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.

  • Stylishly Striped Knit Off-The-Shoulder Mini Dress

    This trendy striped knit mini dress is designed with a chic off-the-shoulder straight neckline with a flattering fold-over design and a bodycon silhouette to show off your curves. Pair with sneakers for a cute everyday look.

    Fit & Features

    • Striped ribbed knit fabric, plenty of stretch
    • Off-the-shoulder straight neckline, fold-over design
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5853

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Raise The Bar Ribbed Knit High Slit Midi Dress

    Raise the bar in this knit high slit midi dress boasting a sultry off-the-shoulder neckline and a form-hugging fit. Pair with boots.

    Fit & Features

    • Ribbed knit fabric, plenty of stretch
    • Off-the-shoulder neckline
    • Fold over accent at bust
    • High side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-2081

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Essential Ribbed Knit High Slit Midi Dress

    Accessorize a ribbed knit midi dress for the perfect fall outfit. The dress features a plunging V-neckline, long fitted sleeves, and a bold high slit. Complete your outfit with thigh-high boots.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch 
    • V-neckline
    • Long fitted sleeves
    • High side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-2079

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty In Plaid Drop Waist A-Line Mini Dress

    This halter dress will make you feel pretty in plaid and flattering with its halter neckline and pleated A-line silhouette.

    Fit & Features

    • Plaid-printed linen-blend woven fabric with woven lining, no stretch
    • Plunge V-neckline
    • Tie-back halter straps
    • Partially open back, hidden zipper with hook-eye closure
    • Drop waist
    • Mini-length pleated A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5852

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artsy Nature Sleeveless Abstract Mesh Mini Dress

    A sleeveless mesh mini dress features a crew neckline and flattering side ruched seams to enhance your curves along the bodycon silhouette. The mesh fabric showcases an artsy abstract print for a unique look.

    Fit & Features

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

    Style Number/Barcode: 05102-5851

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Look Long Sleeve Abstract Mini Dress

    An abstract print mesh mini dress features sheer fitted long sleeves, a boat neckline, and a flattering bodycon silhouette. Perfect for a party or gallery opening.

    Fit & Features

    • Abstract print, sheer mesh fabric, slip knit lining
    • Fitted long sleeves
    • Boat neckline
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5850

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Class Act Cowl Neck Polka Dot Midi Dress

    A sleeveless polka dot midi dress features a flattering cowl neckline, spaghetti straps, and a flowy silhouette with a front slit. Perfect for styling with stiletto heels for any occasion.

    Fit & Features

    • Polka dot print, mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Cowl neckline
    • Front slit
    • Flowy midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5849

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Sweet Tie-Strap Eyelet Mini Dress

    Keep your summer date outfit sweet with the cutest eyelet mini dress! Designed with a lightweight eyelet knit fabric, this adorable short dress will bring the charm. It features a sleeveless square neckline with ruching at the bust, tie-shoulder straps, and a bodycon silhouette with a mini-length hem to flaunt your figure. Style with sneakers for a casual look or mules for a dressier vibe!

    Fit & Features

    • Sheer eyelet knit fabric with knit lining
    • Moderate stretch
    • Ruched square neckline
    • Tie-shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5452

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Setting The Trend Long Sleeve Cutout Mini Dress

    This long sleeve mini dress sets the trend! It features a stylish crew neckline adorned with cutout and lattice accents that capture all the attention and a bodycon silhouette. Complete the look with chic boots.

    Fit & Features

    • Soft, stretchy rib knit fabric
    • Fitted long sleeves
    • Crew neckline
    • Cutouts with lattice accents
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2067

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Staple Ribbed Knit Skater Dress

    A chic staple skater dress featuring a flirty off-the-shoulder folded neckline and a short-length perfect for styling with boots or heels.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Off-the-shoulder neckline, fold-over accent
    • Long fitted sleeves
    • Short-length hem
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000459

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Sweet Silhouette Rosette Ruffled Knit Mini Dress

    The knit mini dress features a sleeveless scoop neckline accented with a dainty rosette detail for an adorable touch. The tiered ruffled mini-length hem and bodycon fit add a flirty feel while highlighting your curves.

    Fit & Features

    • Ribbed knit fabric with knit lining, plenty of stretch
    • Scoop neckline with rosette detail
    • Spaghetti straps
    • Tiered ruffled mini-length hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5846

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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:
    • Sale
  • 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:
    • Sale
  • 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:
    • Sale
  • 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:
    • Ships Free
  • 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:
    • Ships Free
  • 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:
    • Ships Free
  • 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:
    • Ships Free
  • 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