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.

  • Social Butterfly Crochet Knit Mini Dress

    Style up this adorable crochet knit mini dress for a casual party vibe! It features a sleeveless V-neckline with the cutest butterfly crochet embroidered design, spaghetti straps, a mini-length hem, and a form-hugging silhouette. The smooth knit fabric includes a full-length lining and offers plenty of stretch. Complete the look with hoop earrings and espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Butterfly crochet embroidered design
    • Spaghetti straps
    • Mini-length hem
    • Form-hugging fit
    • Knit fabric, full-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5065

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swept Off Your Feet Button Ruffle Maxi Dress

    Oh-so-breezy! Sweep the room off their feet when you enter in this maxi dress featuring a sleeveless V-neckline, adjustable spaghetti straps, button-down front closures, and a flowy ruffled hem with a skin-flaunting front slit. The dress is composed of a smooth woven fabric with a sewn-in knit stretchy lining. Complete the look in espadrille wedges for a trip to the coast!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Button-down front closures
    • Front slit design
    • Flowy ruffled maxi-length hem
    • Smooth woven fabric, sewn-in knit stretchy lining
    • Runs true to size

    Style Number/Barcode: 05102-5061

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Date Night Allure Side Slit Midi Dress

    Give off an enticing allure on your next date night in this sleek knit midi dress! It features a sleeveless square neckline, thin tank shoulder straps, an asymmetric midi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Complete the look with strappy stilettos.

    Fit & Features

    • Sleeveless square neckline
    • Thin tank shoulder straps
    • Asymmetric midi-length hem, high side slit
    • Curve-hugging fit
    • Knit fabric, full lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5057

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Encore Crepe Slit Maxi Dress

    Prepare for a standing ovation whenever you're seen in this crepe maxi dress perfect for casual wine nights by the fire pit or a spring getaway! Featuring a sleeveless square neck, spaghetti straps, a curve-hugging silhouette, and a sultry high slit along the flowy long hem. Complete the look in cute flat sandals.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Curve-hugging silhouette
    • Front high slit
    • Flowy maxi-length hem
    • Crepe knit fabric, mini-length knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5058

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Beauty Chiffon A-Line Midi Dress

    Create a truly beautiful look for spring and summer weddings in this floral chiffon midi dress! The airy chiffon fabric showcases a blooming floral print and includes a stretchy knit lining for coverage. The tea-length dress is shaped with a sleeveless square neckline and adjustable spaghetti straps for a perfect customized fit. Smocking at the back provides added stretch and features a secure zipper closure. The fitted high waist seam flows out to a classic A-line silhouette with a front slit for extra movement. Style this pretty midi dress with sleek hoops and block heels.

    Fit & Features

    • Sheer chiffon fabric with stretchy knit lining, floral print
    • Sleeveless square neckline, no-slip strip, adjustable spaghetti straps
    • Stretchy smocked back, zipper with hook and eye closure
    • High waist seam, front slit
    • A-line silhouette
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05101-2356

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Mode Tropical V-Neck Midi Dress

    Enter vacay mode with the perfect tropical midi dress that'll have you looking fabulous! It features a sleeveless V-neckline, adjustable spaghetti straps, a form-hugging silhouette, and a sultry side slit cutout. Complete the look in chic mules for a dinner by the beach!

    Fit & Features

    • Sleeveless V-neckline 
    • Adjustable spaghetti straps
    • Form-hugging silhouette
    • Side slit cutout, slit
    • Midi-length hem
    • Tropical palm leaf print, stretchy knit fabric, bust lining
    • Runs true to size

    Style Number/Barcode: 05102-5056

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt With Confidence Strappy Back Midi Dress

    Blow kisses to all of your admirors as you pass by in this chic one-shoulder midi dress! It features a wide shoulder strap and an asymmetrical strappy back design, a bodycon silhouette, and a center back slit accent on stretchy ribbed knit fabric. Complete the look with a sleek bracelet and clutch. 

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Wide shoulder strap, asymmetrical strappy back design
    • Bodycon silhouette
    • Center back slit accent
    • Midi-length hem
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5054

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Room To Grow Floral Cutout Midi Dress

    You'll flourish this season in this fresh floral midi dress perfect for outdoor parties, family gatherings, and baby showers! The dress features adorable puff short sleeves, a sweetheart neck, a ruched bust seam with a cutout accent, a stretchy smocked back, and a flowy midi-length hem with a flirty side slit. Complete the look in platform wedges.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck
    • Ruched bust seam, stretchy smocked back
    • Cutout accent
    • Flowy midi-length hem, side slit
    • Floral print, airy woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2358

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacation Mode Tropical Print Maxi Dress

    Activate vacation mode with this sultry tropical print maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, ruching down the side seam leading to an alluring thigh-high slit, an asymmetric maxi-length hem, and a bodycon silhouette that will hug your curves. The stretchy knit fabric features an all-over bold tropical palm leaf pattern. Style with strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back design
    • Ruched side seam, high side slit
    • Asymmetric maxi-length hem, bodycon silhouette
    • Tropical palm leaf print
    • Smooth knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5055

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 70s Groove Floral Tie-Back Skater Dress

    Get into the groove of this 70s-inspired printed floral dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a flattering skater short-length silhouette. Complete the look in rhinestone mules for a dressy date!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back design
    • Skater silhouette
    • Short-length hem
    • 70s-inspired floral print
    • Woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5053

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The Perfect Basic Knit Mini Dress

    This casual knit mini dress is the perfect basic for creating cute everyday 'fits! It features a V-neckline, short fitted sleeves, a mini-length hem, and a form-hugging fit. The cotton-blend fabric offers a moderate stretch. Style with hoop earrings and strappy mules.

    Fit & Features

    • V-neckline
    • Short fitted sleeves
    • Mini-length hem
    • Form-hugging fit
    • Cotton-blend smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5050

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready To Ruffle V-Neck Mini Dress

    You'll bring the flirty flare with this mini dress for bridal showers or day dates! The dress features a sleeveless ruffle V-neckline, straps with ruffle trim, and a bodycon silhouette on stretchy and smooth knit fabric with lining. Complete the look in trendy flat sandals and a purse!

    Fit & Features

    • Sleeveless ruffle V-neckline
    • Straps with ruffle trim
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy, smooth knit fabric with lining
    • Runs true to size

    Style Number/Barcode: 05102-5049

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfectly Striped Shirt Skater Dress

    Step out in this perfectly striped shirt dress to look cute for picnics in the park, family gatherings, or graduations! It features long sleeves with buttoned cuffs, a collar v-neckline, a corset-seam illusion waist, a cutout lace-up back design, and a short skater silhouette. Complete the look with teardrop earrings.

    Fit & Features

    • Long sleeves, buttoned cuffs
    • Collar v-neckline
    • Corset-seam illusion waist
    • Cutout lace-up back design
    • Skater silhouette, short-length hem
    • Striped print, poplin non-stretch woven fabric
    • Runs true to size

    Style Number/Barcode: 05102-5048

    Category Name: Casual Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Walks Ditsy Floral Chiffon Dress

    For your walks through garden parties or outdoor weddings, this ditsy floral chiffon dress brings the charm! It features a sleeveless sweetheart neck, adjustable spaghetti straps with ruffle trim, a skater silhouette, and a flirty lace-up back with tie closure and a ruffled short-length hem. Complete the look in statement heeled mules.

    Fit & Features

    • Sleeveless sweetheart neck
    • Adjustable spaghetti straps, ruffle trim
    • Skater silhouette
    • Lace-up back, tie closure
    • Ruffled short-length hem
    • Ditsy floral print, chiffon fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2347

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everlasting Bliss Ditsy Floral Mini Dress

    You'll be blissful all season with this ditsy floral mini dress in your closet! Blossom into florals for spring bridal showers, graduations, and casual parties. Featuring a sleeveless square neck, adjustable spaghetti straps, and side ruched seams to accentuate your natural curves along the bodycon silhouette. Complete the look in strappy sandals.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti traps
    • Side ruched seam
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print
    • Lined knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5046

    Category Name: Casual Dresses

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Charm Swiss Dot Chiffon Midi Dress

    Unlock your sweet charm in this chiffon midi dress perfect for bridal showers, graduation parties, and more! It features a sleeveless V-neck with a twisted bust, adjustable spaghetti straps, a flirty tie-back design, and a flowy silhouette and ruffled hem. The dress is composed of an airy chiffon fabric with a swiss dot pattern and a smooth woven lining. Complete the look in faux pearl heels.

    Fit & Features

    • Sleeveless V-neck, twisted bust
    • Adjustable spaghetti straps
    • Tie-back design
    • Flowy silhouette, ruffled midi-length hem
    • Airy chiffon fabric, swiss dot pattern, smooth woven lining
    • No stretch
    • Runs true to size

    Style Number/Barcode: 05102-5047

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless And Breezy Short T-Shirt Dress

    Style up this effortless and breezy short T-shirt dress for your casual weekend plans! It features a crew neckline, short sleeves, dual side pockets, a loose T-shirt fit, a short-length hem, and an A-line silhouette. The cotton-blend fabric has a moderate stretch. Pair with hoop earrings and strappy sandals.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Dual side pockets
    • Loose T-shirt fit
    • Short-length hem, A-line silhouette
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5044

    Category Name: Casual Dresses

    Price: $8.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Oopsy Daisy Print Knit Mini Dress

    It's no mistake if this casual mini-dress makes its way into your cart! Perfect for weekend outings and day dates, this daisy print dress features a sleeveless V-neck, spaghetti straps, a center bust ruched seam for a cute scrunched look, and a bodycon silhouette. Complete the look in strappy platform sandals.

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Center bust ruched seam
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy daisy print
    • Rib knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5041

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playful Touch Crepe Daisy Print Short Dress

    Add a playful touch to your closet with this adorable crepe daisy print dress to wear for birthdays or family parties! It features puff short sleeves, a sweetheart neckline, a flirty bust tie, a stretchy smocked back, hidden side pockets for keeping your hands warm, and a tiered ruffled short-length hem. Complete the look with dainty earrings.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neckline
    • Bust tie front, stretchy smocked back
    • Hidden side pockets
    • Tiered ruffled short-length hem
    • Daisy print, 

    Style Number/Barcode: 05101-2338

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winter Chic Style Midi Sweater Dress

    You'll adore the winter chic style of this midi sweater dress! Featuring a mock neckline, long fitted sleeves, a midi-length hem, and a form-hugging silhouette, this sweater dress is a perfect choice for casual holiday parties. The cozy brushed ribbed knit fabric offers plenty of stretch for comfortable wear. Style with ankle booties.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Midi-length hem
    • Form-hugging fit
    • Brushed ribbed knit fabric, knit lining down the body
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5039

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pleated Princess Bow Back Skater Dress

    Look and feel like a princess in this skater dress for cocktail wedding showers or graduation parties! It features a sleeveless square neck, adjustable spaghetti straps, a pleated bodice with a pretty bow on the back, and a fit-and-flare short silhouette. Complete the look in stiletto mules and a clutch.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Pleated bodice, back bow, zipper closure
    • Skater, fit and flare silhouette
    • Short-length hem
    • Cotton-blend fabric, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2333

    Category Name: Casual Dresses

    Price: $5.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirt And Twirl Chiffon Open Back Skater Dress

    Flirt and twirl in this sassy little chiffon dress perfect for date nights or parties! It features adorable sheer puff short sleeves, a ruched square neck with a bust tie and keyhole, an open back with tie closure, and a flowy short skater silhouette. Complete the look in platform block heels.

    Fit & Features

    • Sheer puff short sleeves
    • Ruched square neck, bust tie, keyhole
    • Open back, tie closure
    • Flowy skater silhouette
    • Short-length hem
    • Airy chiffon fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5040

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Styling Ribbed Knit Midi Dress

    This casual-chic ribbed knit midi dress will create effortless styling for everyday wear! It features a sleeveless scoop neckline, tank shoulder straps, a midi-length hem that hits mid-calf, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a layered charm necklace and clear mules.

    Fit & Features

    • Sleeveless scoop neckline, scoop back design
    • Tank shoulder straps
    • Midi-length hem
    • Form-hugging fit
    • Ribbed knit fabric, top lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5037

    Category Name: Casual Dresses

    Price: $19.00 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • First Pick Henley Knit Maxi Dress

    Cute and stylish, this maxi dress will be your first pick for looking good always! It features fitted long sleeves, a v-neckline with button front closures, a bodycon silhouette, and is composed of stretchy rib-knit fabric. Style with booties to complete the look!

    Fit & Features

    • Fitted long sleeves
    • V-neckline
    • Button-front closures
    • Bodycon silhouette
    • Maxi-length hem
    • Rib-knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5036

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale