Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and your calendar.
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Everyday Ease: Casual Dresses for Transitional-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. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.
Laid-Back & Versatile
Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler 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 nuetral 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!
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Go With Florals Mini Dress
Go with florals this season to channel gorge vibes!
Fit & Features
- Scoop Neckline | Spaghetti Straps
- Lattice Back
- Floral Print
- Lined Scuba Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0325
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Chic Satin Midi Dress
Sleek and chic, this satin midi dress will be your new go-to! It features a sleeveless cowl neckline, dual spaghetti straps that lead to a cross-back design, and a mid-length fitted silhouette with a subtle flared hem. Style this dress with clear heels and a trendy shoulder bag.
Fit & Features
- Sleeveless cowl neckline
- Dual spaghetti straps
- Cross-back design
- Mid-length fitted silhouette
- Satin fabric
- Runs true to size
Style Number/Barcode: 05101-0942
Category Name: Casual Dresses
Price: $20.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Glam Tie Dye Ruched Mini Dress
Keep it glam with a retro mini dress! The dress features a sleeveless square neckline, adjustable spaghetti straps, a tie-dye print, a ruched body, and a mini-length silhouette. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Tie-dye print
- Ruched body
- Mini length silhouette
- Form hugging fit
- Runs true to size
Style Number/Barcode: 05102-1377
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Twist Ribbed Knit Midi Dress
Give your midi dress a stylish twist with chic details! The dress features a sleeveless crew neckline, a twist knot accent at the back with a lower back keyhole, 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 look with mules.
Fit & Features
- Sleeveless crew neckline
- Twist knot accent at back
- Lower back keyhole
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0942
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Moves Eyelet Mini Dress
Make some seriously stylish moves with this mini dress! The dress features a square neckline, short puff sleeves, an eyelet design, an open back with tie-back straps, and a mini-length silhouette. Complete look with wedges.
Fit & Features
- Square neckline
- Short puff sleeves
- Eyelet design
- Open back with tie back straps
- Mini length silhouette
- Form hugging fit
- Runs true to size
Style Number/Barcode: 05101-1003
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Affair Long Sleeve Ruched Midi Dress
Make a casual-chic impression in this long sleeve ruched midi dress showcasing a folded off-the-shoulder neckline and a bodycon silhouette. Pair with heels.
Fit & Features
- Smooth knit-lined fabrication, moderate stretch
- Off-the-shoulder neckline, foldover accent
- Fitted long sleeves
- Ruching
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3723
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Frenzy Off The Shoulder Skater Dress
Start a frenzy with a floral dress that brings the romance! The dress features an off-the-shoulder neckline with a sweetheart bust, quarter-length short sleeves, a floral print, and a skater-length silhouette. Complete look with wedges and a floppy hat.
Fit & Features
- Off the shoulder neckline
- Sweetheart bust
- Quarter-length short sleeves
- Floral print
- Skater length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4179
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish And Lovely Eyelet Mini Dress
Keep it stylish and lovely with a mini dress that brings sweet details! The dress features a sleeveless square neckline with a mini tie front, adjustable spaghetti straps, an eyelet pattern, and a mini-length silhouette. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Mini tie-front
- Adjustable spaghetti straps
- Eyelet pattern
- Mini length silhouette
- Form hugging fit runs true to size
Style Number/Barcode: 05102-1276
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Sweet Puff Sleeve Mini Dress
Rock a look that's so sweet this season! The mini dress features an off-the-shoulder neckline with a sweetheart bust, short puff sleeveless, ruching at the bodice, and a mini-length silhouette. Complete your look with statement earrings and wedges.
Fit & Features
- Off the shoulder neckline, sweetheart bust
- Short puff sleeves
- Ruching
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1551
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Chic Cutout Midi Dress
Keep it chic with a midi dress that brings all the appeal. The dress features a sleeveless scoop neckline, a midriff cutout, spaghetti straps, a mini-length silhouette with a midi length overlay. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with wedges.
Fit & Features
- Sleeveless scoop neckline
- Midriff cutout
- Spaghetti straps
- Mini length silhouette with overlay
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0995
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Drawn In With Glam Ruched Mini Dress
Get drawn in with glam in a cute mini dress! The dress features a sleeveless V-neckline, spaghetti straps, a ruched drawstring at the center, and a mini-length silhouette. The dress is composed of a textured knit fabric that offers a form-hugging fit. Complete the look with hoops and mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Ruched drawstring at center
- Mini length silhouette
- Textured knit fabric
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-1496
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Florals Ribbed Knit Mini Dress
Bring the charm with a floral mini dress that is perf for your next brunch date! The dress features a sleeveless sweetheart neckline, tie-front, spaghetti straps, ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with wedges.
Fit & Features
- Sleeveless sweetheart neckline
- Tie-front
- Spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4062
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Passion Sleeveless Mini Dress
Channel the romance with a floral mini dress that brings charm to your look. The dress features a sleeveless V-neckline, tie-front, spaghetti straps, ditsy floral print, and mini-length silhouette. Complete look with mules and a charm necklace.
Fit & Features
- Sleeveless V-neckline
- Tie-front
- Spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2692
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Headed To The Tropics Mini Dress
Get ready to head to the tropics with this mini dress! The dress features a sleeveless scoop neckline, adjustable spaghetti straps, tropical palm leaf print, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Tropical palm leaf print
- Mini length silhouette
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0480
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Vibes Smocked Mini Dress
Channel those floral vibes with a smocked mini dress that nails those lowkey vibes just right! The dress features a sleeveless square neckline, spaghetti straps, a floral print, a mini-length silhouette, and a smocked body throughout. The dress offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Floral print
- Mini length silhouette with ruffled hem
- Smocked fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0802
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Into Florals Maxi Dress
Spring into the season with a maxi dress that ushers in the romance. The dress features a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a floral print, and a flowy A-line silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross back
- Floral print
- A-line silhouette, mini skirt length lining
- Floral print
- Lined chiffon fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-0979
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Darling Gingham Print Mini Dress
Stay on trend with a pretty mini dress that is perf for brunch with the squad! The dress features a sleeveless square neckline, spaghetti straps, gingham print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Gingham print
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4074
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Sweetheart Smocked Mini Dress
You'll be a total summer sweetheart in this adorable mini dress! It features a sleeveless square neckline with a ruffle trim, a tie-front bust detail, tie-shoulder spaghetti straps, a smocked body, and a mini-length, curve-hugging silhouette. Style this dress with casual sandals.
Fit & Features
- Sleeveless square neckline, ruffle trim
- Tie-front bust detail
- Tie-shoulder spaghetti straps
- Smocked body
- Short, form-hugging fit
- Woven fabric
- Runs true to size
Style Number/Barcode: 05102-0496
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Day Crochet Knit Midi Dress
Keep it casual with a midi dress that will have you channeling your bohemian side. The dress features a sleeveless V-neckline, spaghetti straps, a tie waist belt, and a midi length silhouette, The dress is composed of a crochet knit fabric that offers a relaxed fit with a slight stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tie-waist belt
- Midi length silhouette
- Crochet knit fabric
- Relaxed fit, slight stretch
- Runs true to size
Style Number/Barcode: 06005-0921
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty And Chic Paisley Printed Mini Dress
Showcase a pretty and chic vibe in this on-trend paisley printed mini dress. It features a sleeveless V-neckline, a tie accent at the bust, ruffle detailed shoulder straps, and a mini-length, curve-hugging silhouette. Style this dress with wedges for weekend brunch with the girls.
Fit & Features
- Sleeveless V-neckline
- Tie-front at the bust
- Ruffled shoulder straps
- Smocked back
- Short, form-hugging fit
- Paisley printed chiffon fabric
- Runs true to size
Style Number/Barcode: 05102-0571
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glitzy Look Glitter Strapless Skater Dress
Channel all the glitz and glam in this adorable glitter knit skater dress featuring a strapless straight neckline, ruched side seams, and a subtle drop waist. The pleated skater silhouette flares out to a trendy uneven mini-length hem. Style with metallic heels for a school dance or party!
Fit & Features
- Stretchy glitter knit fabric
- Strapless straight neckline
- Ruched side seams
- Subtle drop waist
- Pleated skater silhouette
- Uneven mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5809
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feelin' Fab Tie-Dye Mini Dress
You'll be feelin' oh-so-fab in this trendy tie-dye mini dress. It features a sleeveless scoop neckline, spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. This dress would be perf for a casual date styled with a cute crossbody purse and clear heels.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Ruched detailing, drawstrings at the hem
- Short, form-hugging fit
- Ribbed knit fabric, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-1334
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ditsy Floral Daze Ribbed Knit Mini Dress
Get caught in a floral daze with this cute mini dress! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, 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 mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ditsy floral print
- Mini-length silhouette, ruching down the sides
- Ribbed knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-3119
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy Vacay Vibes Maxi Dress
Bring the dreamy vacay vibes to your next getaway in this gorgeous maxi dress. It features a sleeveless V-neckline, adjustable spaghetti straps, a high waist, and a flowy floor-length silhouette with a chic front slit. The mesh fabric has a tropical floral print, making the maxi dress a perf pick for summer. Complete the look with strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Back zipper closure
- High waist
- Flowy floor-length silhouette, front slit
- Mesh fabric, floral print
- Runs true to size
Style Number/Barcode: 05101-0523
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale