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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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
- Dark wash denim
- 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
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: $39.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M
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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
- 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: $22.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
Product Badge:- Sale
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Pretty Plans Eyelet Mini Dress
Caught feelings for this one instantly. This eyelet dress feels light and playful, perfect for brunch dates, daytime plans, or wherever the mood takes you.
Fit & Features
- Eyelet knit fabric, smooth knit lining
- V-neckline
- Adjustable spaghetti straps
- Fitted bodice
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000471
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: L
Product Badge:- Sale
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Picture Perfect Lace Trim Floral Woven Skater Dress
You booked the brunch. Now match the vibe. This lace trim floral lace-up skater dress snatches at the corset bodice and flares into a twirl-ready mini made for parties, day dates, and every camera roll moment in between.
Fit & Features
- Floral printed woven fabric with lining, dainty lace trims
- Strapless straight-across neckline, ruched bust, tie detail
- Corset-style bodice, V-shaped drop waist
- Lace-up back design, tie closure
- Mini-length skater silhouette, pleated detailing
- Runs true to size
Style Number/Barcode: 05101-000973
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wrapped In Charm Off-Shoulder Mini Dress
This mini dress is that perfect mix of soft and sculpted—the one you reach for when you want to look undone in a chic way. The foldover off-shoulder neckline adds a flirty twist, while the rib knit hugs you with just the right amount of confidence.
Fit & Features
- Soft rib knit fabric with stretch
- Foldover off-shoulder neckline with subtle twist detail
- Fitted long sleeves
- Bodycon silhouette
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000469
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bare It All Open Back Bodycon Midi Dress
Clean lines, confident fit, no extra effort required. This ribbed midi dress keeps things sleek and minimal with a body-hugging silhouette that feels just as good as it looks. Perfect for dressing up or down.
Fit & Features
- Soft ribbed knit fabric with comfortable stretch
- Square neckline with slim spaghetti straps
- Sleeveless bodycon silhouette
- Low open back design
- Midi length that hits below the knee
- Runs true to size
Style Number/Barcode: 05102-000467
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Getaway Mood Tropical Floral Halter Maxi Dress
Lightweight, curve-loving, and made to move with you. The airy sheer mesh fabric and tropical floral print bring a bold edge that feels right for nights out and getaway moods.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Tropical floral print
- Sleeveless V-neckline
- Metal flower hardware accent, keyhole cutout
- Tie-back halter spaghetti straps, partially open back
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000464
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirt With The Breeze Skater Mini Dress
This flowy skater dress was made for sunny days. It features a flattering V-neckline and a breezy silhouette that moves with you from brunch to beachside strolls.
Fit & Features
- Cotton fabric, woven cotton lining, delicate embroidery
- V-neckline
- Adjustable spaghetti straps
- Tiered ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000465
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Plans Chiffon And Lace Skater Dress
Booked, busy, and dressed like it. This chiffon and lace skater dress gives you that soft, floaty fit that moves with you from daytime plans to whatever the night turns into.
Fit & Features
- Lightweight chiffon fabrication, lace trim woven lining
- Sleeveless V-neckline with delicate lace insert
- Spaghetti straps
- Flared skater silhouette
- Adjustable waist tie
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000463
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet On Arrival Floral Skater Dress
Sweet, light, and made for daytime plans. This strapless skater dress features a soft sweetheart neckline and delicate floral details that feel easy and feminine, perfect for brunch dates, bridal celebrations, and plans that turn into golden hour.
Fit & Features
- Ditsy floral print, woven fabric
- Strapless sweetheart neckline with delicate trim
- Skater silhouette with pleating
- Mini-length flared hem
- Runs true to size
Style Number/Barcode: 05101-000956
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Daytime Darling Eyelet Mini Dress
Caught the vibe and didn’t think twice. This puff sleeve eyelet mini dress hugs just right with a flirty tie front—perfect for brunch dates, daytime plans, and those “I look cute today” moments.
Fit & Features
- Eyelet knit fabric
- Sweetheart neckline, tie bust keyhole cutout accent
- Puff short sleeves
- Princess seam detailing
- A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000462
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Polished Mock Neck Mini Dress
This is the kind of dress you reach for when you want to look pulled together without overthinking it. Clean lines, a smooth ribbed fit, and a mock neck give it that quiet confidence that works day to night with a quick switch of shoes.
Fit & Features
- Soft ribbed knit fabric with comfortable stretch
- Mock neckline
- Long fitted sleeves
- Bodycon silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000460
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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A Bit Flirty Lace Halter Dress
This lace mini dress gives you that effortless twirl moment with a light, easy fit that feels made for bridal celebrations, birthdays, graduations, and every dressed-up moment.
Fit & Features
- Lace-lined fabric
- Halter neckline with tie straps
- A-line silhouette
- Layered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000950
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Golden Hour Groove Crochet Halter Maxi Dress
Vacation energy, locked in. This striped texture crochet knit maxi dress features a plunge halter neckline with wooden hoop inserts and an open back that feels equal parts effortless and elevated. Pair with strappy sandals for your upcoming getaway.
Fit & Features
- Crochet striped texture knit, smooth knit lining
- Plunge halter neckline with wood hoop inserts, tie closure
- Open back
- Side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000461
Category Name: Casual Dresses
Price: $10.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: XS, S
Product Badge:- Sale
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Naturally Cool Denim Lace-Up Skater Dress
Easy, relaxed, and low-key cool. This strapless denim skater dress keeps it casual up top with a structured fit that feels effortless from daytime plans to concerts.
Fit & Features
- Denim light wash fabric with slight stretch
- Strapless neckline, non-slip grip trim
- Structured bodice with front lattice lace-up detail
- Skater silhouette
- Flared mini-length hem, built-in knit stretchy shorts lining
- Back zipper and hook-eye closure
- Runs true to size
Style Number/Barcode: 05102-000738
Category Name: Casual Dresses
Price: $54.90
Availability: In Stock
Available Color: BLACK, DENIM
Available Size: XS, S, M, L