Casual Dresses

Loading...

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.

  • Button Up Babe Denim Strapless Mini Dress

    Look and feel like a total babe in this denim mini dress at concerts or parties! The short dress features a sweetheart neckline, bust seam detailing, a trendy asymmetrical button front design, a flattering bodycon silhouette, and a mini-length hem. Complete the look with a mini handbag.

    Fit & Features

    • Strapless sweetheart neckline
    • Bust seam detailing
    • Back zipper closure
    • Asymmetrical button front design
    • Bodycon silhouette, mini-length hem
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5443

    Category Name: Casual Dresses

    Price: $19.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cadet Babe Cargo Pocket Mini Dress

    Take rank as a cadet babe in this sleeveless mini dress perfect for elevating your basics! It features a square neckline, spaghetti straps, cargo flap pockets with pull tabs, and a flattering bodycon silhouette on stretchy rib knit fabric. Complete the look with a denim jacket.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Cargo flap pockets, pull tabs
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5399

    Category Name: Casual Dresses

    Price: $5.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking For The One Basic Long Sleeve Maxi Dress

    Dare to be bold this season and fall in love with this basic maxi dress! Its fitted long sleeves, crew neckline, and bodycon silhouette hug your figure in all the right places all the way down to the maxi-length hem. The dress is composed of a double-lined rib knit fabric with plenty of stretch. Complete the look in block heels and a handbag for any day or night occasion!

    Fit & Features

    • Fitted long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Maxi-length hem
    • Double-lined rib knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5375

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Delightfully Cute Plaid Cargo Mini Dress

    This delightfully cute plaid mini dress dares you to stand out from the crowd! It features a square neckline, spaghetti straps, trendy side cargo flap pockets, a flattering bodycon silhouette, and a mini-length hem. Layer with a cropped jacket for casual hangs or school!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Side cargo flap pockets
    • Bodycon silhouette, mini-length hem
    • Plaid print
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5372

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • I'm So Rare Marble Long Sleeve Mini Dress

    Look one-of-a-kind in this marble print mini dress! The short dress features sheer fitted long sleeves, a crew neck, a flattering bodycon silhouette, and a mini-length hem on marble-printed mesh fabric. Dare to be rare and style the mini dress with a ring set for day or night plans!

    Fit & Features

    • Sheer fitted long sleeves
    • Crew neck
    • Bodycon silhouette
    • Mini-length hem
    • Marble print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5327

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • She's All That Strapless Midi Dress

    Feel confident in this stylish midi tube dress! The knee-length dress features a soft and comfortable textured knit fabric, combined with its strapless neckline and bodycon silhouette, making this the perfect look for any occasion. Style the midi dress with sleek heels for a birthday brunch.

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Midi-length hem
    • Textured knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5311

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drama Meets Paradise Floral Maxi Dress

    Giving goddess energy with every step you take. This mesh maxi dress clings in all the right places with a daring cowl neckline and a strappy open back made to be seen.

    Fit & Features

    • Floral print, mesh fabric, soft stretchy knit lining
    • Plunging cowl neckline
    • Strappy open back with hoop insert
    • Form-hugging fit
    • Flowy maxi hem and front slit
    • Runs true to size

    Style Number/Barcode: 05101-000352

    Category Name: Casual Dresses

    Price: $21.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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
  • Essential Chic Off-The-Shoulder Mini Dress

    This essential chic off-the-shoulder mini dress is the perfect pick for the new season. It features an off-the-shoulder neckline with a cute fold-over design, long fitted sleeves, a mini-length hem, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Style this mini dress with over-the-knee boots for a fall happy hour!

    Fit & Features

    • Off-the-shoulder neckline, fold-over design
    • Long fitted sleeves
    • Mini-length hem
    • Bodycon silhouette
    • Ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5376

    Category Name: Casual Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cadet Cutie Cargo Pocket Mini Dress

    Rise up in rank looking cute in this mini dress! The short dress features a sweetheart neckline, adjustable spaghetti straps, cargo-flap pockets along the bust, snap-button down closures, belt loop accents and side pockets, and a flattering bodycon silhouette. Complete the look in sleek hoop earrings for a day out with the girls!

    Fit & Features

    • Sleeveless sweetheart neckline, adjustable spaghetti straps
    • Cargo-flap pockets along the bust
    • Snap-button down closures
    • Belt loop accents, side pockets
    • Bodycon silhouette, mini-length hem
    • Texture woven fabric, minimal stretch
    • Runs small, recommend to size up

    Style Number/Barcode: 05102-5441

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Draw The Line Striped Sweater Midi Dress

    Draw the line at basic and reach for this sensational striped sweater dress! It features a trendy off-the-shoulder neckline, fitted long sleeves, a flattering bodycon silhouette, and dual tie-back closures, and a cutout design. Complete the look with a chic crossbody bag for day or evening plans.

    Fit & Features

    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Dual tie-back closures, cutout design
    • Bodycon silhouette
    • Midi-length hem
    • Striped pattern, stretchy sweater knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5360

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Chic Paisley Mesh Ruched Midi Dress

    Dreamy boho and chic come together on this paisley print mesh midi dress you'll love for wine nights with bae! It features a cowl neckline  adorned with a shoulder strap and bungee spaghetti strap, a flattering bodycon silhouette, and a side ruched seam atop a slit and asymmetrical hem. Complete the look with strappy heels and earrings.

    Fit & Features

    • Sleeveless cowl neckline
    • Shoulder strap, bungee spaghetti strap
    • Bodycon silhouette, side ruched seam
    • Side slit, asymmetrical midi-length hem
    • Paisley print, mesh fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2924

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Obsession Marble Print Midi Dress

    The obsession you'll have with this fabulous marble print midi dress is so real! It features a V-neckline with a twist-front design, an alluring front waist cutout to showcase some skin, long fitted sleeves, a ruched side seam that leads to a high-cut side slit, and a midi-length hem with a form-hugging silhouette. The stretchy knit fabric features a trendy marble print pattern. Style this midi dress with spiral heels!

    Fit & Features

    • V-neckline, twist-front design
    • Front waist cutout
    • Long fitted sleeves
    • Ruched side seam, high side slit
    • Midi-length hem, form-hugging fit
    • Marble print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5309

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Artistic Muse Abstract Strapless Midi Dress

    You'll be the artsy muse in this abstract print mesh midi dress for gallery openings or an evening downtown! It features a strapless cowl neckline, flattering side ruched seams that accentuate your curves, a bodycon silhouette, and a side slit accent. Complete the look in clear strap heels for a seamless style!

    Fit & Features

    • Strapless cowl neckline
    • Back zipper and hook-eye closure
    • Side ruched seams, side slit
    • Bodycon silhouette, midi-length hem
    • Abstract print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5295

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    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
  • Make It Cute Sleeveless Ruched Slit Midi Dress

    For casual plans and outings, make your look cute in this sleeveless midi dress perfect for inspiring your inner fashionista! It features a square neck, spaghetti straps, a form-hugging fit, a side ruched seam that accentuates your curves, a side slit, and a midi-length hem. Complete the look with a crop jacket and heels!

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Form-hugging fit
    • Side ruched seam, slit
    • Midi-length hem
    • Stretchy brushed knit soft fabric
    • Runs true to size

    Style Number/Barcode: 05102-5290

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Isn't She A Beauty Woven Lace Skater Dress

    Let everyone admire your beauty in this woven skater dress! The sassy sweet dress features a sleeveless sweetheart neckline and shoulder straps with delicate sheer lace trim, a front bust tie, and a corset-seam bodice leading to the flowy short-length hem. The airy woven fabric includes a stretchy knit lining. Complete the look with heeled sandals.

    Fit & Features

    • Sleeveless bodice, sheer lace trim
    • Sweetheart neckline, shoulder straps
    • Corset seam bodice, bust tie
    • High waist seam, skater silhouette
    • Flowy short-length hem
    • Airy woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5439

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stop And Flare Smocked Skater Dress

    Stroll on by making everyone stop and stare at you in this flirty skater dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a cutout bust accent, a stretchy smocked bodice, and a flattering skater short-length hem. Complete the look in statement sandals for a brunch or day date!

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Cutout bust accent
    • Stretchy smocked bodice
    • Skater silhouette, short-length hem
    • Cotton fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5337

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Something Special Lace Satin Tie Skater Dress

    Look and feel like something special in this lace skater dress and enter your romance era! The dress features a sweetheart neckline with a satin ribbon tie, an underwire bust for support, adjustable satin spaghetti straps, and a satin ribbon tie waist that leads to the flattering skater silhouette and ruffled short-length hem. Complete the look in sparkly sandals for a day date or party!

    Fit & Features

    • Sleeveless sweetheart neckline, satin ribbon tie
    • Underwire bust, adjustable satin spaghetti straps
    • Back zipper and hook-eye closure
    • Satin ribbon tie waist
    • Skater silhouette, ruffled short-length hem
    • Delicate sheer lace, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5336

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All In The Flirt Halter Mini Dress

    Catch all the compliments. This mini halter dress features a fitted bodice and a flirty, layered skirt, perfect for your next sunny day brunch or a cute date night!

    Fit & Features

    • Smooth knit fabric
    • Square neckline
    • Wide shoulder straps
    • Low-back cut design
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000228

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Day Dreamer Strapless Abstract Midi Dress

    Make your daydream come true and wear this mesh midi dress for a gorgeous look this weekend! It features a strapless neckline with non-slip grip lining, flexible boning inserts along the bodice for structure, and ruched seams to accentuate your figure along the bodycon silhouette. The dress is designed with an abstract print on mesh fabric with a sewn-in knit lining. Complete the look with hoop earrings.

    Fit & Features

    • Strapless neckline, non-slip grip lining
    • Flexible boning inserts
    • Side zipper and hook-eye closure
    • Ruched seams, bodycon silhouette
    • Midi-length hem
    • Abstract print, mesh fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5363

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Extra Flare V-Neck Skater Dress

    Give your look extra flare in this sweet sleeveless skater dress! It features a V-neckline, tank shoulder straps, and a flattering fit and flare short-length silhouette. The dress is composed of a smooth knit fabric with plenty of stretch. Complete the look in rhinestone stiletto heels for a birthday or a dressy date night!

    Fit & Features

    • Sleeveless V-neckline
    • Tank shoulder straps
    • Skater silhouette
    • Short-length hem
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5292

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free