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.
-
Smocked Sweetheart Gingham Mini Dress
Yes girl, it's the perfect daytime date dress! Perfectly pair the look with some clean white sneakers or heeled sandals!
Fits & Features
- Elastic Sweetheart Neckline & Cuffs
- Tie Design & Cut Out At The Bust
- Woven Short Sleeves I Can Be Worn Off Shoulder
- Smocking Throughout
- Mini Length Hemline With Ruffle Trim
- Gingham Print Design
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0688
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Purrfectly Fierce Smocked Mini Dress
Look purrfectly fierce in this so of the moment leopard printed mini dress! Its smocked detailing will flatter your curves.
Fit & Features
- Strapless sweetheart neckline
- Tie front detail
- Front cut out
- Stretchy smocked body
- Short, form hugging fit
- Leopard print
Style Number/Barcode: 05102-0682
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
That Girl Energy Cutout Tube Midi Dress
Steal the scene and leave them speechless. This sleek strapless midi hugs your curves with a smooth, sculpted fit perfect for date nights, parties, or whenever you’re feeling that girl energy.
Fit & Features
- Brushed knit soft fabric, knit lining, moderate stretch
- Strapless tube neckline
- Cutout back, lower ruched seam
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000176
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
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
Product Badge:- Ships Free
-
Ruched To Perfection Midi Dress
This stunning midi dress is ruched to perfection, and will look so gorgeous on you! Paired with some strappy heels, it's totally date night material.
Fit & Features
- Spaghetti straps
- Cowl neckline
- High waist
- Ruched side detailing | Drawstring at hem
- Mid-length, asymmetric hem
- Stretchy knit fabric
- Form hugging fit
Style Number/Barcode: 05101-0727
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Girly In Gingham Smocked Mini Dress
Look oh so gorgeous and girly in this gingham smocked mini dress babe! Pair with some cute wedges and you'll have a spring ready look!
Fit & Features
- Tie shoulder spaghetti straps
- Notched V neckline | Ruffle trim
- Stretchy smocked body
- Short, form hugging fit
- All over gingham print
Style Number/Barcode: 05102-0683
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Tie shoulder spaghetti straps
-
Effortless Beauty Eyelet Mini Dress
You've got that effortless beauty babe! Wear this gorg eyelet mini dress and have the perfect spring time look!
Fit & Features
- Adjustable spaghetti straps
- Wrap front V neckline
- Hidden back zipper | Hook and eye closure
- Side tie detail
- Wrap front skirt
- Eyelet detail woven fabric | No stretch
Style Number/Barcode: 05102-0686
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Mesmerizing In Mesh Lace Dress
Show off a little skin in this sexy dress! The sleek inner bodysuit provides perf coverage against the mesh skirt!
Fits & Features
- Adjustable Spaghetti Straps
- Unlined, Lace & Mesh Bodice I Underwire Bust
- Elastic Waistband
- Maxi Length Silhouette I Mesh Skirt
- Built-In Bodysuit With Dual Snap Button Closure I Cheeky Coverage
- Moderate Stretch
Style Number/Barcode: 05101-0397
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Pick Of The Bunch Floral Chiffon Skater Dress
It's finally spring and that means adding more floral additions to your wardrobe! Brighten up your look with these fresh prints!
Fits & Features
- Adjustable Shoulder Straps
- V Neckline I Back Zip With Hook & Eye Closure
- Mini Length Hem I Skater Style Silhouette
- Lined Chiffon Fabric I Floral Prints Throughout
- 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: 05101-0313
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Denim Dreamer Tie Front Dress
Look oh so dreamy in denim in this adorable tie front dress! Perf for a spring day out with your gal pals.
Fit & Features
- Collared | Half snap button down front
- Long sleeves | Single buttons to cuff
- Two buttoned chest pockets
- Tie front detail | Front waist cut out
- Two slanted pockets at the waist | Two back pockets
- Front button | Hidden zipper closure
- Short, form hugging fit
Style Number/Barcode: 05102-0435
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
New Love Ditsy Smocked Mini Dress
Something sweet, something new. Charm them all by slipping into the New Love mini dress! Pair with some sneakers for a girls' day and switch to some heels for date night with the boo!
Fits & Features
- Adjustable Spaghetti Straps
- Square Neckline
- Mini Length Silhouette
- Woven Fabric I All Over Smocking
- Ditsy Floral Print I Tiered Ruffle Design
- Form Hugging Fit I Ample Stretch
Style Number/Barcode: 05102-0522
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Crochet Chic High Low Dress
Keep it cute in crochet girl! This dress is giving us major boho vibes and perfectly pairs with your fav headband and wedges!
Fit & Features
- V-Neckline
- Floral Crochet Bodice
- Adjustable Spaghetti Straps
- Smocked Back
- High Low Silhouette| Mini Skirt Length Knit Lining
- Lightweight Woven Fabric
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05102-0617
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Ribbed Knit Mock Neck Mini Dress
The everyday sweater dress you need in your life. Add to cart!
Fit & Features
- Mock neckline
- Long fitted sleeves
- Short, curve hugging fit
- Ribbed knit fabric | Knit lining
- Plenty of stretch
Style Number/Barcode: 06002-0329
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Bring The Romance Off Shoulder Long Sleeve Skater Dress
Date night calls for a sweet and pretty look! Style with some soft curls, a cute crossbody, and sparkly finishing touches and you'll be ready for the night!
Fits & Features
-
Elasticized, Off Shoulder Neckline I Tie At Center Front
- Off Shoulder Long Sleeves I Elastic Cuffs
- Crochet Waist Design
- Mini Length, Skater Style Skirt
- Brushed Knit Design I Floral Print
- Plenty Of Stretch
Style Number/Barcode: 05101-0401
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Elasticized, Off Shoulder Neckline I Tie At Center Front
-
Ready For Tonight Chiffon Blouson Mini Dress
Ooh girl, you look so ready for a night out! Bring the drama with its off-shoulder neckline and fit-and-flare blouson sleeves!
Fits & Features
- Ruffle-Trim Square Neckline, Cuffs, Hem
- Sheer Blouson Sleeves With Circle Embroidery Detail
- Mini Length Silhouette With Drawstring At Center Front
- Smocking All Over
- Bodycon Fit I Ample Stretch
Style Number/Barcode: 05102-0560
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Lovely In Linen Smocked Mini Dress
Look oh so lovely in linen in this perf springtime mini! The smocked detailing make it all the more flattering!
Fit & Features
- Long sleeves | Smocked cuffs
- Square neck | Eyelet trim detail
- Front tie | Keyhole cut out
- Stretchy smocked skirt
- Short, ruffle hem
- Linen fabric
Style Number/Barcode: 05102-0681
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Playful In Polka Dots Mini Dress
Get a playful look in adorable polka dots with this LBD! The short puff sleeves make it all the more trendy.
Fit & Features
- Short sheer puff sleeves
- Sweetheart neckline
- Front ruched detailing
- Short, curve hugging fit
- Sheer mesh fabric with all over polka dot print
- Knit lining
- Plenty of stretch
Style Number/Barcode: 05101-0729
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Own the Moment Tube Floral Slit Bodycon Maxi Dress
This strapless bodycon maxi dress brings major drama with a bold floral print and side thigh-high slit made to steal the spotlight at a beach brunch or on vacation!
Fit & Features
- Statement floral print, slinky knit stretchy fabric
- Tube neckline
- Side slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000286
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Spring It On Floral Mini Dress
Bring on the sunny, spring weather! Look fresh in florals with the Spring It On mini dress! Wear your sleeves up or soak up some vitamin C by wearing it off the shoulder!
Fits & Features
- Short Sleeves With Elastic Shoulders & Cuffs I Can Be Worn Off Shoulder
- V Neckline I Square Back
- Keyhole Opening With Adjustable Ties
- Mini Length Silhouette
- Stretchy Woven Textured Mesh I Floral Prints
- Form Hugging Fit I Moderate Stretch
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0392
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Leopard Purrfection Satin Midi Dress
Tap into your instincts with this fiercely-inspired print! This midi dress only needs a pair of booties and dainty pieces to complete the look!
Fit & Features
- V-Neckline
- Spaghetti Straps
- Leopard Print
- Side Slit
- Lined Satin Fabric
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05101-0599
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Such A Sweetheart Mini Dress
Show off your sweet side in this must-have mini dress! Pair with block heels and layers of dainty pieces to complete your look!
Fit & Features
- Sweetheart Neckline | Padded Cups
- Short Puff Sleeves
- Double-Lined Brush Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0539
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Snake A Difference Side Tie Mini Dress
Move over LBD! Work your charm in this fiesty mini dress!
Fits & Features
-
Spaghetti Straps
- Square Neckline
- Mini Length Silhouette
- Drawstring & Ruching At Side Hem
- Knit Fabric
- Curve Hugging Fit I Plenty Of Stretch
- Zipper Not Featured
Style Number/Barcode: 05102-0537
Category Name: Casual Dresses
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Spaghetti Straps
-
Own Knit Open Back Midi Dress
Own your look bb! You know how to werk it, especially in this sultry open back knit midi dress!
Fit & Features
- Mock neckline
- Long fitted sleeves
- Open back | Twist back detail | Lower back cut out
- Curve hugging fit
- Ribbed knit fabric | Plenty of stretch
Style Number/Barcode: 05102-0656
Category Name: Casual Dresses
Price: $9.97 $36.90
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