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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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
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Leopard Purrfection Satin Midi Dress
Tap into your instincts with this fiercely-inspired print! This midi dress only needs a pair of booties and dainty pieces to complete the look!
Fit & Features
- V-Neckline
- Spaghetti Straps
- Leopard Print
- Side Slit
- Lined Satin Fabric
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05101-0599
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Burnout Floral Mock Neck Mini Dress
We can't get enough of these burnout floral dresses! This mini version is complete with a trendy mock neck and a short, curve hugging fit.
Fit & Features
- Mock neckline
- Back zipper closure
- Long sheer fitted sleeves
- Sheer insets at the neckline
- Sheer back
- Mesh burnout floral sheer fabric | Knit lining
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0597
Category Name: Casual Dresses
Price: $14.97 $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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V Cozy Button Down Sweater Dress
Bundle up with the V Cozy sweater dress!
Fits & Features
- V Neckline I Button-Down Front
- Fitted Long Sleeves With Rolled Cuffs
- Slip Hand Pockets & Hem With Subtle Frill Design
- Detachable Waist Tie
- Midi Length Silhouette
- Ribbed Knit
- Form-Hugging Fit I Ample Stretch
Style Number/Barcode: 06005-0551
Category Name: Casual Dresses
Price: $6.97 $46.90
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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The One For You Mini Sweater Dress
This chic knit mini sweater dress is def the one for you! Pair with some statement earrings and strappy mules and werk it bb!
Fit & Features
- One shoulder neckline
- Single long fitted sleeve
- Short, curve hugging fit
- Ribbed knit fabric
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06005-0540
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Just A Lil' Knit Mini Dress
Show just a lil' when you slip into this knit mini dress with a peep of sexy!
Fit & Features
- Crew neckline
- Long Sleeves
- Cut out detail above the bust
- Form fitting silhouette
- Ribbed knit material
- Moderate stretch | Form fitting silhouette
- Mini length hemline
Style Number/Barcode: 06005-0536
Category Name: Casual Dresses
Price: $6.97 $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
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Floral Beauty Sleeveless Chiffon Maxi Dress
Radiate beauty in a floral maxi dress that brings the charm. Perfect for that next bridal shower this maxi dress features a sleeveless plunging v-neckline, a crochet lace detailed lace, and an all-over floral print. Complete your romantic outfit with duster earrings and clear heels.
Fit & Features
- Sleeveless plunging v-neckline
- Crochet lace detailed waistband
- Floral print
- Maxi length silhouette
- Chiffon knit fabric
- Relaxed fit
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0596
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Comfy Cozy Chic Mini Dress
Comfy, cozy, and chic, the ultimate combo. This mini dress is beyond perf for fall and winter.
Fits & Features
- Turtleneck
- Long Sleeves
- Mini Silhouette
- Ribbed Knit
- Form Hugging Fit | Moderate Stretch
- No Zipper
Style Number/Barcode: 06005-0475
Category Name: Casual Dresses
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Sweetheart Mini Dress
Show off your sweet side in this must-have mini dress! Pair with block heels and layers of dainty pieces to complete your look!
Fit & Features
- Sweetheart Neckline | Padded Cups
- Short Puff Sleeves
- Double-Lined Brush Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0539
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Get With The Program Crepe Mini Dress
Give them a little attitude when you step out in a mini dress with a little sass! Pair with your go to heels, and a pair of door knocker earrings, and stun in 2020's color of the year!
Fit & Features
- Square neckline
- Bungee spaghetti straps
- Vertical flattering seams
- Mini side slit
- Form fitting silhouette
- Fully lined
- Crepe | 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: 05102-0533
Category Name: Casual Dresses
Price: $11.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweetheart Neck Ruffled Ditsy Print Mini Dress
Keep on trend in a floral ruffle dress. The ditsy floral dress features a sweetheart neckline, ruffled shoulder straps and an-all over ditsy floral print. The relaxed fit waist leads to a mini length silhouette that offers a curve-hugging fit with slight stretch. Complete your outfit with hoops and dad sneakers for a casual vibe.
Fit & Features
- Sweetheart neckline
- Ruffled shoulder straps
- Ditsy floral print
- Mini length silhouette
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0538
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance