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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Casual Staple Wrap-Front Mini Dress
Update your wardrobe with this cute and casual mini dress that is a stylish staple! It features a crew neckline, short sleeves, a trendy wrap-front design at the waist with a tie closure, a form-hugging fit, and a mini-length hem. The soft brushed knit fabric offers plenty of stretch for comfort. Complete the look with ankle booties.
Fit & Features
- Crew neckline
- Short sleeves
- Wrap-front design at the waist, tie closure
- Form-fitting silhouette
- Mini-length hem
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5007
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Getaway Tropical Print Midi Dress
Get a gorgeous look for your next vacay getaway with this alluring tropical print midi dress. It features a sleeveless square neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, ruching at the waist, a midi-length hem with an asymmetric high side slit, and a curve-hugging silhouette. The all-over palm leaf pattern on the stretchy knit fabric will bring those tropical vacation vibes. Style with cute wedges.
Fit & Features
- Sleeveless square neckline, spaghetti straps
- Open back, cross-back lace-up strappy design, tie closure
- Ruched detailing at the waist
- Midi-length hem, asymmetric high side slit
- Curve-hugging silhouette
- Tropical palm leaf print, knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5008
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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That 70s Chick Retro Print Mini Dress
Inspired by the groovy era, you'll look like a cute chick in this retro mini dress perfect for parties! It features a sleeveless square neck, spaghetti straps, side ruched seams that hug your figure, a bodycon silhouette, and a geometric-retro print design. Complete the look with bold earrings.
Fit & Features
- Sleeveless square neck, spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Geometric-retro print
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5005
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Time To Slay Bodycon Midi Dress
It's your time to slay in this simple yet chic bodycon midi dress! It features an asymmetrical boat neckline with a partial off-the-shoulder design, long fitted sleeves with thumb hole accents, a midi-length hem, and a curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Style with strappy heels.
Fit & Features
- Asymmetrical boat neckline, partial off-the-shoulder design
- Long fitted sleeves, thumb hole accents
- Midi-length hem
- Curve-hugging fit
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5006
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Escape With Me Tropical Mini Dress
Escape to an island getaway with this tropical mini dress perfect for a sunset dinner by the shore! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a knotted bust accent, and a bodycon silhouette. The smooth lined knit fabric offers a moderate stretch. Complete the look in trendy sandals.
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Knotted bust accent
- Bodycon silhouette, mini-length hem
- Tropical print
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5004
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Showcase Your Charm Sheer Lace Maxi Dress
Showcase your charm in this airy sheer lace flowy maxi dress. It features a V-neck and back with wrap designs, tie-back straps, short billowy bell sleeves with slit accents, a stretchy smocked high waist, a partial button-down design leading to a high front slit, a maxi-length silhouette with an adorable ruffled hem, and an A-line fit. The dainty sheer lace fabric includes a partial mini-length woven lining. Complete your look with espadrille wedges for a summer party.
Fit & Features
- V-neck and back, wrap designs, tie-back straps
- Short bell sleeves, slit accents
- Stretchy smocked high waist
- Partial button-down design, high front slit
- Maxi-length silhouette, ruffed hem, A-line fit
- Sheer lace fabric, partial mini-length woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-5003
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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True Colors Marble Print Mini Dress
Show your true colors of style in this marble print dress perfect for casual plans! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a mini-length hem. Style with trendy heels and a denim jacket to complete the look!
Fit & Features
- Sleeveless square neck, spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Marble print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5000
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Striking Style Marble Print Midi Dress
Showcase a striking style and a stunning look in this curve-hugging marble print midi dress! It features a sleeveless cowl neckline, spaghetti straps, an asymmetric midi-length hem creating a sultry thigh-high side slit, a bodycon silhouette, and an all-over alluring marble print pattern. The smooth knit fabric offers plenty of stretch. Complete the look with clear mules.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Asymmetric midi-length hem, high side slit
- Bodycon fit
- Marble print
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5001
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Catching Flights O-Ring Halter Midi Dress
Catch flights not feelings! This halter midi dress is bringing those getaway vibes. It features a sleeveless halter neckline with a tank strap, an O-ring bust insert with a cutout accent and a form-hugging silhouette. Complete the look in cute flat sandals for a sunset cocktail hour!
Fit & Features
- Sleeveless halter neckline, tank strap
- O-ring bust insert, cutout accent
- Form-hugging silhouette
- Midi-length hem
- Stretchy rib knit fabric, knit lining
- Runs true to size
Style Number/Barcode: 05102-5002
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Romance Tropical Print Maxi Dress
Give off a romantic allure at your sunset dinner date in this form-hugging maxi dress! It features a sleeveless cowl neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, a floor-length hem with a sultry asymmetric high side slit to showcase some leg, ruched detailing, and an all-over tropical palm leaf print. Style with hoop earrings and espadrille wedges.
Fit & Features
- Sleeveless cowl neckline, spaghetti straps
- Open back, cross-back lace-up strappy design, tie closure
- High waist seam, floor-length hem, asymmetric high side slit
- Form-hugging fit, ruched detailing
- Tropical palm leaf print
- Knit fabric. lined bust, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4996
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Soak Up The Sun Tropical Print Maxi Dress
You'll be ready for those relaxing beachside strolls in this gorgeous tropical print maxi dress. It features a sleeveless V-neckline, spaghetti straps, an alluring backless design, a flowy, floor-length hem, and a thigh-high front slit. The smooth knit fabric showcases a tropical palm leaf print. Style with slip-on sandals.
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Backless design, single lattice strap
- Flowy floor-length hem, high front slit
- Tropical palm leaf print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4997
Category Name: Casual Dresses
Price: $5.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Getaway Bound Tropical Cowl Neck Maxi Dress
You'll be ready for your getaway with this tropical maxi dress in your carry-on! It features a sleeveless cowl neckline, spaghetti straps that crisscross in the back, a curve-hugging slim silhouette, and a flirty front slit. Complete the look in espadrille wedges and sunnies!
Fit & Features
- Sleeveless cowl neckline, bust lining
- Spaghetti straps, crisscross back
- Curve-hugging, slim silhouette
- Front slit
- Maxi-length hem
- Tropical print, smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4999
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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She Knows Style Eyelet Lace Skater Dress
Breeze into every occasion in this stylish eyelet lace skater dress! It features a sleeveless square neck, spaghetti straps, a ruched bust, and a flattering fit and flare short-length hem. The sheer eyelet lace fabric includes a full knit lining and offers plenty of stretch. Complete the look with statement block heels for a wedding shower or birthday lunch!
Fit & Features
- Sleeveless square neck, spaghetti straps
- Ruched bust
- Fit and flare, skater silhouette
- Short-length hem
- Sheer eyelet lace fabric, full knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4998
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lovely In Floral Lace Trim Midi Dress
You'll be a sight for sore eyes in this lovely floral midi dress - a flirty option for garden weddings, dressy birthdays, and day dates! The sleeveless dress features a sweetheart neckline with a romantic eyelash lace trim, adjustable spaghetti straps, a curve-hugging bodice, and a slit accent along the flowy hem. Complete the look with earrings and heels.
Fit & Features
- Sleeveless sweetheart neckline, padded wired bust, eyelash lace trim
- Adjustable spaghetti straps, back zipper, hook and eye closure
- Curve-hugging bodice
- Slit accent, midi-length hem, A-line silhouette
- Delicate floral print
- Sheer woven fabric, full lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2228
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Picnic Time Gingham Mini Dress
You'll be the cutest girl in this gingham casual dress at the picnic! It features ruffle trim puff short sleeves, a sweetheart neck with a lace-up bust, a bodycon silhouette, and a mini-length hem on stretchy rib knit fabric. Complete the look in sandals.
Fit & Features
- Ruffle trim puff short sleeves
- Sweetheart neck, lace-up bust
- Bodycon silhouette
- Mini-length hem
- Gingham print
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-4995
Category Name: Casual Dresses
Price: $27.90
Availability: Out of Stock
Product Badge:- Sale
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Flirtatious Charm Cutout Midi Dress
Say hello to this adorable cutout midi dress that will bring those cute and fun vibes! This midi dress features an off-the-shoulder sweetheart neckline and short fitted sleeves. The center knot detail at the bust with a tie-front adds a charming touch, while the dual waist cutouts add a hint of playfulness. The midi-length hem with a high side slit showcases your legs for a sassy look. With its form-hugging silhouette and ribbed knit fabric offering plenty of stretch, this dress ensures both comfort and style. Complete your outfit with a pair of sandals to bring that flirtatious charm!
Fit & Features
- Off-the-shoulder sweetheart neckline
- Center knot detail at the bust, tie-front design
- Dual waist cutouts
- Midi-length hem, high side slit
- Form-hugging fit
- Ribbed knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4992
Category Name: Casual Dresses
Price: $6.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Freshly Picked Floral Skater Dress
Freshly picked from the garden. This floral skater dress is ready for your springtime festivities! It features short puff sleeves, a sweetheart neck with a tie-front closure, an open lace-up back design, and a tiered ruffled short-length hem. Complete the look in trendy new mules.
Fit & Features
- Short puff sleeves
- Sweetheart neck, tie-front closure
- Open lace-up back design
- Skater silhouette
- Tiered ruffle short-length hem
- Watercolor floral print, non-stretch fabric, woven lining
- Runs true to size
Style Number/Barcode: 05102-4993
Category Name: Casual Dresses
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Color Me Cute Linen V-Neck Skater Dress
Color you cute in this linen skater dress perfect for layering over your swimsuit on a beach day or pool party! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty ruffled underbust trim, and a tiered color block ruffled short-length silhouette. Style with trendy espadrille wedges.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Ruffled underbust trim
- Tiered ruffle layered skater silhouette
- Short-length hem
- Color block pattern
- Airy woven linen fabric, partial lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4994
Category Name: Casual Dresses
Price: $5.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Flare To Remember Skater Dress
You'll be unforgettable in this short skater dress perfect for twirling into baby showers, brunches, and family parties! Featuring a sleeveless plunge v-neckline, spaghetti straps that cross and tie along the open back, and a fit-and-flare silhouette. The dress is composed of airy printed chiffon fabric with a smooth woven lining. Style with strappy mules and a clutch!
Fit & Features
- Sleeveless plunge v-neckline
- Spaghetti straps
- Open back, cross strap design, tie closure
- Fit and flare skater silhouette
- Short-length hem
- Airy printed chiffon fabric, smooth woven lining
- Runs true to size
Style Number/Barcode: 05102-4988
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Like Honey Linen Skater Dress
You'll be sweet like honey in this breezy linen skater dress for afternoon tea or a weekend brunch! The dress features adorable puff short sleeves, a ruffle trim sweetheart neck, a ruched bust, and a fit and flare silhouette with a ruffled hem. Style with heeled sandals to complete the look.
Fit & Features
- Puff short sleeves
- Ruffle trim sweetheart neck, ruched bust
- Back zipper and hook-eye closure
- Fit and flare skater silhouette
- Ruffle short-length hem
- Linen fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4991
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Marvel Lace-Up Mini Dress
Everyone will marvel at you in this marble print mini dress featuring a sleeveless square neck, spaghetti straps that lace up along the back, and a bodycon silhouette. The mini-length dress is composed of a marble-printed mesh fabric with a stretch knit lining. Complete the look in platform wedges for dinner by the beach!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Lace-up back
- Bodycon silhouette
- Mini-length hem
- Marble print, mesh fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05102-4990
Category Name: Casual Dresses
Price: $5.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Modern Marvel One-Shoulder Mini Dress
Strut looking like a modern work of art in this marble-printed mini dress all over town! It features a sleeveless one-shoulder neck, an adjustable spaghetti strap, a side adjustable ruched string, and a bodycon silhouette. Complete the look with hoop earrings.
Fit & Features
- Sleeveless one-shoulder neck
- Adjustable spaghetti straps
- Side ruched string
- Bodycon silhouette
- Mini-length hem
- Marble-printed mesh fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05102-4989
Category Name: Casual Dresses
Price: $5.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In Paradise Tropical Print Midi Dress
You'll be ready for your paradise getaway with this tropical print midi dress! It features a sleeveless V-neck, spaghetti straps, a sultry cutout back, a bodycon silhouette, and an asymmetrical side slit cutout. Complete the look in wedges.
Fit & Features
- Sleeveless V-neck, spaghetti straps
- Cutout back
- Bodycon silhouette
- Asymmetrical side slit cutout
- Midi-length hem
- Tropical print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-4987
Category Name: Casual Dresses
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Art Show Marble Print Midi Dress
Look like a work of art in this marble print midi dress all over town! It features a sleeveless cowl neckline, spaghetti straps, a form-hugging fit with ruching down one side, and an asymmetrical side slit cutout on a smooth and stretchy knit fabric. Complete the look with hoop earrings.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Form-hugging fit, ruching down one side
- Asymmetrical side slit cutout
- Midi-length hem
- Marble print, smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4986
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale