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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Dose Of Sweetness Bodycon Floral Mini Dress
Ditsy florals add sweetness to this bodycon mini dress you'll adore for casual summer plans! Designed with a sheer eyelet knit fabric with a knit lining, this dress offers plenty of stretch for comfortable wear. It features adjustable spaghetti straps, a sleeveless square neckline with a dainty lace trim, ruching at the bust accented with a mini flower detail, and a flattering bodycon fit with a mini-length hem. Complete the look with earrings and sneakers.
Fit & Features
- Ditsy floral print
- Sheer eyelet knit fabric with knit lining, plenty of stretch
- Adjustable spaghetti straps
- Square neckline, dainty lace trim
- Ruched bust with mini flower detail
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5730
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fun And Games Tie Strap Bodycon Floral Mini Dress
This floral mini dress is here for fun and games this summer! Perfect for casual weekend fun, this dress features spaghetti strap ties, a sweetheart neckline, and all-over ruched seams that accentuate your curves along the bodycon fit. Complete the look with a trendy purse.
Fit & Features
- Floral ditsy print, brushed knit fabric
- Spaghetti strap ties
- Sweetheart neckline
- Ruched bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5728
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Breezy Look Ruffled Cutout Woven Maxi Dress
Create a breezy-chic look with this woven maxi dress that will prove to be a summer staple! Designed with a lightweight woven fabric accented with ruffled trims, the long dress features a sleeveless square neckline with a keyhole cutout and tie-front detail, adjustable spaghetti straps for a customized fit, and dual cutouts at the stretchy smocked waist that lead to an open lower back. The tiered flowy A-line silhouette will give you an effortlessly pretty look. Style with strappy sandals.
Fit & Features
- Woven fabric, ruffled trims, short knit stretchy lining
- Square neckline, keyhole cutout with tie-front
- Adjustable spaghetti straps
- Stretchy smocked waist
- Dual cutouts leading to open lower back
- Tiered flowy A-line fit
- Runs true to size
Style Number/Barcode: 05102-5729
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fabulous Destination Tropical Cowl Neck Maxi Dress
Look fabulous heading to your destination in this tropical maxi dress for the cutest look on the island or beach resort! The cowl neckline creates a flattering drape and spaghetti strap tie while the low cowl back adds a touch of allure. The flowy maxi silhouette will make you feel like you're on a tropical escape! Complete the look in sunnies.
Fit & Features
- Tropical palm print, stretchy knit fabric
- Cowl neckline
- Low cowl back, spaghetti strap tie
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5727
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Modern Romance Sleeveless Lace-Up A-Line Midi Dress
Designed for a modern-day romance, this sleeveless woven midi dress is perfect for day dates! The sweetheart ruched neckline and adjustable straps are flattering, while the lace-up design cinches your waist for a beautiful silhouette. The front slit adds a touch of allure to this A-line midi-length dress. Complete the look in strappy wedges.
Fit & Features
- Texture woven fabrication with a woven lining
- Sweetheart neckline, ruched bust, dainty lace trim
- Adjustable straps
- Lace-up waist, stretchy smocked back
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5722
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Best Feeling Scoop Neck Cutout A-Line Midi Dress
There's nothing better than enjoying a sunny day in this scoop neck midi dress! With adjustable straps and a stretchy smocked bodice with a flirty cutout, this dress offers the perfect look for any occasion. The A-line silhouette and midi-length hem add a touch of playful style. Complete the look with dainty earrings and sandals.
Fit & Features
- Modal blend woven fabric with lining
- Adjustable spaghetti straps
- Scoop neckline
- Stretchy smocked bodice with cutout
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5718
Category Name: Casual Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Make Hearts Flutter Short Sleeve Cutout Maxi Dress
You'll instantly be crushing on this maxi dress perfect for weekend dinner parties or vacation! The flutter sleeves and plunging neckline create a playful vibe, while the elasticized waist and side cutouts show a hint of skin along the flowy maxi-length silhouette. Complete the look in strappy sandals.
Fit & Features
- Gauze woven fabric, short knit stretchy lining
- Flutter short sleeves
- Plunge V-neckline and V-cut back
- Elasticized strappy waist with side cutouts
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5719
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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To Be Adored Scoop Neck Floral Lace Mini Dress
You're certain to be adored in this floral lace mini dress wherever you go! The scoop neckline with a bust tie adds a touch of feminine charm while the adjustable spaghetti straps provide a perfect fit. Its bodycon silhouette and mini-length hem accentuate your curves, making you feel confident and stylish. Complete the look with a mini handbag.
Fit & Features
- Ditsy floral print, lace fabric lined with stretchy knit
- Adjustable spaghetti straps
- Scoop neckline with bust tie
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5717
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Follow Your Heart Sleeveless Ruffled Lace Maxi Dress
Follow your heart and it'll lead you to this lace maxi dress! Perfect for bridal showers, dressy brunches, or parties. This sleeveless dress brings an allure of romance in a square neckline with adjustable spaghetti straps, a stretchy smocked bodice, and a tiered ruffled silhouette. Complete the look in strappy heeled sandals.
Fit & Features
- Lace fabric, stretchy knit lining
- Adjustable spaghetti straps
- Square neckline
- Tiered ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-3382
Category Name: Casual Dresses
Price: $28.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Talking Sweet One-Shoulder Cutout Eyelet Lace Dress
Dress to impress in this sweet one-shoulder cutout eyelet lace dress guaranteed to turn heads as the lovely bride-to-be or graduate! Made from eyelet lace fabric, this bodycon dress will hug your curves in all the right places. This stunning mini-length dress features a trendy one-shoulder neckline, a flirty puff sleeve, and a sultry side drawstring cutout so you can customize the look. Style this dress with sandals and a tote bag.
Fit & Features
- Eyelet lace fabric lined with stretchy knit
- Drawstring side cut-out
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5715
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sure To Love Floral Woven Puff-Sleeve Skater Dress
You'll love wearing this sweet floral puff-sleeve skater dress all summer long! The lightweight woven fabric is detailed with a soft floral print for a pretty feminine look. The short dress features a scoop neckline with ruching and a tie-front accent, short puff sleeves with elastic cinched hems, a stretchy smocked high waist, and an adorable fit-and-flare silhouette with a ruffled hem for a flirty vibe. Style with sneakers for a cute and casual outfit.
Fit & Features
- Floral print
- Woven fabric with smooth woven lining
- Ruched scoop neckline with tie-front detail
- Short puff sleeves with elastic cinched hems
- Stretchy smocked high waist
- Fit-and-flare silhouette, ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5716
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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True Devotion Strapless Ruffle Skater Mini Dress
Express your true devotion to flirty style in this strapless skater dress perfect for strolling a beach city or a brunch! Featuring a flattering strapless neckline with a tie and stretchy elasticized bands for a comfortable, secure fit. The skater silhouette and ruffled mini-length hem add a touch of flirty fun. Complete the look in strappy sandals.
Fit & Features
- Cotton woven fabric with non-stretch lining
- Strapless neckline with tie
- Skater silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5711
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Getaway Bound Cutout Tropical Mesh Midi Dress
You'll be ready for your trip with this tropical mesh midi dress! This dress features a square neckline, spaghetti straps, and a bodycon fit for a flattering silhouette. The side cutout drawstring adds a touch of fun while the side slit and midi-length offer a sultry feel. Complete the look in trendy sandals.
Fit & Features
- Tropical palm leaf print
- Mesh fabric, stretchy knit lining
- Spaghetti straps
- Square neckline
- Side cutout drawstring
- Bodycon fit, side slit
- Runs true to size
Style Number/Barcode: 05102-5710
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Special Stunner One-Shoulder Cutout Ombre Maxi Dress
Leave everyone in awe when you're in this ombre maxi dress for sunset cocktails! Featuring a unique one-shoulder neckline with an adjustable spaghetti strap and flirty side cutout, this dress hugs your curves and shows off your legs with a high-side slit along the maxi-length hem and form-hugging silhouette. Complete the look with sparkly bracelets.
Fit & Features
- Ombre mesh fabric, stretchy knit lining
- One-shoulder neckline, adjustable spaghetti strap
- Side cutout
- High side slit
- Form-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5708
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Blis Sleeveless Bodycon Knit Midi Dress
Sit back and watch the compliments roll in when you're seen in this knit midi dress over the weekend! Crafted from a unique knit fabric offering a stretchy knit lining for comfort. It features adjustable spaghetti straps, a square neckline with a flirty bust tie, and a flattering bodycon midi-length silhouette. Complete the look in strappy sandals and a purse.
Fit & Features
- Unique knit fabric, stretchy knit lining
- Adjustable spaghetti straps
- Square neckline, bust tie
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5712
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Truly Charming Sleeveless A-Line Mini Dress
Unlock a truly charming style in this sleeveless mini dress at BBQs to summer picnics! Features a square neckline and adjustable spaghetti straps for the perfect fit. Its A-line silhouette flatters every figure, and the mini-length hem adds flirtatiousness. Complete the look with sunglasses and wedges.
Fit & Features
- Woven fabric, minimal stretch
- Square neckline
- Adjustable spaghetti straps
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5704
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Remarkable Vibe One Shoulder Printed Mesh Mini Dress
This mini-length dress features a flattering one-shoulder neckline and a bodycon silhouette. The stretchy mesh-lined fabric boasts a multi-print design that keeps your style fresh.
Fit & Features
- Multi-print, mesh-lined fabric, moderate stretch
- One-shoulder neckline
- Shoulder strap
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5701
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feel The Romance Sweetheart Button Lace Trim Maxi Dress
Instantly feel the romance of this sleeveless maxi dress for a chic and breezy look at showers or parties! It has a sweetheart neckline, adjustable straps, and a ruched bust, so it effortlessly highlights your figure. The button accents and sheer lace trims add delicate touches, while the high waist and flowy maxi silhouette create a flattering and ethereal look. Style this maxi dress with trendy sandals and earrings.
Fit & Features
- Airy woven fabric, short woven lining, no stretch
- Sweetheart neckline
- Adjustable spaghetti straps
- Button and sheer lace trim accents
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5706
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Jetset Babe One Shoulder Tropical Maxi Dress
Jetset off on vacation like a babe in this tropical maxi dress! With a flirty and flattering one-shoulder neckline, ruched seams, and a bodycon silhouette, you'll be turning heads. Plus, the side slit and maxi-length hem add a touch of allure. Complete the look in sandals and sunglasses.
Fit & Features
- Tropical palm leaf print, stretchy knit
- One shoulder neckline
- Bodycon silhouette
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5702
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Vacation Long Sleeve V-Neck Cutout Mini Dress
This V-neck mini dress pairs perfectly with your next vacation or pool party! This playful and stylish dress features long sleeves with flare cuffs, a V-neckline with a hoop insert, and cutout details on the bodice and back. Its bodycon fit and mini-length hem will highlight your curves while you explore exotic destinations or the resort bar! Complete the look with sunnies.
Fit & Features
- Texture knit fabric, sewn-in knit lining, minimal stretch
- V-Neckline with hoop insert
- Cutout bodice and back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5705
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Out Of Town Strapless Floral Crepe Mini Dress
The perfect floral crepe mini dress to take with you out of town! Boasting a strapless neckline, this mini-length dress has a trendy contrast foldover design and a bodycon silhouette that flatters your curves. Complete the look in sandals and sunnies!
Fit & Features
- Floral print, crepe fabric lined with stretchy knit
- Contrast foldover design
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-3364
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Colorful Essence Sleeveless Marble Print Mini Dress
You'll be the most colorful babe on the scene in this marble print mini dress! Perfect for art gallery openings and date nights, this sleeveless dress boasts a square neckline, adjustable spaghetti straps for a custom fit, and side ruched seams and a bodycon fit to accentuate your curves. Complete the look with a clutch and stiletto heels.
Fit & Features
- Marble print, mesh fabric, sewn-in knit lining, moderate stretch
- Square neckline
- Adjustable spaghetti straps
- Ruched side seams
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5691
Category Name: Casual Dresses
Price: $42.90
Availability: Out of Stock
Product Badge:- Sale
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Bold Allure One-Shoulder Cutout Waist Knit Midi Dress
Bring the bold allure to your summer 'fits with this sultry cutout waist midi dress! Made with a lined stretchy ribbed knit fabric, the mid-length dress features a sleeveless one-shoulder neckline and a tank strap with a trendy twisted-back design. The asymmetric goes around the waist, accented with a chic O-ring cutout at the front. The midi-length hem is detailed with a high-cut side slit along the figure-flaunting bodycon silhouette. Style with lace-up sandals for a weekend getaway!
Fit & Features
- Stretchy ribbed knit fabric, knit lining
- One-shoulder neckline, tank strap with twisted-back design
- Asymmetric waist cutout
- Front O-ring cutout
- High side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5697
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stun And Only Mock Neck Floral Mesh Mini Dress
Leaving people speechless is easy with this floral mesh mini dress! Crafted from a mesh fabric showcasing a cute floral print perfect for mixing it up this season. This dress features sheer fitted long sleeves with slit flare cuffs, a stylish mock neck, and a flattering bodycon fit. The mini-length hem adds a touch of sass to this stunning dress. Complete the look in stiletto heels.
Fit & Features
- Floral print, mesh fabric, stretchy knit lining
- Mock neck
- Sheer long sleeves with slit flare cuffs
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5698
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale