Casual Dresses

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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.

  • Such A Sweetheart Ribbed Knit Mini Dress

    You'll look like such a stylish sweetheart in this adorable ribbed knit mini dress! It features a ruffled sweetheart neckline with a button-down front and a curve-hugging fit. Pair this cute and casual dress with some sneakers for an effortless, everyday vibe.

    Fit & Features

    • Spaghetti straps
    • Ruffled sweetheart neckline
    • Button-down front
    • Short, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-1016

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keeping Knit Classy Sleeveless Mini Dress

    Class up your basic mini dress with details that stand out! The dress features a sleeveless crew neckline, dramatic shoulder pads, and a mini length silhouette. The dress is composed of a cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with chunky sneakers for a casual vibe.

    Fit & Features

    • Crew neck
    • Sleeveless bodice
    • Shoulder pads
    • Mini length silhouette
    • Cotton knit fabric
    • Relaxed fit
    • Moderate stretch 

    Style Number/Barcode: 05102-1033

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Basic Ribbed Mini Dress

    Keep your look basic and chic in this ribbed mini dress you can totally dress up or down! It features a mini length silhouette and a form-hugging fit to enhance your curves. Elevate your outfit by pairing this adorable dress with chunky sneakers for a more casual vibe.

    Fit & Features

    • Bungee spaghetti straps
    • Scoop neckline
    • Short, form-hugging fit
    • Ribbed fabric

    Style Number/Barcode: 06002-0611

    Category Name: Casual Dresses

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty In Plaid Knit Mini Dress

    Look oh-so-pretty in plaid in this adorable knit mini dress! Featuring a trendy square neckline and a short, form-hugging fit, this dress is a fall must-have. Pair with strappy heels and layer on a chic faux leather jacket for a date night.

    Fit & Features

    • Spaghetti straps
    • Square neck and back
    • Mini length silhouette
    • Form-hugging fit
    • Plaid print
    • Knit fabric

    Style Number/Barcode: 05102-0585

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Get On-Trend Tie Dye Knit Mini Dress

    Get on-trend in this adorable tie dye knit mini dress! It features an open back detail with a tie closure and ruched, form-hugging fit to enhance your curves. Pair this dress with chunky sneakers for a casual-chic everyday look.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Open back detail with tie closure
    • Ruched detailing
    • Short, form-hugging fit
    • Tie dye knit fabric

    Style Number/Barcode: 05102-0861

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Angelic Beauty Ruched Mini Dress

    Look like such an angelic beauty in this gorgeous ruched mini dress! Featuring a curve-hugging fit with an allover angelic print and front ruched detailing, this dress will make you look oh so dreamy. Pair it with some clear heels for a date night.

    Fit & Features

    • Adjustable spaghetti straps
    • Cowl neckline
    • Back zipper closure
    • Front ruched detailing with slit and drawstring accent
    • Ruffle detail at hem
    • Mesh fabric
    • Allover angelic print

    Style Number/Barcode: 05101-0914

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Best Life Square Neck Mini Dress

    Live your best life in a mini dress that can be dressed up for a night out with the squad. The dress features a sleeveless square neckline, sleek bungee straps, and a mini-length silhouette. Complete your look with sleek black heels.

    Fit & Features

    • Sleeveless square neckline
    • Bungee straps
    • Mini-length silhouette
    • Smooth knit fabric
    • Form-hugging fit
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1000

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Buttoned Up Off The Shoulder Midi Dress

    Get all buttoned up in this adorable off the shoulder midi dress! It features a complete button-down front with a curve-hugging, mid-length fit. Perfect for everyday, pair this dress with heeled booties to take your look into fall.

    Fit & Features

    • Off the shoulder neckline
    • Short fitted sleeves
    • Complete button-down front
    • Mid-length, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-0943

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Knit Off-The-Shoulder A-Line Mini Dress

    Channel that cute and cozy vibe in this adorable soft ribbed knit mini dress featuring an off-the-shoulder straight neckline with a fold-over design, long fitted sleeves, and a short A-line silhouette. Style with knee-high boots for a fall date!

    Fit & Features

    • Soft ribbed knit fabric
    • Off-the-shoulder straight neckline, fold-over design
    • Long fitted sleeves
    • Mini-length A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5892

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ribbed Knit Crew Neck Bodycon Mini Dress

    Keep it casually chic in a mini dress that is a total must-have! The short dress features a crew neckline with a racerback design, a mini-length hem, and is composed of a form-hugging ribbed knit fabric. Put your hair in an updo and style with strappy mules for a cute look!

    Fit & Features

    • Crew neckline
    • Sleeveless bodice 
    • Racerback design
    • Mini-length hem
    • Ribbed knit fabric, fully lined 
    • Form-hugging fit, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-0689

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twist of Glamour Brushed Knit Mini Dress

    Bring a twist of glam to this mini dress! The dress features a plunging V-neckline with a twist knot accent, a midriff keyhole, and a mini length silhouette with an envelope hem. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules

    Fit & Features

    • V-neckline
    • Twist-knot accent at the center of the bodice
    • Long sleeves
    • Mini length silhouette with an envelope hem 
    • Brushed knit fabric
    • Form hugging fit, moderate stretch

    Style Number/Barcode: 05102-0830

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • In Tulum One-Shoulder Tropical Maxi Dress

    Perfect for your vacay in Tulum, this one-shoulder tropical maxi dress was made for sunset dinners and dancing! 

    Fit & Features

    • Tropical print, smooth knit fabric with short stretchy lining
    • One-shoulder neckline
    • One shoulder strap with metal accents
    • Front ruffled slit
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6073

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Break The Rules Ruched Knit Mini Dress

    Dare to bold up your look in a mini dress that showcases curves. The mini dress features a trendy square neckline, fitted long sleeves, and a ruched mini-length silhouette with an envelope hem. Complete look with chunky sneakers for a casual affair. 

    Fit & Features

    • Square neckline
    • Long sleeves
    • Ruched body
    • Mini-length silhouette 
    • Envelope hem
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0872

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Totally Chic Ruched Knit Mini Dress

     Keep it totally chic in a ruched mini dress! The dress features an off the shoulder neckline, long fitted sleeves, and a ruched drawstring center. The dress is composed of a ribbed knit fabric that hugs curves in all the right places. Complete look with sneakers for a casual look. 

    Fit & Features

    • Off the shoulder neckline
    • Long fitted sleeves
    • Ruched drawstring center
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05102-0932

    Category Name: Casual Dresses

    Price: $14.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The One Basic One Shoulder Ribbed Mini Dress

    This ribbed dress is the one that you can't live without! Dress up this beauty with duster earrings and mules for a glam night out outfit. The dress features a one-shoulder neckline, a ruched mini length silhouette, and composed of a ribbed knit fabric. 

    Fit & Features

    • Sleeveless bodice
    • One-shoulder neckline
    • Ruched body
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit

    Style Number/Barcode: 05102-0997

    Category Name: Casual Dresses

    Price: $10.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Own Knit Ruched Mini Dress

    Own your gorgeous look in this adorable knit mini dress! It features a trendy mock neckline, ruched detailing down the back, and a sexy curve-hugging fit. Pair this dress with some chic heels for a night out.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Open back
    • Ruched back detailing
    • Short, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-0971

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Open Back Ruched Ribbed Knit Midi Dress

    Style up this basic ribbed knit midi dress for the perfect everyday look! It features a partial lower open back, ruched detailing and a curve-hugging mid-length silhouette. Pair the dress with chunky sneakers to get that casual, cute vibe.

    Fit & Features

    • Scoop neckline
    • Long fitted sleeves
    • Partial lower open back
    • Ruched detailing
    • Form-hugging fit
    • Midi length
    • Ribbed knit fabric

    Style Number/Barcode: 05102-0977

    Category Name: Casual Dresses

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cut To The Chase Knit Mini Dress

    Let's cut to the chase - this knit mini dress is so chic! Featuring trendy cut outs and a sexy, curve-hugging fit, this dress is perf for a girl's night out. Pair it with chunky gold hoops to give the look some glam.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Waist cut out
    • Ruched detailing
    • Short, form-hugging fit
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05102-0974

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In Knit To Win It Midi Dress

    You'll be totally in it to win it in this adorable knit midi dress! It features a double-lined knit fabric and a mid-length, curve-hugging silhouette. Wear this dress with chunky sneakers for an adorable everyday look.

    Fit & Features

    • Spaghetti straps
    • Scoop neckline
    • Mid-length form-hugging fit
    • Double lined knit fabric

    Style Number/Barcode: 05102-0877

    Category Name: Casual Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Slay In Style Ribbed Scoop Neck Midi Dress

    Slay in this midi dress that brings some major chic vibes! The dress features a scoop neckline, tank-straps, and a chic tie-waist belt to create an hourglass illusion. Complete your night-out look with a faux leather jacket.

    Fit & Features

    • Scoop neckline
    • Tank-straps
    • Tie-waist belt 
    • Ribbed sweater knit fabric
    • Midi-length silhouette
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-0929

    Category Name: Casual Dresses

    Price: $4.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • What's The Scoop Cutout Ribbed Knit Mini Dress

    Serve up a chic look in the ribbed dress! Perfect for your next brunch date, this mini dress brings the drama! The dress features a scoop neckline with shoulder cutouts, tank-like straps, and a mini length silhouette. Style dress with a fab top knot and door knocker earrings

    Fit & Features

    • Scoop neckline with tank-like straps
    • Shoulder cutouts
    • Long sleeves
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit

    Style Number/Barcode: 05102-0903

    Category Name: Casual Dresses

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruched And Ribbed Knit Crew Neck Mini Dress

    This ruched and ribbed knit mini dress is the casual-chic piece you need in your closet! It features a form-hugging fit with ruched detailing to enhance your curves. This dress can be worn as a mini or pulled down and styled as a midi. Wear it with simple slides or elevate the look in heels.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Ruched sides
    • Adjustable ties at hem
    • Rib-knit, moderate stretch, fits true to size

    Style Number/Barcode: 05102-1092

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Slaying Knit Sleeveless Ribbed Midi Dress

    Slay it in a ribbed knit dress that stuns for your next date night in! The dress features a sleeveless square neckline, sleek bungee straps, and a curve-hugging midi-length silhouette. Complete look with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Midi length silhouette
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0964

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Attention-Worthy Camo Print Bodycon Mini Dress

    Create an attention-worthy 'fit in this camo-printed woven mini dress featuring a strapless straight-across neckline accented with dual flap pockets, a secure back zipper closure, cargo-style pockets on each side, and a bodycon silhouette to showcase your curves. Complete the look with a bomber jacket and combat boots!

    Fit & Features

    • Camouflage printed twill woven fabric
    • Strapless straight neckline, dual flap pocket accents
    • Back zipper hook-eye closure
    • Dual cargo flap pockets
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5909

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free