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.
Now Trending
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.
-
Preppy Spirit Collared Midi Dress
Get some pep in your step by styling this casual midi dress for art shows or family dinners! The mid-length dress features a collared V-neckline, long fitted sleeves, and a bodycon silhouette on stretchy ribbed knit fabric. Style with knee-high boots to complete the look!
Fit & Features
- Collared V-neckline
- Long fitted sleeves
- Bodycon silhouette
- Midi-length hem
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4785
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Basic Bae Crew Neck Slit Maxi Dress
A cute basic maxi dress for looking trendy on your off-duty days! It features short sleeves, a crew neck, a bodycon silhouette, and a high side slit to show off some leg! The dress is composed of a brushed knit stretchy fabric. Complete the look in flat sandals and a handbag.
Fit & Features
- Short sleeves
- Crew neck
- High side slit
- Bodycon silhouette
- Maxi-length hem
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-4786
Category Name: Casual Dresses
Price: $18.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Minimalistic Sultry Midi Dress
Chanel a sultry minimalistic wardrobe for fall in this staple crepe midi dress featuring a sleek sleeveless V-neckline, bungee spaghetti straps, a curve-hugging silhouette, and a front slit accent. Complete the look in low-heeled mules and a chic hat.
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Curve-hugging silhouette
- Front slit accent
- Midi-length hem
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4782
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
She's Got Bold Style Midi Dress
Showcase your fearless bold style in this alluring and chic midi dress! It features a sleeveless one-shoulder neckline with an asymmetrical shoulder strap, a center O-ring cutout, dual waist cutouts, and a midi-length, curve-hugging silhouette with a thigh-high side slit. Complete the look with hoop earrings.
Fit & Features
- Sleeveless one-shoulder neckline
- Asymmetrical single shoulder strap
- Center O-ring cutout
- Dual waist cutouts
- Midi-length hem, bodycon silhouette, high side slit
- Smooth knit fabric, partial knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4774
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Major Obsession Marble Print Midi Dress
The obsession you'll have with this fabulous marble print midi dress is so real! It features a V-neckline with a twist-front design, an alluring front waist cutout to showcase some skin, long fitted sleeves, a ruched side seam that leads to a high-cut side slit, and a midi-length hem with a form-hugging silhouette. The stretchy knit fabric features a trendy marble print pattern. Style this midi dress with spiral heels!
Fit & Features
- V-neckline, twist-front design
- Front waist cutout
- Long fitted sleeves
- Ruched side seam, high side slit
- Midi-length hem, form-hugging fit
- Marble print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5309
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Struck By Sultry Halter Mini Dress
Get struck by this sultry halter mini dress sure to capture every eye in the room! The knit dress features a sleeveless halter neck with tie closure, a strappy cutout waist, and a form-hugging silhouette. Complete the look in sassy platform heels.
Fit & Features
- Sleeveless halter neck with tie closure
- Strappy cutout waist
- Form-hugging silhouette
- Mini-length hem
- Lined slinky knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4776
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Swirl Of Splash Crew Mini Dress
A splash of this swirl print mini dress will instantly give your closet a fresh look! The dress features long fitted sleeves, a crew neckline, and a bodycon silhouette on smooth knit fabric with a moderate stretch. Complete the look in a crop denim jacket for a day out with friends!
Fit & Features
- Long fitted sleeves
- Crew neckline
- Bodycon silhouette
- Mini-length hem
- Swirl print
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4779
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Simple Life Crew Tank Midi Dress
All a girl needs is this basic crew tank midi dress perfect for dressing up or down! It features a sleeveless bodice, wide tank shoulder straps, a midi-length hem, and a bodycon silhouette on lined ribbed knit fabric with plenty of stretch. Style this mid-length dress with a jacket and suede booties.
Fit & Features
- Sleeveless crew neckline
- Wide tank shoulder straps
- Midi-length hem
- Bodycon silhouette
- Lined ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4772
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Stylish Links Chain Strap Midi Dress
This stylish midi dress entered the chat! It features a sleeveless V-neckline with trendy chain link shoulder straps, a bodycon silhouette, and a front slit on stretchy, double-lined ribbed knit fabric. Complete the look in clear strap heels.
Fit & Features
- Sleeveless V-neckline
- Chain link shoulder straps
- Bodycon silhouette
- Front slit
- Midi-length hem
- Double-lined, rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4773
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Everyday Slay Ribbed Knit Midi Dress
Showcase an everyday slay in this curve-hugging midi dress! It features a sleeveless square neckline, spaghetti straps, an open back with a double strap design, a midi-length hem with a bodycon silhouette, and a thigh-high side slit for a sultry accent. The ribbed knit fabric offers plenty of stretch. Style with clear mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open back, double strap design, tie closure
- Midi-length hem, bodycon silhouette
- High side slit
- Ribbed knit fabric, lining at the bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4770
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Effortless Beauty Floral Mini Dress
Radiate effortless beauty in this gorg floral mini dress! It features a square neckline, sheer long peasant sleeves to add a chic flair, all-over ruching, a mini-length hem with a form-hugging fit, and an all-over blooming floral print. The sheer chiffon fabric includes a partial knit lining down the body of the dress. Style with dainty duster earrings and a pair of neutral heels.
Fit & Features
- Square neckline
- Sheer long peasant sleeves, elastic cinched hems
- All-over ruching, back zipper, hook and eye closure
- Mini-length hem, form-hugging fit
- Floral print
- Sheer chiffon fabric, partial knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1860
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
So Irresistible Mesh Midi Dress
You'll be a vision in this simply irresistible mesh midi dress perfect for an engagement party or cocktail soiree! It features a sleeveless plunge v-neck, adjustable straps, a back slit accent, and ruched seams that accentuate your curves along the bodycon silhouette. Complete the look in stiletto heels.
Fit & Features
- Sleeveless plunge v-neck
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Ruched seams, back slit accent
- Bodycon, midi-length hem
- Mesh fabric, sewn-in knit lining, minimal stretch
- Fits true to size
Style Number/Barcode: 05101-1857
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Basic Must-Have Ribbed Knit Mini Dress
This ribbed knit mini dress is a basic must-have that needs to be in your wardrobe! It features a classic crew neckline, long fitted sleeves, and a short, form-hugging fit. The ribbed knit fabric offers a moderate stretch. Style with hoop earrings and knee-high boots.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Mini-length hem, form-fitting silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1407
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirty Floral Vibes Ruched Mini Dress
Capture a sweet romantic look in this flirty floral mini dress! It features a sleeveless V-neckline with ruching at the bust, spaghetti straps, a mini-length hem, and a form-hugging fit. The stretchy ribbed knit fabric features an all-over ditsy floral print for an adorable summer style. Pair with espadrille sandals for a day date.
Fit & Features
- Sleeveless V-neckline
- Ruching at the bust
- Spaghetti straps
- Mini-length hem, form-hugging fit
- Ditsy floral print
- Ribbed knit fabric, smooth knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4760
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Add Some Spice Mini Dress
This fiery bodycon mini dress will add some spice to your night-out look! It features a sleeveless square neckline, trendy chain-link shoulder straps, and a short, curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Style this sexy mini dress with platform heels.
Fit & Features
- Sleeveless square neckline
- Chain-link shoulder straps
- Mini-length hem, bodycon silhouette
- Smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4755
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Happily In Love Scoop Neck Mini Dress
You'll be happily in love with how stunning you look in this sleeveless mini dress for a graduation or birthday brunch! It features a scoop neck with a flirty bust tie, spaghetti straps, and a bodycon silhouette on rib knit fabric with a stretchy knit lining. Complete the look in trendy wedges.
Fit & Features
- Sleeveless scoop neck, spaghetti straps
- Bust tie
- Bodycon silhouette
- Mini-length hem
- Rib knit, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4754
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Pretty In Paradise Strappy Cutout Maxi Dress
You'll be pretty in paradise in this stunning maxi dress for vacation or a bachelorette weekend! The dress features a sleeveless V-neckline, spaghetti straps that lace up along the open back, flirty waist cutouts, and a high front slit along the flowy hem. Complete the look with earrings and clear block heels for a chic style!
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Lace-up open back
- Waist cutouts, high front slit
- Maxi-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4752
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
One Love Sweetheart Sweater Dress
The sweater dress your wardrobe needs! It features a sleeveless, sweetheart neckline, shoulder straps, a ruched bust seam, and a flirty cutout waist leading to the bodycon, mini-length silhouette. Complete the look in statement earrings.
Shop More Styles: The Sweater Collection
Fit & Features
- Sleeveless, sweetheart neckline, shoulder straps
- Ruched bust seam
- Cutout waist
- Bodycon silhouette
- Mini-length hem
- Hacci ribbed-knit fabric
- Runs true to size
Style Number/Barcode: 05102-4751
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Fall Ritual Poplin Shirt Dress
Your new fall favorite for wearing all season! This poplin shirt dress features long sleeves with buttoned cuffs, a collared neckline, front button-down closures, a fitted waist, a lower open-back design with lace-up, and a pleated, short skater silhouette. Complete the look in chic Panama hat and booties.
Fit & Features
- Long sleeves with buttoned cuffs
- Collared neckline
- Front button-down closures
- Fitted waist, lower open-back, lace-up
- Pleated, short skater silhouette
- Non-stretch poplin fabric
- Fits true to size
Style Number/Barcode: 05101-1771
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Wonderful Winter Sweater Midi Dress
Slay all season no matter the weather in this sweater midi dress perfect for casual or dressy events! It features fitted long sleeves, a mock neck, a bust cutout, and a form-hugging silhouette with a flirty front slit. The dress is composed of a stretchy rib-knit fabric. Pair with booties to complete the look.
Fit & Features
- Fitted long sleeves, mock neck
- Bust cutout
- Form-hugging silhouette
- Front slit accent
- Midi-length hem
- Rib-knit sweater fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1579
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Winter Chic Off-The-Shoulder Sweater Dress
This adorable ribbed knit sweater dress will give you a chic look for the winter season! It features an off-the-shoulder neckline with a fold-over design, long fitted sleeves, a midi-length, curve-hugging silhouette, and a high front slit. The knit fabric offers a moderate stretch for comfortable wear. Style with knee-high boots.
Fit & Features
- Off-the-shoulder neckline, fold-over design
- Long fitted sleeves
- Midi-length hem, fitted bodycon silhouette
- High front slit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1578
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Style Warm Up Sweater Knit Dress
Cozy up this season in style! This sweater mini dress is the best of both worlds featuring cozy dolman sleeves, a surplice v-neckline, belted tie-front waist, and a bodycon silhouette. The dress is composed of soft cable and rib-knit fabric that offers plenty of stretch. Style with knee-high boots to complete the look!
Fit & Features
- Dolman sleeves
- Surplice v-neckline
- Belted tie-front waist, belt loop accents
- Bodycon silhouette, mini-length
- Cable and rib-knit sweater fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1572
Category Name: Casual Dresses
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
So Adorable Mock Neck Mini Dress
So adorable and perfect for chilly days, this long sleeve mini dress is what your closet needs! The mini dress features a mock neck and a bodycon silhouette composed of hacci rib-knit fabric with moderate stretch. Complete the look in over-the-knee boots for a movie date!
Fit & Features
- Long fitted sleeves
- Mock neck
- Bodycon silhouette
- Mini-length hem
- Hacci rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5227
Category Name: Casual Dresses
Price: $5.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Major Flirt Polka Dot Two Tone Mini Dress
Showcase your flirty side with a mini dress that brings some seriously sultry appeal! The dress features a sleeveless sweetheart neckline with mesh trim, a plunging lace-up front, bungee spaghetti straps, ruching throughout, and a stylish swiss dot design. The dress is composed of a lined mesh fabric that reveals a two-tone effect. Complete date night outfit with heels and rhinestone duster earrings.
Fit & Features
- Sleeveless sweetheart neckline, mesh trim
- Adhesive bra recommended, bungee spaghetti straps
- Lace-up front
- Ruching
- Swiss dot design
- Lined mesh fabric, two-tone color
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-4746
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale