit fabric. Complete the look in trendy boots.

    Fit & Features

    • Short sleeves
    • Collared V-neckline
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4412

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale