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.
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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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Soiree Hour Lace-Up Ruffled Floral Midi Dress
When the cocktails are poured and the music starts playing it's time to unveil this floral chiffon midi dress! Perfect for daytime soirees or showers, this midi dress features a flattering scoop neckline adorned with adjustable spaghetti straps. The lace-up back and flowy ruffled silhouette offer a touch of trendiness to this midi-length dress! Complete the look with earrings and wedges.
Fit & Features
- Floral print, chiffon fabric lined with woven fabric
- Scoop neckline
- Adjustable spaghetti straps
- Lace-up back, zipper and hook-eye closure
- Flowy ruffled silhouette
- Runs true to size
Style Number/Barcode: 05101-3411
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flouncin' Around Strapless Ruffle Mini Dress
Show off your fun and flirty side in this strapless mini dress at parties and on dates! Featuring a figure-hugging bodycon fit, side ruched seams, and a playful ruffled mini-length hem, this dress is perfect for any occasion. Complete the look with block heels.
Fit & Features
- Double-lined smooth knit stretchy fabric
- Strapless neckline
- Bodycon fit
- Ruffled
- Runs true to size
Style Number/Barcode: 05102-5771
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flattering Look A-Line Ruffled Mini Dress
This A-line mini dress gives you a flattering look for every social event on your calendar! The V-neckline adds a touch of elegance to this fun, versatile piece. Perfect for a variety of occasions, this dress will keep you looking stylish. Complete the look with dainty earrings.
Fit & Features
- Soft model-blend knit fabric, lined, moderate stretch
- V-neckline
- A-Line silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5769
Category Name: Casual Dresses
Price: $7.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Sweetie Open Back Bow Skater Dress
Arrive like the stunning sweetie you are in this short skater dress as the bride-to-be, graduate, or birthday girlie! This dress features a square neckline and shoulder straps, with an attention-grabbing open back and statement bow detail. The drop waist skater silhouette is flattering, and the short-length hem is perfect for showing off your legs. Complete the look in block heels.
Fit & Features
- Woven fabric, tulle and stretchy knit lining
- Square neckline, shoulder straps
- Open back, statement bow
- Back zipper and hook-eye closure
- Drop waist seam, skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3410
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Never A Dull Moment Strapless Cutout Maxi Dress
Bring a stunning look in this strapless maxi dress for your look-back-it moment! The strapless neckline and cutout bust add a touch of allure, while the strappy back and form-hugging fit emphasize your figure. With a center-back slit, you'll be able to move in style. Complete the look with earrings and a clutch!
Fit & Features
- Rib knit fabric, sewn-in knit lining, moderate stretch
- Strapless neckline
- Cutout bust, strappy back
- Form-hugging fit
- Center back slit
- Runs true to size
Style Number/Barcode: 05102-5766
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutest Spirit Short Sleeve Knot Tie Mini Dress
This short sleeve mini dress is the cutest for casual outings! Made from soft and stretchy rib knit fabric, this dress will keep you comfy and stylish all day long. With a flattering bodycon fit and a unique front knot tie detail, this dress exudes charm. The asymmetrical mini-length hem adds a touch of playfulness, making this a must-have. Complete the look in platform sneakers.
Fit & Features
- Rib knit fabric, moderate stretch
- Crew neckline
- Bodycon fit
- Front knot tie detail
- Runs true to size
Style Number/Barcode: 05102-5762
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Style Leopard And Floral Print Mini Dress
Create a weekend look exuding trendy style with this multi-print mini dress! The stretchy sheer mesh fabric is detailed with a leopard and rose print for a sweet and sassy vibe. The short dress features a sleeveless V-neckline accented with a dainty sheer lace trim, spaghetti straps, and a flowy A-line silhouette with a mini-length hem. Style with cowgirl boots!
Fit & Features
- Leopard and rose-print
- Stretchy sheer mesh fabric with knit lining
- V-neckline with sheer lace trim
- Spaghetti straps
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5764
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Baby Got Open Back Poplin Woven Mini Dress
Get ready to turn heads in this open back poplin woven mini dress! This bodycon mini dress features a square neckline, spaghetti tie straps, and a spaghetti tie back strap for a playful twist along the sultry open back. Made with a lightweight poplin woven fabric, this dress is perfect for hot days and even hotter nights! Complete the look in heeled sandals and a purse.
Fit & Features
- Poplin woven fabric lined with stretchy knit
- Spagehtti tie straps and back strap
- Open back
- Hidden side zipper and hook-eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5760
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Upgrading V-Neck Lace Up Bodycon Mini Dress
Upgrade your style with this sleeveless mini dress for weekend plans! The sleek V-neckline and spaghetti straps accentuate your feminine figure, while the front lace-up and slit add a touch of allure to the mini-length hem. Complete the look with a sleek layered necklace.
Fit & Features
- Stretchy ribbed knit fabric
- Spaghetti straps
- V-neckline
- Lace-up front and slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-2004
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Chic Sleeveless Wrap Mini Dress
You'll look forever chic in this sleeveless wrap mini dress perf for everyday styling! Designed with a stretchy brushed knit fabric, it features a double-lined design at the top for added coverage. The mini-length dress is shaped with a square neckline, thin tank shoulder straps, a faux wrap-front with the cutest tie detail at the waist, and a form-hugging fit to showcase your curves. Pair with slip-on sandals.
Fit & Features
- Stretchy brushed knit fabric, double-lined top
- Square neckline
- Tank straps
- Faux wrap-front with tie detail
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5761
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
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Charming Presence Strapless Slit Floral Maxi Dress
Your presence will always be charming in this ditsy floral maxi dress at wedding showers, brunch, or casual parties! Adorned in a stunning disty floral print, this strapless dress features a ruffle trim neckline and padded bra cups for flattering support. The curve-hugging silhouette, front slit, and maxi-length hem create a captivating look, while the brushed knit stretchy fabric ensures comfort. Pair with earrings and strappy sandals.
Fit & Features
- Ditsy floral print
- Brushed knit stretchy fabric
- Padded bra cups
- Front slit
- Curve-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5541
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elevated Chic Off-The-Shoulder A-Line Mini Dress
Elevate any casual day in this off-the-shoulder mini dress! This stunning dress features a twisted bust accent for a trendy touch, an A-line silhouette, and a mini-length hem that creates a flattering fit on the smooth knit-lined fabric. Complete the look with luxe earrings for a dinner party!
Fit & Features
- Smooth knit lined fabric, moderate stretch
- Off-the-shoulder neckline
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5755
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Serving Vibes Cutout Geometric Mesh Maxi Dress
Serve major vibes in this geometric mesh maxi dress out by the beach this weekend or for a getaway! The square neckline, adjustable spaghetti straps, and form-hugging fit show off your curves while the cutout sides and back add a touch of sass. Complete with a center-back slit and maxi-length hem for effortless movement. Style this sleeveless dress with earrings and sandals.
Fit & Features
- Geometric print, mesh fabric lined with stretchy knit
- Adjustable spaghetti straps
- Square neckline
- Cutout sides and back
- Form-hugging fit
- Center back slit
- Runs true to size
Style Number/Barcode: 05102-5759
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Deets Cap Sleeve Open Twist Back Midi Dress
This crew neck midi dress may look basic from the front but the open back reveals sultry deets! Featuring classic cap sleeves and a twisted open back design to flaunt some skin, and a bodycon silhouette that hugs your curves. Complete the look with a clutch for a dinner party!
Fit & Features
- Brushed knit fabric lined with stretchy knit
- Crew neckline
- Twisted open back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5754
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Allure Strapless Ruffled Skater Dress
Give off a flirty allure in this adorable skater dress at summer parties! Designed with a stretchy knit fabric, the short dress features a strapless straight-across neckline, ruching at the waist, and a double-layered ruffled skater silhouette for a sweet and sassy look. Style with a dainty necklace and sneakers for a casual vibe.
Fit & Features
- Stretchy knit fabric lined with knit
- Strapless straight neckline
- Ruched waist
- Double-layered ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5758
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweeten The Occasion V-Neck Bow Lace Mini Dress
No matter the occasion, you'll always look sweet in this lace mini dress! With its faux suede spaghetti straps and V-neckline trim adorned with a bow tie, this dress offers a bodycon fit and a mini-length hem for a flattering and stylish look. Complete the look in a crop denim jacket.
Fit & Features
- Lace fabric lined with stretchy knit
- Faux suede spaghetti straps and V-neckline trim with bow
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5752
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ahead Of The Curve Crew Neck Bodycon Mini Dress
A sleeveless mini dress that's ahead of the curve in every way! With a flattering bodycon fit and a mini-length hem, this dress will accentuate your curves in all the right places. The crew neckline and side ruched seam add unique details to this stylish dress. Complete the look with a crop jacket and sandals for any plans!
Fit & Features
- Slinky knit fabric lined with stretchy knit
- Crew neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5753
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swoon Over You Strapless Lace Mini Dress
This stunning strapless lace mini dress will make everyone swoon over your beauty at summer parties! Crafted with an airy sheer lace fabric with a knit lining for coverage, this mini-length dress is the charming style you need for the season. It features a strapless straight-across neckline with a dainty trim, a ruched seam to accentuate your curves leading to an adjustable drawstring and side slit, a ruffled hem for a flirty vibe, and a bodycon fit to flaunt your figure. Complete your look with hoop earrings and espadrille sandals.
Fit & Features
- Sheer lace fabric with knit lining, moderate stretch
- Strapless straight neckline
- Ruched seam, adjustable drawstring
- Side slit
- Ruffled hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3405
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Admire You Scoop Neck Layered Lace Mini Dress
Everyone will admire you in this lace mini dress perfect for any plans. Designed with layered sheer lace fabric, this dress is a total flirt. The adjustable spaghetti straps create a perfect fit, while the delicate scoop neckline enhances the bodycon fit and mini-length hem. Complete the look with a dainty necklace.
Fit & Features
- Layered sheer lace fabric with plenty of stretch
- Adjustable spaghetti straps
- Scoop neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5750
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Follow The Sun Lace-Up Tropical Midi Dress
Follow the sun to your next destination in this tropical midi dress! This bodycon dress flatters your figure with a square neckline, spaghetti straps, and a lace-up back. The side ruched seam and slit add a touch of chic to the midi-length hem. Complete the look in sunglasses and sandals!
Fit & Features
- Tropical print, stretchy knit fabric, bust lining
- Square neckline
- Spaghetti straps
- Lace-up back
- Bodycon silhouette
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5745
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty In Italy Halter Button Striped Mini Dress
Look pretty strolling the streets of Italy in this striped mini dress for a darling allure! With a halter V-neckline and tie-front bust, this dress is perfect for showing off your curves. The front button-down closures add a flirty touch, while the mini-length hem keeps stylish. Complete the look in trendy sandals and sunglasses!
Fit & Features
- Striped pattern, linen blend fabric, no stretch
- Halter V-neckline with tie closure
- Tie-front bust, button-down closures
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5741
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunshine On My Mind Strapless Tropical Skater Dress
This tropical skater dress will inspire sunshine on your mind! Perfect for vacations or a beach day, this strapless dress features a stretchy waist leading to the skater silhouette and a flirty ruffled mini-length hem. Complete the look in espadrille wedges.
Fit & Features
- Tropical palm print, gauze woven fabric, bust lining
- Strapless neckline
- Skater silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5744
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Thoughts Sleeveless Cutout Crochet Maxi Dress
Get summer vibes in an instant wearing this crochet maxi dress perfect for vacation or strolling the boardwalk! Featuring a flattering square neckline, spaghetti straps, and a stunning cutout back with an adjustable drawstring insert and a front slit for movement along the maxi-length silhouette. Complete the look with sunglasses and sandals.
Fit & Features
- Crochet knit fabric lined with stretchy knit
- Spaghetti straps
- Square neckline
- Cutout back, adjustable drawstring insert
- Front slit
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5742
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale