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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Coastal Getaway Printed Mini Dress
Your vacation itinerary just found its favorite outfit. This printed mini dress brings playful resort vibes with a chic A-line silhouette and postcard-inspired details, perfect for your next trip.
Fit & Features
- Linen-like fabric, woven lining
- Resort/paradise script and graphic pattern
- Square neckline, adjustable spaghetti straps
- Side zipper and hook-eye closure
- Side pockets, button-up front closures
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000817
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Subtle Glow Sequin Bodycon Mini Dress
Subtle shimmer is having a major moment. This bodycon mini dress updates the sequin trend with tiny clear embellishments, a clean halter neckline, and a low open back. The result feels fresh, streamlined, and ready for vacation plans and weekend dates.
Fit & Features
- Knit sweater fabric with mini clear sequin embellishments
- Sweater knit lining, high stretch
- Halter neckline
- Low open back
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000432
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Modern Textured Bodycon Mini Dress
The styling is simple, but the details are not. This bodycon mini dress combines textured knit, a scoop halter neckline, and a double-twist open back for a clean look with extra interest. Add a metallic bag and heels to finish it off.
Fit & Features
- Textured knit fabric with stretch
- Scoop halter neckline
- Double-twist open back
- Bodycon mini-length fit
- Runs true to size
Style Number/Barcode: 06005-000433
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L
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Petals & Prosecco V-Neck Midi Dress
This dress feels like brunch reservations, bridal showers, and having lunch in a European city. The soft floral print, delicate ruffle details, and floaty chiffon fabric make every entrance feel extra pretty.
Fit & Features
- Dainty floral print, chiffon-lined fabric
- V-neckline, spaghetti straps
- Back zipper and hook-eye closure
- Curve-hugging fit
- Ruffled midi-length hem
- Runs true to size
Style Number/Barcode: 05101-001478
Category Name: Casual Dresses
Price: $29.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Curve Outline Cutout Bodycon Midi Dress
The contrast trim knows exactly where to draw the eye. This rib knit midi dress frames the halter neckline and waist cutout with bold piping, while the bodycon shape keeps the look streamlined.
Fit & Features
- Rib knit fabrication, moderate stretch
- Halter straps with square neckline
- Front waist cutout
- Contrast piping detail
- Open back with bodycon fit, midi hem
- Runs true to size
Style Number/Barcode: 06005-000428
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: M, L
Product Badge:- Sale
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Kiss Me Quick Satin Mini Dress
Serving flirt first, plans second. This satin mini dress features a plunge V-neckline, lace trim details, and a bust tie front that feels like a vintage-inspired romance.
Fit & Features
- Woven satin fabric
- Sleeveless plunge lace trim V-neckline
- Lace trim wide shoulder straps
- Hidden side zipper and hook-eye closure
- Bust tie-front detail
- Curve-hugging, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000807
Category Name: Casual Dresses
Price: $42.90
Availability: Out of Stock
Product Badge:- Ships Free
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Picnic Flirt Eyelet Mini Dress
Sweet, but with a little attitude—just how we like it. This eyelet skater dress shapes you with a corset bodice and flexible boning, while the flutter sleeves and lace-up back keep it playful for every dressy event.
Fit & Features
- Eyelet woven fabric, woven lining
- Sweetheart neck, ruffle trim, bust tie
- Flutter short sleeves
- Lace-up back, zipper and hook-eye closure
- Corset bodice, flexible boning
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001431
Category Name: Casual Dresses
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Western Chic Faux Suede Mini Dress
Western chic is the vibe. This faux suede mini dress brings the attitude with a plunging halter neckline, studded embroidery, and a bodycon fit made for concerts, parties, and spontaneous plans.
Fit & Features
- Faux suede fabric with knit lining, moderate stretch
- Western-style embroidery, studded embellishments
- Sleeveless deep V-neckline
- Tie-back halter straps, partially open back
- Back zipper with hook-eye closure
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000805
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Rare Find Animal Print Maxi Dress
A little wild, a little glamorous, and impossible to scroll past. This animal print mesh maxi dress pairs a sweetheart neckline, cutout details, hardware accents, and a dramatic front sash for the kind of entrance people remember.
Fit & Features
- Multi-animal print, lined mesh fabric
- Strapless sweetheart neckline
- Hardware bust insert with cascading sash
- Cutout bodice
- Curve-hugging, maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000803
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunday In Bloom Strapless Midi Dress
This midi dress feels like a soft yes to every pretty plan on your calendar. The delicate floral print, smocked bodice, and flowy silhouette make it perfect for vacations, brunch, or any sunny day plans.
Fit & Features
- Floral borderprint, cotton woven fabric, smooth woven lining
- Strapless smocked bodice with stretch
- Back zipper and hook-eye closure
- Flowy A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000798
Category Name: Casual Dresses
Price: $51.00 $72.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: M, L
Product Badge:- Sale
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Fresh Cut Florals Strapless Midi Dress
This strapless midi dress features a soft floral print, smocked bodice, and flowy midi length that's polished, pretty, and just a little romantic. Pair it with strappy heels or keep it casual with flats.
Fit & Features
- Floral print, linen-blend woven fabric, woven lining
- Strapless neckline, non-slip grip lining
- Stretchy smocked bodice detail
- Ruffled A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000799
Category Name: Casual Dresses
Price: $32.97 $72.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mixed Instinct Animal Print Maxi Dress
Plans just got a little wilder. This animal-print maxi dress pairs a ruched bodice, halter neckline, and open back with a front slit, keeping the look fun and current. Wear it for vacations, birthday dinners, cocktail parties, or date night.
Fit & Features
- Mixed animal print, lined mesh fabric
- Halter neckline with beaded detail
- Ruched fitted bodice
- Open back design
- Front slit
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000802
Category Name: Casual Dresses
Price: $54.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Wild Card Printed A-Line Mini Dress
Vacation mood: activated. This printed A-line mini dress combines a flattering ruched fit with playful ruffles, making it an easy pick for rooftop drinks, weekend getaways, and every photo op in between.
Fit & Features
- Mesh fabric, knit lining, high stretch
- Tropical floral and animal multi-print pattern
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Ruched bodice, V-shaped drop waist
- Tiered ruffled design with mini-length hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000796
Category Name: Casual Dresses
Price: $21.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: GREEN
Available Size: L
Product Badge:- Sale
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Worth The Stare Striped Knit Midi Dress
This striped sweater dress does all the hard work the second it’s on. The body-hugging fit and trending striped pattern were made for dinners out, cocktail parties, and walking in fashionably late.
Fit & Features
- Ribbed knit fabric, metallic threading woven throughout, high stretch
- Vertical striped pattern
- Strapless sweetheart neckline
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000420
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Back For More Halter Mini Dress
All eyes on you always. This knit mini dress hugs your shape with side ruching and an open-back moment that keeps the focus on you.
Fit & Features
- Sweater knit fabric, moderate stretch
- High halter neckline with tie straps
- Open back, adjustable strap
- Side ruched seams
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000419
Category Name: Casual Dresses
Price: $8.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Striking Zebra Mesh Bodycon Mini Dress
Animal print is back in its boldest form. This mesh mini dress updates the trend with a curve-skimming fit, halter neckline, and ruffled hem for added movement. It’s made for nights when a minimal outfit is not the plan.
Fit & Features
- Zebra print, lined mesh fabric
- Halter V-neckline
- Curve-hugging fit
- Asymmetrical ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000795
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In Your Good Graces Halter Mini Dress
Sweet, but make it a little unexpected. This halter mini skims your shape with a soft, textured feel and a lace trim hem that adds just enough detail for showers, graduations, or dressy brunch plans.
Fit & Features
- Textured chiffon fabric, sewn in knit stretchy lining
- High halter neckline with tie straps
- Open back
- Bodycon mini silhouette
- Lace trim hem
- Runs true to size
Style Number/Barcode: 05102-000794
Category Name: Casual Dresses
Price: $20.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: M, L
Product Badge:- Sale
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Late Dinner Plans Tube Maxi Dress
This is what you wear when the evening calls for something a little elevated. This tube maxi dress hugs through the bodice with a ruched finish, then falls into a soft shark hem that moves with every step.
Fit & Features
- Soft jersey knit fabric, stretchy lining
- Strapless tube neckline, non-slip grip lining
- Ruched fitted bodice
- Flowy curve-hugging silhouette
- Shark-cut maxi hem
- Runs true to size
Style Number/Barcode: 05102-000787
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Booked Midi Dress
The kind of dress that makes last-minute reservations feel completely intentional. This open back midi dress combines a sleek body-skimming fit with a draped sash detail for an elevated look that works everywhere from cocktail parties to weddings.
Fit & Features
- Slinky knit double-lined fabric
- Sleeveless boat neckline
- Open back, center back slit
- Form-hugging midi silhouette
- Runs true to size
Style Number/Barcode: 05102-000816
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
Product Badge:- Sale
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Weekend Romance Floral Cotton Midi Dress
Feels like a soft yes to every plan on your calendar. This flowy ruffle midi dress brings an easy, romantic fit with a smocked waist and tie back, perfect for brunch, showers, or vacations.
Fit & Features
- Dainty floral pattern, cotton woven fabric and lining
- Sleeveless ruffle trim V-neckline
- Button front bust accents, stretchy smocked panel
- Tie-back design
- A-line silhouette, ruffled midi-length hem
- Runs true to size
Style Number/Barcode: 05101-001392
Category Name: Casual Dresses
Price: $29.97 $64.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Sale
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RSVP To Sunshine Striped Mini Dress
This striped halter mini dress hugs in all the right places with a flattering curve-hugging fit that’s made for brunch, beach city strolls, and vacations.
Fit & Features
- Striped pattern, ribbed knit fabric, knit lining, high stretch
- Halter V-neckline with tie straps
- Partially open back
- Curve-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000785
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: GREEN
Available Size: XS, S, M, L
Product Badge:- Sale
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Chic Agenda Plunge Maxi Dress
From meetings to martinis without missing a beat. This cap sleeve maxi dress with a center drape accent and front slit keeps it polished for work hours and chic for after-hours plans.
Fit & Features
- Smooth knit stretch fabric
- Cao sleeves with shoulder pads for structure
- Plunge V-neckline
- Center front drape and slit designs
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000784
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Romantic Eyelet Lace Skater Mini Dress
Romantic details make this dress feel polished. The lace bodice and embroidered eyelet skirt create rich texture, while the scalloped hem adds a delicate finish. It’s an easy pick for brunches, showers, and daytime celebrations.
Fit & Features
- Airy cotton-blend woven fabric with lining, no stretch
- V-neckline with ruffled trim, wide tank straps
- Sheer lace bodice with embroidered detailing, lined bust
- Front hook-eye closures
- Smocked back panel
- Eyelet skater mini-length skirt with scalloped hem
- Runs true to size
Style Number/Barcode: 05102-000783
Category Name: Casual Dresses
Price: $19.97 $45.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK, WHITE
Available Size: S, M, L
Product Badge:- Sale
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Pretty Little Tie-Back Skater Dress
The kind of dress that makes plans for you. This chiffon skater dress with a sweetheart neckline, lace trim, and tie-back detail feels light, flirty, and ready for any plans.
Fit & Features
- Swiss dot chiffon fabric, smooth woven lining
- Sweetheart lace trim neckline
- Adjustable spaghetti straps
- Open tie-back design, stretchy smocked panel
- Sheer lace trim waist insert
- Skater silhouette, lace trim ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000779
Category Name: Casual Dresses
Price: $24.97 $59.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
Product Badge:- Sale