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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In Check Plaid Mini Dress
Get your look in check with this cute plaid mini dress!
Fits & Features
- Narrow Spaghetti Strap
- Scoop Neckline I Square Back
- Mini Length Silhouette
- Fully Lined, Textured Knit Fabric I Plaid Print Throughout
- Bodycon Fit I Moderate Stretch
- Zipper Not Included
Style Number/Barcode: 05102-0554
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Smooth Like Satin Mini Dress
It's the perfect combo of sleek & sweet. Combat the chilly temps by throwing on a knit turtleneck underneath or a chunky sweater over.
Fits & Features
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Elastic Cord Straps
- Elastic Square Neckline With Vertical Darts At The Bust
- Mini Length Silhouette
- Fully Lined, Satin Fabric
- Curve Hugging Fit I Minimal Stretch
- Zipper Not Included
Style Number/Barcode: 05102-0405
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Elastic Cord Straps
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Keepin' Knit Cozy Sweater Dress
Keep it cozy and chic in this knit sweater dress.
Fits & Features
- Off-Shoulder Boat Neckline
- Long Sleeves With Faux Buttoned Cuffs
- Tie Front At Waist
- Short, Form-Hugging Fit
- Knit Fabric
- Plenty Of Stretch For Comfortable Wear
Style Number/Barcode: 05102-0547
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Mesh Well Ruched Mini Dress
A stunning little ruched dress is just what you need to show off those never-ending curves!
Fits & Features
- Elastic Cord Straps
- Square Neckline With Elastic Interior Band
- Mini Length Silhouette With Ruching Down The Sides
- Fully Lined, Mesh Fabric
- Curve Hugging Fit | Ample Stretch
- Zipper Not Included
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0432
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Scoop Neck Midi Dress
This must-have midi will give you an endless amount of OOTDs to wear and pair.
Fits & Features
- Spaghetti Straps
- Scoop Neckline I Square Back
- Midi Length Silhouette
- Stretchy, Jersey Knit Fabric I Fully Lined
- Curve Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0528
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cute But Chill A-Line Mini Dress
Looks like a serve, feels like a chill day 'fit. This nylon mini dress comes through with a flattering silhouette and hidden shorts, so you can dance, lounge, or do your thing without a second thought.
Fit & Features
- Smooth nylon fabric, moderate stretch
- Sleeveless square neckline
- Spaghetti straps
- Short front slit
- Mini-length hem, hidden shorts
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000031
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Knits An Essential Off Shoulder Maxi Dress
Sure it's winter, but it doesn't mean you have to stash away your dresses. Toss on a leather jacket, add a scarf, grab your fave bag, and you're all ready to go girlie!
Fits & Features
- Off Shoulder Neckline
- Fitted Long Sleeves
- Ruching Down The Side Seams
- Maxi Length Silhouette I Slit At The Side
- Ribbed Knit Composition
- Curve Hugging Fit I Ample Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0354
Category Name: Casual Dresses
Price: $12.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vivid Viper Mini Dress
Be prepared to pave the way to the dance floor in this seductive snake dress!
Fits & Features
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High Neckline
- Fitted Long Sleeves
- Deep V At The Back
- Ruching Along The Sides & Center Back
- Mid Thigh Length Silhouette
- Stretchy Knit I Snake Print Throughout
- Curve Hugging Fit I Ample Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0382
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Neckline
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Captivated In Floral Halter Bodycon Midi Dress
Look captivating and contoured in this floral midi dress while on vacay! The twist halter neckline adds a unique touch while the bodycon silhouette accentuates your curves along the midi-length hem.
Fit & Features
- Floral print, mesh-lined fabric
- Twist halter neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000197
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sheer I Come Mesh Ruched Midi Dress
Better fashionably late than never! Make an entrance in this sultry midi.
Fits & Features
- Spaghetti Straps
- Elastic Square Neckline & Back
- Ruched Accent Along Sides
- Midi Length Silhouette
- Lined, Mesh Fabric
- Curve Hugging Fit I Plenty Of Stretch
- Zipper Not Included
Style Number/Barcode: 05102-0423
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Livin' With Finesse Skater Dress
Finesse that closet with a perfectly designed skater dress!
Fits & Features
- V Neckline
- Double Spaghetti Straps Leading To Cross Over At Back
- High Waist Bodice
- Mini, A-Line Skirt
- Ponte Fabric I Fully Lined
- Moderate Stretch
Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0147
Category Name: Casual Dresses
Price: $14.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fuzzy Feels Sweater Dress
This sweater dress has us in our feels!
Fits & Features
- Turtle Neckline
- Long Sleeves With Ribbed Cuffs
- Mini Length Silhouette With Matching Ribbed Hem
- Unlined, Knit Composition
- Stretchy, Form-Hugging Fit With Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06005-0207
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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The Fuzz Sweater Dress
Mini dresses are all the fuzz! Featuring a crew neckline, long sleeves and a ribbed design. Hem of dress hits mid thigh and dress is composed of an eyelash knit material that offers moderate stretch. Perfect for the winter season!Style Number/Barcode: 06005-0152
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cozy Crush Sweater Dress
A cozy and crush-worthy sweater dress to include in your winter wardrobe.
Fits & Features
- Surplice V Neckline
- Long Bishop Sleeves
- Mid Thigh Length Hem
- Midweight Rib Knit Fabric
- Curve-Hugging Fit
- Ample Stretch
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06005-0231
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Snake It Away Metallic Mini Dress
Take on the night with this sassy mini dress!
Fits & Features
- Bungee Cord Spaghetti Straps
- Square Neckline & Back
- Metallic Knit With A Snake-Inspired Print
- Mini Length Silhouette
- Curve Hugging Fit
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0385
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic With An Edge Sweater Dress
You love a chic look with a little edge to it. This sweater dress has just that.
Fit & Features
- Turtleneck
- Long fitted sleeves
- Tie front belt at the waist
- Sultry side cut out
- Ribbed knit fabric
- Moderate stretch
Style Number/Barcode: 05102-0544
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Caught In The Midi Turtleneck Sweater Dress
A look you wouldn't mind being spotted in. Channel cozy-chic vibes with this turtleneck midi!
Fits & Features
- Turtleneck
- Long Roomy, Bell Sleeves
- Detachable Waist Tie
- Midi Length Silhouette
- Midweight, Ribbed Knit
- Ample Amount Of Stretch
Style Number/Barcode: 06005-0553
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Viper Vixen Knot Mini Dress
Vamp it out girl with statement snake print in this trendy mini dress! It features a deep V neckline with a knot front detail, long fitted sleeves, and a curve-hugging, mini length silhouette with a wrap skirt detail. Pair this dress with strappy heels and a faux leather jacket.
Fit & Features
- Plunging V neckline
- Knot bodice
- Long fitted sleeves
- Snake print
- Mini length silhouette
- Form-hugging fit
- Smooth knit fabric with moderate stretch
Style Number/Barcode: 05102-0357
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ribbed Knit Turtleneck Mini Dress
Stay comfy and look stylish doing it! This ribbed mini is the perfect foundation for your layered looks.
Fits & Features
- Turtleneck
- Quarter-Length Sleeves
- Mini Length Silhouette That Hits Mid-Thigh
- Stretchy Ribbed Knit Composition
- Curve-Hugging Fit I Ample Stretch
Style Number/Barcode: 05102-0347
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Oh-La-Lace Up Sweater Dress
Oh-la-la! Flaunt your curves in this lace-up, body-hugging mini dress!
Fits & Features
- Mock Neckline
- Fitted Long Sleeves
- Empire Waist I Linear Seaming Details At The Front
- Decorative Lace-Up Design I Metal Eyelets
- Mini Length Silhouette
- Ribbed Knit
- Ample Stretch
Style Number/Barcode: 06005-0552
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Open Back Eyelash Knit Sweater Dress
Get in the winter wonderland spirit with this fuzzy knit sweater dress!
Fit & Features
- Turtleneck
- Long sleeves with ribbed cuffs
- Large open back detail
- Form hugging fit
- Ribbed hems
- Soft, eyelash knit fabric | Moderate stretch
Style Number/Barcode: 06005-0566
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Perfect Collar Short Sleeve Mini Dress
There's nothing more perfect for warmer temps than this rib knit mini dress for an effortless athleisure vibe! This bodycon dress features a chic collar and short sleeves making it ideal for sunny days while the subtle side slit adds a flirty look.
Fit & Features
- Rib knit stretchy fabric
- Collar V-neckline
- Short sleeves
- Bodycon silhouette
- Side slit accent
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000127
Category Name: Casual Dresses
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Angora Knit Leopard Print Sweater Dress
Cozy and chic, this leopard print sweater dress is purrfect for the season.
Fit & Features
- Turtleneck
- Long sleeves
- Ribbed hems
- Leopard print
- Angora fuzzy knit fabric | Moderate stretch
- Relaxed, comfortable fit
Style Number/Barcode: 06005-0507
Category Name: Casual Dresses
Price: $4.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake You Out Sweater Dress
A look so fierce and cozy, you'll definitely want to put it on repeat.
Fits & Features
- Surplice V Neckline At Front & Back
- Bar Strap Accent At Back
- Long Sleeves
- Removable Waist Tie
- Hits Mid-Thigh
- Form Hugging Fit I Ample Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-0532
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance