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.
Now Trending
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.
-
Gorgeous Muse Asymmetrical Midi Dress
Catch all the glances like the gorgeous muse you are in this printed midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a midi-length, asymmetrical hem, a curve-hugging silhouette, and an all-over geometric multi-print pattern. Complete the look with sleek hoop earrings.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Midi-length, asymmetrical hem, ruching down one side
- Form-fitting silhouette
- Geometric multi-print pattern
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5302
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Swirl Fun Chain Strap Midi Dress
Perfect for your next getaway, this swirl midi dress is a must to pack in your carry-on! It features a sleeveless square neck, half chain and adjustable spaghetti straps, a bodycon silhouette, and a flirty side slit. The dress is composed of a swirl print slinky-knit fabric with a sewn-in knit lining. Complete the look in heeled sandals.
Fit & Features
- Sleeveless square neck
- Half chain, adjustable spaghetti straps
- Bodycon silhouette
- Side slit, midi-length hem
- Swirl print
- Slinky knit fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5301
Category Name: Casual Dresses
Price: $6.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Vineyard Gal Floral Woven Skater Dress
This vintage-inspired floral woven dress is perfect for vineyard weddings, wine tastings, and daytime soirees! The skater dress features adorable short puff sleeves, a sweetheart neckline with a bust tie, a lace-up back design, and a tiered fit-and-flare skater silhouette with a short hem. The lined woven fabric showcases a vintage floral print pattern. Style this short dress with on-trend strappy mules.
Fit & Features
- Short puff sleeves
- Sweetheart neckline, bust tie
- Lace-up back design, tie closure
- Tiered fit-and-flare skater silhouette
- Short-length hem
- Vintage floral print, lined woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-2966
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Oh-So-Cute Puff Sleeve Lace-Up Gingham Mini Dress
Oh-so-cute and sweet! This gingham mini dress is sure to charm at brunch and picnics. You'll have comfort and style, made from a gauze woven fabric boasting a cheery gingham print line with a stretchy knit. With puff sleeves and a V-neckline, this bodycon dress flatters your figure and adds a fun touch with its lace-up back. The mini-length hem and playful gingham print make it perfect for any spring-to-summer event. Complete the look in sandals and sunnies!
Fit & Features
- Gingham print, gauze woven fabric lined with stretchy knit
- V-neckline
- Lace-up, back zipper and hook-eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5438
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Feeling Amore Tie-Back A-Line Eyelet Mini Dress
Fall in love with this adorable eyelet mini dress perf for weekend plans. The flirty tie-back detail and ruffled A-line silhouette will get you all the compliments.
Fit & Features
- Eyelet knit fabric lined with stretchy knit
- Adjustable spaghetti straps
- Tie-back design
- Ruffled trim
- Short A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5434
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Pretty Vibes Eyelet Knit Layered Skater Dress
Show off pretty vibes in this adorable layered skater dress made with breezy eyelet knit fabric. Pair with sneakers for a cute casual look or wedges for a dressier style.
Fit & Features
- Stretchy sheer eyelet knit fabric, partial knit lining
- Square neckline
- Spaghetti straps
- Double-layered skater skirt
- Short fit-and-flare silhouette
- Runs true to size
Style Number/Barcode: 05102-5428
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirty Day Ruffled Ditsy Floral Skater Dress
You'll love every moment spent in this ditsy floral skater dress! The square neckline and spaghetti tie straps add a flirty touch, while the stretchy smocked bodice ensures a comfortable fit. With a playful ruffled skater silhouette and a mini-length hem, this dress is perfect for any occasion. Complete the look in wedges.
Fit & Features
- Ditsy floral print, woven fabric lined with knit
- Spaghetti tie strap
- Square neckline
- Ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5425
Category Name: Casual Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Charming Appeal Puff Sleeve Eyelet Knit Skater Dress
The sweet eyelet design and adorable details give this puff sleeve skater dress a charming appeal! Made with an airy sheer eyelet knit fabric with a partial knit lining, this short dress is perfect for your spring and summer weekend outings. It features a square neckline with chic ruching at the bust, sheer short puff sleeves with a dainty ruffled trim, a sheer corset-style bodice to create a cinched look, and a fit-and-flare skater silhouette for a flirty vibe. Complete your outfit with hoop earrings!
Fit & Features
- Sheer eyelet knit fabric, partial knit lining, plenty of stretch
- Square neckline with ruched bust
- Sheer short puff sleeves, ruffled trim, elastic cinched hems
- Sheer corset-style bodice, stretchy high waist seam
- Fit and flare skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5427
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Catch A Cutie Short Sleeve Cutout Eyelet Skater Dress
Catch yourself a cutie wearing this eyelet skater dress to day parties this season! With playful puff sleeves and a flirty cutout. The sweetheart neckline and bust drawstring add a touch of romance, while the skater silhouette and tiered ruffled hem keep it fun and flirty. Complete the look in wedge sandals.
Fit & Features
- Eyelet fabric lined with stretchy knit
- Sweetheart neckline
- Adjustable bust drawstring, cutout
- Skater silhouette
- Tiered ruffles
- Runs true to size
Style Number/Barcode: 05102-5430
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Always Sweet Ruffled Bodycon Eyelet Lace Mini Dress
Make your sweet impression in this eyelet lace mini dress at bridal showers, graduations, or birthdays! Crafted from an eyelet lace fabric that adds a touch of chic to this mini-length dress boasting a square neckline, ruffled straps, and a flattering bodycon fit. Complete the look with a sleek choker.
Fit & Features
- Eyelet lace fabric lined with stretchy knit
- Ruffled straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5429
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
City Of Love V-Neck Ruffle Babydoll Dress
Grab your baguette, passport, and this babydoll dress cause the city of love is calling your name! The playful ruffled shoulder straps and convenient side pockets add a touch of whimsy to this flirty dress. The babydoll silhouette and ruffled tiered hem make it perfect to sweep through Paris looking adorable! Complete the look in strappy sandals and a purse.
Fit & Features
- Woven fabric
- Ruffled shoulder straps
- Side pockets
- Babydoll silhouette
- Ruffled tiered short-length hem
- Runs true to size
Style Number/Barcode: 05102-5423
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sweetie Status Halter Crochet Trim Babydoll Dress
You'll look absolutely adorable in this babydoll dress at showers, birthdays, or backyard parties! The halter neckline and cutout bodice add a touch of allure, while the crochet trim and babydoll silhouette create a delicate and feminine look along the short-length hem. Complete the look in sandals and hoop earrings.
Fit & Features
- Gauze woven fabric, woven lining, no stretch
- Halter neckline with spaghetti strap ties
- Cutout bodice
- Crochet trim
- Babydoll silhouette
- Runs true to size
Style Number/Barcode: 05102-5421
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sunny Days Square Neck Tie-Back Skater Short Dress
Sunny days pair perfectly with this skater short dress for casual occasions or day dates! Made from lightweight cotton, this dress boasts a square neckline and elasticized cap sleeves for a perfectly feminine touch. The smocked bodice and tie-back waist ensure a flattering fit, while the tiered skater silhouette adds a playful flair. Complete the look with sandals, sunglasses, and a purse for a cute style!
Fit & Features
- Lightweight cotton fabric with woven lining
- Stretchy smocked bodice
- Tie-back waist
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5417
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Beyond Precious V-Neck Ruffle Babydoll Dress
You'll be looking beyond precious in this babydoll dress - the perfect summer staple! The ruffle trim shoulder straps and v-neckline create a delicate and alluring look, while the ruffled babydoll silhouette and side pockets add a touch of playful charm to the short-length hem. Complete the look in trendy sandals.
Fit & Features
- Woven fabric, bust lining, no stretch
- Ruffle trim shoulder straps
- V-neckline
- Ruffle babydoll silhouette
- Side pockets
- Runs true to size
Style Number/Barcode: 05102-5422
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Spice Things Up V-Neck Cutout Skater Dress
Casual gets a sultry upgrade with this short skater dress perfect for showers and birthdays! This flirty skater dress boasts flowy sleeves, a front and back V-neckline, and a cutout bodice for an alluring look. The gauze fabric adds breezy comfort while the skater silhouette and short length keep you on-trend. Complete the look in strappy wedges.
Fit & Features
- Gauze woven fabric lined with stretchy knit
- V-Neckline front and back
- Cutout bodice, elasticized straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5419
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Simply Sunny Scoop Neck Skater Eyelet Mini Dress
Sunshine days are ahead and this skater mini dress is perfect for enjoying the weekend and weather! Crafted from an adorable eyelet knit fabric, this mini dress is designed with a flattering scoop neckline, adjustable spaghetti straps for a perfect fit, and a flirty tie-back detail to show off your style. The skater silhouette and tiered ruffled hem allow for movement and a fashionable sway with every step! Complete the look in heeled sandals.
Fit & Features
- Eyelet knit fabric, sewn-in knit lining
- Adjustable spaghetti straps
- Tie-back detail
- Skater silhouette
- Tiered ruffles
- Runs true to size
Style Number/Barcode: 05102-5426
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Make A Debut Plaid Strapless Pleated Mini Dress
Make a debut in classic plaid and on-trend silhouette! This plaid mini dress is sure to stand out from any crowd. Featuring a strapless neckline, form-hugging bodice, belt loop accents, and a flirty pleated mini-length hem. Complete the look in lug boots for an edgy vibe!
Fit & Features
- Strapless neckline
- Back zipper closure
- Form-hugging bodice
- Belt loop accents
- Pleated mini-length hem
- Plaid print, woven fabric, knit lining at the bust, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5415
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Cherry On Top Lace-Up Cutout Chiffon Skater Dress
Nothing says wow like this chiffon skater dress that puts the cherry on top of your look at brunch, birthdays, or shower celebrations! Designed with a V-neckline, adjustable ruffled straps, and a pleated bust, this dress accentuates your curves. The cutout waist and back with lace-up detailing add a playful touch, while the skater silhouette and tiered ruffled hem give a flirty and flattering fit! Complete the look in fashionable platform sneakers.
Fit & Features
- Chiffon fabric lined with woven fabric
- Adjustable ruffled straps
- Lace-up, back zipper hook-eye closure
- Cut out sides and back
- Ruffled
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2947
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Love Game Plunge V-Neck Bubble Skater Dress
Win hearts in this adoring bubble skater dress perfect for dressy occasions! Boasting a flattering skater silhouette, this poplin woven dress is designed with a plunge V-neckline and back to show some skin, short ruffled bubble sleeves, and a bubble short-length hem. Complete the look in strappy sandals.
Fit & Features
- Poplin woven fabric, sewn-in knit lining
- Plunge V-Neckline
- Short ruffled bubble sleeves
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2935
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Ready For Romance Floral Velvet Lace Mini Dress
Unleash your inner daring in this floral velvet mini dress on an evening out! With a lace-trim V-neckline, sleek adjustable bungee spaghetti straps, and a low-cut back, this bodycon dress will turn heads. The front bow adds a touch of romance, while the floral velvet pattern on mesh fabric adds an alluring texture. Complete the look with a clutch, heels, and a bolero for a stylish head-to-toe outfit!
Fit & Features
- Floral velvet pattern, mesh fabric lined with knit
- Bungee adjustable spaghetti straps
- Lace trim and bow inset
- Back zipper and hook-eye closure
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-5315
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Chic Girl Energy Houndstooth Knit Mini Dress
Bring the chic girl energy to your fall wardrobe with this trendy mini dress! It features a sleeveless square neckline, spaghetti straps, a mini-length hem, and a bodycon silhouette to showcase your curves. The knit fabric features an all-over houndstooth pattern for an elevated vibe. Style this mini dress with a faux leather moto jacket and combat boots!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Mini-length hem
- Bodycon silhouette
- Houndstooth pattern
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5410
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Always Stylish And Classic Plaid Mini Dress
This stylish mini dress features a classic plaid print and a bodycon silhouette in soft knit fabric. Its square neckline, spaghetti straps, and mini-length hem make it perfect for a trendy, dressy look for layering. Style with a chic moto jacket and boots for an evening out!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Plaid print, knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5411
Category Name: Casual Dresses
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Zip It Long Sleeve Cargo Pocket Mini Dress
This casual mini dress is perfect for the fashionista with an eye for style! Its fitted long sleeves, crew neckline, and zipper closure give a classic feel, while the bodycon silhouette, side cargo flap pockets, and mini-length hem on lined rib knit fabric create a flattering and unique style. Complete the look with booties for day or night plans!
Fit & Features
- Fitted long sleeves, crew neckline
- Front zipper closure
- Bodycon silhouette
- Side cargo flap pockets
- Mini-length hem
- Lined stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5407
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Shine All Way Metallic Woven Skater Dress
Shine all way to and from the party in this breezy skater dress! It features a sleeveless V-neck, adjustable spaghetti straps, a stretchy smocked waist, and a flattering skater silhouette with a ruffled short-length hem. The dress is crafted from an airy woven fabric with shimmering metallic threads and has a stretchy knit lining. Complete the look in stiletto heels.
Fit & Features
- Sleeveless V-neck
- Adjustable spaghetti straps
- Stretchy smocked waist
- Skater silhouette
- Ruffled short-length hem
- Metallic threads, airy woven fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5405
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale