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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Captivating Floral Mesh Mini Dress
Captivate in this gorgeous floral mini dress! It features a sleeveless, scoop neckline, spaghetti straps, ruched bust and side seams, and a bodycon silhouette. Complete the look in espadrille wedges for a lunch date.
Fit & Features
- Sleeveless, scoop neck, spaghetti straps
- Lightly padded bust with ruching
- Side ruched seams
- Bodycon silhouette
- Floral mesh-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4553
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Charm Floral Mesh Mini Dress
Showcase your stylish charm in this adorable floral mesh mini dress. It features a sleeveless sweetheart neckline, bungee spaghetti straps, all-over ruched detailing, and a short, form-fitting silhouette that will hug your curves. Complete the look with strappy mules for weekend brunch.
Fit & Features
- Sleeveless sweetheart neckline
- Bungee spaghetti straps
- All-over ruching
- Mini-length, form-hugging fit
- Floral print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4541
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Babe Cutout Mini Dress
For looking and feeling like a total babe. Let your legs out in this sleeveless mini dress featuring an on-trend square neck, spaghetti straps, a cutout bodice, side ruched seams and a bodycon fit. Complete the look in strappy heels for a party.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Cutout bodice
- Bodycon fit, side ruched seams
- Mini-length hem
- Textured knit-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4545
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Palm Perfect Tropical Midi Dress
Look perfect in paradise wearing this palm print midi dress featuring a sleeveless, v-neck, spaghetti straps, a form-fitting silhouette, and a front slit accent on stretchy knit fabric. Complete your vacation look in wedges.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Form-fitting silhouette
- Front slit accent
- Midi-length hem
- Palm print, knit fabric with moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4542
Category Name: Casual Dresses
Price: $6.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mocktail Sleeveless Rib Knit Mini Dress
This chic mini dress was made for cocktail hour! It features a sleeveless, mock neck, bodycon silhouette, and is composed of stretchy rib-knit lined fabric. Complete the look in a hair clip to create a stunning updo.
Fit & Features
- Sleeveless, mock neck
- Bodycon silhouette
- Mini-length hem
- Stretchy rib-knit lined fabric
- Fits true to size
Style Number/Barcode: 05102-4546
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Deets Knit Mini Dress
You'll love the trendy deets of this ribbed knit mini dress! It features a crew neckline, short sleeves, a cute side cutout with ruching and an adjustable drawstring, and a short, form-hugging fit. Style with clear mules.
Fit & Features
- Crew neckline
- Short fitted sleeves
- Side cutout, ruching, adjustable drawstring
- Mini-length, form-fitting silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4544
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Basic Knit Mini Dress
This simple yet stylish ribbed knit mini dress is a must-have for your everyday looks. It features a sleeveless crew neckline, tank shoulder straps, an alluring lower back cutout, and a short, curve-hugging fit. Style with a denim jacket for the day and dress it up with a faux leather jacket for the night!
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Lower back cutout
- Mini-length, form-fitting silhouette
- Ribbed knit fabric, knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4543
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Innocent Charm Eyelet V-Neck Dress
Innocently charming! Bring the flirtiness in this eyelet v-neck dress featuring a sleeveless ruffle trim bodice with tie-front closure, spaghetti straps, a cutout accent, and a form-fitting silhouette. Complete the look in a dainty choker necklace for a day date.
Fit & Features
- Sleeveless, v-neck, ruffle trim, spaghetti straps
- Tie-front closure
- Cutout accent
- Form-fitting silhouette
- Mini-length hem
- Eyelet knit-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4536
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Total Beauty Floral Maxi Dress
Radiate your beauty in this blooming floral printed maxi dress! It features a romantic off-the-shoulder neckline, short ruffled drape sleeves, an empire waist, and a flowy floor-length silhouette with dual high front slits. Style this dress with strappy sandals.
Fit & Features
- Off-the-shoulder neckline
- Short ruffled drape sleeves
- Empire waist
- Floor-length silhouette, flowy fit, dual front slits
- Floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4535
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Getaway Vibes Mini Sweater Dress
This chic mini sweater dress was made for weekend getaways. It features a sleeveless V-neckline, tank shoulder straps, a square back design, a braided knit trim, and a short, form-fitting silhouette. Complete the look with sleek hoops and your fave shades.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Square back design
- Braided knit trim
- Mini-length, form-fitting silhouette
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1425
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Leave An Impression Halter Sweater Mini Dress
Leave an impression in this sweater mini dress for dates or weekend getaways! The rib knit dress features a sleeveless halter neckline, a partially open back, a bodycon silhouette, and a mini-length hem with a flirty slit. Complete the look in heeled sandals.
Fit & Features
- Sleeveless halter neckline
- Partially open back
- Bodycon silhouette
- Mini-length hem, slit accent
- Rib-knit sweater fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1424
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hot And Cold Sweater Mini Dress
Sweaters may be for cold weather but this mini dress is too hot not to be seen this summer! It features an off-the-shoulder neckline, short sleeve cuffs, a form-fitting silhouette, and a mini-length hem on stretchy rib-knit fabric. Complete the look in platform heels.
Shop More Sweater Styles: Shop The Collection
Fit & Features
- Off-the-shoulder neckline
- Short sleeve cuffs
- Form-fitting silhouette
- Mini-length hem
- Sweater rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1423
Category Name: Casual Dresses
Price: $7.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Island Retreat Mesh Mini Dress
Look like you're ready to jet-set off to an island retreat in this mesh mini dress! It features a sleeveless square neckline, spaghetti straps, ruched detailing down the side seams, and a short, curve-hugging fit. The lined mesh fabric features an all-over tropical palm leaf print. Complete your look with espadrille wedges.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ruching down the side seams
- Mini-length, form-fitting silhouette
- Tropical palm leaf print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4534
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keep It Light Sweater Midi Dress
Keep your look light and effortless in this sweater midi dress perfect for any day or night summer event! It features a sleeveless, v-neck, spaghetti straps, a bodycon silhouette, and a sultry front slit. Complete the look in strappy sandals.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Bodycon silhouette
- Front slit accent
- Midi-length hem
- Sweater rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1420
Category Name: Casual Dresses
Price: $16.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep It Cool Crew Neck Mini Dress
Keep it cool and casual in this effortless knit mini dress for hangs with friends! It features short sleeves, a crew neck, a bodycon silhouette, and a ruched drawstring that lets you customize the style. The dress is composed of a stretchy brushed knit fabric. Complete the look in cute flat sandals.
Fit & Features
- Short sleeve, crew neck
- Bodycon silhouette
- Ruched, adjustable drawstring
- Bodycon silhouette
- Mini-length hem
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4856
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take A Look Sweater Midi Dress
Let everyone take a look at you in this sweet sweater midi dress perfect for the autumn season! This dress features a sleeveless halter neck with tie closure, a bodycon silhouette, and a cutout waist with a front slit along the hem. Complete the look in pointy-toe booties.
Fit & Features
- Sleeveless halter neck with tie closure
- Bodycon silhouette
- Cutout waist, front slit
- Midi-length hem
- Rib-knit sweater fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1416
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep It Cute Cable Knit Mini Dress
Keep it cute and light in this cable knit mini dress perfect for a casual day date! It features a sleeveless scoop neckline, spaghetti straps, a lower back cutout, underbust trim, and a bodycon silhouette. The cable knit fabric offers a moderate stretch. Complete the look in a dainty necklace and heels.
Fit & Features
- Sleeveless scoop neckline, spaghetti straps
- Lower back cutout
- Underbust trim
- Bodycon silhouette
- Mini-length hem
- Cable knit design, knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1412
Category Name: Casual Dresses
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take Me On A Getaway Midi Dress
Pack this alluring and chic midi dress for your next weekend getaway. It features a sleeveless halter neckline with thin straps, front ruched detailing with an adjustable drawstring, a bold front waist cutout, and a midi-length, curve-hugging fit with a high side slit. Style this dress with sleek hoop earrings and strappy sandals.
Fit & Features
- Sleeveless halter neckline, thin straps that tie at the back of the neck
- Front ruching, adjustable drawstring
- Front waist cutout
- Midi-length, form-fitting silhouette, side slit
- Ribbed sweater knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1414
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Beachy Vibes Maxi Sweater Dress
Bring the beachy vibes to your summer look with this effortlessly chic maxi sweater dress. It features a sleeveless scoop neckline, spaghetti straps, an open back with a cross-back strap design, and a fitted, maxi-length silhouette with a high side slit. The sweater knit fabric features pretty crochet detailing. Style this dress with sandals.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Open back, cross-back strap design
- Fitted, maxi-length silhouette, side slit
- Sweater knit fabric, crochet detailing, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1421
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Everyday Perfection Ribbed Knit Mini Dress
This comfortable ribbed knit mini dress is perfect for everyday 'fits! It features a classic crew neckline, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric offers a moderate stretch. Keep it casual with sneakers and a denim jacket, or elevate the look with sleek hoops and strappy mules.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Form-fitting silhouette
- Mini-length hem
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1272
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cool Girl Vibes Space Dye Mini Dress
Bring the cool girl vibes in this trendy curve-hugging mini sweater dress! It features a sleeveless halter neckline with tie-back straps, a center O-ring accent at the bust, a front waist cutout, and a fitted mini-length silhouette. The sweater knit fabric features a space dye design. Style this dress with gold hoops and cute mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless, halter neckline, tie-back straps
- Center O-ring accent at the bust
- Front waist cutout under the bust
- Short, form-fitting silhouette
- Sweater knit fabric, moderate stretch
- Space dye knit design
- Runs true to size
Style Number/Barcode: 06005-1400
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Daydream Graphic Cutout Tunic Top
You gotta hustle girl! Work for your dreams while showcasing your edgy style in this tunic top featuring short sleeves, a V-notch neckline, and graphic front detail with side drawstring cutouts and a fitted hem. Complete the look in retro boots.
Fit & Features
- Short sleeves, V-notch neckline
- Graphic front detail
- Script reads, "Hustle Daydream"
- Side drawstring cutouts
- Fitted hem
- Jersey knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1257
Category Name: Casual Dresses
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Good Times Marble Halter Dress
Let the good times flow in this marble print mini dress perfect for vacation and sipping mojitos! It features a sleeveless, halter neckline with a ruched drawstring and tie closure, a cutout bodice, and a form-hugging fit on the knit-lined fabric. Complete your fab look with lucite mules.
Fit & Features
- Halter neckline, ruched drawstring, tie closure
- Cutout bodice
- Form-hugging fit
- Mini-length hem
- Marble print knit-lined fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4531
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Animal Kingdom Zebra Satin Dress
You'll be the head of the animal kingdom in this fierce and femme zebra satin mini dress! It features a sleek and sleeveless cowl neck, spaghetti straps, and a curve-hugging silhouette. Complete the look in strappy heels for a wild night out!
Fit & Features
- Sleeveless cowl neck
- Spaghetti straps
- Curve-hugging silhouette
- Mini-length hem
- Zebra pattern
- Smooth satin with minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4532
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale