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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Spring Knits Halter Midi Dress
The cooler spring days call for your best knits! Set the tone in this halter midi sweater dress featuring a sleeveless high neck, adjustable spaghetti straps, space-dye knit pattern, bodycon silhouette, and a side slit accent to showcase some leg. Complete the look in cute mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless high neck, halter design
- Adjustable spaghetti straps
- Bodycon silhouette
- Side slit, midi-length hem
- Space-dye knit pattern
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1257
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Paisley Babe V-Neck Midi Dress
Look like a babe in this paisley midi dress to bring those retro vibes! It features a sleeveless V-neck, adjustable spaghetti straps, a bodycon silhouette, and an asymmetrical midi-hem with a trendy ruched seam. Complete the look in block heels for happy hour.
Fit & Features
- Sleeveless V-neck, adjustable spaghetti straps
- Bodycon silhouette
- Ruched side seam
- Asymmetrical midi-length hem
- Paisley pattern
- Stretchy and soft knit fabric
- Runs true to size
Style Number/Barcode: 05102-4380
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Siesta Keys Tropical Maxi Dress
Take a vacation to Siesta Keys looking fab in this tropical maxi dress! It features a sleeveless, v-neck, spaghetti straps, and a tie-front bust atop a cutout bodice leading to the form-fitting silhouette with a sultry side slit. Complete your vacay look in a straw hat and your fave sunglasses.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Tie-front bust
- Cutout bodice
- Form-fitting silhouette
- Side slit, maxi hem
- Tropical print
- Fits true to size
Style Number/Barcode: 05102-4377
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Cruise Floral Midi Dress
You'll be ready for a sunset cruise on the water in this chic floral midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, side ruched detailing, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some leg. The dress features an all-over tropical floral print. Complete the look with strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross-back strap design
- Side ruching
- Midi-length, form-fitting silhouette, asymmetrical hem
- Tropical floral print
- Stretchy knit fabric, partial lining at the bust
- Runs true to size
Style Number/Barcode: 05102-4375
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Jetset Getaway Tropical Midi Dress
Wanna get away? Jetset off to paradise with this tropical floral dress in your lineup! It features a sleeveless scoop neck, spaghetti straps, a cross-back strap design with a tie closure, a form-fitting silhouette, a side ruched seam, and an asymmetrical midi hem with a side slit. Complete the look in lace-up heels.
Fit & Features
- Sleeveless, scoop neck, spaghetti straps
- Open-back, cross-back strap design, tie closure
- Form-fitting silhouette
- Side ruched seam
- Asymmetrical midi-length hem, side slit
- Tropical floral print, stretchy knit-lined fabric
- Runs true to size
Style Number/Barcode: 05102-4373
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Walk Floral Midi Dress
Take a stroll at sunset on your relaxing vacay in this chic floral midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, an asymmetrical midi-length hem creating an alluring side slit, and a curve-hugging silhouette. The all-over tropical floral print pairs perfectly with strappy sandals. Complete the look with hoop earrings.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross-back design
- Asymmetrical midi-length hem, ruching, side slit
- Form-fitting silhouette
- Tropical floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4374
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Tropic Strappy Back Midi Dress
Flaunt your figure on vacay girl! This floral tropic midi dress is perfect for a dinner with a view. Featuring a sleeveless V-neckline, spaghetti straps, a strappy open-back, a bodycon silhouette, and an asymmetrical hem. Complete the look in chic wedges.
Fit & Features
- Sleeveless, V-neck, spaghetti straps
- Strappy open-back, tie closure
- Bodycon silhouette
- Asymmetrical midi-length hem
- Floral tropic print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4376
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Beauty Ruffled Floral Dress
Showcase your beauty in this sweet floral chiffon dress! It features short puff sleeves, a sweetheart neckline, a high waist with a fit and flare silhouette, and a short flowy skirt with a charming ruffled hem. The sheer chiffon fabric features an all-over dainty floral print and includes a lightweight woven lining. Style this dress with cute espadrille sandals.
Fit & Features
- Short puff sleeves, elasticized hems
- Sweetheart neckline, ruching at the bust, partially smocked back
- High waist seam, fit and flare silhouette
- Mini-length flowy skirt, ruffled hem
- Floral print
- Sheer chiffon fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1430
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Idyllwild Floral Bust Tie Mini Dress
Put your curves on display in this cute floral mini dress designed in a sleeveless, sweetheart neck with a ruched bust tie, spaghetti straps, and side ruched seams. Composed of a brushed knit fabric with a moderate stretch. Finish the look in hoop earrings.
Fit & Features
- Sleeveless, sweetheart neck, ruched bust tie
- Spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Floral pattern, brushed knit fabric
- Fits true to size, moderate stretch
Style Number/Barcode: 05102-4369
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Views Tropical Cowl Mini Dress
You may be in paradise but you'll be the main view in this tropical mini dress! Features a sleeveless, cowl neck, sleek spaghetti straps, bodycon silhouette, and an asymmetrical mini-length hem with a side ruched tie. Complete the look in hoop earrings and heels.
Fit & Features
- Sleeveless, cowl neck, spaghetti straps
- Bodycon silhouette
- Asymmetrical mini-length hem
- Side ruched tie
- Tropical pattern
- Texture knit fabric, moderate stretch, fits true to size
Style Number/Barcode: 05102-4366
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Moves Midi Dress
Make the trendiest of moves in this cool printed midi dress. It features a sleeveless halter neckline with spaghetti straps that lead to an open back with a strappy lattice design, a fitted bodice leading to a subtle flowy silhouette with a thigh-high front slit, and an all-over splattered tie-dye print. Style this dress with clear mules.
Fit & Features
- Sleeveless halter neckline, spaghetti straps
- Open back, strappy lattice design, tie closure
- Fitted bodice, flowy silhouette, high front slit
- Spattered tie-dye print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4371
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paradise Calls Tropical Midi Dress
Vacation on the mind? You're going to need this tropical midi dress with paradise written all over it! Features a sleeveless, v-neck, adjustable spaghetti straps, a form-fitting silhouette, and a side ruched seam on an asymmetrical midi hem. Complete the look in lace-up sandals for a dinner with a view.
Fit & Features
- Sleeveless, v-neck, adjustable spaghetti straps
- Form-fitting silhouette
- Side ruched seams
- Asymmetrical midi hem
- Tropical pattern
- Texture knit fabric, moderate stretch. fits true to size
Style Number/Barcode: 05102-4367
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Trendsetter Ruched Mini Dress
Keep your look sweet and trendy with this adorable bodycon mini dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruched side detailing, a short, curve-hugging fit, and an all-over butterfly print. Style this dress with a pair of cute mules for an outing with the girls.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruched side detailing
- Mini-length, form-fitting silhouette
- Butterfly print
- Brushed knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4370
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beachside Brunch Swim Coverup Dress
Strut down the pier looking so fab in this maxi coverup dress featuring a sleeveless V-neckline, tank straps, and a form-fitting silhouette with a sultry front slit. The coverup dress is composed of an unlined semi-sheer knit fabric that offers a form-hugging fit. Perf for layering over your bikinis, complete the look in sandals.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless V-neckline, tank straps
- Surplice accent
- Form-fitting silhouette
- Front slit
- Maxi-length hem
- Unlined, semi-sheer sweater-knit fabric, no stretch
- Runs true to size
Style Number/Barcode: 06005-1250
Category Name: Casual Dresses
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bold Impressions Sleeveless Midi Cutout Dress
Make a bold impression with a midi dress that cuts a sultry look! The midi dress features a plunging V-neckline, spaghetti straps, sexy cutouts at the waist, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Dual cutouts at the waist
- Midi-length silhouette
- Sheer ribbed knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1967
Category Name: Casual Dresses
Price: $34.90
Availability: Out of Stock
Product Badge:- Sale
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Sunday Girl Floral Chiffon Skater Dress
Look cute for Sunday brunch in this floral chiffon skater dress featuring three-quarter length puff sleeves, a square neck, and a pleated waistband on the skater silhouette. Showcase a peek of skin in the open-back design with tie closure and ruffled short-length hem. Composed of a chiffon floral lined fabric with no stretch. Perfect for styling with knee-high boots.
Fit & Features
- Three-quarter length puff sleeves, elastic cinched hems
- Square neckline
- Pleated waistband, skater silhouette
- Ruffled short-length hem
- Open-back, tie closure, back zipper, hook and eye closure
- Chiffon floral lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-1706
Category Name: Casual Dresses
Price: $25.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Nothing Bud Fun Floral Halter Dress
Have nothing but fun in this flirty floral halter dress perfect for a brunch date! It features a sleeveless, halter v-neck with adjustable neck tie, a babydoll style bodice leading to a flowy, ruffled short hem. Showcase some skin in the open-back with tie closure. Complete the look in lace-up sandals.
Fit & Features
- Sleeveless, halter v-neck, adjustable necktie
- Babydoll style bodice
- Flowy ruffled short hem
- Open-back, tie closure
- Ditsy floral print, woven-lined fabric
- Fits true to size, no stretch
Style Number/Barcode: 05102-4364
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lotus Floral Mesh Bodycon Dress
Look lovely in this floral mesh bodycon dress for a trendy afternoon tea look! Features a sleeveless, cowl neckline, adjustable spaghetti straps, on a mini-length hem. Complete the look in cute heels and a straw hat.
Fit & Features
- Sleeveless, cowl neckline, adjustable spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Floral mesh-lined fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4363
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Getaway Sleeveless Maxi Dress
Get ready for a gorgeous getaway in this alluring sleeveless maxi dress! It features a V-neckline, spaghetti straps, a cross-back strap design, a fitted high waist seam, and a floor-length silhouette with a chic high front slit. The knit fabric features an all-over tropical palm leaf print. Style this dress with strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross-back strap design
- Fitted high waist seam
- Floor-length silhouette, high front slit
- Palm leaf print
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-4362
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Earn Your Stripes Sweater Midi Dress
Earn your stripes in style rocking this sweater midi dress for all-day slays! It features a sleeveless square neck, adjustable spaghetti straps, a striped pattern, and a bodycon silhouette. Composed of a rib-knit fabric with a moderate stretch. Style with chic booties.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Striped pattern
- Bodycon midi-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1240
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Essential Sleeveless Midi Dress
The perfect sleeveless midi sweater dress for every occasion! It features a V-neck, tank straps, and a bodycon silhouette on ribbed knit fabric with a moderate stretch. Complete the look in sleek hoops and heels.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless V-neckline, tank straps
- Bodycon silhouette
- Midi-length hem
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1239
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetie Puff Sleeve Mini Dress
You'll look so sweet in this mini dress for a cute brunch fit. It features adorable short puff sleeves along the sweetheart neck with a cutout bust tie. The side ruched seams accentuate your curves on slinky knit-lined fabric with a moderate stretch. Complete the look in PVC mules.
Fit & Features
- Short puff sleeves, elastic cinched hems
- Sweetheart neck, cutout bust tie
- Side ruched seams, bodycon fit
- Mini-length hem
- Slinky knit-lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4361
Category Name: Casual Dresses
Price: $5.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Stunner Striped Halter Short Dress
Keep it stylish in a short sweater dress that wows and keeps it effortless. The dress features a halter neck with an adjustable neck tie, a striped pattern, and a short-length hem. The dress is composed of an unlined knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with wedges.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Halter neck
- Adjustable neck ties
- Striped pattern
- Short-length hem
- Knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1231
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Day To Night Snap Button Midi Dress
Go from office hours to happy hour in a snap with this classy sweater midi dress! It features long sleeves, a rounded neckline, a bodycon silhouette, and a side slit with snap button accents. Composed of a ribbed knit fabric with a moderate stretch. Style with a chic jacket and heels.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Long fitted sleeves
- Round neckline
- Bodycon silhouette
- Side slit, snap button accents
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1219
Category Name: Casual Dresses
Price: $18.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale