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.

  • Back Beauty Linen Halter Skater Dress

    They'll love to watch you leave in this gorgeous skater dress featuring a sleeveless, halter neck with tie closure, and a smocked bodice that leads to a flowy, skater short silhouette with an open back and lattice bar accents. Complete the look in sleek hoop earrings for a day date. 

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • Smocked bodice
    • Flowy skater silhouette
    • Short-length hem
    • Open-back, lattice bar accents
    • Linen fabric, lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4404

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Babe Of Funk Halter O-Ring Mini Dress

    Bring back the funk babe! This retro-inspired halter dress features a sleeveless plunge V-neck with an O-ring inset, a bodycon silhouette, and a mini-length hem. Complete the look in pointed-toe booties.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, plunge V-neck, halter strap
    • O-ring inset
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1292

    Category Name: Casual Dresses

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty In Florals Short Dress

    Keep it pretty in a short dress that brings the charm! The dress features a pretty daisy print, a halter neck with neck ties, a square-neck smocked bodice, and a triple-row bar strap design at the back. The slim fit bodice leads to a fluttery A-line short-length hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules. 

    Fit & Features

    • Halter neck with adjustable neck ties
    • Square-neck smocked bodice
    • Triple-row bar strap design 
    • Floral print
    • A-line, short length hem
    • Lined lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4401

    Category Name: Casual Dresses

    Price: $46.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Budding Romance Chiffon Skater Dress

    Isn't a new romance so exciting! Enter into your new spring fling in this floral chiffon skater dress featuring a sleeveless, ruffled V-neck, adjustable spaghetti straps, an open back with cross straps, and a tiered ruffle trim skirt. Complete the look in lucite mules for the perf day date.

    Fit & Features

    • Sleeveless, ruffled V-neck, adjustable spaghetti straps
    • Open-back, cross straps, back zipper closure
    • Tiered ruffle trim skirt
    • Skater-style silhouette
    • Floral pattern
    • Chiffon fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1482

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Too Sweet Floral Ruffled Skater Dress

    These florals are too sweet not to fall for! Twirl all day in this chiffon skater dress featuring a sleeveless, v-neck, ruffled trim straps, waist tie, open-back design with tie closure, and a tiered ruffled skirt. Complete the look in statement earrings.

    Fit & Features

    • Sleeveless, v-neck, ruffled trim straps
    • Open-back with tie closure
    • Tie waist, tiered ruffled skirt
    • Skater silhouette
    • Floral pattern, back zipper closure
    • Chiffon fabric, inner knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1481

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty In Floral Chiffon Babydoll Dress

    It may start out as flirty but this floral babydoll dress is in for the long haul. It features a sleeveless, ruffle-trim V-neckline, adjustable spaghetti straps, open-back with cross straps, and a fitted bodice atop a tiered, flowy mini skirt. This dress is composed of airy chiffon fabric with an inner lining. Complete the look in chic sandals.

    Fit & Features

    • Sleeveless, ruffle-trim V-neck, adjustable spaghetti straps
    • Open-back, cross straps, fitted bodice
    • Hidden back zipper and hook and eye closure
    • Tiered flowy mini skirt
    • Floral pattern
    • Chiffon fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1474

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Freedom Vibes Graphic Tunic

    Show up and stun with this edgy distressed graphic tunic. It features a crew neckline, long fitted sleeves, a center eagle and flames graphic with the scripts "Freedom Vibes" and "Wild and Free," slashed detailing down the front, and a short, form-hugging fit. Style this tunic with combat booties.

    Fit & Features

    • Crew neckline, long sleeves
    • Eagle and flames graphic
    • Scripts that read "Freedom Vibes" and "Wild and Free"
    • Slashed detailing
    • Mini-length, form-hugging fit
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06002-1119

    Category Name: Casual Dresses

    Price: $11.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Let It Flow Crochet V-Neck Skater Dress

    Flowy and flirty! Twirl all day in this crochet V-neck skater dress featuring a sleeveless bodice with adjustable spaghetti straps, an open back with tie closure, and a tiered short hem. Composed of a gauze woven fabric with an inner lining. Finish the look in trendy mules.

    Fit & Features

    • Sleeveless bodice, crochet V-necklined
    • Adjustable spaghetti straps
    • Open-back, tie closure
    • Tiered short hem
    • Skater silhouette
    • Airy gauze woven fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4397

    Category Name: Casual Dresses

    Price: $21.97 $47.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruffle Party Chiffon V-Neck Babydoll Dress

    Make a ruffle at the party in this chiffon babydoll dress featuring a sleeveless V-neckline, adjustable spaghetti straps, criss-cross back, flowy silhouette, and a ruffled trim throughout. Composed of a chiffon woven fabric with an inner skirt lining. Perfect for styling with a mini tote bag.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Criss-cross back
    • Babydoll flowy silhouette
    • Ruffled trim throughout
    • Chiffon woven fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1465

    Category Name: Casual Dresses

    Price: $6.67 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Classic Chic Shirt Dress

    This classic chic mini shirt dress is everything you need and more. It features a collar, a plunging V neckline with lace-up ties, long sleeves with buttons to cuff, a high waist seam, and a mini-length silhouette. The dress is composed of a woven fabric with no stretch. Complete look with thigh-high boots and a cabby hat. 

    Fit & Features

    • Collar, V-neckline
    • Lace-up front 
    • Long sleeves, buttoned cuffs
    • High waist seam 
    • Mini length silhouette
    • Woven fabric 
    • Form hugging fit, minimal stretch, runs true to size 

    Style Number/Barcode: 05101-1464

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jungle Queen Leopard Satin Slip Dress

    Clearly, you're the queen of the jungle in this leopard satin mini! It features sleek, adjustable spaghetti straps, a v-neckline, and a slightly flared hem with a slit accent. Composed of a luxe satin-lined fabric with no stretch. Style with chic block heels.

    Fit & Features

    • Sleeveless, V-neckline
    • Sleek adjustable spaghetti straps
    • Slit accent, Back zipper closure
    • Slightly flared hem
    • Leopard pattern
    • Luxe satin-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1461

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropic Beauty Strappy Midi Dress

    Unveil your beauty on your tropical getaway in this figure-flattering midi dress featuring a square neckline, spaghetti straps, an open strappy back design, and a bodycon silhouette on an asymmetrical midi-length hem. Complete the look in lace-up stilettos.

    Fit & Features

    • Square neckline
    • Spaghetti straps
    • Open strappy back design
    • Bodycon silhouette
    • Asymmetrical midi-length hem
    • Tropical print fabric
    • Fits true to size

    Style Number/Barcode: 05102-4389

    Category Name: Casual Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Nights V-Neck Midi Dress

    Enjoy your nights in paradise in this tropical floral midi dress featuring a sleeveless, v-neck, adjustable criss-cross spaghetti straps, and a bodycon silhouette leading to the asymmetrical slit hem. Complete your vacay look in strappy heels.

    Fit & Features

    • Sleeveless, v-neck
    • Adjustable criss-cross spaghetti straps
    • Bodycon silhouette
    • Asymmetrical slit, side ruching
    • Midi-length hem
    • Tropical floral print, texture-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1455

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bora Bora Floral Chiffon Maxi Dress

    Got vacay on the mind? This floral chiffon maxi dress is perfect for a trip to Bora Bora! Features a sleeveless, halter neck with tie-closure, ruched bust, and a cutout bodice atop a flowy, tiered maxi skirt. Complete the look in wedges and chic sunglasses. 

    Fit & Features

    • Sleeveless, halter neck, tie-closure
    • Ruched bust
    • Cutout bodice
    • Flowy, tiered maxi skirt
    • Floral print
    • Airy chiffon fabric, inner lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4391

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whatever Rib Takes Cutout Mini Dress

    Take on the day in style wearing this mini dress featuring a trendy, sleeveless, high neck, bodycon silhouette, and a cutout accent for a flash of skin. Complete the look in sunnies and sandals for the perf day date look.

    Fit & Features

    • Sleeveless, high neck
    • Bodycon silhouette
    • Cutout accent
    • Mini-length hem
    • Rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1270

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Spotted In Floral Mesh Ruffle Hem Dress

    Spotted in floral for spring! Refresh your closet with this flirty mini dress featuring a ruffle trim v-neck, adjustable spaghetti straps, a bodycon silhouette, ruffled hem, and a trendy front drawstring so you can customize the length. Composed of mesh-lined fabric with a moderate stretch. Finish the look in mules for a day date.

    Fit & Features

    • Sleeveless, ruffle trim v-neck
    • Adjustable spaghetti straps
    • Side ruched seams, front drawstring
    • Bodycon silhouette
    • Mini-length ruffled hem
    • Floral pattern, mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1453

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • That Edgy Look Slash Corset Hoodie Tunic

    Edge up your everyday look in this cool tunic featuring long cuffed sleeves, a drawstring hoodie neckline, a corset-style bodice, and slash accents throughout. Composed of a soft knit fabric with plenty of stretch. Style with knee-high boots.

    Fit & Features

    • Long cuffed sleeves
    • Drawstring hoodie neckline
    • Corset-style bodice
    • Slash accents throughout
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1110

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Free The Butterfly Ruche Mini Dress

    Spread your wings butterfly babe! Look cute in this mini dress featuring a sleeveless, square neckline, adjustable spaghetti straps, and side ruched seams to accentuate your curves on the mini-length hem. Composed of a soft knit-lined fabric with a moderate stretch. Style with platform heels for a fun night out.

    Fit & Features

    • Sleeveless square neckline, adjustable spaghetti straps
    • Side ruched seams, bodycon silhouette
    • Butterfly print
    • Mini-length hem
    • Knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4385

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picnic Date Eyelet Lace V-Neck Dress

    The cutest picnic date dress ever! Make an adorable impression in this eyelet lace dress featuring a sleeveless V-neck, ruffled straps, and a pencil silhouette on a short hem. Complete the look in wedges.

    Fit & Features

    • Sleeveless, V-neck, ruffled straps
    • Pencil silhouette
    • Short-length hem
    • Back zipper, hook and eye closure
    • Eyelet lace fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4386

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Airy Floral Skater Dress

    Chic and airy, this floral printed skater dress is ready for all your fun weekend festivities! It features a sleeveless V-neckline, adjustable spaghetti straps, an open back with an adorable tie-back design, and a high waist leading to a short skater skirt with a flirty fit and flare silhouette. Style this dress with strappy mules.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Open back, tie closure
    • High waist seam, short skater skirt, fit and flare silhouette
    • Ditsy floral print
    • Sheer woven fabric, full knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4384

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Express Yourself O-Ring Bandeau Midi Dress

    Express your stylishly bold self in this midi dress! It features a strapless, bandeau top with a string tie o-ring, cutout bodice, and midi bodycon skirt with a sultry side slit. Composed of ribbed knit fabric with a moderate stretch. Finish the look in oversized sunglasses.

    Fit & Features

    • Strapless bandeau top
    • String tie o-ring, cutout bodice
    • Midi bodycon skirt
    • Side slit 
    • Ribbed knit fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 06005-1263

    Category Name: Casual Dresses

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Weekend Getaway Floral Midi Dress

    Pack this adorable floral printed midi dress in your carry-on for your next weekend getaway! It features a sleeveless square neckline, spaghetti straps, ruched detailing down one side leading to a slit, and a midi-length, curve-hugging fit. Style this dress with your fave oversized shades and espadrille wedges.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down one side leading to a slit, adjustable drawstring
    • Midi-length, form-fitting silhouette
    • All-over floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4383

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set the Bar Linen Cutout Mini Dress

    This flare mini dress sets the bar high! Showcase your daring side in this sleeveless dress featuring a plunge v-neck on the front and back, a smocked bodice, and side elasticized bar cutouts that lead to a flirty mini-length hem. Complete the look in wedges and dainty earrings.

    Fit & Features

    • Sleeveless, dual plunge v-neck
    • Smocked bodice
    • Side elasticized bar cutouts
    • Flare mini-length hem
    • Linen gauze fabric
    • Runs true to size

    Style Number/Barcode: 05102-4831

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrapped In Chic Style Midi Sweater Dress

    Get wrapped up in chic style in this ribbed knit sweater dress. It features a sleeveless V-neckline, tank shoulder straps, a trendy knot-front design with a small center keyhole cutout, and a mid-length, curve-hugging fit. Complete the look with strappy mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline
    • Tank shoulder straps
    • Knot-front design, center keyhole cutout
    • Midi-length, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1256

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free