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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Sun Ready Strapless High Slit Maxi Dress
If sandy beaches are what you seek this maxi dress is ready for fun under the sun! It features a strapless neckline, a side O-ring metal insert atop the sexy high slit, and a flowy long hem on slinky knit fabric. Complete the look in strappy sandals and sunglasses!
Fit & Features
- Strapless neckline
- Side O-ring insert, high side slit
- Flowy maxi silhouette
- Long hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5263
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Electric Love Chiffon Floral Maxi Dress
Look absolutely electric in this 70s-inspired chiffon maxi dress at parties and vacations! It features a sleeveless V-neckline, adjustable spaghetti straps that cross along the open back, an empire waist, and a flowy maxi-length silhouette on floral print chiffon fabric with a smooth woven lining. Complete the look with a sleek arm cuff bracelet and heels.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross-open back
- Empire waist
- Flowy maxi-length silhouette
- Floral print
- Airy chiffon fabric, smooth woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-5264
Category Name: Casual Dresses
Price: $5.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elite Summer Style Marble Print Maxi Dress
Show off an elite summer style in this eye-catching marble print maxi dress! It features a sleeveless scoop neckline, spaghetti straps, an alluring lower back cutout, a maxi-length hem with a thigh-high side slit to showcase some leg, and a bodycon silhouette that will hug your curves. The stretchy knit fabric features a trendy multi-colored marble print pattern. Complete the look with strappy heels for sunset happy hour.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps, lower back cutout
- Maxi-length hem, high side slit
- Bodycon silhouette
- Multi-colored marble print
- Slinky knit fabric, short knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5261
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Show Up And Stun Geometric Print Midi Dress
Show up and stun for casual drinks with the girls in this trendy midi dress! It features a sleeveless square neckline, spaghetti straps, a midi-length hem, a form-hugging silhouette, and a color block geometric printed pattern to catch everyone's eye. The buttery-smooth lined knit fabric offers plenty of stretch for comfortable wear. Style with clear mules!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Midi-length hem
- Form-hugging silhouette
- Color block geometric print
- Smooth and stretchy knit fabric, full knit lining
- Runs true to size
Style Number/Barcode: 05102-5260
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swirls Of Attraction Strappy Marble Print Midi Dress
Attract all the attention when you step out in this marble print midi dress for dinner and drinks! It features a sleeveless scoop neckline, spaghetti straps, an open strappy back design, a bodycon silhouette, and a flattering side ruched seam and slit along the asymmetrical hem. Complete the look with a fab earrings set and heels.
Fit & Features
- Sleeveless scoop neckline, spaghetti straps
- Open strappy back design
- Bodycon silhouette
- Side ruched seam and slit
- Asymmetrical midi-length hem
- Marble print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5259
Category Name: Casual Dresses
Price: $5.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Artsy Dreamer One Shoulder Abstract Maxi Dress
Dreaming of an artsy wardorbe? Look no further than this abstract print maxi dress perfect for an art show or gallery opening! It features a sleeveless one-shoulder neckline, tank strap, a bodycon silhouette, and a side ruched seam atop a sultry high slit to show some skin. Complete the look with a rhinestone bracelet and heels.
Fit & Features
- Sleeveless one-shoulder neckline, tank strap
- Bodycon silhouette
- Side ruched seam, high side slit
- Maxi-length hem
- Abstract print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5258
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Artsy Play Abstract Mock Neck Mini Dress
Play up your artsy side in this mesh mini dress totally giving those Y2K vibes! The mini dress features fitted long sleeves with split cuffs, a mock neckline, and a bodycon silhouette on mesh abstract printed fabric with a sheer mesh stretchy lining. Complete the look in chunky platform heels for a party!
Fit & Features
- Fitted long sleeves, split cuffs
- Mock neckline
- Bodycon silhouette
- Mini-length hem
- Abstract print on mesh fabric, sheer mesh stretchy lining
- Runs true to size
Style Number/Barcode: 05102-5398
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Knit Talks Mock Neck Sleeveless Sweater Dress
This knit sweater dress speaks for itself! Flaunt your classic style in this sleeveless dress featuring a ribbed mock neck, a flattering bodycon silhouette, and a mini-length hem with a flirty slit accent. Complete the look with a chic mini handbag and knee-high boots for a daytime outing!
Fit & Features
- Sleeveless
- Ribbed mock neck
- Bodycon silhouette
- Slit accent
- Mini-length hem
- Stretchy sweater knit fabric
- Runs true to size
Style Number/Barcode: 06005-1726
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mesmerized By You Marble Print Mini Dress
Make them mesmerized by your allure in this trendy marble print mini dress! It features a strapless angled neckline with flexible boning inserts to provide structure, a sultry corset-style bodice, a high waist seam, a mini-length hem, and a bodycon silhouette that will flaunt your figure. The lined crepe fabric features an all-over marble print pattern for an eye-catching look. Pair with lace-up heels for a night out.
Fit & Features
- Strapless angled neckline, flexible boning inserts
- Corset-style bodice, back zipper, hook and eye closure
- High waist seam
- Mini-length hem, bodycon silhouette
- Marble print
- Crepe fabric, full-length knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5254
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Best Spot To Be Off-The-Shoulder Polka Dot Mini Dress
Wherever you are in this off-the-shoulder polka dot mini dress is the best spot to be! The ruffled neckline with non-slip grip lining adds a flirty touch while the stretchy smocked bodycon silhouette highlights your curves. The tiered ruffle mini-length hem and polka print add a playful and chic vibe to this woven dress. Complete the look with earrings and cute booties!
Fit & Features
- Polka dot print, lined woven fabric
- Ruffled off-the-shoulder neckline
- Stretchy smocked bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5553
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Leave An Impression Abstract Midi Dress
Leave an impression everywhere you go in this abstract midi dress! It features a sleeveless square neckline, spaghetti straps, side ruched seams to accentuate your curves, and a flattering bodycon silhouette. The dress is designed with a figure-flattering abstract print on knit fabric with a stretchy lining. Complete the look in cute sandals for a lunch date.
Fit & Features
- Sleeveless square neckline, spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Midi-length hem
- Abstract print, smooth knit fabric, stretchy lining
- Runs true to size
Style Number/Barcode: 05102-5252
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Well Played Denim Bodycon Wrap Midi Dress
Well played! This denim midi dress is the perfect pick for having all eyes on you. It features a square neckline, adjustable straps, and a side pleated seam that creates the bodycon silhouette with an asymmetrical wrap slit hem. Complete the look in cute stiletto mules for a day or night out!
Fit & Features
- Sleeveless square neckline, adjustable straps
- Back zipper and hook-eye closures
- Side pleated seam
- Bodycon silhouette, asymmetrical wrap slit
- Midi-length hem
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5251
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Staple Tie-Front Midi Dress
This trendy tie-front midi dress is a stylish summer staple! It features a sleeveless V-neckline, a tie-front design at the bust with a small keyhole cutout, spaghetti straps, a midi-length hem, and a bodycon silhouette that will hug your natural curves. The ribbed knit fabric offers plenty of stretch. Pair with espadrille sandals for happy hour.
Fit & Features
- Sleeveless V-neckline
- Tie-front design, small keyhole cutout
- Spaghetti straps
- Midi-length hem
- Bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5250
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Check It Out Gingham Plaid Mini Dress
Make a statement in this gingham plaid mini dress! The square neckline and spaghetti straps make it the perfect dress for flaunting your curves, while the bodycon silhouette and mini-length hem radiate confidence. Complete the look by layering a long sleeve top for a preppy vibe!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Gingham plaid print
- Texture knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5243
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Caught In The Midi Crew Neck Tank Dress
A midi dress you wouldn't mind being spotted in! The dress features a sleeveless crew neck, a bodycon silhouette, and a fitted midi-length hem on stretchy rib knit fabric. Complete the look in a sleek layered necklace for lunch with friends!
Fit & Features
- Sleeveless crew neck
- Bodycon silhouette
- Fitted midi-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5242
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Vision Abstract Mesh Midi Dress
You'll be a stunning vision in this mesh midi dress out for a day date or brunch! It features a sleeveless square neckline, adjustable spaghetti straps, side ruching that accentuates your natural curves, and a flattering bodycon silhouette. The dress is designed with an artsy abstract print on mesh fabric and has a sewn-in knit lining. Complete the look with a trendy denim crop jacket.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Side ruching, bodycon silhouette
- Midi-length hem
- Abstract print, mesh fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5496
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfectly Seasoned Plaid Crew Neck Mini Dress
Fabulous and flavor-filled, step into this plaid mini dress for the new season! The mini dress features fitted long sleeves, a classic crew neckline, and a flattering bodycon silhouette on stretchy knit fabric with a trendy plaid print. Complete the look in a moto jacket for a coffee shop hang!
Fit & Features
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Mini-length hem
- Plaid print
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5247
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Element Turtleneck Long Sleeve Mini Dress
Soft and lightweight ribbed knit fabric crafts this trendy mini dress perfect for styling day to night! The mini-length dress features fitted long sleeves, a folded turtleneck, and a flattering bodycon silhouette on double-lined ribbed knit fabric. Complete the look in an oversized blazer and boots for brunch downtown or date night!
Fit & Features
- Double-lined ribbed knit fabric, moderate stretch
- Fitted long sleeves
- Folded turtleneck
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5245
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Muse Scoop Neck Mini Dress
A casual mini dress that's sure to become your fashion muse! The mini-length dress features fitted long sleeves, a scoop neckline, a built-in shelf bra for extra support, and a flattering bodycon silhouette on stretchy rib knit fabric. Complete the look in a moto jacket and boots for day or evening plans!
Fit & Features
- Fitted long sleeves
- Scoop neckline
- Built-in shelf bra
- Bodycon silhouette, mini-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5244
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Staple Tie-Front Ribbed Knit Midi Dress
This adorable tie-front midi dress is a stylish staple for an effortlessly chic look! It features a crew neckline, long fitted sleeves, a tie-front design at the waist, a mid-length hem with a high side slit, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Pair with ankle booties!
Fit & Features
- Stretchy ribbed knit fabric
- Crew neckline
- Long fitted sleeves
- Tie-front waist design
- High side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5248
Category Name: Casual Dresses
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stand Out Marble Print Cutout Midi Dress
Stand out this season and have all eyes on you in this marble print midi dress perfect for weekend getaways or sunset cocktails! The dress features a sleeveless square neck, spaghetti straps, a cutout bodice, and side ruched seams that accentuate your curves along the bodycon silhouette. Complete the look with a sleek choker necklace.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Cutout bodice
- Side ruched seams, bodycon silhouette
- Midi-length
- Marble print, smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5235
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Curve Allure Mock Neck Maxi Dress
Bring the allure to your look in this curve-flaunter maxi dress perfect for a dinner out with friends or date night! It features a sleeveless mock neck, bodycon silhouette, and side slit accent, and is crafted from smooth knit fabric with lining. Complete the look with a cute crop jacket.
Fit & Features
- Sleeveless mock neck
- Bodycon silhouette
- Side slit accent
- Maxi-length hem
- Smooth knit fabric, lined, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5232
Category Name: Casual Dresses
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Check Me Out Plaid Bodycon Mini Dress
You'll be the object of everyone's gaze in this trendy plaid bodycon mini dress! It features a sleeveless square neckline, bungee spaghetti straps, a stylish lower back cutout, a mini-length hem, and a bodycon silhouette that will hug your natural curves. The stretchy brushed knit fabric features a chic windowpane plaid print. Complete your look with clear mules!
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Lower back cutout
- Mini-length hem, bodycon silhouette
- Plaid print
- Brushed knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5230
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Throwback Blues Denim Print Mini Dress
Let this printed denim mini dress cure your throwback blues! It features a sleeveless square neckline, tank shoulder straps, a bodycon silhouette, and a mini-length hem on smooth and stretchy knit fabric. Complete the look with classic hoop earrings.
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Bodycon silhouette
- Mini-length hem
- Printed denim, smooth, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5229
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale