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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Cutest Picnic Gingham A-Line Eyelet Mini Dress
From BBQs, picnics, to summer parties, this gingham mini dress will make the cutest impression! The faux button accents add a touch of vintage charm, while the A-line silhouette and eyelet ruffled trim create a flattering and playful look.
Fit & Features
- Gingham print, cotton-blend woven fabric, woven lining
- Sweetheart neckline, eyelet trim
- Adjustable spaghetti straps
- Stretchy smocked back panel
- Faux button accents
- A-Line fit, eyelet ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000067
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Staple Ribbed Knit Bodycon Midi Dress
A stylish staple like this bodycon midi dress needs to be in your closet. The ribbed knit fabric offers plenty of stretch, while the form-hugging fit flaunts your curves.
Fit & Features
- Lined ribbed knit fabric, high stretch
- Sleeveless square neck and back design
- Spaghetti straps
- High side slit
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000066
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
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Cutout Crush Hour Midi Dress
Warning: This midi dress is sure to cause double takes. From the front-tie detail to the high leg slit, it’s giving effortless bombshell, perfect for pool parties or a cute brunch!
Fit & Features
- Sweater knit stretchy fabric
- V-neckline with tie bust design
- Adjustable spaghetti straps
- Underbust cutout accent
- Front slit
- Bodycon fit, midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000014
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
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Sweet And Off-The-Shoulder Sweater Skater Dress
Look sweet on chilly days in this darling sweater mini dress featuring a cute folded, off-the-shoulder neckline and forever flattering skater silhouette.
Fit & Features
- Rib knit stretchy fabric
- Folded off-the-shoulder neckline
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000013
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
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Favorite Staple Striped Cutout Mini Dress
Slip into this striped mini dress with a flirty cutout and bodycon fit - it'll be your favorite staple all season long!
Fit & Features
- Striped pattern, stretchy rib knit fabric
- Strapless neckline
- Cutout accent
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000015
Category Name: Casual Dresses
Price: $38.90
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty And Flowy Ribbed Knit Strapless Skater Dress
Ready before the group chat even replies. This ribbed knit strapless skater dress hugs through the bodice with a flirty drop waist and flowy skirt that moves with you from brunch plans to last-minute invites.
Fit & Features
- Ribbed knit fabric, high stretch
Strapless straight-across neckline - Drop waist design
- Godet detailing
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 06005-000008
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Ribbed knit fabric, high stretch
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Paisley and Playful Halter Skater Dress
Flirty, floaty, and made for dancing under the sun. With a smocked bust and ruffled skater fit, this halter mini dress is your go-to for festivals, vacays, or just looking way too good for no reason.
Fit & Features
- Paisley print, woven fabric, bust lining
- Halter V-neckline, spaghetti strap tie
- Stretchy smocked bust
- Open tie-back detail
- Flowy skater silhouette
- Ruffled trim short hem
- Runs true to size
Style Number/Barcode: 05102-000065
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laced Up And Lovely Floral Corset Dress
Giving a fairytale with a flirty twist. This corset mini dress brings the drama with lace trim, a lace-up back, and a twirl-worthy skater skirt perfect for celebrations or garden soirees!
Fit & Features
- Floral print, woven fabric, woven lace trim lining
- Sweetheart lace trim neckline, bust tie, underwire bust
- Lace trim, adjustable shoulder straps
- Corset lace and pleated trim bodice, flexible boning
- Back zipper and hook-eye closure, lace-up back detail
- Drop waist seam, voluminous skater silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000067
Category Name: Casual Dresses
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
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Heartbreaker Hourglass Midi Dress
Soft, sleek, and serving curves. This bodycon midi dress is your go-to when you want to keep it simple but still shut it down—with flattering bust detail and a bodycon fit perfect for showing off on date night or a chic party.
Fit & Features
- Soft modal fabric, smooth knit lining, moderate stretch
- Sweetheart neckline, bust detail
- Spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000064
Category Name: Casual Dresses
Price: $18.97 $39.90
On Sale: Yes
Availability: Out of Stock
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Definitely Darling Tie Back Babydoll Mini Dress
Fall in love with this darling eyelet mini dress!. Featuring an open tie-back design and a charming babydoll silhouette, this dress is perfect for brunch, shower celebrations, or graduations.
Fit & Features
- Eyelet fabric, stretchy knit lining
- Short puff sleeves
- Square neckline
- Open tie-back design
- Babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000061
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Heatwave Floral Halter Mini Dress
Cause a major heatwave in this sultry mini dress designed with a large floral print on smooth, stretchy knit fabric. The plunging halter V-neck and short, curve-hugging silhouette are alluring details you'll love.
Fit & Features
- Lined knit fabric, high stretch
- Large floral print
- Sleeveless plunging V-neckline
- Halter strap, partially open back
- Ruching
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000063
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sophisticated Vibe Double-Breasted Longline Vest
Redefine business casual in this longline vest, perfect for polishing your everyday look! This vest has a lapel collar neckline, double-breasted buttons, and a belted waist, It's a chic layer to have in your closet.
Fit & Features
- Woven fabric, sewn-in knit lining
- Lapel collar neckline
- Double-breasted button closures
- Belted waist
- Longline hem
- Runs true to size
Style Number/Barcode: 06204-000004
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Eyes On You High Slit Maxi Dress
Giving "I didn’t come to play, I came to slay" energy. With a draped neckline, leggy side slit, and flattering ruching—this dress is a total scene-stealer from cocktail hour to afterparty.
Fit & Features
- Soft knit fabric with stretch, full knit lining
- Draped cowl neckline with adjustable spaghetti straps
- Side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000059
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beauty So Bold Floral Mesh Maxi Dress
Stroll like a bold beauty in this floral mesh maxi dress for any occasion! Its strapless design and curve-hugging fit accentuate your natural beauty, while the flowing maxi hem adds elegant movement.
Fit & Features
- Bold floral print, mesh fabric, stretchy knit lining
- Strapless neckline
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000058
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wanting More Strapless Lace Knit Maxi Dress
Leave everyone wanting more when you're in this lace knit maxi dress! Perfect for any summer plans, this dress flaunts a sleek strapless neckline and form-hugging fit that flares out into a long hem.
Fit & Features
- Lace knit fabric, lined
- Strapless neckline
- Form-hugging fit
- Flared maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000057
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Romantic Flair Floral Lace-Up Maxi Dress
Bring the romantic flair in this gorgeous floral print maxi dress with a form-hugging silhouette to highlight your curves. The alluring open lace-up back will turn heads and capture all the attention.
Fit & Features
- Knit fabric, high stretch
- Floral print
- Sleeveless V-neckline
- Open back, cross-back lace-up design
- Maxi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000055
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Courtside Style Cutout Pleated Skater Dress
Look cute courtside in this stylish tennis-inspired skater dress! Featuring a trendy cutout back and a flattering skater silhouette, this pleated dress combines playful charm with modern flair.
Fit & Features
- Attached panty lining
- Scoop neckline, tank shoulder straps
- Double-lined soft knit bodice
- Cutout back design
- Woven pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000055
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beachy Breeze Strapless Slit Maxi Dress
Enjoy a sunset dinner by the beach in this chic strapless maxi dress showcasing a high slit for effortless movement and a flattering bodycon silhouette.
Fit & Features
- Texture knit fabric, stretchy knit lining
- Strapless sweetheart neckline, twist accent
- Bodycon silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000052
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Eyes On You Lace-Up Slit Maxi Dress
Not just a dress—this is the moment. From date nights to rooftop dinner parties, this linen maxi dress boasts a cutout bodice and leg-baring slit that does all the flirting for you!
Fit & Features
- Gauze linen-blend woven fabric, stretchy knit lining
- Halter neckline, spaghetti strap ties
- Lace-up back
- Cutout accents
- High front slit
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000053
Category Name: Casual Dresses
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold And Beautiful Rosette Halter Cutout Maxi Dress
Step out like a bold beauty in this printed maxi dress for brunch, shower celebrations, or parties! This stunning maxi features an elegant halter neckline adorned with rosette detail, flirty cutouts that flatter your silhouette, and a flowing skirt that moves gracefully with every step.
Fit & Features
- Abstract print, woven fabric
- Halter neckline with rosette detail, bust knit lining
- Side cutout accents
- Flowy ruffled maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000054
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Muse Floral Mesh Maxi Dress
You'll be a gorgeous vacay muse in this curve-flaunting maxi dress designed with a large floral print on airy mesh fabric. Perf for pairing with wedges!
Fit & Features
- Sheer mesh fabric, full-length knit lining, high stretch
- Large floral print
- Sleeveless V-neckline
- Spaghetti straps
- Maxi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000056
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Mode Tropical Print One-Shoulder Maxi Dress
You'll be on vacay mode in this sultry tropical print maxi dress featuring a one-shoulder neckline with a chic O-ring accent and an alluring bust cutout. The floor-length fitted silhouette will flaunt your stunning curves.
Fit & Features
- Mesh fabric, high stretch, knit lining
- Tropical print
- Sleeveless one-shoulder neckline, O-ring accent
- Asymmetric bust cutout
- Asymmetric back strap
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000050
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Mode Halter Cutout Maxi Dress
Amp up the sultry vibes of your summer 'fits with this sleek knit maxi dress featuring a halter square neck, an asymmetric waist cutout, and a curve-hugging silhouette.
Fit & Features
- Smooth knit fabric with knit lining, high stretch
- Sleeveless square neckline
- Tie-back halter spaghetti straps, partially open back
- Asymmetric side cutout
- Ruching
- Maxi-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000051
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylishly Sweet Smocked Tube Skater Dress
Stylishly sweet, this smocked tube skater dress is perfect for weekend brunch! It features a strapless straight neckline, a V-shaped waist, and a short A-line silhouette for that flirty flair.
Fit & Features
- Poplin cotton-blend woven fabric, stretchy knit lining
- Strapless straight-across neckline
- Stretchy smocked bodice
- V-shaped waist
- Pleating
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000049
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free