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.

  • Trendy New Vibe One-Shoulder Skater Dress

    This adorable sleeveless skater dress will give off a trendy new vibe that will get all the compliments. It features an asymmetric one-shoulder neckline, dual adjustable spaghetti straps that continue to an asymmetric back strappy design, dual vertical seams down the front, a short-length hem, and a flared-out skater silhouette. The buttery-smooth knit fabric includes a full lining and has plenty of stretch. Style with clear mules!

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Dual adjustable spaghetti straps
    • Asymmetric back strappy design
    • Dual vertical seams down the front
    • Short-length hem, skater silhouette
    • Smooth knit fabric, full-length lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5291

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casual Flirt Sleeveless A-Line Short Dress

    Breeze in looking casual and flirty in this short dress at parties and date nights! It features a sleeveless square neck, spaghetti straps, and a flattering A-line silhouette on smooth knit fabric. Complete the look in a necklace and earrings set.

     Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • A-line silhouette
    • Short-length hem
    • Smooth knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5287

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casually Effortless Smooth Knit Bodycon Mini Dress

    Enjoy an effortless day or night out with this casual smooth knit mini dress! Its strapless neckline and bodycon silhouette are perfect for showing off those curves, while the mini-length hem ensures you get noticed! The dress is composed of a slinky smooth knit fabric with a stretchy knit lining. Complete the look in sassy lace-up sandals.

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Slinky smooth knit fabric, stretchy knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5289

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Classic Allure Sleeveless A-Line Short Dress

    Showcase a classic allure in this chic sleeveless A-line short dress. It features a high mock neckline with tie-back straps, an open-back design, a fitted high waist seam, a short-length hem, and a flowy A-line silhouette. The buttery-smooth knit fabric includes a full lining and has plenty of stretch. Complete your look for happy hour with sleek pumps.

    Fit & Features

    • Sleeveless high mock neckline, tie-back straps
    • Open back
    • Fitted high waist seam
    • Short-length hem
    • A-line silhouette
    • Smooth knit fabric, full-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5288

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's The Main Rib Knit Strapless Midi Dress

    Flaunt your look with ease and chicness with this midi dress this season! The knee-length dress features a strapless neckline, a flattering bodycon silhouette, and a fitted maxi-length hem on soft and stretchy rib knit fabric with a short knit lining. Style with the matching bolero and heels for weekend plans!

    Shop Matching Bolero: She's The Main Rib Knit Slouchy Bolero

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Fitted midi-length hem
    • Soft and stretchy
    • Rib knit fabric, short knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5872

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playful Prints Satin Pleated Skater Dress

    Play up your colorful side in this satin skater dress perfect for summer! It features a sleeveless V-neckline, adjustable spaghetti straps, a ruched tie-front bust, a stretchy smocked back, a flirty cutout, and a pleated short-length hem. The dress is designed with a multi-colored geometric print on smooth woven satin fabric. Complete the look in lace-up heels.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Ruched tie-front bust, stretchy smocked back
    • Cutout accent, skater silhouette
    • Pleated short-length hem
    • Multi-colored geometric print
    • Smooth woven satin fabric, no stretch, bust lining
    • Runs true to size

    Style Number/Barcode: 05102-5284

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Down Low Denim Strapless Midi Dress

    Take your look on the down low in this denim midi dress! The knee-length dress features a strapless neckline, stretchy smocked back, and button-down front closures, this bodycon dress will have you breaking the fashion barriers. With belt loop accents, three-pocket styling, and a midi-length hem, this denim stunner gives you the power to take risks and turn heads! Style this midi dress with a purse and block heels for a birthday brunch!

    Fit & Features

    • Strapless neckline
    • Stretchy smocked back
    • Button-down front closures
    • Bodycon silhouette, midi-length hem
    • Belt loop accents, three-pocket styling
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5283

    Category Name: Casual Dresses

    Price: $5.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Loved In Lace V-Neck Long Sleeve Short Dress

    A divine lace short dress for modern brides, birthday babes, or any dressy occasion! The mini dress features sheer lace long sleeves with flared cuffs, a V-neckline, a bodycon silhouette that hugs your curves and is composed of a lace knit fabric with stretchy knit lining. Complete the look with fringe earrings and heels.

    Fit & Features

    • Sheer long sleeves, flared cuffs
    • V-neckline
    • Bodycon silhouette
    • Short-length hem
    • Lace knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-3171

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Curves For Days Off-The-Shoulder Midi Dress

    Serve major curves in this off-the-shoulder midi dress at parties and dressy occasions! Featuring a flattering off-the-shoulder sweetheart neckline and a tie-front bust, this dress accentuates your figure in all the right ways. The cutout bodice adds a flirty charm, while the ruched seams and bodycon fit hug your figure for a sultry silhouette on mesh-lined fabric. Complete the look in stiletto heels.

    Fit & Features

    • Mesh fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Tie-front bust, cutout bodice
    • Side ruched seams
    • Center back slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-2623

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fashion Zilla Mock Neck Texture Mini Dress

    A fashionista like you will go crazy for this iconic mini dress! It features a mock neckline, cap sleeves, and a flattering bodycon silhouette on stylish textured mesh fabric with a stretchy knit lining. Complete the look in sleek sunglasses and booties for an edgy-fab vibe!

    Fit & Features

    • Mock neckline
    • Cap sleeves
    • Bodycon silhouette
    • Mini-length hem
    • Textured mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5278

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Colorful Sensation Abstract Print Maxi Dress

    Be the colorful sensation in whatever room you walk into wearing this abstract print midi dress! It features a sleeveless square neckline, spaghetti straps, a bodycon silhouette, and an adjustable ruched drawstring atop a sultry slit. Complete the look with a chic handbag for an art gallery opening or sunset cocktails!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Adjustable ruched drawstring, high slit
    • Maxi-length hem
    • Abstract print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5279

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off My Mind Cutout Long Sleeve Ribbed Knit Midi Dress

    Make an unforgettable appearance in this long-sleeved midi dress at brunch or casual parties! The midi dress is designed with an off-the-shoulder neckline, a twisted bust with a sultry cutout, and a bodycon fit on stretchy ribbed knit fabric. Complete the look in strappy heels.

    Fit & Features

    • Ribbed knit fabric with moderate stretch
    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Twisted bust, cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5280

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreaming In Marble Asymmetrical Midi Dress

    Finished with a gorgeous marble print, this midi dress will be the star of the night! The knee-length dress features a sleeveless V-neckline, adjustable spaghetti straps, a crisscross back, and a  bodycon silhouette and side ruched seam that flatters your curves, while the asymmetrical midi-length hem and high side slit show off your legs. Style the midi dress with basic stiletto heels for a sunset dinner.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Crisscross back
    • Bodycon silhouette
    • Side ruched seam, high side slit
    • Asymmetrical midi-length hem
    • Marble print, bust knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5274

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Colorful Style Strapless Abstract Mini Dress

    Showcase a colorful style in this abstract print mini dress out and about with the girls! The dress features a strapless neckline, bodycon silhouette, and a fitted hem on mesh fabric with a stretchy knit lining. Complete the look with a sleek choker and sandals!

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Mini-length fitted hem
    • Abstract print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5275

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Crush Marble Print Maxi Dress

    They'll totally be crushing on you in this alluring abstract marble print maxi dress! It features a strapless straight-across neckline, ruching down one side seam with an adjustable drawstring, a sultry high-cut side slit, and an asymmetric maxi-length hem. The fitted bodice leads to a flowy silhouette. The marble-printed sheer mesh fabric includes a mini-length knit lining. Style with gemstone earrings.

    Fit & Features

    • Strapless straight-across elastic-banded neckline
    • Ruching down one side seam, adjustable drawstring
    • High-cut side slit, asymmetric maxi-length hem, lettuce-edge trim
    • Fitted bodice, flowy silhouette
    • Abstract marble print
    • Sheer mesh fabric, mini-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5276

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Living In Color Chiffon Halter Maxi Dress

    Live life in color! Easy and breezy, this chiffon maxi dress is perfect for all of your summer activities. It features a sleeveless halter V-neckline, a unique braided neck strap with tie closure, a stretchy smocked back, and a flowy silhouette. The dress is designed with an airy chiffon fabric showcasing a watercolor print and a woven lining. Complete the look with a sleek arm cuff bracelet.

    Fit & Features

    • Sleeveless halter V-neckline
    • Braided neck strap, tie closure
    • Stretchy smocked back
    • Flowy silhouette
    • Maxi-length hem
    • Airy chiffon fabric, watercolor print, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-5269

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fresh In Floral Ruched Mesh Midi Dress

    Keep your summer style fresh with this pretty floral printed mesh midi dress! It features a sleeveless square neckline, adjustable spaghetti straps to customize the fit, all-over ruched detailing, a midi-length hem with a side slit accent, and a bodycon silhouette that will hug your natural curves. The airy floral printed sheer mesh fabric includes a smooth knit lining and offers plenty of stretch. Complete the look with strappy mules.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • All-over ruching
    • Midi-length hem, side slit, bodycon silhouette
    • Floral print
    • Sheer mesh fabric, smooth knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5267

    Category Name: Casual Dresses

    Price: $10.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miss. Fashion Strapless Marble Print Mini Dress

    They'll call you Miss. Fashion when you step out in this mesh mini dress! It features a strapless neckline, a bodycon silhouette, an adjustable side drawstring that lets you customize the style, a slit accent, and an asymmetrical hem. Style with lucite heels for a seamless-chic look!

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Adjustable side drawstring, slit accent
    • Asymmetrical mini-length hem
    • Marble print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5268

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Lovely Off-The-Shoulder Ruffled Skater Dress

    You'll look oh-so-lovely in this adorable ruffled skater dress! It features an off-the-shoulder sweetheart neckline with a ruffled trim and short sleeve cuffs, ruching at the bodice, a pointed high waist seam, a short skater skirt with a ruffled tiered design, and a fit and flare silhouette. The woven fabric has minimal stretch. Complete the look with rhinestone hoops and clear heels for a flirty date look.

    Fit & Features

    • Off-the-shoulder sweetheart neckline
    • Ruffled trim, short sleeve cuffs
    • Ruching at the bodice, pointed high waist seam
    • Hidden back zipper, hook and eye closure
    • Short skater skirt, ruffled tiered design, fit and flare silhouette
    • Woven fabric, knit lining at the bodice, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5271

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Fab Marble Print Mesh Mini Dress

    Oh so fab, you'll turn heads in this alluring marble print mesh mini dress. It features a sleeveless cowl neckline, adjustable spaghetti straps to customize the fit, a mini-length hem with a cute lettuce-edge trim, and a bodycon silhouette that will hug your natural curves. The airy sheer mesh fabric includes a full knit lining and features an all-over marble print pattern. Style with lace-up heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Mini-length hem, lettuce-edge trim
    • Bodycon silhouette
    • Marble print
    • Sheer mesh fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5509

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Babe Satin A-Line Mini Dress

    Embody the beauty of sunset hour in this satin marble print mini dress perfect for a rooftop lounge! It features a sleeveless front and back cowl neckline, adjustable spaghetti straps, crisscross back straps, and a flattering A-line silhouette. Complete the look in lace-up heels.

    Fit & Features

    • Sleeveless front and back cowl neckline
    • Adjustable spaghetti straps
    • Crisscross back straps
    • A-line silhouette
    • Mini-length hem
    • Marble print, smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5273

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Enchanting Entrance Chiffon Floral Maxi Dress

    Make an enchanting entrance into a tropical destination wedding in this effortless chiffon floral maxi dress! It features a sleeveless V-neckline, flirty ruffled spaghetti straps, a stretchy smocked back, a ruched bust, and a flowy tiered ruffled silhouette with a flattering front slit. Complete the look with a dainty layered choker necklace and heels.

    Fit & Features

    • Sleeveless V-neckline, ruffled spaghetti straps, adjustable
    • Stretchy smocked back, ruched bust
    • Flowy tiered ruffled silhouette, front slit
    • Maxi-length hem
    • Tropical floral print
    • Airy chiffon fabric, short smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5270

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Curve Flaunter Mesh Ruched Midi Dress

    Flaunt your best assets in this curve appeal of a midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a ruched bust with trim, a bodycon silhouette, a side slit, and all-over ruching. Complete the look in striking rhinestone sandals for an engagement party or birthday!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Ruched bust with trim
    • Bodycon silhouette
    • Side slit, midi-length hem, all-over ruching
    • Mesh fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5266

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wanna Getaway Chiffon Geometric Print Maxi Dress

    'Tis the season for day trips, weekend getaways, or booking a flight out of town! This chiffon maxi dress will keep you stylish for it all. It features a sleeveless surplice V-neckline, spaghetti straps that crisscross along the open back, a tie-waist design, and a flowy silhouette with a flattering high front slit. Complete the look in statement sandals.

    Fit & Features

    • Sleeveless surplice V-neckline
    • Spaghetti straps, crisscross open back
    • Flowy silhouette, tie waist design
    • High front slit, back zipper and hook-eye closure
    • Maxi-length hem
    • Geometric print, airy chiffon fabric, smooth woven lining
    • Runs true to size

    Style Number/Barcode: 05102-5265

    Category Name: Casual Dresses

    Price: $5.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale