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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Modern Minimalist Long Sleeve Midi Dress
Keep it sleek in a smooth knit dress that features a square neckline, fitted long sleeves, and a midi-length hem. Channel those casual vibes when you pair this midi dress with statement sneakers.
Fit & Features
- Smooth knit fabrication
- Square neckline
- Fitted long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5966
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fresh Lines Sleeveless Pinstripe Mini Tube Dress
Look fresh this season in this strapless pinstripe mini dress boasting a sleek bodycon silhouette and faux front pockets. Pair with chic flats.
Fit & Features
- Woven knit fabrication
- Sleeveless square neckline
- Pinstripe pattern
- Faux front pockets
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-5963
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sculpted Chic Ribbed Knit Midi Dress
The ribbed knit dress features a sweetheart neckline with a twist accent at the bust, long sleeves, and a midi-length hem. Channel a casual vibe with chunky sneakers.
Fit & Features
- Ribbed knit fabrication
- Sweetheart neckline with twist accent
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5962
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Girl Short Sleeve Bodycon Slit Mini Dress
Enter a chic girl era in this sultry LBD designed in a flattering bodycon silhouette that flaunts your curves and a flirty front slit along the mini-length hem.
Fit & Features
- Smooth knit stretchy fabric
- Short sleeves
- Square neck
- Bodycon silhouette
- Front slit accent
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5961
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
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Casually Classic Long Sleeve Midi Dress
The midi-length dress is composed of a cashmere-like soft knit fabrication, features an off-the-shoulder neckline with a popover accent, and long sleeves. Complete look with knee-high boots.
Fit & Features
- Cashmere-like knit fabrication, stretchy knit lining
- Off-the-shoulder neckline
- Popover accent
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5960
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ravishing Florals High-Slit Ruched Maxi Dress
Usher in romance in a maxi dress that features a sleeveless square neckline with spaghetti straps, an abstract floral pattern, ruching throughout to enhance curves, and a high side slit. Complete the look with block heels that will have you ready for your next brunch date!
Fit & Features
- Lined mesh fabrication
- Sleeveless square neckline
- Spaghetti straps
- Abstract floral pattern
- Ruching
- High side slit
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05101-3859
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simply Chic Strapless Ribbed Knit Midi Dress
Simply chic, this strapless ribbed knit midi dress is a closet staple. The asymmetric seams and form-hugging silhouette will show off your gorgeous curves.
Fit & Features
- Ribbed hacci knit fabric with knit lining, high stretch
- Strapless straight neckline
- Asymmetric seams
- Midi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5956
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Short And Sweet V-Neck Bodycon Mini Dress
Keep your style short and sweet in this sassy bodycon mini dress perf for casual weekend plans or dressing up with a cute jacket and heels!
Fit & Features
- Stretchy knit fabric
- Short sleeves
- V-neckline
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5957
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The Essential High-Slit Ribbed Knit Midi Dress
The ribbed knit dress features a turtleneck, fitted long sleeves, and a midi-length hem accented with a high side slit. Pair it with ankle booties to complete the look.
Fit & Features
- Ribbed knit fabrication, stretchy knit lining
- Turtleneck
- Long sleeves
- High side slit
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5959
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Charm Halter Pleated Denim Skater Dress
Showcase a darling charm in this halter denim skater dress with convenient side pockets and a flattering pleated hem!
Fit & Features
- Denim fabric
- Square halter neckline, button closures
- Side zipper and hook-eye closure
- Stretchy smocked back
- Skater silhouette, side pockets
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5954
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Impressive Blossom Strapless Floral Maxi Dress
Impress in this floral maxi dress showcasing a sleek strapless neckline and a column silhouette that flatters your figure. Style the dress with a choker.
Fit & Features
- Statement floral print
- Mesh fabric lined with soft, stretch knit
- Column silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-5953
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Chic Floral Strapless Skater Dress
Live out your cottagecore dreams in this chic floral strapless skater dress, perfect for sunny days. You'll love the tie-back bow design and adorable fit-and-flare silhouette.
Fit & Features
- Swiss dot woven fabric
- Small floral pattern
- Strapless straight neckline
- Ruched high waist, tie-back bow design
- Short pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3852
Category Name: Casual Dresses
Price: $11.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Contemporary Sleek Bodycon Midi Dress
Made in a soft rib knit fabric that snatches your figure, this sleeveless midi dress offers a contemporary and sleek style with a sleeveless square neckline and a bodycon silhouette. Pair with hoop earrings and a blazer.
Fit & Features
- Soft rib knit fabric, moderate stretch
- Square neckline
- Wide angled shoulder straps
- Bodycon silhouette
- Center back slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5951
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Edgy In Plaid Scoop Neck Mesh Mini Dress
Show your edge in this plaid mesh mini dress featuring a flattering scoop neckline and form-hugging fit with a hanky-style hem. Complete the look with a cardigan.
Fit & Features
- Plaid print, mesh fabric, stretchy knit lining
- Spaghetti straps
- Scoop neckline
- Form-hugging fit
- Hanky-style mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5952
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Fave Open Back Long Sleeve Knit Mini Dress
This trendy ribbed knit mini dress features a crew neckline, long fitted sleeves, and a bold lower open back with a tie-back strap design. The short bodycon silhouette will highlight your curves and is perf for pairing with knee-high boots.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Crew neckline
- Long fitted sleeves
- Open lower back with tie-back straps
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5948
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sharp Lines Asymmetrical Long Sleeve Midi Dress
Strike a fierce impression in a ribbed knit dress with an asymmetrical off-the-shoulder neckline, a pleated popover accent, fitted long sleeves, and a midi-length hem. Complete the look with strappy heels for the perfect work-to-happy hour look!
Fit & Features
- Ribbed knit fabrication
- Asymmetrical off-the-shoulder neckline
- Pleated popover accent at the neckline
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5947
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Inspired Art Abstract Bodycon Mini Dress
Bring a little extra artsy glamour to any plans in this abstract bodycon mini dress sure to inspire many compliments!
Fit & Features
- Abstract print, mesh-lined fabric
- Adjustable spaghetti straps
- Square neckline, padded bra cups
- Front ruched drawstring
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-5952
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elevated Button-Down Drop Waist Mini Dress
So elevated, this adorable mini dress is designed with a textured knit fabric and a sleek button-down front. It features a sleeveless square neckline with tank straps, a drop waist, and a short pleated A-line silhouette for that cute flair.
Fit & Features
- Textured knit fabric, sewn-in knit lining
- Square neckline
- Tank shoulder straps
- Button-down front
- Drop waist
- Mini-length pleated A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3842
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Adored Sleeveless Bow Trim Crepe Mini Dress
Embrace romance in this crepe mini dress that features a sleeveless square neckline with tank-like straps, a charming bow accented trim under the bust, and a flared mini-length hem with an A-line silhouette. Complete your look with sleek flats!
Fit & Features
- Crepe fabric with knit lining, moderate stretch
- Sleeveless square neckline, dart seams
- Tank-like shoulder straps
- Bow accented trim under bust
- Back zipper closure
- Flared mini-length hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3840
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trend Moment Denim Belted Pleat Mini Dress
Hit the streets in this of-the-moment denim mini dress with a trendy belted design and flirty pleated hem!
Fit & Features
- Denim fabric, moderate stretch
- Strapless neckline
- Back zipper and hook-eye closure
- Belted design
- Bodycon fit
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5944
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always A Good Time Long Sleeve Midi Dress
A basic midi dress every fashionista needs to create bold looks. The dress features side ruched seams and a bodycon silhouette to accentuate your curves while the midi-length hem makes it perfect for styling with boots or heels.
Fit & Features
- Rib knit fabric, stretchy knit lining
- Fitted long sleeves
- Square neckline
- Side ruched seams
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5940
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Vibes Off The Shoulder Knit Midi Dress
Keep it sleek and stylish in a ribbed knit dress that features a v-neckline that can be worn off-the-shoulder, fitted long sleeves, and a midi-length hem. Complete the look with sneakers to add a casual touch!
Fit & Features
- Lined ribbed knit fabrication
- V-neckline and off-the-shoulder
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5942
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mesmerizing Glam Abstract Ruched Midi Dress
Step out and mesmerize in a midi dress that features a sleeveless square neckline, ruching throughout to enhance curves, and an abstract marble print. Complete look with strappy heels for a look that's ready for date night!
Fit & Features
- Lined mesh fabrication
- Sleeveless square neckline
- Ruching
- Abstract marble print
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5937
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute Flirt Drop Waist Ruffled Hem Mini Dress
Show off your stunning figure in this smooth knit mini dress featuring a boat neckline, long fitted sleeves, a cute scoop back, a drop waist design, and a short tiered ruffled hem with an A-line fit for that flirty flair. Style with strappy mules!
Fit & Features
- Smooth nylon knit fabric, plenty of stretch
- Boat neckline
- Long fitted sleeves
- Scoop back
- Drop waist
- Tiered ruffled mini-length hem, A-line fit
- Runs true to size
Style Number/Barcode: 05102-5938
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free