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.
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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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Love's A Picnic Strapless Gingham A-Line Midi Dress
Be loved and admired by everyone who sees you in this gingham midi dress showcasing a flattering A-line silhouette with convenient side pockets to keep your hands warm!
Fit & Features
- Gingham print, woven fabric, tulle and woven linings
- Strapless neckline
- Back zipper closure, stretch smocked panel
- Side pockets
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3870
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweetly Sultry Floral Bodycon Midi Dress
So sweet and sultry in every way, this floral midi dress flaunts a sleek, flattering strapless neckline and bodycon fit perfect for shower celebrations or casual events.
Fit & Features
- Floral print, eyelet fabric, sewn-in knit lining
- Strapless neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000169
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Belt It Babe Strapless Denim Mini Dress
This denim tube dress understood the assignment—snatched waist, pleats for drama, and grommets for edge. The belted fit hugs you just right, and the mini hem? Major moment.
Fit & Features
- Denim fabric
- Strapless tube neckline with grommet trim
- Fitted bodice with seam detail
- Adjustable belted waist
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000171
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
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Cute Soiree Sweetheart Skater Short Dress
Keep any occasion cute in this sweetheart skater dress with adorable tie shoulder straps and a flattering drop waist seam to accentuate your figure!
Fit & Features
- Poplin woven fabric, multiple tulle and stretchy knit linings
- Sweetheart neckline
- Tie shoulder straps
- Lace-up back, stretch smocked panel
- Drop waist seam
- Skater silhouette, short-length hem
- Runs true to size
Style Number/Barcode: 05101-3986
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
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Dearest Charm Bow Print Skater Dress
Show off your charm in this bow print skater dress boasting flirty details like puff sleeves and a short-length hem perfect for styling with sandals.
Fit & Features
- Bow print, woven fabric, woven lining
- Puff short sleeves
- Square neckline, bust tie
- Stretchy smocked bodice
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3981
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Playful Mood Strapless Ruffled Skater Dress
Frolicking is expected in this playful ruffled skater dress at brunch, shower celebrations, or graduation parties!
Fit & Features
- Chiffon lined fabric
- Strapless sweetheart neckline
- Stretchy smocked bodice
- Ruffled skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3999
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Total Attraction Cutout Bodycon Midi Dress
Look and feel like a babe in this bodycon midi dress with a flirty cutout twist back design and side slit for effortless movement! Pair with cute sandals.
Fit & Features
- Texture knit fabric, stretchy knit lining
- Scoop neckline, spaghetti straps
- Twist cutout back design
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2281
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Back In Stock
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Sway With Me Halter V-Neck Paisley Skater Dress
This breezy skater dress brings the romance with a halter neckline and swingy silhouette made to float with you. Perfect for golden hour snaps, weekend wandering, or spontaneous getaways!
Fit & Features
- Paisley print, woven fabric, bust lining
- Halter V-neckline with spaghetti strap ties
- Stretchy smocked bust
- Tie back design
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5575
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bubbly and Booked Striped Collar Dress
For the girl with plans, lattes, and an effortless look. This striped dress keeps it crisp with a collar button-down design and a bubble hem that adds a little bounce to every step.
Fit & Features
- Striped print, cotton fabric, sewn-in woven lining
- Collared neckline
- Button-down closures
- Belted waist
- Bubble short hem
- Runs true to size
Style Number/Barcode: 05102-000182
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Carefree Energy Halter Bodycon Mini Dress
Be a cute sight in this halter mini dress boasting a flattering bodycon fit that perfectly flaunts your curves on vacay or a chic staycation!
Fit & Features
- Texture knit stretchy fabric
- Halter neckline, spaghetti strap ties
- Knotted bust accent
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2302
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Chic Floral Strapless Skater Dress
Live out your cottagecore dreams in this chic floral strapless skater dress, perfect for sunny days. You'll love the tie-back bow design and adorable fit-and-flare silhouette.
Fit & Features
- Swiss dot woven fabric
- Small floral pattern
- Strapless straight neckline
- Ruched high waist, tie-back bow design
- Short pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3852
Category Name: Casual Dresses
Price: $11.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Gorgeous Vibe Floral Bodycon Mini Dress
Radiate a gorgeous vibe in this bold floral print mini dress designed with a strapless neckline and bodycon silhouette to flaunt your curves.
Fit & Features
- Smooth knit fabric with knit lining, high stretch
- Large floral print
- Strapless straight neckline, no-slip strip
- Mini-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000147
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blissful Darling Halter Lace Skater Mini Dress
Twirl with bliss in this darling lace skater mini dress with a flirty halter neckline and open back. It's perfect for shower celebrations or a dressy date night!
Fit & Features
- Lace knit fabric, stretchy knit lining
- Halter V-neckline, tie closure
- Open back
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4157
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunshine Romance Floral Babydoll Dress
Indulge in the romantic allure of this floral dress for dressy events! With delicate ruffled shoulder straps and a charming babydoll silhouette, this dress offers a flirty and feminine look.
Fit & Features
- Floral print, chiffon fabric
- Square neckline
- Ruffled shoulder straps
- Babydoll silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3467
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sun And Blooms Floral Chiffon Skater Dress
Sunny weather is finally here to show off this floral chiffon skater dress with a flirty ruffled short-length hem! This dress is perfect for dressy occasions.
Fit & Features
- Floral print, chiffon fabric, stretchy knit lining
- V-neckline, back zipper and hook-eye closure
- Adjustable spaghetti straps
- Skater silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-3470
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunshine Cutie Strapless Ruffle Eyelet Mini Dress
Created for the cuties, this eyelet mini dress is a cute look for shower celebrations or casual parties! Designed to hug your form for a flattering fit, the strapless neckline and ruffled mini hem add a flirty and playful touch.
Fit & Features
- Eyelet fabric, stretchy knit lining
- Strapless neckline
- Form-hugging fit
- Ruffled layer mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000187
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Breezy Chic Belted A-Line Maxi Dress
Breezy chic, this A-line maxi dress is made with an airy gauze woven fabric accented with sheer lace insets. The belted waist leads to a long tiered flowy fit for that effortless vibe.
Fit & Features
- Gauze woven fabric with sheer lace insets
- Strapless sweetheart neckline with ruffled trim
- Bust cutout with tie-front detail, ruching, underbust seam
- Faux leather belted waist, gold metal buckle
- Maxi-length hem
- Tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6106
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Babe Striped Drop Waist Skater Dress
So darling, this striped woven skater dress is effortless perfection. The sleeveless square neckline is accented with a mini bow detail, and the drop waist design leads to a pleated fit-and-flare silhouette.
Fit & Features
- Striped woven fabric
- Sleeveless square neckline, eyelet trim, mini bow detail
- Tank shoulder straps
- Square back, zipper closure
- V-shaped drop waist
- Short pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000145
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Booked Floral Maxi Dress
Already picturing the dinner plans in this one. This tropical floral maxi dress features a soft cowl neckline and an open back that brings just the right amount of drama for your getaway lineup.
Fit & Features
- Tropical floral print, mesh-lined fabric, high stretch
- Cowl neckline
- Adjustable spaghetti straps
- Open strappy back
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000189
Category Name: Casual Dresses
Price: $9.97 $42.90
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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Coastal Chic Linen Halter Maxi Dress
Meet your vacay soulmate. This breezy maxi serves minimal effort with major impact thanks to its sleek halter neckline, open tie back, and flowy fit made for golden hour strolls or rooftop cocktails.
Fit & Features
- Linen-blend woven fabric
- High halter neckline, spaghetti strap tie
- Open back with spaghetti strap tie, lower zipper and hook-eye closure
- High side slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000026
Category Name: Casual Dresses
Price: $11.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Sweet Floral And Plaid Patchwork Mini Dress
Create the perfect weekend look in this oh-so-sweet mini dress designed with a floral and plaid patchwork pattern. The crochet bust trim and tie-front detail are dainty details you'll adore.
Fit & Features
- Woven fabric, no stretch
- Ditsy floral and plaid patchwork pattern
- Sleeveless sweetheart neckline, crochet trim and tie-front detail, ruched bust
- Adjustable spaghetti straps
- Hidden back zipper, hook-eye closure
- Mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-000178
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Girlie Lace-Up A-Line Mini Dress
Say hello to your new favorite mini dress for celebrations to brunch! Featuring flutter sleeves for a touch of flirtiness, a lace-up back for a customizable fit, and an a-line silhouette to flatter any figure.
Fit & Features
- Woven fabric, lace trims, stretchy knit lining
- Square neckline, with keyhole bust tie
- Flutter sleeves
- Lace-up back
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4108
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flawlessly Chic Strapless High Slit Maxi Dress
You'll look flawlessly chic in this textured knit maxi dress featuring a strapless neckline and high-cut side slit. Style with stiletto heels for a rooftop bar!
Fit & Features
- Sheer knit fabric, textured pattern, full-length lining
- Strapless straight neckline
- Back zipper closure
- High side slit
- Maxi-length fitted silhouette
- Runs true to size
Style Number/Barcode: 05102-000141
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free