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.

  • Layered In Glam Ribbed Knit Long Sleeve Maxi Dress

    Nail that layered look in a ribbed knit dress featuring a plunging square neckline, a bralette inset with lace trim, fitted long sleeves, and a maxi-length hem with a back slit accent. Complete the look with trendy ankle booties for the ultimate vibe.

    Fit & Features

    • Ribbed knit fabrication, plenty of stretch
    • Square neckline
    • Bralette inset with lace trim
    • Fitted long sleeves
    • Long hem length
    • Back slit
    • Runs true to size

    Style Number/Barcode: 05102-5848

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Alluring Moment Faux Suede Lattice Cutout Mini Dress

    Fit & Features

    • Faux suede fabric with knit lining, moderate stretch
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Back zipper with hook-eye closure
    • Dual lattice side cutouts at bodice and waist
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5782

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Unforgettable Cutie Bow A-Line Ponte Mini Dress

    Bring an unforgettable cute vibe in this strapless ponte mini dress perfect for semi-formal events or brunch! Featuring a strapless neckline with a charming bow and contrast trim, this dress boasts an A-line silhouette and a mini-length hem for a flirty and flattering look. Complete the look with a necklace.

    Fit & Features

    • Ponte knit fabric, moderate stretch
    • Strapless neckline, contrast trim and bow
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3636

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ray Of Romance A-Line Lace Mini Dress

    Radiate a ray of romance in this sleeveless lace mini dress featuring a V-neckline accented with a dainty lace and ribbon bow trim and a flattering A-line silhouette. Style with heels for a date.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • V-neckline with lace and ribbon bow trim
    • Spaghetti straps
    • Mini-length A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3626

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Loving Halter Strappy Floral Mini Dress

    You'll love this floral mini dress all summer for brunch, picnics, and casual parties! Featuring a halter V-neckline with spaghetti strap ties, an open back with spaghetti strap ties, this bodycon dress is perfect for a fun and flirty look. Style this dress with trendy flat sandals.

    Fit & Features

    • Floral print, knit fabric with stretchy knit lining
    • Halter V-neckline with spaghetti strap ties
    • Open back with spaghetti strap ties
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5807

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Bohemian-Chic Geometric Striped Halter Maxi Dress

    Channel a bohemian chic vibe with this breezy halter maxi dress perfect for summer. The lightweight woven fabric showcases a geometric striped print in stylish neutral hues. The long dress features a sleeveless plunging V-neckline, halter spaghetti straps that can be crossed in the front for a trendy look, and a tie-back design at the neck. The alluring open back leads to lower tie-back straps and a lower cutout accent. You'll love the hidden side pockets and high side slit on the effortless, flowy silhouette. Complete the look with strappy sandals.

    Fit & Features

    • Geometric striped print
    • Woven fabric, no stretch
    • Plunge V-neckline, halter spaghetti straps, tie-back design
    • Open back, lower tie-back straps, lower cutout
    • Side pockets
    • Side slit, flowy fit
    • Runs true to size

    Style Number/Barcode: 05102-5842

    Category Name: Casual Dresses

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Definite Beauty V-Neck A-Line Mini Dress

    Everyone will watch as you walk in wearing this sleeveless mini dress to the school dance or party! Made from smooth lined knit fabric, it's perfect for any occasion.  With its flattering V-neckline and shoulder straps, this dress offers a stunning A-line silhouette and a mini-length hem. Compliment your look with statement heels and a clutch.

    Fit & Features

    • Smooth lined knit fabric
    • V-neckline
    • Shoulder straps
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5844

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Always Strapless Cutout Ruffle Maxi Dress

    Have all eyes on you in this strapless maxi dress boasting a sweetheart twist neckline and a cutout bodice. The smooth knit fabric hugs your curves along the form-hugging silhouette and creates a front center ruffle design. 

    Fit & Features

    • Smooth knit lined fabric, moderate stretch
    • Strapless sweetheart twist neckline
    • Cutout bodice
    • Center front ruffle design
    • Form-hugging, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3601

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whimsical Glam Bow and Lace Mini Dress

    This whimsical bow and lace mini dress features adorable cap sleeves and a square neckline that leads to the lace-up back that makes every head turn. Complete the look with statememt flats.

    Fit & Features

    • Lined rayon knit fabric with plenty of stretch
    • Square neckline with lace trim inset and mini bow detail
    • Cap sleeves
    • Open back with lace-up bungee strap design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5839

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Adorably Chic Lace Trim Plaid Mini Dress

    This adorable plaid mini dress features sheer lace trims at the neckline and hem and a center bow detail to add a chic touch of femininity. The bodycon silhouette will hug your gorgeous curves, a perfect option for date night.

    Fit & Features

    • Plaid printed woven fabric with sheer lace trims, moderate stretch
    • Square neckline with small bow detail
    • Spaghetti strap
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5838

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Most Lovely Tie Back Ruffled Skater Floral Romper

    A sleeveless floral romper features a flirty surplice V-neckline, a strappy back with a lower tie closure for head-turning detail, and a flattering ruffled skater silhouette. Perfect for the school dance or a dressy brunch.

    Fit & Features

    • Floral pattern, woven fabric, sewn-in knit lining
    • Surplice V-neckline
    • Adjustable spaghetti straps
    • Strappy back, tie-back closure, zipper and hook-eye closure
    • Ruffled skater short-length silhouette
    • Runs true to size

    Style Number/Barcode: 06403-0572

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Flirty Ditsy Floral Eyelet Strapless Mini Dress

    Keep your summer date 'fits flirty and stylish with this floral eyelet strapless mini dress! The airy lightweight eyelet knit fabric is detailed with a sweet ditsy floral print and features a brushed knit lining for coverage. The mini-length dress is shaped with a strapless straight-across elasticized neckline for added stretch and a bodycon silhouette to highlight your curves. Pair with platform sandals and hoop earrings.

    Fit & Features

    • Ditsy floral print
    • Stretchy eyelet knit fabric with knit lining
    • Strapless straight neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5799

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Ditsy Floral Eyelet Strapless Mini Dress

    Keep your summer brunch vibe sweet and stylish in this floral eyelet strapless mini dress! The airy lightweight eyelet knit fabric is detailed with a flirty ditsy floral print and features a brushed knit lining for coverage. The mini-length dress is shaped with a strapless straight-across elasticized neckline for added stretch and a bodycon silhouette to highlight your curves. Pair with espadrille wedges and a mini handbag.

    Fit & Features

    • Ditsy floral print
    • Stretchy eyelet knit fabric with knit lining
    • Strapless straight neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5800

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightful Impact Corset Slit Chiffon Midi Dress

    A sleeveless chiffon midi dress boasts a sweetheart tie neckline, a corset-inspired bodice with a lace-up back, and a front slit for a stylish flair. Perfect for styling with heels for a dressy occasion.

    Fit & Features

    • Burnout pattern, chiffon fabric lined with stretchy knit
    • Sweetheart tie neckline, shoulder straps
    • Underwire bust, side zipper and hook-eye closure
    • Corset bodice, lace-up back
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3591

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Preppy Chicness Lace Trim Plaid Bodycon Dress

    This plaid mini dress features a lace rose trim square neckline, spaghetti strap ties, and a flattering bodycon silhouette perfect for casual plans. 

    Fit & Features

    • Plaid print, knit fabric with minimal stretch
    • Lace rose trim square neckline
    • Spaghetti strap ties
    • Back zipper closure
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5836

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Chic Ruched Ribbed Knit Maxi Dress

    Effortlessly elevate your everyday looks with this casual chic ribbed knit maxi dress. It features a sleeveless boat neckline, tank shoulder straps with a trendy twist-back design, ruched side seams at the waist to accentuate your curves, and a fitted A-line silhouette with a maxi-length hem to flaunt your figure. Style with hoop earrings and strappy mules.

    Fit & Features

    • Stretchy ribbed knit
    • Boat neckline
    • Tank shoulder straps, twist-back design
    • Side ruching at the waist
    • Fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5834

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flawless Puff Sleeve Corset Midi Dress

    A flawless midi dress with femme details from the corset bodice to the puff short sleeves and flattering A-line silhouette - you'll feel like a dream in this dress! Complete the look with strappy sandals.

    Fit & Features

    • Lined woven fabric, dainty sheer lace trim, minimal stretch
    • Sweetheart neckline, ruched bust, keyhole cutout, bow-front detail
    • Corset bodice, bust underwire, flexible boning
    • Short puff sleeves, elastic cinched hems
    • Smocked lace-up back, hidden zipper with hook-eye closure
    • V-shaped drop waist
    • Midi-length A-line silhouette, front slit
    • Runs true to size

    Style Number/Barcode: 05101-3573

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Side Lace Trim Floral A-Line Mini Dress

    A floral mini dress that shows your sweet side in a flattering scoop neckline, spaghetti straps, and a lace trim with a bow accent along the A-line silhouette. The floral printed knit fabric offers stretch and comfort. 

    Fit & Features

    • Floral printed knit fabric, bust lining, moderate stretch
    • Spagehtti straps
    • Scoop neckline
    • Lace trim bow accent
    • A-Line mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5833

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Easy Bliss Turtleneck Striped Mini Dress

    This sleeveless knit mini dress boasts a turtle neckline and a bodycon silhouette with a trendy striped pattern. Style with simple hoop earrings for any casual plans.

    Fit & Features

    • Striped pattern, stretchy knit fabric
    • Turtle neckline
    • Bodycon mini-length fit
    • Runs true to size

    Style Number/Barcode: 06005-2045

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Style Ruched Knit Halter Skater Dress

    Show off your sassy style at weekend outings in this adorable halter skater dress. Made with stretchy smooth knit fabric, it features a sleeveless V-neckline, trendy tie-back halter straps leading to a partially open back, ruched seams at the waist to accentuate your curves, a short double-layered skater skirt for a flirty vibe, and a fit-and-flare silhouette. Complete the look with a charm necklace and strappy mules!

    Fit & Features

    • Stretchy smooth knit, top knit lining
    • V-neckline, tie-back halter straps
    • Partially open back
    • Ruched seams at the waist
    • Double-layered skater skirt
    • Fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5832

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Whimsical Cutie Butterfly Polka Dot Satin Maxi Dress

    Soar toward any celebration in this whimsical and cute polka dot satin maxi dress! Featuring cap sleeves and a gorgeous butterfly lace trim sweetheart neckline, this dress adds a touch of elegance. The button-down back with a cutout accent completes the maxi silhouette, making you the center of attention! Complete the look in strappy block heels and a necklace.

    Fit & Features

    • Polka dot print, satin fabric, no stretch
    • Butterfly lace trim sweetheart neckline
    • Button-down back and zipper hook-eye closures
    • Cutout back accent
    • Maxi length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3555

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picture Perfect V-Neck Smocked A-Line Midi Dress

    You'll be the picture of perfection in this adorable A-line midi dress at showers or birthday brunch! With its flattering V-neckline and stretchy smocked bodice, this dress hugs your body in all the right places. The tie spaghetti straps add a touch of delicacy, while the V-cut waist seam and A-line silhouette create a flattering look along the midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Woven fabric lined with non-stretch woven
    • Tie spaghetti straps
    • V-neckline
    • Stretchy smocked bodice
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3560

    Category Name: Casual Dresses

    Price: $11.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Style Tie-Back Bodycon Slit Zebra Midi Dress

    This sleeveless bodycon midi dress features a flattering scoop neckline and spaghetti straps that shape the tie-back design and a side slit. The stretchy knit material boasts a zebra print perfect for brunch or parties.

    Fit & Features

    • Stretchy knit material, zebra print, sewn-in knit lining
    • Scoop neckline
    • Spaghetti straps
    • Tie-back design
    • Side slit
    • Bodycon midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5830

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Marvelous Blooms Lace-Up Corset Floral Skater Dress

    Stay stunning all night in this floral skater dress at prom, birthdays, or dressy events! With adjustable spaghetti straps and a drawstring sweetheart neckline, this dress offers a perfect fit every time. The underwire bust, flexible boning, and a lace-up back provide support and a flattering silhouette, while the mini-length hem adds a playful touch. Complete the look in chic block heels.

    Fit & Features

    • Floral print, woven fabric, woven lining, no stretch
    • Adjustable spaghetti straps
    • Drawstring sweetheart neckline
    • Side zipper and hook-eye closure
    • Underwire bust
    • Flexible boning, lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3550

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale