Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on your calendar.
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Casual Dresses Made for Everyday Fall Plans
Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.
Easy Prints, Textures & Layers for the Season
Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.
What Makes a Dress Casual?
A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.
How Do You Transition a Casual Dress From Summer to Fall?
Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.
Which Fabrics Work Best for Everyday Dresses?
Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.
How Can You Style One Casual Dress for Different Plans?
Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.
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Petal Perfection Cowl Neck Midi Dress
Charm them all in this pretty midi dress! Soft watercolored petals and a trendy cowl neckline make a romantic combination for this wedding guest dress!
Fits & Features
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Spaghetti Straps That Cross At The Back
- Cowl Neckline
- Midi Length Silhouette
- Stretchy Floral Knit Fabric
- Form Hugging Fit I Moderate Stretch
- Zipper Not Featured
Style Number/Barcode: 05101-0662
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spaghetti Straps That Cross At The Back
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Own The Night Mini Dress
Own the night with this chic little mini dress! Pair this head-turner with strappy stilettos and an envelope clutch for a classy night out with the squad bby!
Fit & Features
- V-Neckline
- Double Row of Spaghetti Straps
- Cross-Back Straps
- Mini Length Silhouette
- Lined Crepe Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05103-0762
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready For Tonight Chiffon Blouson Mini Dress
Ooh girl, you look so ready for a night out! Bring the drama with its off-shoulder neckline and fit-and-flare blouson sleeves!
Fits & Features
- Ruffle-Trim Square Neckline, Cuffs, Hem
- Sheer Blouson Sleeves With Circle Embroidery Detail
- Mini Length Silhouette With Drawstring At Center Front
- Smocking All Over
- Bodycon Fit I Ample Stretch
Style Number/Barcode: 05102-0560
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Turn On The Charm Square Neck Midi Dress
Slip into this midi dress and watch that confidence skyrocket! Pair this dress with some fab heels and layer on the dainty deets.
Fits & Features
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Bungee Spaghetti Straps
- Square Neckline
- Midi Length Hemline
- Smooth, Double-Layered Jersey Knit Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0561
Category Name: Casual Dresses
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bungee Spaghetti Straps
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Romance In Ruffles Mini Dress
Fall for romantic ruffles as they fall for you in this sweet mini dress! It features short sheer puff sleeves and ruched, lined mesh fabric with a form-hugging fit. Dress up with some fab heels for a night out with your girls, or keep it chill with some chunky sneakers for a day date.
Fit & Features
- Square neckline
- Puff sleeves with a ruffled trim
- Ruched
- Lined mesh fabric
- Rounded hem
- Form-hugging fit
- Moderate stretch
Style Number/Barcode: 05103-0755
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Warming Sign Midi Sweater Dress
All signs are pointing to *add to cart* with this cozy midi dress!
Fits & Features
- Off Shoulder Neckline
- Cuffed, Roomy Blouson Sleeves
- Midi Length Silhouette I Side Slit
- Midweight Ribbed Knit
- Comfortable Relax Fit I Plenty Of Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0558
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Chick Mock Neck Mini Dress
Pair this basic necessity with some thigh-high boots, take cover with your fave jacket, and you're all ready for a night out!
Fits & Features
- Mock Neckline
- Long, Balloon Sleeves With Elastic Cuffs
- Mini Length Silhouette
- Lightweight Ribbed Fabric I Best Paired With Tonal Shaper
- Curve Hugging Fit I Ample Stretch
Style Number/Barcode: 05102-0559
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Knit Mini Tie-Waist Sweater Dress
Keep it cute and cozy in a soft sweater dress that has an effortlessly classy finish!
Fit & Features
- High neckline
- Long flared sleeves
- Long hemline
- High waist slits
- Tie waist
- Knit material | Moderate stretch
Style Number/Barcode: 06005-0588
Category Name: Casual Dresses
Price: $21.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Posh In Polka Dot Smocked Mini Dress
You'll be looking oh-so-chic and posh in this pretty polka dot mini!
Fits & Features
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Square Neckline & Back
- Organza Sleeves With Puff Shoulders & Elasticized Cuffs
- Smocked Bodice & Mini Length Skirt
- Mesh, Ruffle Trim At The Neckline & Hem
- Velvet Polka Dots Throughout
- Form Hugging Fit I Ample Stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0806
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Square Neckline & Back
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Flirty Florals Blouson Mini Dress
Look fresh and effortlessly in this flirty mini dress! A perf day-time look for coffee dates or brunch with your girls!
Fits & Features
- Sweetheart Neckline With Twist At Center Front
- Cut Out Underneath Bust
- Unlined, Sheer Fitted Long Sleeves I Smocked Cuffs
- Back Zipper
- Flowy, Mini Length Skirt With Drawstrings At The Side
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05102-0556
Category Name: Casual Dresses
Price: $18.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Button Up Ribbed Mini Dress
Button up in this classic ribbed dress to channel a cool chick vibe! Step out for a girl's night out or for a casual date night out with bae. The dress features a sleeveless bodice, a trendy square neckline, bungee straps for a secure fit, and a button-down center to create a customized look. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit and a moderate stretch. Pair this baby with your favorite heels to create a standout look and finish off with statement earrings.
Fit & Features
- Square neckline
- Bungee spaghetti straps
- Button-down center closure
- Lined ribbed fabric
- Form hugging fit
- Moderate stretch
Olive Dress: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Black Dress: Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06002-0402
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Slit Floral Knit Maxi Dress
Upgrade your dress with a floral print. The floral maxi dress features a sleeveless bodice, a plunging V-neckline, and spaghetti straps that lead to a partially open back with a square neck. The relaxed fit waist leads to a curve-hugging maxi length silhouette that is accented with a high side slit to reveal a hint of leg. The dress is composed of a smooth knit fabric that offers a form hugging fit. Complete your brunch-ready look with statement heels and extra-large hoops.
Fit & Features
- Sleeveless v-neckline
- Spaghetti straps
- Partially open back
- Floral print
- Maxi length silhouette
- High side slit
- Knit fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0645
Category Name: Casual Dresses
Price: $21.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cable Knit Off Shoulder Sweater Dress
Cozy AF! Maximize the styling potential of this mini sweater dress!
Fits & Features
- Off Shoulder Neckline Design
- Long Sleeves WIth Elasticized Cuffs
- Mini Length Silhouette
- Lined, Knit Fabric I Cable Knit Design
- Form Hugging Fit I Ample Stretch
Style Number/Barcode: 05102-0553
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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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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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All Fleur Love Scuba Mini Dress
Wrap yourself up in florals with this oh-so-lovely and charming mini dress! Easily dress your look up or down by pairing it with some sneakers or heels.
Fits & Features
- Spaghetti Straps
- Square Neckline
- Mini Length Silhouette I Front Slit
- Scuba Knit Fabric
- Form Hugging Fit I Plenty Of Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0626
Category Name: Casual Dresses
Price: $11.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Puff It Up Crepe Mini Dress
Pump up the jams and get your night going in this LBD with statement puff sleeves!
Fits & Features
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Puff Shoulder Short Sleeves
- Plunging V Neckline I Padded Bust
- Square Back I Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0624
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Puff Shoulder Short Sleeves
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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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Knit Girl Mock Neck Sweater Dress
When cozy meets chic. This midi is just what you need for that winter wardrobe!
Fits & Features
- Mock Neckline
- Fitted Long Sleeves
- Midi Length Silhouette
- Ribbed Knit
- Bodycon Fit I Ample Stretch
- Zipper Not Included
Style Number/Barcode: 06005-0569
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simply Stunning Floral Chiffon Skater Dress
Style up this adorable floral chiffon dress for a simply stunning look. It features a sleeveless V neckline, adjustable spaghetti straps, front buttons, a fitted bodice, and a flirty skater skirt silhouette. Complete the outfit with hoop earrings and a straw tote.
Fit & Features
- Sleeveless V neckline
- Adjustable spaghetti straps
- Front buttons
- Fitted bodice, smocked back
- Back zipper closure
- Skater skirt silhouette
- Floral chiffon fabric
- Runs true to size
Style Number/Barcode: 05102-0545
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Floral Stunner Puff Sleeve Mini Dress
You'll be a total stylish stunner in this adorable floral mini dress! It features short puff sleeves, a square neckline with a front keyhole cut out and tie at the bust, and a short, curve-hugging silhouette. The all-over floral print makes the dress a perfect option for brunch dates and shopping trips with your girls. Complete the look with a pair of cute wedges.
Fit & Features
- Short puff sleeves, elasticized hems
- Elastic square neckline
- Front keyhole cut out and tie at the bust
- Back zipper, hook and eye closure
- Mini-length, form-hugging fit, moderate stretch
- Floral print
- Smooth knit fabric, fully lined
- Runs true to size
Style Number/Barcode: 05102-4339
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Major Jetsetter Tropical Print Maxi Dress
Nail your vacay-bound look with a maxi dress that brings those tropical vibes! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a high side slit, and a tropical palm leaf print. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and sunglasses.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross-back
- High side slit
- Tropical palm leaf print
- Maxi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0542
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale