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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Fab Florals Crochet Waist Maxi Dress
Impress with florals in a maxi dress that takes you to paradise! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a crochet waist, a floral print, a high side slit, and a maxi length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Crochet waist
- Floral print
- High side slit
- Maxi length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0196
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet And Smocked Floral Mini Dress
Bring a sweet vibe to your spring style with this adorable floral mini dress! It features an off-the-shoulder square neckline, short ruffle sleeves, and a curve-hugging, mini-length silhouette with a smocked design. Complete the look with hoop earrings and new heels.
Fit & Features
- Off-the-shoulder square neckline
- Short ruffle sleeves
- Short, form-hugging fit
- Floral print
- Chiffon fabric, smocked design
- Runs true to size
Style Number/Barcode: 05102-0339
Category Name: Casual Dresses
Price: $20.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Chiffon Long Sleeve Skater Dress
We're falling for this floral look! It's the perf dress for that special outing you got lined up

Fits & Features
- Surplice V Neckline
- Cuffed & Unlined, Sheer Long Sleeves
- Zipper At Back
- Mini Length | Flowy Skater Skirt
- Lined, Chiffon Fabric
- Minimal Stretch
Style Number/Barcode: 05101-0192
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Still Got Knit Mini Dress
Flaunt your love for knit with this casual mini dress! It features a turtle neck, long fitted sleeves and a curve hugging mini length silhouette that rests at the mid-thigh level. Dress is composed of a cable-knit fabric that offers a relaxed fit with a moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0186
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Alluring Tropical Floral Maxi Dress
Create a stylish and alluring look for your next vacay in this gorgeous maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a lace-up back design, a high waist, a floor-length hem with a chic side slit, and a flowy, relaxed fit. The knit fabric has an all-over tropical floral print, making this dress a perf pick for summer. Complete the outfit with strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Lace-up back design
- High waist
- Floor-length hem, side slit, relaxed fit
- Knit fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 05102-0195
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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That's My Stripe Crepe Triangle Waist Cut Out Mini Dress
This striped crepe waist cut out mini dress will be just your type! Featuring a sultry cutout, a streamlined silhouette, and trendy stripes, this dress checks all the boxes. Opt for some booties and statement earrings to go with this look for a night out.
Fits & Features
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Spaghetti straps
- V Neckline and vertical dart seams
- Square back with no zipper
- Triangular waist cut out
- Mini length silhouette
- Crepe fabric
- Form-hugging fit with moderate stretch
Style Number/Barcode: 05103-0292
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spaghetti straps
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Floral Tropical Surplice Wrap Maxi Dress
Wrap yourself in a floral maxi dress. Bring the vacation vibes this season in this dress that features an all-over tropical floral print, a sleeveless surplice wrap neckline, and spaghetti straps. The relaxed fit waist leads to a carefree maxi length silhouette. The dress is composed of a lightweight smooth knit fabric that offers a form hugging fit. Complete your outfit with dainty bracelets and face-framing sunglasses.
Fit & Features
- Sleeveless
- Wrap v-neckline
- Spaghetti straps
- Tropical floral print
- Maxi length silhouette
- Smooth knit fabric
- Form hugging fit
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 05102-0194
Category Name: Casual Dresses
Price: $21.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral The Right Reasons High Neck
Brunch? Wedding guest? Winery? This floral mini dress is perfect for all these special occasions!
Fits & Features
- Adjustable Spaghetti Straps
- Lace Zipper Back
- High Neckline
- Mini Length Silhouette | Skater Skirt
- Smooth Scuba Fabric With Floral Prints
- Form Hugging Fit | Moderate Stretch
Style Number/Barcode: 05101-0168
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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City Slicker Satin Mini Dress
A sleek mini, inspired by the trendy city girl in mind!
Fits & Features
- Cowl Neckline
- Adjustable Self Tie Shoulder Straps
- Square Back
- Satin-Like Composition I Fully Lined
- Mini Length Silhouette
- Form-Flattering Fit I Minimal Stretch
Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0350
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Passion Scuba Skater Dress
Get passionate about florals this season bby! This twirl-worthy dress is what dreams are made of!
Fit & Features
- V-Neckline
- Spaghetti Straps
- Floral Print
- Double Layered Skater Skirt
- Lined Scuba Fabric
- Relaxed Fit
- Moderate Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0155
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lovely In Linen Sleeveless Skater Dress
Get a lovely look this season in this flowy linen skater dress! It features a sleeveless bodice, tank shoulder straps, a V-neck and back, a high waist with trendy bar cutouts on each side, and a flirty skater silhouette. Style this dress with sandals for a breezy vacay outfit.
Fit & Features
- Tank shoulder straps
- V-neck and back
- High waist, bar cutouts on each side
- Flowy skater silhouette
- Linen and gauze fabric
- Runs true to size
Style Number/Barcode: 05102-0241
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ribbed Knit Square Neck Midi Dress
Can't get enough of knit! Exude your confidence in this form-flattering midi dress.
Fits & Features
- Tank-Style Shoulder Straps
- Square Neck & Back
- Slit At Center Back
- Midi Length Silhouette
- Curve-Hugging Fit
- Ample Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0349
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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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Long Sleeve Ribbed Knit Midi Dress
Keep it cozy and chic this season with a basic midi! This must have features a turtleneck, long sleeves and a midi length silhouette. Dress is composed of ribbed knit fabric that offers a form hugging fit with a moderate stretch.
Style Number/Barcode: 05102-0344
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Cut Out Mini Dress
Cute and casual, this mini dress needs to be in your closet! It features an elastic banded off the shoulder square neckline, long fitted sleeves, a front waist cut out, and a short, curve hugging fit. Dress is composed of a ribbed knit fabric with plenty of stretch.
Hunter: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Rust: Model is 5'8" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0260
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All Over Ruffled Skater Dress
Get an adorable all over ruffled look in this pretty little skater dress. It features long sleeves with elastic banded ruffle cuffs, a deep V neckline with a ruffle trim, a hidden back zipper and hook and eye closure, ruffle tiered detailing, and a flowy skater skirt. The dress is composed of a linen fabric with no stretch.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0321
Category Name: Casual Dresses
Price: $18.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Get On Knit Long Sleeve Dress
Get on those basic vibes with this sleek mini dress! It features a turtle neck, fitted long sleeves and rounded mini length silhouette. Dress is composed of a semi-sheer smooth knit fabric that offers a curve hugging fit with a moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0185
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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V Mine Ribbed Knit Midi Dress
What's not to love about this perfect layering piece? With unlimited styling possibilities, this dress features a v-neckline, long sleeves, and a midi-length silhouette. The garment is composed of a rib-knit construction and offers a form hugging fit with an ample amount of stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0346
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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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Loving And Living In Knit Midi Dress
We love a basic staple midi dress that pair perfectly with booties to channel those fall vibes! The midi dress features a plunging V neckline, long fitted sleeves and a midi length that sits slightly above the knee. Dress is composed of a soft to the touch lined ribbed knit fabric that offers a curve hugging fit with a moderate stretch.
Olive: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Burgundy: Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Taupe: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0205
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ready To Ruche Mini Dress
Showcase curves in this sultry mini dress! It features a plunging V neckline, fitted long sleeves, a ruched side seam and a mini length silhouette that falls at the mid-thigh length. Dress is composed of a double-lined soft to the touch brushed knit fabric that offers a form hugging fit with a moderate stretch.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 05102-0200
Category Name: Casual Dresses
Price: $13.97 $33.90
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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Precious In Plaid Mini Dress
Make your way into the next season with a perfectly plaid mini dress!
Fits & Features
- Square Neckline
- Thick, Tank Strap
- Mini Length Silhouette
- Smooth Poly Material
- Curve Hugging Fit I Moderate Stretch
- Complete The Look With The Matching Duster (06202-0057)
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0261
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feelin' Sweet Off Shoulder Sweater Dress
Channel your sweet side when you slip into a flattering off shoulder sweater dress gurl!
Fit & Features
- Fold over off shoulder neckline
- Form fitting silhouette
- Banded wrist
- Mini hemline
- Knit woven material
- Moderate stretch
Style Number/Barcode: 06005-0232
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance