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 Stunner Plaid Mini Dress

    You'll be a total trendy stunner in this sultry sleeveless plaid mini dress! It features a square neckline, spaghetti straps, an open back with a strappy design, and a short, curve-hugging silhouette. Complete the look with chic mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, strappy design
    • Mini-length, form-hugging fit
    • Plaid print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4205

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Essential Sleeveless Midi Dress

    The perfect sleeveless midi sweater dress for every occasion! It features a V-neck, tank straps, and a bodycon silhouette on ribbed knit fabric with a moderate stretch. Complete the look in sleek hoops and heels.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline, tank straps
    • Bodycon silhouette
    • Midi-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1239

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Oh Snap Mock Neck Ribbed Midi Dress

    Oh, snap, imagine how cute you'd look in this ribbed midi dress! It features long sleeves, a mock neck, bodycon silhouette, and side snap-button closures on ribbed knit fabric with a moderate stretch. Complete the look in suede booties.

    Fit & Features

    • Long sleeves
    • Mock neck
    • Bodycon silhouette
    • Side snap-button closures
    • Midi-length hem
    • Ribbed knit fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 06005-1124

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Born To Rock Lace-Up Graphic Tunic

    Feel the rockstar vibes in this trendy graphic tunic for all of your jam sessions! It features a sleeveless mock neck, dual side lace-up detail, and a front graphic script that reads, 'Let's Make Some Noise/Born To Be A Rockstar'. Complete the look in lug booties.

    Fit & Features

    • Sleeveless, mock neck
    • Dual side lace-up detail
    • Graphic reads, 'Let's Make Some Noise/Born To Be A Rockstar'
    • Form-fitting bodice
    • Short hem
    • Cotton knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1149

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Be Mine Button-Down Ribbed Midi Dress

    One look at this midi dress and you'll want it to be yours! It features short sleeves, a scoop neck, button-down front closures, a sultry front slit, and a bodycon silhouette. Composed of rib-knit fabric with a moderate stretch. Finish the look in chic hoop earrings.

    Fit & Features

    • Short sleeves, scoop neck
    • Button-down front closures
    • Front slit, midi hem
    • Bodycon silhouette
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4292

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shamrock Shake Ruched Mini Dress

    Look like a treat this St. Patrick's Day! This sleeveless mini dress features an on-trend square neck, spaghetti straps, and dual side ruching with adjustable ties, a shamrock pattern, and a bodycon silhouette. Composed of a brushed knit fabric with a moderate stretch. Finish the look in strappy sandals. 

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Dual side ruching, adjustable ties
    • Shamrock pattern
    • Bodycon silhouette
    • Mini hem
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4430

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Moves Midi Dress

    Make the trendiest of moves in this cool printed midi dress. It features a sleeveless halter neckline with spaghetti straps that lead to an open back with a strappy lattice design, a fitted bodice leading to a subtle flowy silhouette with a thigh-high front slit, and an all-over splattered tie-dye print. Style this dress with clear mules.

    Fit & Features

    • Sleeveless halter neckline, spaghetti straps
    • Open back, strappy lattice design, tie closure
    • Fitted bodice, flowy silhouette, high front slit
    • Spattered tie-dye print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4371

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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

    Keep it lowkey in a dress that brings those casual vibes! The dress features a crew neckline, short sleeves, and a sexy open back with a tie-back accent. The midi dress is composed of a lined ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sneakers and a denim jacket for those girl next door vibes!

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Open back 
    • Tie-back accent
    • Midi-length, high side slit
    • Lined ribbed knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4526

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rodeo Rebel Faux Suede Mini Dress

    Cowgirl, but make it hot. This faux suede mini dress brings western vibes with curve-hugging fit, embroidery details, and a button-front that’s strictly for show.

    Fit & Features

    • Western-embroidery, faux suede fabric, sewn-in knit lining
    • Moderate stretch
    • Strapless tube neckline
    • Side zipper and hook-and-eye closure
    • Faux front buttons
    • Bodycon fit, mini hem
    • Runs true to size

    Style Number/Barcode: 05102-000154

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS

  • Flirty And Flowy Woven Mini Dress

    Flirty and flowy, this adorable woven mini dress is perfect for day dates! It features a V-neckline, long blouson sleeves, a high waist seam, and an A-line silhouette with tiered ruffle detailing. The lightweight woven fabric includes a knit lining. Complete the look with a denim jacket and mules.

    Fit & Features

    • V-neckline
    • Long blouson sleeves, tapered hems
    • Back zipper and hook and eye closure
    • High waist seam
    • A-line silhouette, tiered ruffle detailing
    • Woven fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4280

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ditsy Floral Scoop Mini Dress

    Fall for this ditsy floral mini to revive your springtime wardrobe! It features puff short sleeves, a scoop neckline, a bodycon silhouette, and a short-length hem. Complete the look in chic mules for brunch.

    Fit & Features

    • Puff short sleeves
    • Scoop neckline
    • Bodycon silhouette
    • Short-length hem
    • DItsy floral pattern
    • Fits true to size

    Style Number/Barcode: 05102-4336

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Own It Ribbed Knit Midi Dress

    Own your look with a ribbed dress that makes a head-turning impression! The dress features a crew neckline, long sleeves, a sexy cutout at the waist, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties and a teddy jacket.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Cutout at the waist
    • Midi-length silhouette
    • Ribbed knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1079

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • In The Wild Leopard Mini Dress

    Flaunt your wild side in a leopard mesh mini dress for your next prowl! It features a sleeveless, square neck bodice with spaghetti straps and side ruched seams on a bodycon silhouette. Complete the look in heels.

    Fit & Features

    • Sleeveless bodice, square neck
    • Spaghetti straps
    • Side ruched seams
    • Mini-length bodycon silhouette
    • Leopard print pattern
    • Sheer mesh fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4470

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Perfection Ribbed Knit Mini Dress

    This comfortable ribbed knit mini dress is perfect for everyday 'fits! It features a classic crew neckline, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric offers a moderate stretch. Keep it casual with sneakers and a denim jacket, or elevate the look with sleek hoops and strappy mules.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves 
    • Form-fitting silhouette
    • Mini-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1272

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Collared And Chic Button Down Dress

    Keep it chic with a dress that is part trendy, part casual. The dress features a collared neckline, a button-down front, ruching, long sleeves, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules and gold earrings.

    Fit & Features

    • Collared neckline
    • Button-down front
    • Ruching 
    • Long sleeves
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4235

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Double Take Knit Mini Dress

    Wow in a mini dress that makes them all take a double take! The dress features a mock neck, long sleeves, a sexy cutout at the back, and a mini-length hem. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a trench coat

    Fit & Features

    • Mock neck
    • Long sleeves
    • Cutout at the back 
    • Mini length hem
    • Lined ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06002-1252

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Cutie Puff Sleeve Mini Dress

    Look cute in this mini floral dress for a picnic date or brunch with friends. It features puff short sleeves, a sweetheart neck with keyhole tie, and a short-length hem. Complete the look in trendy sandals.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neck, keyhole tie
    • Dainty floral pattern
    • Short-length fitted hem
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4337

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Winter Florals Ruched Bodycon Dress

    Florals for winter? Absolutely! This bodycon dress features a sleeveless, bungee spaghetti strap on a scoop neck, ruched sides, and a fitted hem. Composed of soft-knit fabric with a moderate stretch. Perfect for styling with a moto jacket.

    Fit & Features

    • Sleeveless, bungee spaghetti straps
    • Scoop neck
    • Ruched sides, fitted hem
    • Floral pattern throughout
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4445

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Show Your Floral Smocked Chiffon Dress

    Show your florals off in this chiffon mini dress for your next girl's day! It features long peasant sleeves, a sweetheart neck with a front knot-tie and keyhole accent, and a smocked short-length hem. Complete the look in chic sunglasses and heels.

    Fit & Features

    • Long peasant sleeves
    • Sweetheart neck
    • Front knot-tie, keyhole accent
    • Floral pattern
    • Smocked mini-length hem
    • Chiffon fabric
    • Fits true to size

    Style Number/Barcode: 05101-1378

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Thinking About Knit Cutout Midi Dress

    You've got knit on the mind, show off in a midi dress that stuns! The dress features a crew neckline, short sleeves, a knot accent at the center with dual cutouts at the waist, and a midi-length silhouette that is accented with a high side slit. The dress is composed of a cotton knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and a clutch.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Twist knot accent
    • Dual cutouts at the waist
    • Midi-length silhouette, high side slit
    • Cotton knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4261

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Go With The Flow Chiffon Skater Dress

    Go with the flow and keep it casual with a dress that can be dressed up or down for a date with bae. The dress features a square neckline, long balloon sleeves, an empire waist with pleating, and a skater length silhouette with a ruffled hem. The dress is composed of a lined chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with block heels and hoops

    Fit & Features

    • Square neckline
    • Long balloon sleeves
    • Empire waist with pleating 
    • Skater length silhouette, ruffled hem
    • Lined chiffon fabric
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1133

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Girl Next Door Slip Dress

    Show off your trendy style in this adorable cow print slip dress! It features a sleeveless V-neckline, bungee spaghetti straps, a stylish small front slit, and a short fitted silhouette. Complete the look with ankle booties.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Short front slit
    • Mini-length fitted silhouette
    • Brushed knit fabric, moderate stretch
    • Cow print
    • Runs true to size

    Style Number/Barcode: 05102-4325

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Frame Long Sleeve Midi Dress

    Bring the sweetness in this long sleeve midi dress featured in a sweetheart neck, bodycon silhouette, and midi-length hem. The dress is composed of a rib-knit fabric offering a moderate stretch. Complete the look with chic booties.

    Fit & Features

    • Long sleeves
    • Sweetheart neckline
    • Bodycon silhouette
    • Midi-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1179

    Category Name: Casual Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Twist Off-The-Shoulder Soft Knit Mini Dress

    The cashmere-like soft knit mini dress features an off-the-shoulder neckline, a popover accent with twist detail, long bell sleeves, faux wrap ties at the waist, and a fitted short-length hem. Complete a cozy stylish outfit with clear heels or ankle booties. 

    Fit & Features

    • Soft cashmere-like knit fabrication
    • Off-the-shoulder neckline
    • Popover accent with twist detail
    • Long bell sleeves
    • Faux wrap ties at the waist
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-6003

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L