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!

  • Fall Nights Satin Button-Up Short Dress

    The perfect satin short dress for a night of wine and dining! Featuring long sleeves with buttoned cuffs, a collar neckline, button-up front closures, a smocked waist, and a curved short-length hem. Complete the look in knee-high boots.

    Fit & Features

    • Long sleeves, buttoned cuffs
    • Collar neckline
    • Button-up front closures
    • Smocked waist
    • Curved short-length hem
    • Smooth satin fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1927

    Category Name: Casual Dresses

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rock Babe Lace-Up Graphic Dress

    If you're a rock babe this graphic short dress is the one for you! It features short sleeves, a crew neck, a front lace-up placket, and graphic detail with a script that reads, "Rock N Roll World Tour" along the fitted hem. Complete the look in over-the-knee boots.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Front lace-up placket
    • Graphic detail/ front reads, "Rock N Roll World Tour"
    • Short and fitted hem
    • Jersey knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1459

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Alluring Marble Mesh Bodycon Dress

    This alluring marble mesh bodycon dress will draw all the attention your way! It features a square neckline, sheer long fitted sleeves, a short, curve-hugging silhouette, and an all-over marble swirl pattern. The partially lined mesh fabric offers plenty of stretch. Style with platform heels.

    Fit & Features

    • Square neckline
    • Sheer long fitted sleeves
    • Mini-length hem
    • Fitted bodycon silhouette
    • Marble swirl pattern
    • Sheer mesh fabric, partial knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4863

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Finding Inspo Scoop Neck Mini Dress

    Casual to dressy, this scoop neck mini dress is perfect for creating all sorts of stylish fits! Featuring long sleeves, a bodycon silhouette, and a slight low-back neckline on ribbed knit fabric. Complete the look in a trendy shacket and booties.

    Fit & Features

    • Long sleeves
    • Scoop neck on front and back
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed knit fabric, double-lined
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4100

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eyes For One Shoulder Sweater Dress

    Everyone will only have eyes for you in this one-shoulder sweater dress featuring a long sleeve, flirty choker neck, a side waist cutout, and a form-hugging midi hem with a slit. Pair with strappy stiletto heels to complete the look!

    Fit & Features

    • One-shoulder, long sleeve
    • Choker neck
    • Side waist cutout
    • Form-hugging silhouette
    • Slit midi-length hem
    • Soft sweater-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1495

    Category Name: Casual Dresses

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Laced Up For The Night Mini Dress

    Heat up the night in this bombshell sleeveless mini dress featuring v-neckline, tank-style straps, a bodycon silhouette, and a cutout side with lace-up straps. Perfect for styling with strappy stiletto heels.

    Fit & Features

    • Sleeveless v-neckline
    • Tank-style straps
    • Bodycon silhouette
    • Cutout side with lace-up straps
    • Mini-length hem
    • Double-lined knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4814

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Live Or Ride Graphic Short Dress

    Live life comfortably or on the edge! Showcase your wild lifestyle in this graphic short dress featuring short sleeves, a crew neck, a front script that reads, "Live Or Ride Legend" and a bustier-style bodice with mesh inserts and a fitted hem. Complete the look in combat boots.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Graphic front with a script, "Live Or Ride Legend"
    • Bustier-style bodice with mesh inserts
    • Fitted, short-length hem
    • Smooth and stretchy cotton fabric
    • Fits true to size

    Style Number/Barcode: 06002-1449

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lowkey Head Turner Open Back Mini Dress

    She’s simple until she turns around. This bodycon mini dress elevates your look with an open back and tie detail that’s anything but basic. Pair with sandals for daytime outings.

    Fit & Features

    • Rib knit fabric, smooth, stretchy knit lining
    • Crew neck
    • Open back with tie detail
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000159

    Category Name: Casual Dresses

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Leave Em' Breathless Sweater Dress

    Leave your crush breathless when they see you in this spicy sweater mini dress! It features an off-the-shoulder neckline, long sleeves, a cutout bust, and a bodycon silhouette. Complete the look in thigh-high boots for everyday slay! 

    Shop More Sweater Styles: The Sweater Collection

    Fit & Features

    • Off-the-shoulder neckline
    • Long sleeves
    • Cutout bust
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1456

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Cable Knit Tie-Front Mini Dress

    Bring all the cozy vibes this season in this adorable cable knit mini dress! It features a V-neck and back with wrap designs, long balloon sleeves with tapered hems, a high waist with a tie-front accent, and a short, form-hugging fit. Style with knee-high boots.

    Fit & Features

    • V-neck and back, wrap design
    • Long balloon sleeves, tapered hems
    • High waist seam, tie-front
    • Mini-length hem, form-hugging fit
    • Cable knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4842

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Color Me Pretty Ombre Midi Dress

    Give your closet some pretty color with this ombre knit midi dress perfect for dressing up! The dress features a sleeveless scoop neck, sleek spaghetti straps, an open lace-up back with tie closure, a bodycon silhouette, and an asymmetrical side slit cutout to showcase some chic strappy heels.

    Fit & Features

    • Sleeveless scoop neck, spaghetti straps
    • Open lace-up back, tie closure
    • Bodycon silhouette
    • Asymmetrical side slit cutout
    • Midi-length hem
    • Ombre lined knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4825

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Draw Attention One-Shoulder Midi Dress

    You'll draw all the attention to you in this one-shoulder midi dress perfect for a casual lunch with friends! The dress features a single long sleeve, an adjustable drawstring waist cutout, a side ruched seam, and a form-hugging fit. Complete the look in chic lattice booties.

    Fit & Features

    • One-shoulder neckline
    • Single long sleeve
    • Adjustable drawstring waist cutout
    • Side ruched seam
    • Form-hugging, midi-length hem
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4803

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made Your Mark X-Back Midi Dress

    Make your mark in this stylish basic midi dress featuring a sleeveless crew neckline, wide shoulder straps that cross along the open back, and a form-hugging fit with a side slit detail. Complete the look in pointed-toe heels for a dinner with friends!

    Fit & Features

    • Sleeveless crew neckline
    • Wide shoulder straps cross along the open back
    • Form-hugging silhouette
    • Side slit detail
    • Midi-length hem
    • Rib-knit fabric, sewn-in lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4621

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Playful Spirit Chiffon Skater Dress

    Play up your flirty side in this adorable chiffon skater dress featuring sheer peasant sleeves, a square neckline, an open-back with tie closure, and a short-length hem. Complete the look in platform heels for a dressy event!

    Fit & Features

    • Sheer peasant sleeves
    • Square neckline
    • Open-back with tie closure
    • Skater silhouette
    • Short-length hem
    • Airy chiffon fabric, woven lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-2162

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually Cute Ribbed Knit Strapless Mini Dress

    Casually cute, this strapless mini dress is perfect for styling from coffee dates to happy hour. The A-line fit adds a flirty flair to the short silhouette.

    Fit & Features

    • Ribbed knit fabric with knit lining, high stretch
    • Strapless straight-across neckline
    • Mini-length hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000123

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Step It Up Henley Knit Midi Dress

    Step up your basics with this rib knit midi dress with subtle detail for a cute, everyday style! The dress features long sleeves, a V-neck, a button-down front with a slit, and a form-hugging silhouette. Complete the look in strappy mules for weekend plans!

    Fit & Features

    • Long sleeves, V-neck
    • Front button-down
    • Slit accent
    • Form-hugging silhouette
    • Midi-length hem
    • Rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4726

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Abstract Idea Mesh Printed Dress

    Wear your art! This abstract mesh mini dress features a sleeveless square neck, adjustable spaghetti straps, front cutouts with rhinestone button accents, side ruched seams, and a bodycon silhouette. Complete the look in glitzy heels and earrings.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Front cutouts with rhinestone button accents
    • Side ruched seams
    • Bodycon, mini-length hem
    • Abstract print, lined-mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4824

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knot Pleasure Crew Neck Midi Dress

    This crew neck midi dress will be pleased to be added to your fashion closet! It features long fitted sleeves, a form-hugging silhouette, and a front knot accent at the waist. The slinky knit fabric offers a moderate stretch. Complete the look with strappy heels.

    Fit & Features

    • Long fitted sleeves
    • Crew neckline
    • Form-hugging silhouette
    • Front knot accent at the waist
    • Midi-length hem
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4807

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cream Of The Crop Cutout Mini Dress

    Look and feel your absolute best in this prize-worthy casual mini dress! It features a sleeveless, one-shoulder neckline with a thin shoulder strap, a sultry cutout waist with a hoop insert, and a bodycon silhouette. Complete the look in clear strap heels for a lunch date.

    Fit & Features

    • Sleeveless, one-shoulder neckline
    • Thin shoulder strap
    • Cutout waist, hoop insert
    • Bodycon silhouette
    • Mini-length hem
    • Double-lined knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4806

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Wonders Square Neck Midi Dress

    This sleek midi dress will do wonders for your curves! It features a sleeveless square neckline with bungee spaghetti straps, and a side ruched seam to accentuate your figure along the asymmetrical slit hem. Complete the look in strappy mules for a brunch!

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Asymmetrical midi slit hem
    • Slinky knit double-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4805

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Weekend Vibes Ribbed Knit Mini Dress

    This cute and cozy ribbed knit mini dress is perf for your weekend plans! It features a crew neckline, long fitted sleeves, ruched detailing down the side seams, and a short, curve-hugging silhouette. The soft ribbed knit fabric offers plenty of stretch. Style with knee-high boots to grab coffee with your friends.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Ruching down the sides
    • Mini-length hem, fitted bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4839

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Staple Bodycon Mini Dress

    This chic mini dress is an elevated staple! It features a sleeveless mock neckline, tank shoulder straps, and a mini-length, form-hugging, bodycon silhouette. Style with strappy mules and a cute handbag.

    Fit & Features

    • Sleeveless mock neckline
    • Tank shoulder straps
    • Mini-length hem
    • Bodycon silhouette
    • Brushed knit fabric, knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4663

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Reap The Rewards Cutout Mini Dress

    You'll be reaping the rewards of this rib mini dress all season long! It features long fitted sleeves and a crew neckline, a twist accent bust with a cutout waist, side ruched ties that let you customize the length, and a bodycon silhouette. Complete the look in booties.

    Fit & Features

    • Long fitted sleeves
    • Crew neckline
    • Twist accent bust, cutout waist
    • Side ruched ties to customize the length
    • Bodycon mini silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4583

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wildly Iconic Animal Print Long Sleeve Mini Dress

    A little wild, a lot iconic—this abstract animal print mini dress brings the heat with its bold vibe and sultry sheer sleeves. Perfect for nights out or when you want your outfit to do all the talking.

    Fit & Features

    • Sheer mesh fabric with partial knit lining, high stretch
    • Abstract animal print
    • Mock neckline
    • Sheer long fitted sleeves, slit accents
    • Mini-length bodycon silhouette
    • Short side slit
    • Runs true to size

    Style Number/Barcode: 05102-000216

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M