Casual Dresses

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.

  • Hint Of Chic Cowl Neck Knit Mini Dress

    You'll love the hint of chic style this cowl neck mini dress gives your look! The soft knit fabric has a double-lined design for a smooth seamless look with plenty of stretch. The short dress is shaped with a sleeveless cowl neckline and thin tank shoulder straps. The bodycon silhouette will hug your curves along the mini-length hem. Pair with a handbag and clear heels for happy hour.

    Fit & Features

    • Stretchy double-lined knit fabric
    • Sleeveless cowl neckline
    • Thin tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5557

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cool Girl Chic Strapless Abstract Mesh Mini Dress

    Keep your going-out look cool girl chic with this sultry strapless abstract mesh mini dress. The airy sheer mesh fabric showcases a trendy abstract print and includes a full-length soft knit lining for coverage. The strapless straight-across neckline features an elastic band for a stretchy and secure fit, while the bodycon silhouette will flaunt your stunning curves. Style this short dress with a layered necklace and lace-up heels for drinks with the girls!

    Fit & Features

    • Stretchy sheer mesh fabric with soft knit lining
    • Abstract print
    • Strapless straight elasticized neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5558

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect And Stylish Scoop Neck Ribbed Knit Midi Dress

    Perfect and stylish for everyday occasions, this basic ribbed knit midi dress is just what you need for coffee dates, shopping downtown, or grabbing dinner with friends! This stunning dress features classic short sleeves, a flattering scoop neckline, and a bodycon silhouette for a sleek curve-flaunting appeal. The side slit offers movement along the mid-length hem, while the soft and stretchy ribbed knit fabric ensures all-day comfort. Style this midi dress with a casual jacket, sandals, and a crossbody bag to complete the look!

    Fit & Features

    • Soft, stretchy ribbed knit fabric
    • Side slit
    • Bodycon silhouette
    • Midi-length 
    • Runs true to size

    Style Number/Barcode: 05102-5554

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crusin' The Tropics Lace-Up Tropical Mini Dress

    Cruise the tropics in this stylish tropical mini dress! Designed with a tropical palm print on knit fabric, this dress is sure to stand out on the island and boat. Featuring a V-neckline and spaghetti straps, a lace-up back that lets you customize the style, and a flattering bodycon fit. Complete the look with sunglasses.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, sewn-in lining
    • Spaghetti straps
    • V-neckline
    • Lace-up back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5549

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty In Paradise One-Shoulder Tropical Maxi Dress

    You'll be looking so pretty as you stroll the beach in paradise in this tropical maxi dress! The smooth stretchy knit fabric showcases a bold tropical print perfect for an island vacay. The long dress is shaped with a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap. The sultry ruched cutout at the waist features an adjustable drawstring for a customized look. Reveal some leg with the sexy high-cut side slit on the maxi-length silhouette. Style this slim-fit dress with espadrille wedges.

    Fit & Features

    • Stretchy knit fabric, knit lining at the bust
    • Tropical print
    • Asymmetric one-shoulder neckline, spaghetti strap
    • Ruched side cutout, adjustable drawstring
    • High side slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5542

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Mode Tropical Floral Mesh Maxi Dress

    Activate vacay mode and radiate dreamy vibes in this alluring tropical maxi dress! Designed with an airy sheer mesh fabric with a mini-length knit lining, this maxi-length dress is accented with a blooming tropical floral print for a stunning look. It features a sleeveless square neckline, spaghetti straps, ruched detailing at the waist to accentuate your curves, and a bodycon silhouette with a thigh-high side slit to showcase some leg. Style with stiletto heels for a sunset dinner!

    Fit & Features

    • Tropical floral print
    • Sheer mesh fabric with mini-length knit lining, plenty of stretch
    • Square neckline
    • Spaghetti straps
    • Ruched waist, side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5543

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Natural Romancer Crew Neck Lace Mini Dress

    Indulge in the effortless romance of this lace mini dress perfect for bridal showers, rehearsal dinners, and parties! This stunning dress features short sleeves, a flattering crew neckline, and a bodycon silhouette that hugs your curves. The sheer lace fabric exudes romance, while the attached knit slip lining provides comfort and coverage. Complete the look with earrings and strappy sandals.

    Fit & Features

    • Sheer lace fabric with stretch
    • Attached slip knit lining
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5548

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lost In Love Strappy Back A-Line Mini Dress

    Everyone will be lost in love once they catch sight of you in this strappy A-line mini dress! Perfect for any occasion, this dress will have you feeling fabulous. This playful A-line mini features a flattering sweetheart neckline, shoulder straps for added support, and a strappy back for flirty fun. Complete the look in block heels.

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Sweetheart neckline
    • Shoulder straps
    • Strappy back
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5544

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Covetable Charm V-Neck Ruffled Maxi Dress

    You'll covet the charm of this sleeveless maxi dress all season!  With a flattering V-neckline and adjustable spaghetti straps, this dress will hug you in all the right places. The crisscross and smocked back add a trendy touch, while the flowy silhouette and ruffled long-length hem offer a breezy style. Complete the look in sandals.

    Fit & Features

    • Woven fabric, bust lining, no stretch
    • Adjustable spaghetti straps
    • Crisscross and smocked back
    • Flowy silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5546

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simplest Statement Sweetheart Rib Knit Midi Dress

    Simple and statement-making! This rib knit midi dress offers any fashionista a stylish adventure. With a flattering sweetheart neckline, twisted bust, and bodycon silhouette that puts your curves on display, you'll feel confident and flirty! The midi-length hem and side slit add a touch of sultry to this simple yet stunning dress. Perfect for casual weekend plans or a date night, style this dress with chic sandals and a necklace.

    Fit & Features

    • Stretchy rib knit fabric
    • Sweetheart neckline with twisted accent
    • Spaghetti straps
    • High side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5545

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sheer Exellence Mock Neck Bodycon Mesh Midi Dress

    Experience sheer excellence in this stunning mesh midi dress perfect for dinners downtown or concerts. The sheer short sleeves and mock neckline add a touch of chic, while the bodycon silhouette flatters your figure. The sheer mesh fabric and smooth knit slip provide a luxurious feel, and adjustable spaghetti straps ensure a perfect fit. Complete the look with this midi dress in block heels and a hair clip for a fashion-forward style!

    Fit & Features

    • Sheer mesh fabric
    • Includes a smooth knit slip, adjustable spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5540

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charmed And Cute Polka Dot Chiffon Skater Dress

    Envoke a charmed and cute style in this polka dot skater dress perfect for showers or graduates! Show off your curves with the sweetheart neckline and skater silhouette, while adding a touch of cuteness with the short puff sleeves. The tie-back adds a flirty detail and the short-length hem is perfect styling with trendy sneakers for a casual vibe.

    Fit & Features

    • Polka dot, chiffon fabric, woven lining, no stretch
    • Sweetheart neckline
    • Padded bra cups
    • Back zipper hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3289

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Free Flowing Cutie V-Neck Ruffle Eyelet Maxi Dress

    Flattering and breezy come together on this charming eyelet lace maxi dress perfect for spring days and summer cuteness! This dreamy dress features a flattering V-neckline, adjustable spaghetti straps, and charming button accents. The cutout waist and flowy silhouette accentuate your figure, while the tiered ruffled maxi hem adds a whimsy touch. Complete the look in wedge sandals and a floppy hat!

    Fit & Features

    • Eyelet lace fabric lined with woven fabric
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Cutout waist
    • Ruffled maxi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3286

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fun And Flirty Halter Neck Skater Dress

    This adorable skater dress is perf for twirling and giving off those fun and flirty vibes at your next party! It features a sleeveless deep V-neckline with halter straps that lead to a tie-back design, an open back, dual high waist seams, and a short skater skirt with a fab fit and flare silhouette. The plisse woven fabric includes a full knit lining. Complete your look with a lariat necklace and platform heels.

    Fit & Features

    • Sleeveless deep V-neckline
    • Halter straps, tie-back design
    • Open back
    • Dual high waist seams
    • Short skater skirt, fit and flare silhouette
    • Plisse woven fabric, full-length knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2908

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Escape Strapless Tropical Midi Dress

    Serve chic looks on your dreamy escape in this tropical print midi dress. The stretchy lined knit fabric showcases a detailed tropical print pattern on the figure-flaunting silhouette. The bodice features a strapless elasticized straight-across neckline, leading to a bodycon fit with a mid-length hem. Style with combat booties to add some edge!

    Fit & Features

    • Stretchy knit fabric with knit lining
    • Tropical print
    • Strapless elasticized straight neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5539

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Vibes High Slit Tropical Knit Maxi Dress

    Give off effortless vacay vibes in this high slit tropical knit maxi dress. The tropical palm leaf print on the lightweight knit fabric will have you looking like you're ready for a getaway, even if you're just grabbing drinks at a local happy hour! The dress is shaped with a sleeveless V-neckline and spaghetti straps, and features a high-cut side slit to showcase some leg on the form-hugging mid-length silhouette. Style with gold hoops and strappy wedges!

    Fit & Features

    • Stretchy knit fabric with a bust lining
    • Tropical print
    • Sleeveless V-neckline
    • Spaghetti straps
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5537

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Polished Perfection Vest Pleated Short Dress

    Capture polished perfection in this chic vest pleated short dress! Designed with a structured twill woven fabric, this dress features a fitted vest top with an A-line skirt. The top is shaped with a sleeveless V-neckline and tank shoulder straps, followed by a button-front design and an angled cropped hem for a snatched look. The chic waist cutout adds a touch of allure, leading to a fitted high waist and a flowy, pleated short-length hem. The dress includes a back zipper closure for effortless styling. Complete your look with gold hoops and strappy mules!

    Fit & Features

    • Non-stretch twill woven fabric
    • Sleeveless V-neckline with tank shoulder straps
    • Button-front design, angled cropped hem
    • Back zipper with hook and eye closure
    • Waist cutout, high-rise skirt with pleating
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5536

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Modern Masterpiece Short Sleeve Marble Midi Dress

    Your look will be a modern masterpiece in this marble print mesh midi dress - a stunning piece for art gallery openings or cocktail parties! The airy sheer mesh fabric is lined with a stretchy knit for comfortable wear. The short sleeves and crew neckline create a classic look, while the bodycon silhouette accentuates your curves down to the midi-length hem with a back slit for movement. Complete the look with a purse and strappy stiletto heels.

    Fit & Features

    • Marble print
    • Sheer mesh fabric lined with stretchy knit
    • Crew neckline
    • Short sleeves
    • Bodycon silhouette
    • Back slit
    • Runs true to size

    Style Number/Barcode: 05102-5535

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Look Ditsy Floral Ruched Knit Mini Dress

    Create the cutest look for your weekend plans in this floral ruched knit mini dress! The adorable ditsy floral print on the soft and stretchy brushed knit fabric will give your casual look a flirtatious vibe! The short dress features a sleeveless square neckline with tie-shoulder spaghetti straps for a trendy detail and customized fit. The ruching down the side seams will show off your curves on the bodycon silhouette. Style this dress with hoop earrings and strappy mules for brunch with your girls!

    Fit & Features

    • Ditsy floral print
    • Stretchy brushed knit fabric
    • Sleeveless square neckline
    • Tie-shoulder spaghetti straps
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5533

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Floral Ruched Mesh Mini Dress

    Walk into any party looking like a dream in this floral ruched mesh mini dress! The bold multi-colored floral print will capture all the attention, while the airy mesh fabric offers breezy comfortable wear. The mini-length dress features a sleeveless square neckline with adjustable spaghetti straps for a customized fit. The trendy ruched detailing down the side seams will accentuate your curves along the alluring bodycon silhouette. Style this short dress with hoop earrings and clear heels.

    Fit & Features

    • Floral print
    • Sheer mesh, sewn-in knit lining
    • Sleeveless square neckline
    • Spaghetti straps
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5534

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Compliment Me High Slit Knit Midi Dress

    You'll spark up all the compliments in this simply chic high slit midi dress! Designed with a stretchy structured knit fabric, this dress is shaped with a sleeveless square neck and back with thin tank shoulder straps. The mid-length hem is accented with a high-cut side slit to show off some leg, and the bodycon silhouette will flaunt your stunning curves. Style with a faux leather jacket and heels to go bar-hopping!

    Fit & Features

    • Stretchy structured knit fabric
    • Sleeveless square neck and back
    • Tank shoulder straps
    • High side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5526

    Category Name: Casual Dresses

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Aura Strapless Floral Tie-Dye Maxi Dress

    Shine bright and serve a gorgeous aura in this strapless floral tie-dye maxi dress perfect for summertime soirees! The strapless neckline and lace-up back design exude effortless elegance, while the form-hugging fit accentuates your curves. The ruffled maxi-length hem adds a playful touch to this stunning dress. Complete the look with a ring set and sandals.

    Fit & Features

    • Floral tie-dye print, smooth knit fabric, moderate stretch
    • Strapless neckline
    • Lace-up back design
    • Form-hugging fit
    • Ruffled maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3277

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Truly Chic High Slit Bodycon Midi Dress

    Create a truly chic look for dinner and drinks in this high slit bodycon midi dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruching down the side seams, an asymmetric midi-length hem creating a thigh-high side slit, and a bodycon fit to showcase your stunning silhouette. The lined smooth knit fabric offers plenty of stretch. Style with rhinestone fringe earrings to add a touch of glam!

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruched side seams
    • Asymmetric midi-length hem, thigh-high side slit
    • Bodycon silhouette
    • Smooth knit fabric, mini-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5521

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Charmer Basic Rib Knit Maxi Dress

    A basic maxi dress that brings everyday charm! This long rib knit dress features a square neckline, spaghetti straps, and a flattering bodycon silhouette, you'll love this maxi dress for any occasion. Complete the look in a cute crop jacket and your favorite sneakers! 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Maxi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5522

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale