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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Casually Chic Smooth Knit Fitted Maxi Dress
This smooth knit fitted maxi dress is the casually chic style you need to elevate your 'fits. It features a strapless straight-across neckline, an all-over curve-hugging silhouette, a maxi-length hem, and a trendy back slit accent. The smooth knit fabric includes an airy sheer mesh lining and offers plenty of stretch for comfortable wear. Complete your looks with strappy mules and a mini handbag.
Fit & Features
- Strapless straight-across neckline
- Curve-hugging silhouette
- Maxi-length hem
- Back slit
- Smooth knit fabric, sheer mesh lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5175
Category Name: Casual Dresses
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Party Energy Cutout Bodycon Mini Dress
You'll bring the party energy in this sexy cutout bodycon mini dress! It features a sleeveless one-shoulder neckline, a sultry asymmetric bust cutout creating two front tank straps, a mini-length hem, and a curve-hugging silhouette that will flaunt your gorgeous figure. The smooth nylon fabric offers plenty of stretch. Style with clear heels.
Fit & Features
- Sleeveless one-shoulder neckline
- Asymmetric bust cutout
- Two front tank shoulder straps
- Mini-length hem
- Curve-hugging fit
- Nylon fabric, sewn-in lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5169
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Noteworthy Flirt Ruffled Lace-Up Mini Dress
Everyone will take note of your flirtiness in this mesh mini dress perfect for daytime parties! It features a sleeveless square neck, spaghetti straps that lace up along the open back, a bodycon silhouette, and all-over ruffled trim detail. Complete the look with statement earrings.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Lace-up, open back
- Bodycon silhouette
- Mini-length hem
- All-over ruffled trim, mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5168
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Call You Sweetheart Ruffle A-Line Dress
Everyone will be calling you sweet in this short A-line dress as the bride-to-be or graduate! It features a sleeveless sweetheart neck, tank shoulder straps, a ruched bust seam, a flattering A-line silhouette, asymmetrical front ruffle trim, and a short-length hem. Complete the look with earrings and block heels.
Fit & Features
- Sleeveless sweetheart neck
- Tank shoulder straps
- Ruched bust seam
- A-line silhouette, asymmetrical ruffle trim
- Short-length hem
- Slinky knit stretchy fabric
- Runs true to size
Style Number/Barcode: 05101-2480
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Preppy Girl Plaid V-Neck Mini Dress
This plaid mini dress is for all the preppy girls! It features a sleeveless V-neckline, spaghetti straps, a bodycon fit, and a flirty front slit accent on stretchy knit fabric. Style with a cropped blazer and booties to complete the look!
Fit & Features
- Sleeveless V-neckline, spaghetti straps
- Bodycon fit
- Front slit accent
- Mini-length hem
- Plaid print
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5161
Category Name: Casual Dresses
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Match Plaid Lace-Up Mini Dress
Find your perfect match in this casual-chic plaid mini dress! Featuring a sleeveless square neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, a mini-length hem, a form-hugging fit, and a classic plaid windowpane print, this dress is a stylish must-have. Pair with hoop earrings and clear mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open back, cross-back lace-up straps, tie closure
- Mini-length hem, form-hugging fit
- Plaid windowpane print
- Lined soft knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5159
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Looking Sensational Smooth Knit Maxi Dress
Rise to the occasion looking sensational in this basic smooth knit maxi dress perfect for dressing up or down! It features a sleeveless scoop neck, sleek spaghetti straps, a bodycon silhouette, and a flirty back-slit accent composed of double-lined smooth knit fabric. Complete the look in lucite mules for a bridal shower or casual party!
Fit & Features
- Sleeveless scoop neck, spaghetti straps
- Bodycon silhouette
- Back slit accent
- Maxi-length hem
- Double-lined smooth knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5158
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Impressions Ruched Mini Dress
Make a bold impression out and about in this mesh mini dress perfect for parties or sexy brides! It features a sleeveless square neck, bungee spaghetti straps, side ruched seams that accentuate your curves, and a bodycon fit. Complete the look with heart-shaped earrings.
Fit & Features
- Sleeveless square neck
- Bungee spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Mesh fabric, nude stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5160
Category Name: Casual Dresses
Price: $5.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Double Take Strappy Back Mini Dress
This casual mini-dress will make everyone do a double-take! It features a sleeveless scoop neckline, spaghetti straps, an open back with a caged strap design, a bodycon silhouette, and a mini-length hem. The dress is composed of a stretchy rib knit fabric with a sewn-in knit lining. Complete the look in hoop earrings for a backyard bbq.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Open back, caged strap design
- Bodycon silhouette
- Mini-length hem
- Rib-knit fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5156
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sassy Speed Racer Graphic Mini Dress
Amp up your bar hopping 'fits with this edgy graphic mini dress! It features a sleeveless crew neckline, a notched V-neck design with safety pin accents, a racecar graphic with various scripts like, "Champions Racing," a mini-length hem, and a bodycon silhouette that will hug your curves. Style with a layered necklace set and sneakers.
Fit & Features
- Sleeveless crew neckline
- Notched V-neck design, safety pin accents
- Racecar graphic, various scripts like "Champions Racing"
- Mini-length hem
- Bodycon silhouette
- Cotton-blend fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1607
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feeling Playful In Floral Babydoll Dress
You'll be feeling playful in this floral babydoll dress perfect for bridal showers or dressy weekend brunches! It features a sleeveless square neck, adjustable spaghetti straps, an empire seam, and a flared short-length hem. The dress is designed with flower appliques on airy chiffon fabric with a woven lining. Complete the look in cute wedges.
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Empire seam, babydoll silhouette
- Flared, short-length hem
- Flower appliques, chiffon fabric, woven lining
- Runs true to size
Style Number/Barcode: 05101-2470
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendsetting Cutie Cable Knit Lace-Up Dress
Step out as a trendsetting cutie in this cable knit midi dress perfect for daytime strolls! It features a sleeveless square neck, thin shoulder straps that create the lace-up back design, a tie-waist belt, a bodycon silhouette, a side slit, and a midi-length hem. Complete the look in flat sandals and sunglasses.
Fit & Features
- Sleeveless square neck, thin shoulder straps
- Lace-up back design
- Tie-waist belt
- Bodycon silhouette
- Side slit, midi-length hem
- Cable knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5155
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Refresh One-Shoulder Bodycon Mini Dress
This chic bodycon mini dress is the summer style refresh you need! It features an asymmetric one-shoulder neckline with an O-ring accent, a thin braided shoulder strap, a mini-length hem, and a curve-hugging silhouette. The double-lined brushed knit fabric offers plenty of stretch. Complete the look with strappy sandals.
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- O-ring accent, thin braided shoulder strap
- Mini-length hem
- Bodycon fit
- Double-lined brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5151
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ready For Sun Rib Knit Mini Dress
Ready for some sun? Let this rib knit mini dress cue the sunshine! It features a sleeveless scoop neckline, a flirty bust tie with a keyhole accent, spaghetti straps, and a bodycon silhouette. Complete the look in trendy flat sandals for a backyard bbq!
Fit & Features
- Sleeveless scoop neckline
- Bust tie, keyhole accent
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5149
Category Name: Casual Dresses
Price: $6.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Appeal Mock Neck Bodycon Mini Dress
A must-have basic for the upcoming season! This dress features fitted long sleeves, a mock neck, a flattering bodycon silhouette, and a mini-length hem. It's composed of a cotton-blend knit fabric with a moderate stretch for comfort. Complete the look in strappy heels for a birthday brunch!
Fit & Features
- Fitted long sleeves
- Mock neck
- Bodycon silhouette
- Mini-length hem
- Cotton-blend knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5153
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Next Level Lace-Up Slit Maxi Dress
A next-level maxi dress to elevate your look for upcoming parties or date nights! It features a sleeveless square neckline, spaghetti straps that form the lace-up back with tie closure, a side ruched seam to show off your figure, a bodycon silhouette, and a sexy side slit on smooth knit stretchy fabric. Complete the look with fringe rhinestone earrings for a touch of glamour!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Lace-up back, tie closure
- Side ruched seam, bodycon silhouette
- High side slit, maxi-length hem
- Smooth knit stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-5147
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In The Details Basic Ruched Midi Dress
The true style of this basic midi dress lies in the detail! Features a sleeveless square neckline, sleek bungee spaghetti straps, ruched seams down the sides to accentuate your curves, and a flattering bodycon silhouette. The dress is composed of a brushed soft knit fabric with a full-length lining. Complete the look with a chic handbag for a dinner date.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ruched side seams
- Bodycon silhouette
- Midi-length hem
- Brushed soft knit fabric, lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5146
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Strappy And Stunning Rib Knit Midi Dress
Step out looking stunning in this rib knit midi dress for a casual beach day with friends or a date! It features a sleeveless V-neckline, spaghetti straps, a head-turning strappy open back, a bodycon silhouette, a side slit cut out, and a midi-length hem. Complete the look in trendy flat sandals and sunglasses!
Fit & Features
- Sleeveless V-neckline, spaghetti straps
- Strappy open back
- Bodycon silhouette
- Side slit cut out
- Midi-length hem
- Rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5144
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Refresh Ruched Bodycon Mini Dress
Update your dress collection with this ruched bodycon mini dress that will be a chic refresh! It features a sleeveless crew neckline, tank shoulder straps, a partially open back with a cross-back strap design for a trendy detail, ruching down the side seams, and a mini-length hem with a bodycon silhouette that will hug your natural curves. The lined ribbed knit fabric offers plenty of stretch. Style with clear lucite heels for happy hour.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Open back, cross-back strap design
- Ruched side seams
- Mini-length hem, bodycon fit
- Ribbed knit fabric, smooth sewn-in knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5143
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Moments A-Line Mini Dress
This gorgeous mini dress was made for sunset dates! It features a sleeveless cowl neckline, spaghetti straps, an open back with a cross-back strap design and a low back draped accent, and a mini-length hem with an A-line silhouette. Style this short dress with a dainty necklace and espadrille wedges.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Open back, cross-back strap design
- Low back draped accent
- Mini-length hem, A-line silhouette
- Lightweight woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-5325
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Taking Care Of Business Collar Tank Mini Dress
Take care of business in preppy style! This sleeveless mini dress features a trendy collared V-neckline, a bodycon silhouette, and a fitted mini-length hem on stretchy rib knit fabric. Complete the look with a dainty bracelet for a coffee shop hang!
Fit & Features
- Sleeveless collared V-neckline
- Bodycon silhouette
- Fitted mini-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5139
Category Name: Casual Dresses
Price: $13.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tag You're Knit Bodycon Midi Dress
Tag you're it to rock this casually cute midi dress all over town! It features a sleeveless scoop neck, spaghetti straps, a flirty bust tie, and a figure-hugging bodycon silhouette with a side slit accent on stretchy rib knit fabric. Complete the look in sparkly teardrop earrings for an outdoor dinner party.
Fit & Features
- Sleeveless scoop neck
- Bust tie, spaghetti straps
- Bodycon silhouette
- Side slit accent
- Midi-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5138
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dial B For Basics Square Neck Mini Dress
Dial B for this basic mini dress that'll inspire all your fashion-forward looks! It features a sleeveless square neckline, sleek bungee spaghetti straps, a form-hugging silhouette, and a mini-length hem. The double-line buttery knit fabric offers a seamless design and plenty of stretch. Style with a minimalistic necklace and earrings to inspire your day or night outfit!
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Form-hugging silhouette
- Mini-length hem
- Double-lined buttery knit fabric, moderate stretch
- Seamless design
- Runs true to size
Style Number/Barcode: 05102-5134
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Passport To Paradise Tropical Print Ruched Midi Dress
Whether you're headed on a weekend getaway or a plane ride to paradise, pack this tropical print midi dress for a gorgeous glow! It features a sleeveless cowl neckline, spaghetti straps, ruching down one side seam, an asymmetric midi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The smooth and stretchy knit fabric features an all-over tropical palm leaf print. Style with espadrille sandals.
Fit & Features
- Sleeveless cowl neckline, spaghetti straps
- Ruched side seam
- Asymmetric midi-length hem, high side slit
- Bodycon fit
- Tropical palm leaf print
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5136
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale