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.
-
Keeping It Fierce Snake Mini Dress
Keep it fierce in snake print! The bodycon features an off the shoulder neckline with ruffled trim, short sleeves, a sweetheart bust, a keyhole with tie front accent, a smocked back and a mini length silhouette. Dress features a snake print to perfectly matching with your favorite solid pieces. Garment is composed of a lined satin fabric that offers a relaxed fit with slight stretch.
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0421
Category Name: Casual Dresses
Price: $9.97 $50.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Turtleneck Ribbed Knit Mini Dress
Layer away! With a trendy turtleneck and a comfy rib-knit construction, this is the perfect starting piece for your layered looks.
Fits & Features
- Turtleneck
- Long Sleeves With Thumb Holes
- Curve-Hugging Fit
- Plenty Of Stretch
- Mini Length Silhouette
- Zipper Not Included
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0422
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Tropical Print Cowl Neck Maxi Dress
Head to the tropics in a maxi dress. The vacation-worthy maxi dress features a draped cowl neck, spaghetti straps that lead to a bold open back and an all-over tropical palm leaf print. The relaxed fit waist leads to a sweeping maxi length silhouette that is accented with a daring high slit. Complete your look with clear heels to let the print speak for itself and a floppy hat.
Fit & Features
- Cowl neck
- Spaghetti straps
- Open back
- High slit, maxi length silhouette
- Tropical palm leaf print
- Smooth knit fabric
- Form hugging fit, moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 05101-0446
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Flower Up Strapless Skater Dress
Recharge your wardrobe by adding some bright floral prints! We know you'll be slaying it in the Flower Up skater dress.
Fits & Features
-
Elastic, Strapless Neckline
- Mini Length Silhouette I Skater Style Skirt
- Chiffon Fabric I Floral Print All Over
- Ruffle-Trim At Hem & Neckline
- Form Hugging Fit
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0418
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Elastic, Strapless Neckline
-
Blossom And Bloom Square Neck Skater Dress
Show that springtime glow in this skater dress! Twirl 'round and 'round and capture everyone's attention with the gorge floral prints!
Fits & Features
- Spaghetti Straps
- Square Neckline With Center Tie Front
- Mini Length Hem I Skater Style Silhouette
- Smooth Knit Fabric I Floral Print Design
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0417
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
All Over Ruffled Skater Dress
Get an adorable all over ruffled look in this pretty little skater dress.
Fits & Features
- Long Sleeves With Elastic Banded Ruffle Cuffs
- Deep V Neckline With Ruffle Trim
- Zipper & Hook And Eye Closure At Back
- Ruffle Tiered Detailing Along Flowy Skater Skirt
- Linen Composition
- No Stretch
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0419
Category Name: Casual Dresses
Price: $18.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Flirty Fleur Tie Front Mini Dress
Show off your soft side! Pretty blooms cover this flirty dress! It's the perfect mini for a day with your gals.
Fits & Features
- Spaghetti Straps
- Square Neckline With Tie Front I Empire Waist
- Mini Length Silhouette
- Knit Fabric I Floral Print
- Form Hugging Fit
Style Number/Barcode: 05101-0445
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Ruched Right In Midi Dress
Slip right into this curve-flattering midi dress. It features fixed shoulder straps, a scoop neck and back, ruching down the side seams, and a midi-length silhouette. The garment is composed of a sleek and smooth knit, and offers a moderate amount of stretch. Zipper not included.
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0411
Category Name: Casual Dresses
Price: $13.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Dreamy In Florals Tie Front Mini Dress
Bring the spring vibes in this cute and dreamy mini dress! We'd love to see you styling this with a pair of white sneakers or chunky heels!
Fits & Features
- Spaghetti Straps
- Plunging V Neckline I Bust Tie With Keyhole Opening I Square Back
- Mini Length Silhouette
- Textured Knit Fabric I Ditsy Floral Print
- Form Hugging Fit I Moderate Stretch
- Zipper Not Included
Style Number/Barcode: 05101-0442
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
One Shoulder Asymmetrical Ribbed Maxi Dress
Show off some skin in this cute AF maxi dress!
Fits & Features
- One Shoulder Strap
- Slanted Neckline
- Maxi Length I Sultry Side Slit
- Ribbed Knit
- Form Hugging I Plenty Of Stretch
Style Number/Barcode: 06005-0341
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sleeveless Leopard Chiffon Maxi Dress
Keep it sassy in spots with this pretty leopard maxi dress! It features a sleeveless bodice, a plunging wrap V neckline, adjustable spaghetti straps that lead to a strappy back design and a relaxed fit bodice that leads to a sweeping maxi length with a ruffled hem. Dress is composed of a semi sheer chiffon fabric that reveals a mini length knit lining. Garment offers a relaxed fit with a minimal stretch. Hidden back zipper closure included.
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0413
Category Name: Casual Dresses
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Floral Flirt Skater Dress
Hey bby! You'll be a total flirt in this pretty floral skater dress! Pair with some strappy sandals and a boho chic panama hat!
Fit & Features
- Spaghetti straps | V neck and back
- Ruched front | Tie closure
- Small front keyhole cut out
- High waist
- Flowy skater skirt
- Stretchy knit fabric
- Small all over floral print
Style Number/Barcode: 05102-0416
Category Name: Casual Dresses
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Season of Stripes Cutout Gauze Mini Dress
Keep it sassy in a striped dress this season to keep on-trend! Make a stunning impression for that upcoming date in a dress that features a plunging V-neckline, sexy bar waist cutouts, and a trendy striped design. Complete look with wedges and fringe earrings to channel bohemian vibes.
Fit & Features
- Sleeveless V-neckline
- Smocked waist
- Bar waist cutouts
- Striped pattern
- Mini length silhouette
- Gauze-linen fabric
- Form hugging fit, minimal stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0414
Category Name: Casual Dresses
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Meow Or Never Leopard Midi Dress
Move fast girl. Snag this purr-fect midi before it's too late!
Fits & Features
- Spaghetti Straps That Cross At The Back
- Self Ties & Keyhole Opening At Back
- Draped Cowl Neckline
- Front Slit At Midi Length Silhouette
- Stretchy Polyester Composition I Form Hugging Fit
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0408
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Ribbed Knit Off Shoulder Mini Dress
Slip into this adorable ribbed knit mini dress!
Fits & Features
- Elastic, Off Shoulder Neckline
- Unlined Long Sleeves
- Fold-Over, Overlay At Center Front
- Mini Length Silhouette
- Fully Lined, Ribbed Knit Composition I Slub Print Throughout
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0407
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Wild Feline Leopard & Tiger Ruched Midi Dress
Spotted: The purrrrrrfect midi dress! Shake up your look and add some animal print in your wardrobe.
Fits & Features
- Bungee Spaghetti Straps
- Elastic Square Neckline
- Ruched Design
- Mixed Leopard & Tiger Inspired Print
- Midi Length Silhouette
- Mesh Composition I Fully Lined
- Little Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0406
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Simply Perfect Knit Mini Dress
Get a simply perfect 'fit with this basic knit mini dress! With its fitted long sleeves and curve-hugging silhouette, this stretchy knit dress is oh-so-flattering. A definite for your next date night, keep it casual with a pair of chunky sneakers or glam it up with some bold block heels.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Short, form-hugging fit
- Ribbed knit fabric
- Plenty of stretch
Style Number/Barcode: 06002-0519
Category Name: Casual Dresses
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Floral Feeling Chiffon Off Shoulder Mini Dress
Bloom, baby! Look absolutely stunning in this floral mini dress!
Fits & Features
- Adjustable Shoulder Straps
- Off Shoulder Neckline & Sleeves
- Layered Ruffles Along Neckline & Hem
- Mini Length Silhouette
- Chiffon Fabric I Lining
- Form Hugging Fit I Minimal Stretch
Style Number/Barcode: 05101-0434
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Snake It To The Top Mini Dress
This ssstylish fierce mini dress is bound to be at the top of your wardrobe rotation!
Fits & Features
- High Neckline
- Sleeveless Bodice
- Mini Length Silhouette
- Knit Composition With Snake Print Design
- Fully Lined
- Form Fitting I Ample Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0399
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Feline This Leopard Midi Dress
Lovin' that look, girl! You're going to be feeling this mini dress as soon as you slip it on!
Fits & Features
- Adjustable Spaghetti Straps
- Cowl Neckline I Square Back
- Zipper With Hook & Eye Closure At Back
- Midi Length Silhouette With Front Slit
- Unlined, Satin-Like Fabric I Tonal Leopard Print Throughout
- Relax Fit I Minimal Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0401
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Feline Good Leopard Print Mesh Mini Dress
Whether you are out on a date night, or out with the gals you'll be feelin' good in this feline inspired leopard print mesh mini dress! Dress up with heels and hoops, or dress down with booties and a leather jacket!
Fit & Features
- Spaghetti straps
- Square neck and back
- Ruched side detailing
- Short, curve hugging fit
- Sheer mesh leopard printed fabric
- Knit lining | Plenty of stretch
- Leopard print pattern
Style Number/Barcode: 05102-0402
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Smooth Like Satin Mini Dress
It's the perfect combo of sleek & sweet. Combat the chilly temps by throwing on a knit turtleneck underneath or a chunky sweater over.
Fits & Features
-
Elastic Cord Straps
- Elastic Square Neckline With Vertical Darts At The Bust
- Mini Length Silhouette
- Fully Lined, Satin Fabric
- Curve Hugging Fit I Minimal Stretch
- Zipper Not Included
Style Number/Barcode: 05102-0405
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Elastic Cord Straps
-
She's A Plaid Girl Mini Dress
It's true. Plaid girls have more fun.
Fits & Features
- Square Neckline
- Bungee Spaghetti Straps
- Mini Length Silhouette
- Textured Knit Composition I Velvet Plaid Print Throughout
- Curve Hugging Fit I Moderate Stretch
- Zipper Not Included
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0400
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Beautifully Buttoned Ribbed Sweater Dress
Button up in this casually chic sweater dress to impress this season! It features a wrap V-neckline, long sleeves, a multi-button down accent on the left seam and a mini length silhouette. Dress is composed of an unlined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Zipper not included.Style Number/Barcode: 06005-0322
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance