Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and 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.
-
Cool Cat Leopard Off Shoulder Mini Dress
Leopard prints FTW. You'll be having a moment everywhere you go in the Cool Cat off shoulder mini dress!
Fits & Features
- Smocked Off Shoulder Neckline
- Roomy Cuffed Long Sleeves
- Elastic, Smocked Skirt
- Subtly Pleated, Mini-Length Hemline
- Form-Hugging Fit WIth Plenty Of Stretch
Style Number/Barcode: 05102-0397
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Smooth Charmer Velvet Mini Dress
Look...but don't touch. You'll be looking extra vivacious in the Smooth Charmer mini dress!
Fits & Features
- Scoop Neckline
- Square Back
- Fixed Spaghetti Straps
- Mini Length Silhouette
- Form-Hugging Fit I Moderate Stretch
- Smooth Velvet Composition I Metallic Snake-Inspired Print Throughout
Style Number/Barcode: 05102-0370
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Spring Fling Ditsy Floral Bodycon Mini Dress
Show off sweet flirty vibes in this adorable ditsy floral mini dress detailed with a ribbon trim and bow detail at the bust. The short bodycon silhouette will flaunt your gorgeous curves.
Fit & Features
- Textured knit fabric, high stretch
- Ditsy floral print
- Sleeveless sweetheart neckline
- Ribbon trim with bow detail at the bust
- Adjustable spaghetti straps
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5763
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Rattle Me Snake Mini Dress
We're rattled by the FIERCE look you're serving!
Fits & Features
- Spaghetti Straps
- Sweetheart Neckline With Padded Cups
- Mini Length Silhouette
- Soft Knit Fabric With Snake Inspired Print Throughout
- Fully Lined
- Curve-Hugging Fit I Ample Stretch
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0377
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Snap Snap Slay Ribbed Sweater Dress
Oh snap she came to play! This sexy sweater dress is designed with a mock neckline, long sleeves, and a mid length hem that hits right passed the knee. Dress has a side slit detailing with faux snap buttons that lead down. Composed of a ribbed knit material that offers a form fit with moderate stretch.
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small
Style Number/Barcode: 06005-0193
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Such A Dream Eyelash Knit Mini Dress
Look like a total dream babe in this adorable eyelash knit mini! The soft knit fabric has plenty of stretch for a total comfy form hugging fit.
Fit & Features
- Off the shoulder neckline
- Short sleeves
- Mid-thigh length hem
- Fuzzy eyelash ribbed knit fabric
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06005-0196
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
V Cozy Button Down Sweater Dress
Bundle up with the V Cozy sweater dress!
Fits & Features
- V Neckline I Button-Down Front
- Fitted Long Sleeves With Rolled Cuffs
- Slip Hand Pockets & Hem With Subtle Frill Design
- Detachable Waist Tie
- Midi Length Silhouette
- Ribbed Knit
- Form-Hugging Fit I Ample Stretch
Style Number/Barcode: 06005-0551
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Long Sleeve Ribbed Midi Dress
We're totally loving knit this season girl! Create some seriously cute looks with a basic midi dress!
Fit & Features
- Off The Shoulder Neckline
- V-Neck Bust
- Fitted Long Sleeves
- Ribbed
- Knit
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0391
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Days In Paradise Strapless Cutout Mini Dress
Indulge in pure paradise in this cutout mini dress! Featuring a sweetheart neckline accented with a stunning hoop and stone insert, this bodycon dress is designed to hug your every curve.
Fit & Features
- Texture knit fabric, stretchy knit lining
- Strapless sweetheart neckline with hoop and stone insert
- Padded bra cups, back zipper and hook-eye closure
- Cutout accent
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6079
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
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
-
Life Is Sweet Eyelet Bodycon Ruffle Mini Dress
The sweetest eyelet mini dress for shower celebrations, graduations, or brunch! It boasts flirty tie shoulder straps, a flattering bodycon silhouette, and a ruffled hem for cute flair.
Fit & Features
- Eyelet fabric
- Square neckline, tie shoulder straps
- Bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6006
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Ribbed Long Sleeve Knit Dress
Fall back this season with a classic knit dress to pair with your fav layers!
Fit & Features
- Mockneck
- Fitted Long Sleeves
- Ribbed
- Lined Knit
- Bust Geometric Cut Out
- Form Fit
- Moderate Stretch
Style Number/Barcode: 05102-0384
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Ruched Hour Mini Dress
This fiery number is calling your name. You'll be stopping traffic in this one!
Fits & Features
- Dual Shoulder Straps
- Square Neckline
- Ruched Drawstring
- Form Hugging Fit
- Moderate Stretch
- Fully Lined
Style Number/Barcode: 05102-0433
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Flow On Chiffon Mini Dress
Let the good times flow in this pretty mini dress!
Fits & Features
- Elastic Square Neckline With Self Ties At Center Front
- Unlined, Cuffed Long Sleeves
- Ruffle-Trim At Mini Length Hem
- Smocked Skirt
- Chiffon Composition I Fully Lined
- Form Flattering Fit I Moderate Stretch
Model is 5'8" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0448
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Off Shoulder Knit Mini Dress
There's no such thing as cold weather blues in this number. Snuggle up to this comfy and cute mini dress!
Fits & Features
- Wide, Off Shoulder Neckline
- Cuffed Quarter Length Sleeves
- Elastic Waistband
- Form-Hugging Silhouette I Moderate Stretch
- Knit Composition I Fully Lined At The Skirt
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0511
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Ribbed Knit Surplice Mini Dress
Sweater dresses are a must for all things winter wear! This knit mini will become a staple in your winter wardrobe.
Fit & Features
- Wrap front V neck and back
- Back bar detail
- Long cuffed dolman sleeves
- High waist seam
- Short, curve hugging fit
- Ribbed knit fabric | Plenty of stretch
Style Number/Barcode: 06005-0222
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
City Slicker Satin Mini Dress
A sleek mini, inspired by the trendy city girl in mind!
Fits & Features
- Cowl Neckline
- Adjustable Self Tie Shoulder Straps
- Square Back
- Satin-Like Composition I Fully Lined
- Mini Length Silhouette
- Form-Flattering Fit I Minimal Stretch
Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0350
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Can't V Bothered Sweater Dress
Chilly? Never heard of her. Stay stylishly festive and warm in the form-flattering and heavy knit Can't V Bothered sweater dress.
Fits & Features
- V Neckline & Back With Surplice Design
- Roomy, Cuffed Dolman Sleeves
- Bar Strap Accent At Back
- Removable, Waist Tie
- Hem Hits Mid Thigh
- Comfortable Form-Fit I Ample Stretch
Black: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
White & Blue: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06005-0500
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Comfy Cozy Chic Mini Dress
Comfy, cozy, and chic, the ultimate combo. This mini dress is beyond perf for fall and winter.
Fits & Features
- Turtleneck
- Long Sleeves
- Mini Silhouette
- Ribbed Knit
- Form Hugging Fit | Moderate Stretch
- No Zipper
Style Number/Barcode: 06005-0475
Category Name: Casual Dresses
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Long Sleeve Ribbed Mini Dress
Add this staple to your closet to create some seriously fab fall looks!
Fits & Features
- Turtleneck
- Long Sleeves
- Mini Silhouette
- Ribbed Knit
- Form Hugging Fit | Moderate Stretch
- No Zipper
Style Number/Barcode: 06005-0474
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Meow You're Talking Leopard Mini Dress
Satin and leopard? Matchmade in heaven. Show your sleek and wild side in the Meow You're Talking mini dress!
Fits & Features
- Cowl Neckline
- Spaghetti Straps
- Adjustable Tie At Back I Low Open Back
- Satin-Like Composition I Minimal Stretch
- Mini Length Silhouette
- Zipper Not Included
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0338
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Ruffle Up Chiffon Off Shoulder Mini Dress
Make every walkway your runway in the Ruffle Up Off Shoulder mini dress!
Fits & Features
- Elastic Off Shoulder Neckline
- Long Sleeves
- Ruffle-Trim At Cuffs, Neckline, Waist, And Hem
- Smocked Skirt And Cuffs
- Mini Length Silhouette
- Chiffon Composition
- Form Flattering Fit I Moderate Stretch
Style Number/Barcode: 05102-0506
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sleek Satin Mini Dress
Keep it sleek in stunning satin to show off those curves girl!
Fit & Features
- Square Neckline
- Tank Straps
- Satin
- Rounded Hem
- Double Lined
- Form Hugging Fit | Moderate Stretch
- No Zipper
Burgundy: Model is 5'8" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Hunter: Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0386
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sun Rays Tropical V-Neck Babydoll Mini Dress
Flaunt beachy perfection in this tropical babydoll dress with a strappy tie-back that turns heads with every wear! Style with sandals for a cute vacation look.
Fit & Features
- Tropical print, woven fabric, bust knit lining
- V-neckline, twisted bust
- Spaghetti straps
- Strappy tie-back design
- Babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000042
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free