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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Styled Chic Button Halter Neck Mini Dress
Serving sculpted and styled without trying too hard. This halter neck mini dress hugs your curves with a sleek ribbed feel and subtle button detail that keeps it chic from every angle.
Fit & Features
- Ribbed knit fabric, high stretch
- Sleeveless V-neckline
- Varied button accents
- Halter strap, partially open back
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000316
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Postcard From Paradise Maxi Dress
Mentally already sipping something fruity by the water. This flowy maxi dress brings vacation dressing to life with a citrus postcard print, flirty front tie detail, and lace-up back that looks good from every angle.
Fit & Features
- Multi-printed design, woven fabric
- V-neckline with trim and tie bust
- Spaghetti straps
- Lace-up tassel back
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000572
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pearls Before Midnight Denim Mini Dress
A little country, a little glamorous, and fully committed to being overdressed. This denim skater mini dress brings together pearl embellishments, a fitted bodice, and flirty volume for the kind of outfit that owns the room before you even say hi.
Fit & Features
- Denim fabric, bust lining
- Sweetheart neckline, adjustable spaghetti straps
- Button front accents. back zipper and hook-eye closure
- Skater silhouette
- Faux pearl embellishments
- Pleated side mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000568
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Plans Tropical Tube Mini Dress
Booked, busy, and already packing this. This floral print mini dress hugs you in all the right places and was made for beach stays, resort destinations, and tropical escapes!
Fit & Features
- Slinky knit-lined stretchy fabric
- Tube strapless neckline
- Statement floral print
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000571
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Sale
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Sweet Talker Floral Eyelet Midi Tube Dress
Soft, fitted, and low-key stealing attention. This floral print eyelet midi tube dress hugs in all the right places with a stretchy feel that’s made for brunch plans, day dates, and everything after.
Fit & Features
- Eyelet knit fabric with sewn-in knit lining, high stretch
- Floral print
- Strapless elasticized straight-across neckline
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000569
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Muse Floral Midi Dress
Soft florals and a sleek silhouette make this one an instant favorite. This strapless floral eyelet bodycon midi dress hugs your curves and adds a polished look for brunch, garden parties, and getaways.
Fit & Features
- Ditsy floral print, eyelet knit fabric, soft lining
- Strapless tube neckline
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000570
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Styled Up Off-Shoulder Mini Dress
Easy, confident, and styled without overthinking. This off-the-shoulder blouson mini dress drapes up top with a fitted bottom that keeps the silhouette clean and pulled together for any plans that pop up.
Fit & Features
- Soft knit fabric with comfortable stretch
- Relaxed blouson top with a fitted mini skirt
- Off shoulder neckline
- Relaxed short sleeves
- Runs true to size
Style Number/Barcode: 05102-000563
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Glow Bodycon Mini Dress
Cute, simple, and effortlessly flattering. This ribbed knit bodycon mini dress hugs in all the right places with a clean square neckline and delicate straps, making it the perfect dress for day dates, brunch, or a casual night out.
Fit & Features
- Rib knit fabric, sewn-in lining
- Square neckline
- Spaghetti straps
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000560
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wine Night Pinstripe Mini Dress
Clock out, but keep the attitude. This pinstripe mini dress brings tailored energy up top and flirty drama at the hem, hugging you in all the right places for wine bar nights and dinner.
Fit & Features
- Pinstriped pattern, woven fabric, sewn-in knit lining
- Strapless lace trim sweetheart neckline
- Padded bra cups
- Back zipper and hook-eye closure
- Ruched side lace panels
- Form-hugging fit, ruffled mini hem
- Runs true to size
Style Number/Barcode: 05102-000558
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Chic Cutout Maxi Dress
The kind of dress that makes every plan feel a little more chic. With its flowy silhouette, flirty cutout detail, and side pockets, this maxi dress was made for vacations, weekend plans, and showers.
Fit & Features
- Gauze cotton woven fabric, woven lining
- Sweetheart neckline, spaghetti straps
- Open tie-back design
- Cutout bodice
- Hidden side pockets
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000559
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Vibe Ribbed Knit Mini Tube Dress
Simple, chic, and such a vibe. This ribbed knit mini tube dress hugs your curves with a comfy stretch fit—made for plans that come together at the last minute, but you still look fab.
Fit & Features
- Hacci ribbed knit fabric, high stretch, knit lining
- Strapless fold-over neckline
- Mini-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000562
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Flirting In Positano A-Line Mini Dress
Meet the dress equivalent of booking the flight before asking questions. With its dreamy coastal print and easy strapless fit, this mini dress was made for European getaways, brunch, and sunny day plans.
Fit & Features
- Multi-print design, linen-blend woven fabric, woven lining
- Strapless neckline, non-slip grip lining
- Side hidden zipper and hook-eye closure
- Bar back accent and cutout
- A-line fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000561
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Plans Ahead Long Sleeve Skater Dress
Soft, cute, and already booked. This ribbed skater dress hugs up top and floats just right at the hem, making it an easy yes for brunches, daytime plans, and V-day dates!
Fit & Features
- Pointelle knit soft stretch fabric
- Crew neckline
- Fitted long sleeves
- Fitted bodice with a defining drop waist seam
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000556
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirt First Strapless Lace Tiered Mini Dress
Sweet at first glance, bold once you turn around. This strapless lace mini dress hugs through the bodice and finishes with playful tiered ruffles—made for nights that start casual and end unforgettable.
Fit & Features
- Stretch lace-lined fabric with a soft, floral texture
- Strapless neckline
- Drop waist silhouette
- Tiered ruffle skirt
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000557
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Desert Heat Faux Suede Strapless Mini Dress
This mini dress is doing the most in the best way. The faux suede strapless dress hugs in all the right places while the curved fringe detail brings the drama for nights out or festival plans.
Fit & Features
- Faux suede fabric, smooth knit lining
- Strapless neckline, non-slip grip lining
- Back zipper and hook-eye closure
- Bodycon fit
- Curved seam detailing, curved front fringe trim
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000555
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Barely Trying Open Back Midi Dress
This is that effortless dress you reach for when you want to feel cute and put together. The open back adds a soft, unexpected moment, while the ribbed fit keeps everything sleek and flattering.
Fit & Features
- Rib knit stretchy fabric
- Scoop neckline
- Spaghetti straps
- Open back
- Side slit
- Form-hugging, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000553
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Favorite Thing Sleeveless Midi Dress
The kind of dress that somehow works for every plan on your calendar. This rib knit bodycon midi dress keeps it chic and simple, perfect for dressing up or down.
Fit & Features
- Rib knit fabric, double-lined, stretchy
- Sleeveless scoop neckline
- Tank shoulder straps
- Bodycon silhouette
- Side slit, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000551
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BROWN, IVORY
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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Stylish Plans Ribbed Knit Bodycon Midi Dress
One of those dresses that somehow does all the styling for you. This ribbed knit bodycon midi dress hugs just right with a notched V-neckline and sleek silhouette that works from casual plans to dressed-up moments.
Fit & Features
- Ribbed knit fabric, high stretch
- Sleeveless scoop neckline, notched V-neckline
- Thin tank shoulder straps
- Back slit accent
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000552
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ultra Game NBA LA Lakers Mini Dress
Game night, but make it stylish. This Los Angeles Lakers tube mini dress snatches with a structured bodice while the embroidered team logo and stud accents keep it bold from every angle.
Fit & Features
- Sleek knit-lined stretchy fabric
- Strapless tube neckline, padded bra cups
- Los Angeles Lakers embroidered team logo, mini stud accents
- Lace-up back design, side zipper and hook-eye closure
- High waist seam
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000549
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS
Product Badge:- Sale
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Ultra Game NBA NY Knicks Mini Dress
Serving courtside energy even when you’re not at the game. This NBA Knicks halter mini dress hugs in all the right places with a sporty lace-up detail that keeps it playful and bold.
Fit & Features
- Jersey knit fabric, smooth knit lining
- Halter contrast trim neckline with tie straps
- Lace-up neckline with front and back Knicks graphic team logo
- Corset bodice, flexible boning
- Side zipper and hook-eye closure
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000548
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Spoken Confidence Rib Knit Mini Dress
Low effort, high payoff. This rib knit foldover off-the-shoulder mini dress hugs just enough while keeping things comfortable, perfect for dinners that turn into late plans.
Fit & Features
- Soft rib knit fabric with stretch and lining
- Foldover off-the-shoulder neckline
- Long sleeve design
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000545
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hot Plans Tropical Tube Mini Dress
Booked, busy, and dressed for it. This tropical floral mini dress hugs in all the right places with a sleek strapless fit—made for vacations, beach weekends, and last-minute plans that turn into everything.
Fit & Features
- Tropical floral print, lined stretchy knit fabric
- Tube strapless neckline, no-slip strip
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000547
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Brunch Flirt Polka Dot Ruffle Skater Dress
Sweet and flirty, this polka dot mesh babydoll dress brings the ruffle, the lace-up back, and that floaty skater shape that’s made for brunch plans and your fab weekend festivities.
Fit & Features
- Mesh fabric with lining
- Dainty polka dot print
- Sleeveless V-neckline, ruched bust and bodice
- Adjustable spaghetti straps
- Open cross-back lace-up design, tie closure
- Tiered ruffled short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-001099
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirting With Plans Puff Sleeve Skater Dress
She’s cute, collected, and already has plans you’ll want in on. This puff sleeve skater dress cinches in all the right places with a breezy fit that works for dinner reservations, summer parties, and every “I had nothing to wear” moment.
Fit & Features
- Linen-blend woven fabric
- Sweetheart neckline, bust tie detail
- Short puff sleeves
- Open tie-back design
- Short skater silhouette, ruffled hem
- Runs true to size
Style Number/Barcode: 05102-000543
Category Name: Casual Dresses
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free