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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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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Delightful Impact Corset Slit Chiffon Midi Dress
A sleeveless chiffon midi dress boasts a sweetheart tie neckline, a corset-inspired bodice with a lace-up back, and a front slit for a stylish flair. Perfect for styling with heels for a dressy occasion.
Fit & Features
- Burnout pattern, chiffon fabric lined with stretchy knit
- Sweetheart tie neckline, shoulder straps
- Underwire bust, side zipper and hook-eye closure
- Corset bodice, lace-up back
- Front slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3591
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blooming Bouquet Sleeveless Floral Mesh Mini Dress
Get ready to bloom in this floral mesh mini dress at a girl's brunch or evening soiree! The sleeveless crew neckline and bodycon silhouette highlight your curves, while the bold floral print and mesh fabric add a touch of feminine charm. Complete the look in simple stiletto heels.
Fit & Features
- Blooming floral print
- Sheer mesh fabric with knit lining, plenty of stretch
- Crew neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5612
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stripes In Style Off The Shoulder Mini Dress
Stay stylish in this trendy off-the-shoulder mini dress showcasing a classic striped pattern and a form-hugging fit. Pair with knee-high boots.
Fit & Features
- Ribbed knit fabrication
- Off-the-shoulder neckline
- Long dolman sleeves
- Stripes
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-5885
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Memorable Vibe Strapless Plaid Pleated Mini Dress
A strapless plaid mini dress features a form-hugging fit with a sassy pleated hem. Perfect for back-to-school styling.
Fit & Features
- Plaid print, woven fabric, slight stretch
- Strapless folded neckline
- Back zipper closure
- Form-hugging fit
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5862
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smooth Silhouette Square Neck Tank Midi Dress
Effortlessly chic and oh-so-flattering, this sleeveless midi dress will become your new favorite go-to. This bodycon dress has a sleeveless square neckline and tank straps and hugs your curves in all the right places. The midi-length hem adds a touch of sophistication, while the rib knit fabric lining ensures comfort all day long. Complete the look in a layered necklace for any occasion!
Fit & Features
- Rib knit fabric, sewn-in knit lining, stretchy
- Bodycon fit
- Midi-length
- Runs true to size
Style Number/Barcode: 05102-5587
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ray Of Beauty Lace-Up Corset Skater Dress
You'll be a ray of beauty in this chic lace-up corset skater dress! Designed with a lightweight woven fabric with a stretchy knit lining, this adorable short dress captures the summer season. It features an alluring sleeveless corset-style bodice with a ruched sweetheart neckline and a tie-front detail at the bust. The thin adjustable tank straps lead to a lace-up strappy back design to find your perfect fit. The angled high waist seam flows out to a fit-and-flare skater silhouette with pleating for a flirtatious vibe. Complete the look with platform heels!
Fit & Features
- Cotton woven fabric, stretchy knit lining
- Corset-style bodice, ruched sweetheart neckline, tie-front bust
- Thin adjustable tank straps
- Lace-up strappy back, tie closure
- Side zipper with hook and eye closure
- Fit-and-flare skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3641
Category Name: Casual Dresses
Price: $11.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Flirt Sweetheart Lace Trim Skater Dress
This sleeveless chiffon skater dress features a lace trim sweetheart neckline and bodice for flirty flair while the drop waist seam accentuates your curves along the mini-length skater silhouette. Perfect for a dressy brunch or party.
Fit & Features
- Sheer chiffon woven fabric with stretchy knit lining
- Lace trim sweetheart neckline with bow detail, bust underwire
- Adjustable lace trim shoulder straps
- Partially smocked back with zipper and hook-eye closure
- Lace trim bodice, drop waist seam
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3461
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Definite Beauty V-Neck A-Line Mini Dress
Everyone will watch as you walk in wearing this sleeveless mini dress to the school dance or party! Made from smooth lined knit fabric, it's perfect for any occasion. With its flattering V-neckline and shoulder straps, this dress offers a stunning A-line silhouette and a mini-length hem. Compliment your look with statement heels and a clutch.
Fit & Features
- Smooth lined knit fabric
- V-neckline
- Shoulder straps
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5844
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elevated Vibes Ribbed Knit High Slit Maxi Dress
This ribbed knit high slit maxi dress will bring elevated vibes to your casual basics! Crafted from a stretchy ribbed knit fabric, this maxi dress features a scoop neckline, long fitted sleeves, a long-length hem with a thigh-high side slit, and a bodycon silhouette that will hug your curves. Style with a faux leather jacket and knee-high boots for a casual-chic date night look!
Fit & Features
- Scoop neckline
- Long fitted sleeves
- Long-length hem
- Thigh-high side slit
- Bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5342
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Look Long Sleeve Abstract Mini Dress
An abstract print mesh mini dress features sheer fitted long sleeves, a boat neckline, and a flattering bodycon silhouette. Perfect for a party or gallery opening.
Fit & Features
- Abstract print, sheer mesh fabric, slip knit lining
- Fitted long sleeves
- Boat neckline
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5850
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Chic Style Long Sleeve Ribbed Knit Midi Dress
The perfect blend of casual and chic, this ribbed knit midi dress features a V-neckline, long fitted sleeves, and a form-hugging silhouette. Style with hoop earrings and sneakers for a cute everyday look.
Fit & Features
- Hacci ribbed knit fabric, plenty of stretch
- V-neckline
- Long fitted sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5920
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Read All About It Newspaper Bodycon Mini Dress
Extra, extra read all about how fine you'll look in this newspaper print mini dress! This dress features a sweetheart neckline with lace trim and adjustable spaghetti straps for a perfect fit. The built-in padded underwire bust ensures support while the bodycon fit and mini-length hem create a flattering silhouette. Complete the look in a crop denim jacket.
Fit & Features
- Newspaper print, knit fabric with stretchy lining
- Adjustable spaghetti straps
- Sweetheart neckline with lace trim
- Back zipper and hook-eye closure
- Built-in padded underwire bust
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5578
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fab Trendsetter Leopard Print Drop Waist Mini Dress
Fab trendsetter will be your vibe in this leopard print mini dress featuring an off-the-shoulder neckline with short sleeves, a drop waist seam, and an asymmetric tiered mini-length hem with an A-line fit. Style with knee-high boots!
Fit & Features
- Leopard-printed brushed knit fabric, plenty of stretch
- Off-the-shoulder neckline, short sleeves
- Drop waist seam
- Asymmetric tiered mini-length hem
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5904
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Gorgeous Aura Strapless Floral Tie-Dye Maxi Dress
Shine bright and serve a gorgeous aura in this strapless floral tie-dye maxi dress perfect for summertime soirees! The strapless neckline and lace-up back design exude effortless elegance, while the form-hugging fit accentuates your curves. The ruffled maxi-length hem adds a playful touch to this stunning dress. Complete the look with a ring set and sandals.
Fit & Features
- Floral tie-dye print, smooth knit fabric, moderate stretch
- Strapless neckline
- Lace-up back design
- Form-hugging fit
- Ruffled maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3277
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flawless Puff Sleeve Corset Midi Dress
A flawless midi dress with femme details from the corset bodice to the puff short sleeves and flattering A-line silhouette - you'll feel like a dream in this dress! Complete the look with strappy sandals.
Fit & Features
- Lined woven fabric, dainty sheer lace trim, minimal stretch
- Sweetheart neckline, ruched bust, keyhole cutout, bow-front detail
- Corset bodice, bust underwire, flexible boning
- Short puff sleeves, elastic cinched hems
- Smocked lace-up back, hidden zipper with hook-eye closure
- V-shaped drop waist
- Midi-length A-line silhouette, front slit
- Runs true to size
Style Number/Barcode: 05101-3573
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smooth Talker Lace Bow Pleated Ponte Mini Dress
Smooth ponte knit fabric shapes this sleeveless mini dress featuring a lace bow trim square neckline, spaghetti straps, and a fitted silhouette that leads to a pleated flare mini-length hem.
Fit & Features
- Smooth pointe knit fabric, minimal stretch
- Lace bow trim square neckline
- Spaghetti straps
- Fitted silhouette
- Pleated flare mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3661
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Fab Drop Waist Halter Skater Dress
Look and feel fabulous in this sleeveless skater dress boasting a flirty halter V-neckline and a trendy mineral wash on the stretchy rib knit cotton fabric. Complete the look with hoop earrings.
Fit & Features
- Ribbed cotton-blend fabric, moderate stretch
- Mineral wash
- Sleeveless halter V-neckline
- Partially open back
- Drop waist
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5857
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Element Turtleneck Long Sleeve Mini Dress
Soft and lightweight ribbed knit fabric crafts this trendy mini dress perfect for styling day to night! The mini-length dress features fitted long sleeves, a folded turtleneck, and a flattering bodycon silhouette on double-lined ribbed knit fabric. Complete the look in an oversized blazer and boots for brunch downtown or date night!
Fit & Features
- Double-lined ribbed knit fabric, moderate stretch
- Fitted long sleeves
- Folded turtleneck
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5245
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cool Staple Ribbed Knit Long Sleeve Midi Dress
This ribbed knit midi dress is designed with a cotton-blend fabric with a cool mineral wash offering plenty of stretch. The dress features a scoop neckline, long fitted sleeves, and a midi-length bodycon silhouette to show off your curves.
Fit & Features
- Cotton-blend ribbed knit fabric, plenty of stretch
- Mineral wash
- Scoop neckline
- Long fitted sleeves
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5829
Category Name: Casual Dresses
Price: $11.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Silhouette Abstract Print Mesh Midi Dress
Showcase a sultry silhouette in this sheer mesh midi dress designed with a multi-colored abstract print for a bold vibe. It features a mock neckline with long fitted sleeves, a bodycon silhouette to hug your curves, and a full-length knit lining with a scoop neckline and spaghetti straps.
Fit & Features
- Abstract printed sheer mesh fabric, plenty of stretch
- Mock neckline
- Long fitted sleeves
- Midi-length bodycon fit
- Full-length knit lining, scoop neckline, adjustable spaghetti straps
- Runs true to size
Style Number/Barcode: 05102-5879
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Iconic Abstract Print Ruched Mini Dress
Step out like the icon you are in a mini dress that features a plunging cowl neckline with halter neck ties for a secure fit, an abstract floral print, and ruching throughout to enhance curves. Style with clear heels.
Fit & Features
- Fitted mesh fabrication, moderate stretch
- Cowl neckline
- Open back, halter neck ties
- Abstract floral print
- Mini length hem
- Ruching
- Runs true to size
Style Number/Barcode: 05102-5786
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ray Of Romance A-Line Lace Mini Dress
Radiate a ray of romance in this sleeveless lace mini dress featuring a V-neckline accented with a dainty lace and ribbon bow trim and a flattering A-line silhouette. Style with heels for a date.
Fit & Features
- Lace fabric lined with stretchy knit
- V-neckline with lace and ribbon bow trim
- Spaghetti straps
- Mini-length A-line fit
- Runs true to size
Style Number/Barcode: 05101-3626
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Beauty Sleeveless A-Line Mini Dress
This sleeveless mini dress features a crew neckline, a flattering A-line silhouette, and a front slit accent. The soft rib knit fabric offers plenty of stretch and comfort.
Fit & Features
- Rib knit fabric, moderate stretch
- Crew neckline
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5631
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale