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.

  • Favorite Tune Sleeveless Tank Midi Dress

    Get ready to sing about this sleeveless midi dress and how much you love it! With a stylish sleeveless square neckline and flattering shoulder straps, this midi dress will hug your curves in the form-hugging silhouette and show some skin with the front slit. Perfect for any occasion, style this midi dress with a denim jacket and long necklace for an effortlessly chic look!

    Fit & Features

    • Sleeveless square neckline, shoulder straps
    • Form-hugging silhouette
    • Front slit
    • Midi-length hem
    • Rib knit fabric, bust knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5397

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Can't Help It Off-The-Shoulder Sweater Dress

    If chic comes naturally, this sweater maxi dress can't help but make your style shine! The maxi dress features an off-the-shoulder folded neckline, fitted long sleeves, a flattering bodycon silhouette, and a side slit on stretchy rib knit fabric. Complete the look in sleek stiletto heels for date nights or holiday parties!

    Fit & Features

    • Off-the-shoulder folded neckline
    • Fitted long sleeves
    • Bodycon silhouette, side slit
    • Maxi-length hem
    • Stretchy rib knit sweater fabric
    • Runs true to size

    Style Number/Barcode: 06005-1793

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Class Mock Neck Long Sleeve Midi Dress

    Enjoy feeling like a boss in this high-class midi dress! The fitted long sleeves with thumbholes offer protection without compromising style, while the mock neckline, bodycon silhouette, and midi-length hem create a sleek and modern look. The stretchy ribbed knit fabric has a full-length lining. Complete the look with statement booties for a dinner downtown!

    Fit & Features

    • Fitted long sleeves with thumbholes
    • Mock neckline
    • Bodycon silhouette
    • Midi-length hem
    • Stretchy ribbed knit fabric, full-length knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5396

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Out And About Long Sleeve Short Dress

    This adorable long sleeve short dress is ideal for those casual days where you're out and about! It features a square neckline with a ruched bust and an adjustable tie-front drawstring, long fitted sleeves, a fitted high waist seam, a short-length hem, and a flowy A-line silhouette. The lined brushed crepe fabric offers plenty of stretch. Style this short-length dress with a chunky knit cardigan and over-the-knee boots for a coffee date!

    Fit & Features

    • Square neckline
    • Ruched bust, tie-front drawstring
    • Long fitted sleeves
    • High waist seam
    • Short-length hem, A-line silhouette
    • Brushed crepe fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5395

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Signature Style Collared Wrap Mini Dress

    This wrap mini dress is perf for showcasing that signature chic style! It features a collared V-neckline with a pleated surplice design, long fitted sleeves, a high waist seam with ruched detailing to highlight your silhouette, a faux wrap-front design leading to an asymmetric mini-length hem, and a form-hugging fit. The knit fabric offers plenty of stretch. Complete your look with knee-high boots.

    Fit & Features

    • Collared V-neckline, pleated surplice design
    • Long fitted sleeves
    • High waist seam, ruching
    • Faux wrap-front design, asymmetric mini-length hem
    • Form-hugging fit
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-2948

    Category Name: Casual Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Momemt To Marvel Chiffon A-Line Short Dress

    Everyone will take a moment to marvel at you in this breezy chiffon short dress perfect for an afternoon lunch date! Featuring a sleeveless cowl neckline adorned with self-tie spaghetti straps, a flirty low back design, a tie-waist belt, an A-line silhouette, and a short-length hem. The dress is designed with a dreamy marble print on airy chiffon fabric with a woven lining. Complete the look with a chic mini handbag and sandals.

    Fit & Features

    • Sleeveless cowl neckline
    • Self-tie spaghetti stra[s
    • Low-back design, hidden zipper and hook-eye closure
    • Tie-waist belt
    • A-line silhouette, short-length hem
    • Marble printed chiffon fabric, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-5393

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Choice Floral Chiffon A-Line Mini Dress

    A sweet floral mini dress for all of your outdoor soirees! This dreamy dress features adorable short sleeves with ruffle trim, a pleated sweetheart neckline, a flirty open back with dual tie closures, a flattering A-line silhouette, and a ruffled hem. Complete the look with butterfly earrings for a whimsy charm.

    Fit & Features

    • Short sleeves, ruffle trim
    • Pleated sweetheart neckline
    • Open back, dual tie closures
    • A-Line silhouette, ruffled mini-length hem
    • Back zipper and hook-eye closure
    • Artsy floral print, chiffon fabric, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-5388

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Obsessed With Floral Chiffon Skater Dress

    Obsessed with floral? Let this chiffon skater dress into your blossoming collection! It features cap sleeves, a scoop neckline, a flirty front lace-up along the stretchy smocked bodice, and a flattering and flowy short-length hem. Complete the look with earrings and heels for a dressy occasion!

    Fit & Features

    • Cap sleeves
    • Scoop neckline
    • Front lace-up, stretchy smocked bodice
    • Skater silhouette, short-length hem
    • Back zipper and hook-eye closure
    • Floral print, airy chiffon fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5391

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Enchanting Romance Floral Chiffon Short Dress

    This airy floral chiffon short dress will make an enchanting entrance on your next date! It features a sleeveless sweetheart neckline with a built-in padded bust, a tie-front design with a small front keyhole cutout, tie-shoulder spaghetti straps, ruffled accents cascading down the dress, a short-length hem, and a flowy A-line silhouette. The blooming floral print chiffon fabric includes a full-length woven lining. Style with clear mules!

    Fit & Features

    • Sleeveless sweetheart neckline, padded bust
    • Tie-front design, small keyhole cutout
    • Tie-shoulder spaghetti straps, gold metal accents
    • High waist seam, hidden back zipper, hook and eye closure
    • Ruffled accents, short-length hem, A-line silhouette
    • Floral print, sheer chiffon fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5390

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picking Daisies Chiffon Strappy Skater Dress

    The perfect dress you'll want to pluck from the garden! This dreamy skater dress features adorable puff short sleeves, a square neckline, and pleated bust, a cutout strappy front and back with ties, and a short-length hem on daisy printed chiffon fabric. Complete the look in cute sandals for a family party!

    Fit & Features

    • Puff short sleeves
    • Square neckline, pleated bust
    • Cutout strappy front and back, tie closure
    • Back hidden zipper and hook-eye closure
    • Skater-silhouette, short-length hem
    • Dainty printed chiffon fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5389

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Can I Have Your Attention Belted Mini Dress

    Capture all the attention in this alluring belted mini dress that will draw in all the compliments! It features a strapless straight-across neckline, front hook and eye closures at the bodice, a high waist seam with a belted design to cinch your silhouette, vertical seams running down the front and back, and a mini-length hem with a bodycon fit. The lined woven fabric has a minimal stretch. Style this edgy-chic dress with hoop earrings and ankle booties!

    Fit & Features

    • Strapless straight-across neckline
    • Front hook and eye closures at the bodice
    • High waist seam, belted waist, double grommet design
    • Vertical seams down the front and back, back zipper, hook and eye closure
    • Mini-length hem, bodycon silhouette
    • Woven fabric, full-length knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5382

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Kiss The Sky Floral Paisley A-Line Dress

    Look sky-high in this adorable floral paisley short dress! This stylish little number features a sleeveless, cowl neckline, crisscross open back, self-tie spaghetti straps that cross along the open back, a flattering A-line silhouette, and a ruffled hem. Complete the look with sassy stiletto heels for a dressy brunch or birthday!

    Fit & Features

    • Sleeveless cowl neckline
    • Self-tie spaghetti straps
    • Crisscross open back, hidden zipper and hook-eye closure
    • A-Line silhouette, short-length ruffle hem
    • Floral paisley print
    • Lined woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5386

    Category Name: Casual Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smooth Silhouette Mock Neck Mini Dress

    Turn heads in this essential mini dress! Crafted with a double-lined smooth seamless knit fabric, the mini-length dress fits your body like a glove and features a mock neckline, fitted long sleeves, and a flattering bodycon silhouette. Make a statement and get compliments wherever you go styling this mini dress with combat boots and jacket.

    Fit & Features

    • Fitted long sleeves
    • Mock neckline
    • Bodycon silhouette
    • Mini-length hem
    • Double mesh lined smooth seamless knit fabric
    • Buttery soft and stretchy
    • Runs true to size

    Style Number/Barcode: 05102-5384

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ray Of Beauty Ruffled Short Skater Dress

    You'll be a bright ray of beauty in this adorable ruffled short skater dress! It features a V-neckline with a cute tie-front design, a front keyhole cutout, short puff sleeves with a ruffled trim, a high-rise stretchy smocked waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight sheer chiffon fabric includes a partial woven lining. Style with hoop earrings and clear mules for a day date!

    Fit & Features

    • V-neckline, tie-front design, front keyhole cutout 
    • Short puff sleeves, ruffled trim
    • High-rise stretchy smocked waist
    • Short skater skirt, tiered ruffled design
    • Fit and flare silhouette
    • Sheer chiffon fabric, partial woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5392

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Destination Tropical Ruffle Maxi Dress

    Arrive at your destination in this tropical maxi dress looking stunning and ready for fun! The maxi dress features a strapless neckline, non-slip grip lining, flexible boning, a form-hugging fit, and an effortless high front slit and ruffled flowy hem. Complete your vacation look with a handbag and sandals!

    Fit & Features

    • Strapless neckline, non-slip grip lining
    • Back zipper and hook-eye closure
    • Flexible boning
    • Form-hugging fit
    • High front slit, ruffled flowy maxi hem
    • Tropical print, airy mesh fabric, partial knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5383

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Find Your Style Button Down Pleated Mini Dress

    Make a style statement in this woven shirt mini dress! Featuring long sleeves with button cuffs, a collar neckline, a button down front, and a flattering A-line silhouette and pleated mini-length hem for an adorable and undeniable stylish look. Complete the look in knee-high boots for brunch downtown!

    Fit & Features

    • Long sleeves with button cuffs
    • Collar neckline
    • Button down front
    • A-line silhouette
    • Pleated mini-length hem
    • Woven poplin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5379

    Category Name: Casual Dresses

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Can't Deny Strapless Cargo Mini Dress

    Cargo will forever be a classic and this strapless mini dress is no exception! It features trendy contrast stitched seams, a flattering bodycon silhouette, side cargo-style flap pockets, and a mini-length hem on textured knit fabric. Style with a cute crop jacket for a casual dinner and movie!

    Fit & Features

    • Strapless neckline
    • Back zipper and hook-eye closure
    • Contrast stitched seams
    • Bodycon silhouette
    • Side cargo-style flap pockets
    • Textured knit fabric, moderate stretch
    • Mini-length hem

    Style Number/Barcode: 05102-5377

    Category Name: Casual Dresses

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Work Or Play Ruffle Strap Button Skater Dress

    Work or play, this cotton skater dress is a charming choice for a stroll downtown or a coffee date! It features a sleeveless V-neckline, adorable ruffled straps, a stretchy smocked bodice, a button-down front, and a flattering short-length hem. Complete the look in strappy heels.

    Fit & Features

    • Sleeveless V-neckline
    • Ruffled straps
    • Stretchy smocked bodice
    • Button-down front
    • Skater silhouette, short-length hem
    • Lightweight cotton fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5369

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    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
  • All Things Cute Cable Knit Sweater Dress

    Wrap yourself up in this cute and casual cable knit sweater dress perfect for pumpkin patches or festivals! It features long sleeves with banded cuffs, a plunge surplice V-neckline and V-cut back, a tie-waist belt, and a short form-hugging fit. Complete the look in trendy knee-high boots.

    Fit & Features

    • Long sleeves, banded cuffs
    • Plunge surplice V-neckline, V-cut back
    • Tie-waist belt
    • Form-hugging fit
    • Short-length hem
    • Cable knit design, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5370

    Category Name: Casual Dresses

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • A Must Have Strapless Twist Midi Dress

    This midi dress is a must-have style for showing off your shoulder for a brunch or party! It features a strapless sweetheart neckline, a padded and twisted bust, a flattering bodycon silhouette, and a center-back slit on stretchy knit fabric. Complete the look with a chic crossbody bag and heels.

    Fit & Features

    • Strapless sweetheart neckline, non-slip grip lining
    • Padded and twisted bust
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5374

    Category Name: Casual Dresses

    Price: $5.97 $36.90

    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
  • Striking And Chic Marble Print Midi Dress

    So striking and chic, this marble print midi dress will capture all the attention at happy hour! It features a sleeveless V-neckline, spaghetti straps, an asymmetric high-cut midi-length hem creating a thigh-high slit, and a bodycon silhouette that will flaunt your figure. The buttery smooth and stretchy knit fabric features an all-over multicolored marble print pattern. Style with clear mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Asymmetric high-cut midi-length hem, high slit
    • Bodycon silhouette
    • Multi-colored marble print
    • Smooth and stretchy knit fabric, full-length sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5231

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale