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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Work Or Play Ruffle Strap Button Skater Dress
Work or play, this cotton skater dress is a charming choice for a stroll downtown or a coffee date! It features a sleeveless V-neckline, adorable ruffled straps, a stretchy smocked bodice, a button-down front, and a flattering short-length hem. Complete the look in strappy heels.
Fit & Features
- Sleeveless V-neckline
- Ruffled straps
- Stretchy smocked bodice
- Button-down front
- Skater silhouette, short-length hem
- Lightweight cotton fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-5369
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Looking For The One Basic Long Sleeve Maxi Dress
Dare to be bold this season and fall in love with this basic maxi dress! Its fitted long sleeves, crew neckline, and bodycon silhouette hug your figure in all the right places all the way down to the maxi-length hem. The dress is composed of a double-lined rib knit fabric with plenty of stretch. Complete the look in block heels and a handbag for any day or night occasion!
Fit & Features
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Maxi-length hem
- Double-lined rib knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5375
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Things Cute Cable Knit Sweater Dress
Wrap yourself up in this cute and casual cable knit sweater dress perfect for pumpkin patches or festivals! It features long sleeves with banded cuffs, a plunge surplice V-neckline and V-cut back, a tie-waist belt, and a short form-hugging fit. Complete the look in trendy knee-high boots.
Fit & Features
- Long sleeves, banded cuffs
- Plunge surplice V-neckline, V-cut back
- Tie-waist belt
- Form-hugging fit
- Short-length hem
- Cable knit design, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5370
Category Name: Casual Dresses
Price: $5.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Must Have Strapless Twist Midi Dress
This midi dress is a must-have style for showing off your shoulder for a brunch or party! It features a strapless sweetheart neckline, a padded and twisted bust, a flattering bodycon silhouette, and a center-back slit on stretchy knit fabric. Complete the look with a chic crossbody bag and heels.
Fit & Features
- Strapless sweetheart neckline, non-slip grip lining
- Padded and twisted bust
- Bodycon silhouette
- Center back slit
- Midi-length hem
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5374
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Delightfully Cute Plaid Cargo Mini Dress
This delightfully cute plaid mini dress dares you to stand out from the crowd! It features a square neckline, spaghetti straps, trendy side cargo flap pockets, a flattering bodycon silhouette, and a mini-length hem. Layer with a cropped jacket for casual hangs or school!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side cargo flap pockets
- Bodycon silhouette, mini-length hem
- Plaid print
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5372
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Striking And Chic Marble Print Midi Dress
So striking and chic, this marble print midi dress will capture all the attention at happy hour! It features a sleeveless V-neckline, spaghetti straps, an asymmetric high-cut midi-length hem creating a thigh-high slit, and a bodycon silhouette that will flaunt your figure. The buttery smooth and stretchy knit fabric features an all-over multicolored marble print pattern. Style with clear mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Asymmetric high-cut midi-length hem, high slit
- Bodycon silhouette
- Multi-colored marble print
- Smooth and stretchy knit fabric, full-length sewn-in knit lining
- Runs true to size
Style Number/Barcode: 05102-5231
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Divine Darling Square Neck Ruffle Mini Dress
Breeze in looking so darling in this sleeveless mini dress for a day date or dinner party! It features a square neckline, adjustable spaghetti straps, an eye-catching tie-back closure, and a flattering wrap hem with ruffle trim. The dress is composed of an airy woven fabric with a stretchy knit lining. Complete the look with strappy block heels.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Tie-back closure
- Wrap mini-length hem, ruffle trim
- Airy woven fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2860
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Retro Luxe Velvet Mock Neck Mini Dress
Embrace a luxurious and retro look in this velvet mini dress! It features fitted long sleeves, a mock neckline, a mini-length hem, and a bodycon silhouette that flatters your curves. The flocked velvet retro pattern gives it a glamorous look and brings a luxe vibe. The sheer mesh fabric features a sleeveless knit lining down the body of the dress. Complete the look in metallic heels for a party!
Fit & Features
- Fitted long sleeves
- Mock neckline, dual back button closures, keyhole cutout
- Mini-length hem
- Bodycon silhouette
- Flocked velvet design, retro pattern
- Sheer mesh fabric, sleeveless knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2856
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Day Dreamer Strapless Abstract Midi Dress
Make your daydream come true and wear this mesh midi dress for a gorgeous look this weekend! It features a strapless neckline with non-slip grip lining, flexible boning inserts along the bodice for structure, and ruched seams to accentuate your figure along the bodycon silhouette. The dress is designed with an abstract print on mesh fabric with a sewn-in knit lining. Complete the look with hoop earrings.
Fit & Features
- Strapless neckline, non-slip grip lining
- Flexible boning inserts
- Side zipper and hook-eye closure
- Ruched seams, bodycon silhouette
- Midi-length hem
- Abstract print, mesh fabric, sewn-in knit lining
- Runs true to size
Style Number/Barcode: 05102-5363
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Hottie Cutout Ruched Midi Dress
This curve-hugging cutout midi dress will show off your major hottie status! The mid-length dress features an off-the-shoulder straight-across neckline, long fitted sleeves, alluring front and back waist cutouts, ruching down the side seams, and a bodycon silhouette to flaunt your figure. The lined knit fabric offers plenty of stretch. Style this midi dress with layered chain necklaces and clear strap heels for a rooftop bar.
Fit & Features
- Off-the-shoulder straight-across neckline, elasticized hem
- Long fitted sleeves
- Front and back waist cutouts
- Ruched side seams
- Midi-length hem, bodycon silhouette
- Knit fabric, sewn-in knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5366
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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It's A Must Collared Denim Mini Dress
This denim mini dress is a must for curating a cute and trendy lineup this season! The short dress features long sleeves, a collar neckline, zipper front closure, dual flap pockets with snap-button closures and lower pockets, an elasticized waist with belt loop accents, a bodycon fit, and a mini-length hem. Complete the look in pointed-toe booties for a day out with friends!
Fit & Features
- Long sleeves, collar neckline
- Zipper front closure
- Flap pockets with snap-button closures
- Lower pockets
- Bodycon fit, mini-length hem
- Rigid denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-5364
Category Name: Casual Dresses
Price: $54.90
Availability: Out of Stock
Product Badge:- Sale
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Simply Fine In Floral A-Line Midi Dress
Take your look to the next level with this gorgeous floral midi dress. With its cowl neckline, adjustable spaghetti straps, A-line silhouette, and a painted floral print on woven fabric, this midi-length dress will make you feel stylish and fine! Complete the look in sleek stiletto heels for a semi-formal soiree.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- A-line silhouette
- Midi-length hem
- Painted floral print
- Lightweight woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-2920
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adorable Style Cable Knit Mini Dress
You'll fall in love with the adorable style of this cable knit mini dress for the cozy winter season. It features a V-neckline with a surplice design, long sleeves, a faux wrap-front creating an asymmetric mini-length hem, and a form-hugging silhouette. The cable knit fabric offers a moderate stretch. Style with a chic trench coat and knee-high boots.
Fit & Features
- V-neckline, surplice design
- Long sleeves
- Faux wrap-front design
- Asymmetric mini-length hem
- Form-hugging silhouette
- Cable knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5359
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy Destination Cutout Tropical Print Maxi Dress
Get ready to jet set to your dreamy destination with this sexy tropical maxi dress! The lightweight woven fabric showcases an abstract tropical print to bring that bold allure to your next getaway. The maxi-length dress features a sleeveless halter neckline with tie-back straps that can be styled as a criss-cross high neck or a sultry plunging design according to your fashion mood! The long dress has a chic center O-ring accent and eye-catching waist cutouts with thin straps that lead to an open back with a tie-back design. The flowy A-line fit will bring those breezy vibes, while the dual thigh-high side slits add a sexy silhouette. Complete your look with heeled sandals!
Fit & Features
- Tropical printed woven fabric
- Sleeveless halter neckline, tie-back straps
- Waist cutouts, O-ring accent
- Open back, lower tie-back straps
- Dual high-cut side slits
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5356
Category Name: Casual Dresses
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Timeless Classic Cable Knit A-Line Dress
Bring beauty and charm in this short dress! The mini dress features a V-neckline, long sleeves with flared cuffs, a short-length hem, and a flattering a-line silhouette on lightweight cable knit fabric. Complete the look with a ring set and boots for a casual occasion!
Fit & Features
- Long sleeves, flared cuffs
- V-neckline
- A-line silhouette
- Short-length hem
- Lightweight cable knit fabric
- Runs true to size
Style Number/Barcode: 05102-5355
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stroll Along Surplice Tie Waist Mini Dress
Stroll along the city streets in this casual mini dress perfect for a day out! The mini dress features relaxed long sleeves with banded cuffs, a V-neckline with a surplice accent, a tie-waist belt, and a flattering bodycon fit on stretchy knit fabric. Complete the look with a crossbody bag.
Fit & Features
- Relaxed long sleeves, banded cuffs
- V-neckline, surplice accent
- Tie-waist belt
- Bodycon fit
- Mini-length hem
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5354
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fashion Lovers Of Basic Mock Neck Mini Dress
Calling all fashion girlies! Check out this basic mini dress perfect for daring bold girls. The mini-length dress is designed with fitted long sleeves, a mock neckline, a front half-zip-up closure, and a flattering bodycon silhouette on smooth rib knit fabric that fits like a glove. Style with a baseball cap, jacket, and your favorite kicks!
Fit & Features
- Fitted long sleeves
- Mock neckline
- Half zip-up closure
- Bodycon silhouette, mini-length hem
- Smooth rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5357
Category Name: Casual Dresses
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Draw The Line Striped Sweater Midi Dress
Draw the line at basic and reach for this sensational striped sweater dress! It features a trendy off-the-shoulder neckline, fitted long sleeves, a flattering bodycon silhouette, and dual tie-back closures, and a cutout design. Complete the look with a chic crossbody bag for day or evening plans.
Fit & Features
- Off-the-shoulder neckline
- Fitted long sleeves
- Dual tie-back closures, cutout design
- Bodycon silhouette
- Midi-length hem
- Striped pattern, stretchy sweater knit fabric
- Runs true to size
Style Number/Barcode: 05102-5360
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Winter Beauty Cable Knit Mock Neck Mini Dress
Showcase your beauty in this cozy cable knit mini dress this winter season! It features a ribbed mock neckline, long balloon-style sleeves with tapered ribbed hems, a mini-length hem, and a form-hugging fit. The classic cable knit fabric offers a moderate stretch. Style this mini dress with over-the-knee boots for a chic look.
Fit & Features
- Ribbed mock neckline
- Long balloon sleeves, tapered ribbed hems
- Mini-length hem
- Form-hugging fit
- Cable knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5358
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Finders Keepers V-Neck Tie Midi Dress
Once you find this sleeveless midi dress you'll want to keep it! Perfect for semi-formal occasions, this midi dress will make you feel chic and effortless. Designed with an adjustable V-neckline with a bust tie, sleek spaghetti straps, and a flattering curve-hugging silhouette that exudes charm. Complete the look with a bolero shrug sweater and strappy stilettos!
Fit & Features
- Woven fabric, no stretch
- Spaghetti straps
- Adjustable bust tie
- Curve-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5551
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Color Splash Tie Dye Glitter Midi Dress
Make a splash this summer in this colorful tie-dye midi dress! It features a sleeveless square neck, adjustable spaghetti straps, side ruched seams that accentuate your curves along the bodycon silhouette, a flirty side slit, and a midi-length hem. The dress is designed with a trendy all-over tie dye print and glitter on mesh fabric with a sewn-in knit lining. Complete the look in heels for an outdoor party!
Fit & Fetaures
- Sleeveless square neck, adjustable spaghetti straps
- Side ruched seams, bodycon silhouette
- Back zipper and hook-eye closure
- Side slit, midi-length hem
- All-over tie-dye print, glitter
- Mesh fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5348
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flaunt Your 'Fit Ruched Bodycon Midi Dress
You'll want to flaunt your sultry 'fit in this ruched bodycon midi dress that will showcase your gorgeous figure! It features a sleeveless sweetheart neckline with a padded bust, a twist-front design with a center keyhole cutout, spaghetti straps, ruching down the side seams, and a midi-length hem with a curve-hugging silhouette. The slinky knit fabric includes a full-length lining and has plenty of stretch. Style with lace-up heels!
Fit & Features
- Sleeveless sweetheart neckline, padded bust
- Twist-front design, center cutout
- Spaghetti straps
- Ruched side seams
- Midi-length hem, bodycon silhouette
- Slinky knit fabric, full-length lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-2817
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Coastal Vacay Tie-Shoulder Ruffled Short Dress
This cute and casual ruffled short dress is perfect for a coastal summer vacay! It features a sleeveless scoop neckline, tie-shoulder tank straps, hidden side pockets, a drop waist seam with a ruffled short-length hem, and a relaxed A-line silhouette. The cotton fabric has no stretch. Style with gold hoops and espadrille sandals!
Fit & Features
- Sleeveless scoop neckline
- Tie-shoulder tank straps
- Hidden side pockets
- Drop waist seam, ruffled short-length hem
- Relaxed A-line silhouette
- Cotton fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-5345
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Style In Check Gingham Skater Dress
Keep your style in check in this flirty gingham skater dress! It features a sleeveless square neck, spaghetti straps, a flattering skater silhouette, and a short-length hem. The dress is designed with an adorable gingham print on brushed knit fabric with a stretchy lining. Complete your look with a statement choker necklace and heels for a party!
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Skater silhouette
- Short-length hem
- Gingham print
- Brushed knit fabric, stretchy lining
- Runs true to size
Style Number/Barcode: 05102-5349
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale