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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Sweet Day Sleeveless Mermaid Denim Midi Dress
Look cute and casual wherever you go in this denim midi dress! Featuring spaghetti straps, a sweetheart neckline, a flattering mermaid silhouette, and a flared midi-length hem, this dress will have you looking and feeling amazing. Complete the look in strappy espadrille wedges.
Fit & Features
- Denim fabric, minimal stretch
- Spaghetti straps
- Sweetheart neckline
- Back zipper and hook-eye closure
- Mermaid silhouette
- Runs true to size
Style Number/Barcode: 05102-5567
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Dreamy Muse Watercolor Chiffon Flowy Midi Dress
You'll be a dreamy muse in this gorgeous watercolor chiffon flowy midi dress! The airy lined chiffon fabric is detailed with a mesmerizing watercolor print for the perf summertime vibe. The mid-length dress features a sleeveless halter neckline with a center stone accent, tie-back spaghetti straps, a partially open back for a touch of allure, and a lower-smocked back design for added stretch. The fitted high waist flows out to a gorgeous A-line silhouette with an asymmetrical hemline for beautiful movement. Style this long dress with espadrille wedges.
Fit & Features
- Watercolor print
- Sheer chiffon fabric with smooth woven lining
- Halter neckline, stone detail, tie-back straps
- Partial open back, lower stretchy smocked back
- Flowy A-line silhouette
- Asymmetrical hemline
- Runs true to size
Style Number/Barcode: 05101-3306
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darling Ditsy Floral V-Neck Mini Dress
This ditsy floral mini dress will have you dreaming of sunshine days! Flaunt your figure with the bodycon fit of this dress showcasing a flattering V-neckline, dainty spaghetti straps, a tie-front bust for added detail, and a mini-length hem on ditsy floral print mesh fabric. Complete the look in sandals and a mini tote bag.
Fit & Features
- Ditsy floral print
- Mesh fabric lined with stretchy knit
- Spaghetti straps
- Slit accent
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5571
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Enchanting A-Line Floral Chiffon Midi Dress
Have everyone under your spell in this floral chiffon midi dress as a stunning wedding guest or to attend a garden party! Featuring a square neckline with a bust tie, elasticized shoulder straps, and an A-line silhouette, this dress flatters any figure. The front slit and midi-length hem add a touch of sophistication. Complete the look in block heels and earrings!
Fit & Features
- Floral print, chiffon fabric, stretchy knit lining
- Elasticized shoulder straps
- Square neckline, bust tie
- Back zipper and hook-eye closure
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3304
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romance Dreamer Sweetheart A-Line Lace Mini Dress
Embrace your romantic side in this lace mini dress to add a whimsical allure to parties, birthdays, and dates! The sweetheart neckline and adjustable spaghetti straps flatter and give you a perfect fit, while the corset-trim fitted bodice and A-line silhouette provide a lovely silhouette along the ruffled mini-length hem. Complete the look with platform heels and a purse.
Fit & Features
- Delicate lace fabric line with stretchy knit
- Adjustable spagehtti straps
- Corset trim fitted bodice
- Ruffled mini-length hem
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05101-3302
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Coastal Dream Lace-Up Ruffled Maxi Dress
A dreamy sleeveless maxi dress perfect for styling for beach city days or coastal vacations! The scoop neckline and bust tie accentuate your figure, while adjustable spaghetti straps provide the perfect fit. The lace-up back adds a touch of charm, while the flowy ruffled silhouette and maxi-length hem exude effortless chicness! Complete the look with strappy sandals and sunglasses.
Fit & Features
- Woven fabric, short knit stretchy lining
- Scoop neckline with bust tie
- Adjustable spaghetti straps
- Lace-up back
- Flowy tiered ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5565
Category Name: Casual Dresses
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Match Sleeveless Striped Ribbed Knit Mini Dress
You and this striped knit mini dress are the perfect match for sunny days! With a playful scoop neckline and cutout back, this mini dress is a cute piece for any fun occasion. Its bodycon fit flatters your figure while the striped pattern adds a touch of quirkiness. The ribbed knit fabric offers a moderate stretch for comfortable wear. Complete the look with flat sandals.
Fit & Features
- Striped pattern
- Ribbed knit fabric with moderate stretch
- Scoop neckline
- Tank shoulder straps
- Cutout back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1940
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stroll The Beach V-Neck Floral Paisley Maxi Dress
Wherever your summer travels take you, always be in style with this casual floral paisley maxi dress! Featuring adjustable spaghetti straps and a stretchy smocked V-neckline, you'll have the perfect fit for a day in the sun. The crisscross back adds a playful touch, while the ruffled hem gives a flirty flair to the flowy silhouette. Complete the look with a cute hair accessory and sandals!
Fit & Features
- Floral paisley print, woven fabric, stretchy knit lining
- Adjustable spaghetti straps, crisscross back
- Stretchy smocked V-neckline
- Flowy silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5566
Category Name: Casual Dresses
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simple Staple Ribbed Knit Bodycon Mini Dress
Comfy and chic, this knit bodycon mini dress is the simple staple you need in your closet! Made with a stretchy ribbed knit fabric, it features a sleeveless scoop neckline, spaghetti straps, and a form-hugging fit to flaunt your curves along the bodycon silhouette. Style this mini-length dress with a denim jacket and sneakers for a cute and casual vibe.
Fit & Features
- Stretchy ribbed knit fabric
- Scoop neckline
- Spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1937
Category Name: Casual Dresses
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Escape Lace-Up Tropical Midi Dress
Have the sweetest look in this tropical midi dress for your next vacay escape! With a flattering square neckline, delicate spaghetti straps, and a lace-up back, this bodycon dress will hug your curves down to the high-cut asymmetrical midi-length hem. Complete the look in espadrille wedges.
Fit & Features
- Tropical print, lined knit fabric, plenty of stretch
- Square neckline
- Spaghetti straps
- Lace-up back
- Asymmetric high-cut hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5564
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Smell The Garden Square Neck Floral Midi Dress
Enter the fresh fragrance of this floral midi dress into your spring and summer lineup! With a square neckline and spaghetti straps, this dress will hug your curves in all the right places with its bodycon fit. The side ruched seams add more detail to this stylish midi-length dress. Complete the look in platform sneakers for a trendy allure.
Fit & Features
- Brushed knit stretchy fabric, floral print, knit lining
- Spaghetti straps
- Square neckline
- Ruched side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5562
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Icon Marble Print Mesh Bodycon Mini Dress
Show up looking stunning like the trendy icon you are in this marble print mesh mini dress! The airy lightweight sheer mesh fabric features a trendy neutral marble print to draw all the attention your way. The sleeveless crew neckline and tank shoulder straps shape the bodice of the mini-length dress, while the bodycon silhouette will flaunt your gorgeous curves. Style with lace-up stiletto heels to get drinks with the squad!
Fit & Features
- Stretchy sheer mesh fabric with knit lining
- Marble print
- Sleeveless crew neckline
- Tank straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5563
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tempting Allure Sweetheart A-Line Lace Mini Dress
A lace A-line mini dress that will captivate everyone in the room! With a playful sweetheart neckline, adjustable spaghetti straps, and an underwire bust, this dress accentuates your curves, while the A-line silhouette and ruffled tie mini-length hem add a touch of whimsy. Complete the look with a clutch for a dressy evening event.
Fit & Features
- Lace fabric lined with stretchy knit
- Sweetheart neckline, adjustable tie
- Adjustable spaghetti straps
- Underwire bust, back zipper and hook-eye closure
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3300
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Enchanting Look V-Neck Button Down Skater Dress
Your day just got sweeter in this sleeveless skater dress perfect for spring and summer occasions! This V-neck skater dress boasts adjustable spaghetti straps and button closures that allow for the perfect fit while the skater silhouette and short-length hem elevate your style. Complete the look with sandals and sunnies!
Fit & Features
- Woven fabric with lining, no stretch
- Adjustable spaghetti straps
- V-Neckline
- Button down front
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5555
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hint Of Chic Cowl Neck Knit Mini Dress
You'll love the hint of chic style this cowl neck mini dress gives your look! The soft knit fabric has a double-lined design for a smooth seamless look with plenty of stretch. The short dress is shaped with a sleeveless cowl neckline and thin tank shoulder straps. The bodycon silhouette will hug your curves along the mini-length hem. Pair with a handbag and clear heels for happy hour.
Fit & Features
- Stretchy double-lined knit fabric
- Sleeveless cowl neckline
- Thin tank shoulder straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5557
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cool Girl Chic Strapless Abstract Mesh Mini Dress
Keep your going-out look cool girl chic with this sultry strapless abstract mesh mini dress. The airy sheer mesh fabric showcases a trendy abstract print and includes a full-length soft knit lining for coverage. The strapless straight-across neckline features an elastic band for a stretchy and secure fit, while the bodycon silhouette will flaunt your stunning curves. Style this short dress with a layered necklace and lace-up heels for drinks with the girls!
Fit & Features
- Stretchy sheer mesh fabric with soft knit lining
- Abstract print
- Strapless straight elasticized neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5558
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect And Stylish Scoop Neck Ribbed Knit Midi Dress
Perfect and stylish for everyday occasions, this basic ribbed knit midi dress is just what you need for coffee dates, shopping downtown, or grabbing dinner with friends! This stunning dress features classic short sleeves, a flattering scoop neckline, and a bodycon silhouette for a sleek curve-flaunting appeal. The side slit offers movement along the mid-length hem, while the soft and stretchy ribbed knit fabric ensures all-day comfort. Style this midi dress with a casual jacket, sandals, and a crossbody bag to complete the look!
Fit & Features
- Soft, stretchy ribbed knit fabric
- Side slit
- Bodycon silhouette
- Midi-length
- Runs true to size
Style Number/Barcode: 05102-5554
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crusin' The Tropics Lace-Up Tropical Mini Dress
Cruise the tropics in this stylish tropical mini dress! Designed with a tropical palm print on knit fabric, this dress is sure to stand out on the island and boat. Featuring a V-neckline and spaghetti straps, a lace-up back that lets you customize the style, and a flattering bodycon fit. Complete the look with sunglasses.
Fit & Features
- Tropical palm print, stretchy knit fabric, sewn-in lining
- Spaghetti straps
- V-neckline
- Lace-up back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5549
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 Paradise One-Shoulder Tropical Maxi Dress
You'll be looking so pretty as you stroll the beach in paradise in this tropical maxi dress! The smooth stretchy knit fabric showcases a bold tropical print perfect for an island vacay. The long dress is shaped with a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap. The sultry ruched cutout at the waist features an adjustable drawstring for a customized look. Reveal some leg with the sexy high-cut side slit on the maxi-length silhouette. Style this slim-fit dress with espadrille wedges.
Fit & Features
- Stretchy knit fabric, knit lining at the bust
- Tropical print
- Asymmetric one-shoulder neckline, spaghetti strap
- Ruched side cutout, adjustable drawstring
- High side slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5542
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Mode Tropical Floral Mesh Maxi Dress
Activate vacay mode and radiate dreamy vibes in this alluring tropical maxi dress! Designed with an airy sheer mesh fabric with a mini-length knit lining, this maxi-length dress is accented with a blooming tropical floral print for a stunning look. It features a sleeveless square neckline, spaghetti straps, ruched detailing at the waist to accentuate your curves, and a bodycon silhouette with a thigh-high side slit to showcase some leg. Style with stiletto heels for a sunset dinner!
Fit & Features
- Tropical floral print
- Sheer mesh fabric with mini-length knit lining, plenty of stretch
- Square neckline
- Spaghetti straps
- Ruched waist, side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5543
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Natural Romancer Crew Neck Lace Mini Dress
Indulge in the effortless romance of this lace mini dress perfect for bridal showers, rehearsal dinners, and parties! This stunning dress features short sleeves, a flattering crew neckline, and a bodycon silhouette that hugs your curves. The sheer lace fabric exudes romance, while the attached knit slip lining provides comfort and coverage. Complete the look with earrings and strappy sandals.
Fit & Features
- Sheer lace fabric with stretch
- Attached slip knit lining
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5548
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lost In Love Strappy Back A-Line Mini Dress
Everyone will be lost in love once they catch sight of you in this strappy A-line mini dress! Perfect for any occasion, this dress will have you feeling fabulous. This playful A-line mini features a flattering sweetheart neckline, shoulder straps for added support, and a strappy back for flirty fun. Complete the look in block heels.
Fit & Features
- Smooth knit fabric lined with stretchy knit
- Sweetheart neckline
- Shoulder straps
- Strappy back
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5544
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Covetable Charm V-Neck Ruffled Maxi Dress
You'll covet the charm of this sleeveless maxi dress all season! With a flattering V-neckline and adjustable spaghetti straps, this dress will hug you in all the right places. The crisscross and smocked back add a trendy touch, while the flowy silhouette and ruffled long-length hem offer a breezy style. Complete the look in sandals.
Fit & Features
- Woven fabric, bust lining, no stretch
- Adjustable spaghetti straps
- Crisscross and smocked back
- Flowy silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5546
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale