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.

  • Wild For Style Strapless Zebra Print Midi Dress

    Let this strapless midi dress tame your worries over having nothing to wear! It features a strapless neckline, a figure-flaunting bodycon silhouette, and a midi-length hem on zebra print knit fabric that gives you a wild style. Complete the look with earrings for any occasion!

    Fit & Features

    • Zebra print, knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5820

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Fave Cable Knit Long Sleeve Mini Dress

    Cozy up in the cutest cable knit mini dress featuring a V-neckline, a surplice wrap front and back design, and long dolman-style sleeves. The tie-front high waist and form-hugging fit will highlight your curves, making it your fave dress of the season.

    Fit & Features

    • Cable knit fabric with plenty of stretch
    • V-neckline, surplice front and back design
    • Back bar strap
    • Long dolman sleeves
    • Tie-front waist
    • Mini-length form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-2101

    Category Name: Casual Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Feeling Sleeveless Bubble Hem Mini Dress

    A sleeveless knit dress features a classic crew neckline, a form-hugging fit, and a trending drop waist seam with a bubble mini-length hem. Style with a denim jacket for casual plans.

    Fit & Features

    • Knit fabric, moderate stretch
    • Crew neckline
    • Form-hugging fit
    • Drop waist seam, bubble mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5873

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Muse Tropical Floral Knit Bodycon Mini Dress

    You'll be a gorgeous vacay muse in this tropical floral mini dress! The sleek stretchy knit fabric showcases a blooming tropical floral print perfect for your summer trips. The short dress features a sleeveless square neckline, spaghetti straps, an alluring ruched waist cutout with an adjustable drawstring, and a bodycon silhouette to flaunt your figure. Style with espadrille wedges.

    Fit & Features

    • Tropical floral print
    • Stretchy knit fabric
    • Square neckline
    • Spaghetti straps
    • Ruching waist cutout, drawstring
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5614

    Category Name: Casual Dresses

    Price: $11.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Modern Stripes Ribbed Knit Long Sleeve Mini Dress

    Capture a modern vibe in this striped rib knit long sleeve mini dress designed with a chic mock neck and flattering bodycon fit. Pair with boots.

    Fit & Features

    • Ribbed knit fabrication
    • Mock neck
    • Fitted long sleeves
    • Multi-stripe pattern
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 06005-2095

    Category Name: Casual Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Embrace Cable Knit Midi Dress

    Embrace a cozy vibe in a cable knit dress that features a trendy v-neckline, fitted long sleeves, and a midi-length hem. Complete look with ankle booties!

    Fit & Features

    • Unlined cable knit fabrication
    • V-neckline
    • Fitted long sleeves
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 06005-2097

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bow Babe Strapless Pleated Ponte Romper

    A strapless ponte romper features a form-hugging fit and a drop waist with an adorable ribbon bow and pleated short-length hem. Perfect for styling with a crop jacket and sandals.

    Fit & Features

    • Ponte knit fabric, slight stretch
    • Strapless neckline
    • Form-hugging fit
    • Drop waist with ribbon bow trim
    • Short pleated hem
    • Runs true to size

    Style Number/Barcode: 06503-1221

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fall Flair Plaid Woven Bubble Hem Skater Dress

    Add some flair to your fall 'fits in this chic skater dress designed with a plaid printed cotton woven fabric. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a trendy V-shaped waist, and a short skater silhouette with the cutest bubble hem.

    Fit & Features

    • Plaid cotton woven fabric with knit lining, minimal stretch
    • Square neckline
    • Adjustable spaghetti straps
    • Back zipper with hook-eye closure
    • V-shaped waist
    • Short skater silhouette, bubble hem
    • Runs true to size

    Style Number/Barcode: 05102-5870

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Abstract Marble Sleeveless Mesh Midi Dress

    A sleeveless abstract marble print mesh midi dress features a sleek crew neckline, a flattering form-hugging fit, and a flirty side slit. Pair with heels.

    Fit & Features

    • Abstract marble printed sheer mesh fabric with brushed knit lining, plenty of stretch
    • Sleeveless crew neckline
    • Tank shoulder straps
    • High side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5869

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seasonal Staple Ribbed Knit Bell Sleeve Mini Dress

    This adorable ribbed knit mini dress will be your fave staple of the season featuring a square neckline, long bell sleeves, and a short form-hugging silhouette. Style with knee-high boots for a casual party.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Square neckline
    • Long bell sleeves
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-2086

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Trendy Striped Slit Maxi Dress

    A trendy maxi dress features a flattering square neckline, form-hugging fit, and a high front slit to show off your shoes. Perfect for styling with a denim jacket and sandals.

    Fit & Features

    • Striped pattern, stretchy knit fabric
    • Square neckline, spaghetti straps
    • High front slit
    • Form-hugging maxi-length fit
    • Runs true to size

    Style Number/Barcode: 05102-5867

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Neutral Babe One-Shoulder Abstract Mini Dress

    A one-shoulder abstract mini dress features side ruched seams that accentuate your curves along the bodycon silhouette perfect for styling with heels.

    Fit & Features

    • Abstract print, mesh fabric, sewn-in knit lining
    • One-shoulder neckline
    • Side ruched seams
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5868

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Forward Strappy Back Skater Dress

    Spring forward in the cutest skater dress showcasing a head-turning strappy tie-back and a flattering ruffled mini-length hem that'll swoon everyone!

    Fit & Features

    • Woven fabric with woven lining
    • Square neckline with bust tie
    • Spaghetti straps
    • Strappy tie-back design
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3687

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Show Off Your Glow Tropical Lace-Up Midi Dress

    Show off your vacation glow in this tropical midi dress all over the island or resort! With a square neckline, spaghetti straps, and a lace-up back, this side slit dress hugs your body in all the right places with side ruched seams and a bodycon fit. Complete the look in sandals.

    Fit & Features

    • Tropical print, mesh fabric, sewn-in knit lining, moderate stretch
    • Spaghetti straps
    • Square neckline
    • Lace-up back
    • Ruched side seams, bodycon fit
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5866

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fiji Feeling Sleeveless Lace-Up Tropical Maxi Dress

    Escape to the island or look like you did in this tropical maxi dress for an effortless summer style! With a flattering V-neckline and delicate spaghetti straps, this dress will keep you stylish all day long. The lace-up back adds a touch of playful detail, while the A-line silhouette and maxi-length hem create a flowy and romantic look.

    Fit & Features

    • Palm leaf tropical and border print, woven fabric with lining, no stretch
    • V-neckline
    • Spaghetti straps
    • Lace-up back
    • A-line maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5864

    Category Name: Casual Dresses

    Price: $11.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Breezes Halter Boho Satin Maxi Dress

    Enter the room in this chic boho satin maxi dress to make a bold impression! The sleeveless dress boasts a halter neckline and a flowy silhouette adorned with a high front slit. Style with stiletto heels.

    Fit & Features

    • Boho print, satin woven fabric. sewn-in woven lining
    • Halter neckline
    • Spaghetti strap
    • Flowy silhouette
    • High front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5865

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Memorable Vibe Strapless Plaid Pleated Mini Dress

    A strapless plaid mini dress features a form-hugging fit with a sassy pleated hem. Perfect for back-to-school styling.

    Fit & Features

    • Plaid print, woven fabric, slight stretch
    • Strapless folded neckline
    • Back zipper closure
    • Form-hugging fit
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5862

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Autumn Attitude Strapless Pleated Plaid Mini Dress

    Embrace the new season in this plaid mini dress featuring a strapless neckline, form-hugging silhouette, and a flirty pleated mini-length hem. Perfect for back-to-school and styling with flats.

    Fit & Features

    • Plaid pattern, knit fabric, moderate stretch
    • Strapless folded neckline
    • Form-hugging silhouette
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5863

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chicest Vibe Drop Waist Bubble Hem Mini Dress

    This chic sleeveless mini dress brings flirtiness to the party or dressy dinner out! The dress boasts a trendy drop waist seam leading to the pleated bubble mini-length hem. Complete the look heels or knee-high boots.

    Fit & Features

    • Ribbed knit and woven fabrics, moderate stretch
    • Mock neckline
    • Tank shoulder straps
    • Drop waist
    • Mini-length pleated bubble hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5861

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Picture Striped Midi Dress

    With an ice cream in hand and strappy sandals on, this striped midi dress will have you looking pretty everywhere you go! Featuring a flattering square neck and curve-hugging fit, this dress accentuates your figure down to the midi hem.

    Fit & Features

    • Striped print, stretchy knit fabric, sewn-in knit lining
    • Square neckline
    • Wide shoulder straps
    • Curve-hugging fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5860

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Talker Lace Bow Pleated Ponte Mini Dress

    Smooth ponte knit fabric shapes this sleeveless mini dress featuring a lace bow trim square neckline, spaghetti straps, and a fitted silhouette that leads to a pleated flare mini-length hem.

    Fit & Features

    • Smooth pointe knit fabric, minimal stretch
    • Lace bow trim square neckline
    • Spaghetti straps
    • Fitted silhouette
    • Pleated flare mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3661

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Fab Drop Waist Halter Skater Dress

    Look and feel fabulous in this sleeveless skater dress boasting a flirty halter V-neckline and a trendy mineral wash on the stretchy rib knit cotton fabric. Complete the look with hoop earrings.

    Fit & Features

    • Ribbed cotton-blend fabric, moderate stretch
    • Mineral wash
    • Sleeveless halter V-neckline
    • Partially open back
    • Drop waist 
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5857

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serving Chic Long Bell Sleeve A-Line Mini Dress

    Serve chic looks in this A-line mini dress featuring a halter V-neckline with flirty cutouts and long fitted bell sleeves to give coverage. Style with earrings.

    Fit & Features

    • Smooth knit fabric with partial lining, plenty of stretch
    • Halter V-neckline, tie-back spaghetti straps
    • Cutout shoulder design
    • Long fitted bell sleeves, slit accents
    • Lower back cutout
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3657

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Attitude Strapless Bodycon Denim Mini Dress

    A strapless denim mini dress features a flattering bodycon silhouette with classic jean styling with pockets. Perfect for casual occasions.

    Fit & Features

    • Denim fabric, moderate stretch
    • Strapless neckline
    • Bodycon mini-length silhouette
    • Front button and zipper closure
    • Flap pockets
    • Runs true to size

    Style Number/Barcode: 05102-5854

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale