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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Bare It Beautiful Floral Tube Midi Dress
No straps, no stress, just compliments. This floral printed midi dress sculpts in a smooth, strapless tube silhouette with a sleek bar back detail that keeps it secure while you own every spring RSVP.
Fit & Features
- Floral printed stretch-lined fabric
- Strapless tube silhouette
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-001188
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All The Compliments Floral Mini Dress
Soft, flirty, and already getting compliments. This floral eyelet mini hugs in all the right places with a sweetheart neckline and ruffle hem that feels made for any occasion.
Fit & Features
- Ditsy floral print, eyelet knit fabric with knit lining, moderate stretch
- Sweetheart neckline, tie bust keyhole cutout
- Short puff sleeves
- Bodycon fit, ruffle trim mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000501
Category Name: Casual Dresses
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Look Eyelet Flutter Sleeve Skater Dress
Caught feelings for this one instantly—she’s light, flirty, and made for plans that turn into pics. This eyelet skater dress hugs up top, then flares just right for brunch, dates, and every RSVP.
Fit & Features
- Woven eyelet fabric with woven lining, no stretch
- Sweetheart neckline, no-slip strip, button-front closures
- Short ruffle flutter sleeves, can be worn off-the-shoulder
- Back zipper with hook-eye closure
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05101-001031
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Escape Ruffle Halter Romper
Light, sculpting, and ready for plans that turn into stories. This halter romper features a plunging neckline, ruched body, and layered ruffle detailing that deserves the spotlight.
Fit & Features
- Smooth knit fabric with high stretch
- Sleeveless plunging V-neckline
- Tie-back halter straps, open back
- Form-hugging bodice, ruched detailing
- Tiered ruffled mini-length overlay, side ruffled accents
- Hidden shorts lining
- Runs true to size
Style Number/Barcode: 06503-000328
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: MAGENTA
Available Size: XS
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Daytime Vibe Floral Eyelet Strapless Midi Dress
Currently planning your next cute daytime moment. This floral eyelet strapless midi dress hugs up top with a smocked fit, then flows out for that easy, throw-on-and-go vibe—perfect for brunch, beach days, or last-minute plans.
Fit & Features
- Woven floral eyelet fabric, woven lining
- Strapless straight-across neckline
- Fitted smocked bodice
- Midi-length flowy A-line silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-000498
Category Name: Casual Dresses
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet With A Twist Polka Dot Halter Mini Dress
Soft, flirty, and just a little daring. This halter mini dress pairs classic polka dots with a lace-trim neckline and open back that feels romantic without trying too hard—easy to dress up, impossible to forget.
Fit & Features
- Polka dot print, knit fabric with lining
- Halter neckline with lace trim detail
- Open back with adjustable tie closure
- Mini-length silhouette, subtle flared hem
- Runs true to size
Style Number/Barcode: 05102-000685
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: S, L
Product Badge:- Sale
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Sunny Days Crochet A-Line Mini Dress
Booked, packed, and already planning the outfit. This A-line mini dress with a crochet bust overlay and lace-up back brings that effortless Euro summer vibe with a flirty, easy fit.
Fit & Features
- Linen-like fabric, smooth woven lining
- V-neckline, crochet bust overlay, tie bust front
- Spaghetti straps
- Strappy tie-back design
- Princess seam, A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000494
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Sale
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Sweet Breeze Eyelet Mini Dress
This one feels like sunshine in dress form. The smocked bodice keeps it easy and flattering, while the tiered eyelet skirt adds flirty movement, perfect for showers, graduations, brunches, and any dressy plans.
Fit & Features
- Eyelet embroidered woven fabric, stretchy knit lining
- Strapless neckline
- Stretchy smocked bodice
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001022
Category Name: Casual Dresses
Price: $44.90
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy Eyelet Ruffle Mini Dress
This sweet eyelet dress brings soft romance with a playful twist. The square neckline, puff sleeves, and tiered ruffle skirt create a flattering A-line silhouette that feels effortlessly feminine. Perfect for brunch dates, garden parties, or sunny day plans.
Fit & Features
- Eyelet fabric, knit lining
- Square neckline
- Short puff sleeves
- Fitted bodice
- Drop waist A-line silhouette
- Tiered ruffle mini hem
- Runs true to size
Style Number/Barcode: 05102-000493
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutie Vibe Lace Strapless A-Line Mini Dress
Cute plans only—this one’s already booked. This lace strapless A-line mini dress hugs up top and flares out with an easy, flirty fit that’s made for last-minute invites.
Fit & Features
- Sheer lace fabric with knit lining, high stretch
- Strapless straight-across neckline, no-slip strip
- Mini-length asymmetric hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000492
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: L
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Picnic Date Lace Cotton Skater Dress
Straight out of your Euro summer mood board. This cotton skater dress with a lace ruffled bodice and tie shoulder straps gives you that floaty, twirl-worthy fit made for brunch, bridal celebrations, and cute getaways.
Fit & Features
- Cotton fabric, tulle and woven linings
- Square neckline, tie shoulder straps
- Hidden side zipper and hook-eye closure
- Mini lace tiered ruffled fitted bodice
- Tie-waist design
- Voluminous skater silhouette, lace trim mini hem
- Runs true to size
Style Number/Barcode: 05101-001009
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready In Five Tie-Back Mini Dress
This A-line mini dress is your “I have nothing to wear” fix—handled. A flirty ruffled dress with a tie-back detail that cinches just right and a flowy skirt made for last-minute plans and weekend brunches.
Fit & Features
- Woven fabric with knit lining
- V-neckline, cinched bust design
- Adjustable spaghetti straps
- Open tie-back design
- A-line fit
- Layered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000488
Category Name: Casual Dresses
Price: $21.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: SAGE
Available Size: XXS, XS, S, M, L, XL
Product Badge:- Sale
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Flirty Flowy Chiffon Strapless Babydoll Dress
Made for spontaneous plans and extra mirror checks. This strapless chiffon babydoll dress brings the flirty vibes with flowy layers, a mini hem, and that effortlessly dressed-up look.
Fit & Features
- Sheer chiffon fabric with lining
- Strapless sweetheart neckline
- Hidden side zipper and hook-eye closure
- Flowy, tiered, ruffle design
- Mini-length hem
- Babydoll silhouette
- Runs true to size
Style Number/Barcode: 05102-000489
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Denim Days Button Front Mini Dress
Denim, but make it plans. This button-up mini dress cinches you in with a flattering fit and an unexpected back buckle moment that turns heads anywhere you go.
Fit & Features
- Cotton-blend dark wash denim fabric, moderate stretch
- Strapless tube neckline
- Button-up front
- Adjustable back buckle
- Curve-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000490
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Flirt Babydoll Mini Dress
Floaty, flirty, and effortless in the best way. This babydoll mini dress brings that easy, throw-on-and-go feel with a breezy fit that moves with you from daytime plans to last-minute outings.
Fit & Features
- Cotton-blend fabric with lining
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Partially smocked back
- Mini-length asymmetric hem, subtle distressed detailing
- Flowy babydoll silhouette
- Runs true to size
Style Number/Barcode: 05102-000485
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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After Hours Bloom Floral Burnout Mesh Mini Dress
Flirty with a side of intention—this one moves differently. The floral burnout mesh mini dress hugs up top, flows below, and shows up perfectly for plans that turn into after-hours moments.
Fit & Features
- Mesh fabric with floral velvet burnout design, knit lining, high stretch
- Strapless straight-across neckline, no-slip strip
- Tube silhouette with a fitted bodice
- Drop waist with tiered ruffle mini skirt for movement
- Runs true to size
Style Number/Barcode: 05101-001329
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: TAUPE, BLACK
Available Size: XS, S, L
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Daydream Bloom Floral Print Midi Dress
This is the kind of dress that makes every plan feel a little prettier. The fitted bodice and flowy skirt create that effortless shape, while the soft floral print keeps things light and romantic.
Fit & Features
- Woven fabric, soft floral print, woven lining
- Square neckline, tie bust keyhole accent
- Adjustable spagehtti straps
- Stretchy smocked back panel, side zipper and hook-eye closure
- Fitted bodice with button accents
- Drop waist seam, a-line midi silhouette
- Runs true to size
Style Number/Barcode: 05102-000481
Category Name: Casual Dresses
Price: $9.97 $62.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Second Look Open Back Midi Dress
Simple from the front, unforgettable from the back. This ribbed halter midi dress features a plunging neckline and open back with subtle ruching that hugs your shape and keeps the look smooth, polished, and confidently put together.
Fit & Features
- Soft rib knit stretch fabric
- Plunge halter neckline
- Open back design with subtle ruching
- Bodycon midi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000482
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M
Product Badge:- Sale
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Effortless Impact Mock Neck Midi Dress
This midi is your secret weapon—clean, sculpting, and quietly commanding. The ribbed knit dress smooths and contours while the mock neck adds that cool, editorial structure that never tries too hard.
Fit & Features
- Rib knit fabric
- Mock neckline
- Smooth bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000479
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunshine State Of Mind Eyelet Mini Dress
This eyelet skater mini dress offers a breezy fit and ruffled details—perfect for graduations, showers, or brunch.
Fit & Features
- Eyelet woven fabric with knit lining
- Sweetheart neckline
- Smocked shoulder straps and bust
- Flowy skater silhouette
- Ruffle trim mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000988
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Fab Polka Dot Halter Mini Dress
This polka dot halter mini dress is ready for your weekend plans. It features a draped cowl neckline and curve-hugging bodycon fit that keeps you looking flirty, fab, and right on time for every outing.
Fit & Features
- Sleek knit fabric with high stretch
- Polka dot print
- Sleeveless V-neckline, draped cowl design
- Tie-back halter straps, partially open back
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000475
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Serving Sweetness Denim Mini Dress
This lace-up denim skater dress features a plunge V-neckline, structured bodice, and a playful drop waist skirt that’s made for concerts, festivals, and every plan in between.
Fit & Features
- Denim fabric, built-in pant knit lining, some stretch
- Plunge halter V-neckline
- Structured bodice with lace-up design
- Drop waist seam
- Back zipper with hook-eye closure
- Pleated skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000752
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: XS, S, M, L
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Sunny Day Invites Eyelet Knit Skater Dress
This adorable eyelet knit skater dress will have you instantly weekend-ready. The short dress hugs up top, flares just right, and is basically made for last-minute brunches and sunny day invites.
Fit & Features
- Eyelet knit fabric with knit lining, high stretch
- Sleeveless V-neckline
- Halter tie-back straps, partially open back
- Drop waist design, V-shaped seam
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000476
Category Name: Casual Dresses
Price: $31.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Backstage Flirt Denim Skater Dress
Caught feelings for a denim moment this good. This plunge halter mini dress brings the drama with an open tie back and skate silhouette that’s made for weekend plans and concerts.
Fit & Features
- Denim fabric, slight stretch, built-in panty lining
- Plunge halter neckline, tie straps
- Button front closures
- Open back with tie
- Drop waist seam
- Skater silhouette, mini-length raw hem
- Runs true to size
Style Number/Barcode: 05102-000474
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: M, L
Product Badge:- Sale