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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Trendy Twist Knot Open Back Ribbed Mini Dress
Stun in a dress that makes them take a double-take with bold details! The dress features a crew neckline, fitted long sleeves, and a stunning open back with a twist knot bar strap accent. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules.
Fit & Features
- Crew neckline
- Fitted long sleeves
- Open back
- Twist knot bar strap
- Ribbed knit fabric
- Mini length silhouette
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0991
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Sweetheart Ribbed Knit Mini Dress
You'll look like such a stylish sweetheart in this adorable ribbed knit mini dress! It features a ruffled sweetheart neckline with a button-down front and a curve-hugging fit. Pair this cute and casual dress with some sneakers for an effortless, everyday vibe.
Fit & Features
- Spaghetti straps
- Ruffled sweetheart neckline
- Button-down front
- Short, form-hugging fit
- Ribbed knit fabric
Style Number/Barcode: 05102-1016
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keeping Knit Classy Sleeveless Mini Dress
Class up your basic mini dress with details that stand out! The dress features a sleeveless crew neckline, dramatic shoulder pads, and a mini length silhouette. The dress is composed of a cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with chunky sneakers for a casual vibe.
Fit & Features
- Crew neck
- Sleeveless bodice
- Shoulder pads
- Mini length silhouette
- Cotton knit fabric
- Relaxed fit
- Moderate stretch
Style Number/Barcode: 05102-1033
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keep It Basic Ribbed Mini Dress
Keep your look basic and chic in this ribbed mini dress you can totally dress up or down! It features a mini length silhouette and a form-hugging fit to enhance your curves. Elevate your outfit by pairing this adorable dress with chunky sneakers for a more casual vibe.
Fit & Features
- Bungee spaghetti straps
- Scoop neckline
- Short, form-hugging fit
- Ribbed fabric
Style Number/Barcode: 06002-0611
Category Name: Casual Dresses
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty In Plaid Knit Mini Dress
Look oh-so-pretty in plaid in this adorable knit mini dress! Featuring a trendy square neckline and a short, form-hugging fit, this dress is a fall must-have. Pair with strappy heels and layer on a chic faux leather jacket for a date night.
Fit & Features
- Spaghetti straps
- Square neck and back
- Mini length silhouette
- Form-hugging fit
- Plaid print
- Knit fabric
Style Number/Barcode: 05102-0585
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get On-Trend Tie Dye Knit Mini Dress
Get on-trend in this adorable tie dye knit mini dress! It features an open back detail with a tie closure and ruched, form-hugging fit to enhance your curves. Pair this dress with chunky sneakers for a casual-chic everyday look.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Open back detail with tie closure
- Ruched detailing
- Short, form-hugging fit
- Tie dye knit fabric
Style Number/Barcode: 05102-0861
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Angelic Beauty Ruched Mini Dress
Look like such an angelic beauty in this gorgeous ruched mini dress! Featuring a curve-hugging fit with an allover angelic print and front ruched detailing, this dress will make you look oh so dreamy. Pair it with some clear heels for a date night.
Fit & Features
- Adjustable spaghetti straps
- Cowl neckline
- Back zipper closure
- Front ruched detailing with slit and drawstring accent
- Ruffle detail at hem
- Mesh fabric
- Allover angelic print
Style Number/Barcode: 05101-0914
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Best Life Square Neck Mini Dress
Live your best life in a mini dress that can be dressed up for a night out with the squad. The dress features a sleeveless square neckline, sleek bungee straps, and a mini-length silhouette. Complete your look with sleek black heels.
Fit & Features
- Sleeveless square neckline
- Bungee straps
- Mini-length silhouette
- Smooth knit fabric
- Form-hugging fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1000
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Buttoned Up Off The Shoulder Midi Dress
Get all buttoned up in this adorable off the shoulder midi dress! It features a complete button-down front with a curve-hugging, mid-length fit. Perfect for everyday, pair this dress with heeled booties to take your look into fall.
Fit & Features
- Off the shoulder neckline
- Short fitted sleeves
- Complete button-down front
- Mid-length, form-hugging fit
- Ribbed knit fabric
Style Number/Barcode: 05102-0943
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Knit Off-The-Shoulder A-Line Mini Dress
Channel that cute and cozy vibe in this adorable soft ribbed knit mini dress featuring an off-the-shoulder straight neckline with a fold-over design, long fitted sleeves, and a short A-line silhouette. Style with knee-high boots for a fall date!
Fit & Features
- Soft ribbed knit fabric
- Off-the-shoulder straight neckline, fold-over design
- Long fitted sleeves
- Mini-length A-line fit
- Runs true to size
Style Number/Barcode: 05102-5892
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ribbed Knit Crew Neck Bodycon Mini Dress
Keep it casually chic in a mini dress that is a total must-have! The short dress features a crew neckline with a racerback design, a mini-length hem, and is composed of a form-hugging ribbed knit fabric. Put your hair in an updo and style with strappy mules for a cute look!
Fit & Features
- Crew neckline
- Sleeveless bodice
- Racerback design
- Mini-length hem
- Ribbed knit fabric, fully lined
- Form-hugging fit, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-0689
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Twist of Glamour Brushed Knit Mini Dress
Bring a twist of glam to this mini dress! The dress features a plunging V-neckline with a twist knot accent, a midriff keyhole, and a mini length silhouette with an envelope hem. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules.
Fit & Features
- V-neckline
- Twist-knot accent at the center of the bodice
- Long sleeves
- Mini length silhouette with an envelope hem
- Brushed knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0830
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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In Tulum One-Shoulder Tropical Maxi Dress
Perfect for your vacay in Tulum, this one-shoulder tropical maxi dress was made for sunset dinners and dancing!
Fit & Features
- Tropical print, smooth knit fabric with short stretchy lining
- One-shoulder neckline
- One shoulder strap with metal accents
- Front ruffled slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6073
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Break The Rules Ruched Knit Mini Dress
Dare to bold up your look in a mini dress that showcases curves. The mini dress features a trendy square neckline, fitted long sleeves, and a ruched mini-length silhouette with an envelope hem. Complete look with chunky sneakers for a casual affair.
Fit & Features
- Square neckline
- Long sleeves
- Ruched body
- Mini-length silhouette
- Envelope hem
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0872
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Totally Chic Ruched Knit Mini Dress
Keep it totally chic in a ruched mini dress! The dress features an off the shoulder neckline, long fitted sleeves, and a ruched drawstring center. The dress is composed of a ribbed knit fabric that hugs curves in all the right places. Complete look with sneakers for a casual look.
Fit & Features
- Off the shoulder neckline
- Long fitted sleeves
- Ruched drawstring center
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0932
Category Name: Casual Dresses
Price: $14.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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The One Basic One Shoulder Ribbed Mini Dress
This ribbed dress is the one that you can't live without! Dress up this beauty with duster earrings and mules for a glam night out outfit. The dress features a one-shoulder neckline, a ruched mini length silhouette, and composed of a ribbed knit fabric.
Fit & Features
- Sleeveless bodice
- One-shoulder neckline
- Ruched body
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0997
Category Name: Casual Dresses
Price: $10.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Own Knit Ruched Mini Dress
Own your gorgeous look in this adorable knit mini dress! It features a trendy mock neckline, ruched detailing down the back, and a sexy curve-hugging fit. Pair this dress with some chic heels for a night out.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Open back
- Ruched back detailing
- Short, form-hugging fit
- Ribbed knit fabric
Style Number/Barcode: 05102-0971
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Open Back Ruched Ribbed Knit Midi Dress
Style up this basic ribbed knit midi dress for the perfect everyday look! It features a partial lower open back, ruched detailing and a curve-hugging mid-length silhouette. Pair the dress with chunky sneakers to get that casual, cute vibe.
Fit & Features
- Scoop neckline
- Long fitted sleeves
- Partial lower open back
- Ruched detailing
- Form-hugging fit
- Midi length
- Ribbed knit fabric
Style Number/Barcode: 05102-0977
Category Name: Casual Dresses
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cut To The Chase Knit Mini Dress
Let's cut to the chase - this knit mini dress is so chic! Featuring trendy cut outs and a sexy, curve-hugging fit, this dress is perf for a girl's night out. Pair it with chunky gold hoops to give the look some glam.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Waist cut out
- Ruched detailing
- Short, form-hugging fit
- Knit fabric with plenty of stretch
Style Number/Barcode: 05102-0974
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In Knit To Win It Midi Dress
You'll be totally in it to win it in this adorable knit midi dress! It features a double-lined knit fabric and a mid-length, curve-hugging silhouette. Wear this dress with chunky sneakers for an adorable everyday look.
Fit & Features
- Spaghetti straps
- Scoop neckline
- Mid-length form-hugging fit
- Double lined knit fabric
Style Number/Barcode: 05102-0877
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Slay In Style Ribbed Scoop Neck Midi Dress
Slay in this midi dress that brings some major chic vibes! The dress features a scoop neckline, tank-straps, and a chic tie-waist belt to create an hourglass illusion. Complete your night-out look with a faux leather jacket.
Fit & Features
- Scoop neckline
- Tank-straps
- Tie-waist belt
- Ribbed sweater knit fabric
- Midi-length silhouette
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0929
Category Name: Casual Dresses
Price: $4.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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What's The Scoop Cutout Ribbed Knit Mini Dress
Serve up a chic look in the ribbed dress! Perfect for your next brunch date, this mini dress brings the drama! The dress features a scoop neckline with shoulder cutouts, tank-like straps, and a mini length silhouette. Style dress with a fab top knot and door knocker earrings.
Fit & Features
- Scoop neckline with tank-like straps
- Shoulder cutouts
- Long sleeves
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0903
Category Name: Casual Dresses
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruched And Ribbed Knit Crew Neck Mini Dress
This ruched and ribbed knit mini dress is the casual-chic piece you need in your closet! It features a form-hugging fit with ruched detailing to enhance your curves. This dress can be worn as a mini or pulled down and styled as a midi. Wear it with simple slides or elevate the look in heels.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Ruched sides
- Adjustable ties at hem
- Rib-knit, moderate stretch, fits true to size
Style Number/Barcode: 05102-1092
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Slaying Knit Sleeveless Ribbed Midi Dress
Slay it in a ribbed knit dress that stuns for your next date night in! The dress features a sleeveless square neckline, sleek bungee straps, and a curve-hugging midi-length silhouette. Complete look with clear mules.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0964
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance