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.

  • Floral Scene V-Neck Mini Dress

    Make a scene in this floral mini dress sure to cause compliments! Featuring a sleek, sleeveless v-neckline, bungee spaghetti straps, and a bodycon silhouette atop a mini-length hem with a flirty slit accent. Complete the look in chic sandals for a fun day out.

    Fit & Features

    • Sleeveless, v-neckline
    • Bungee spaghetti straps
    • Bodycon silhouette
    • Mini-length hem, slit accent
    • Floral pattern
    • Stretch-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4419

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Prowlin' Leopard Mini Slip Dress

    On the prowl and looking fierce! This leopard mini slip dress features a sleeveless V-neckline, sleek bungee spaghetti straps, a bodycon silhouette, and a front slit accent. Complete the look in classy hoop earrings.

    Fit & Features

    • Sleeveless V-neck, bungee spaghetti straps
    • Bodycon silhouette
    • Front slit accent
    • Mini-length hem
    • Leopard pattern
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4418

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Brunch Vibes Eyelet Skater Dress

    Sweet and flirty, this eyelet knit skater dress is a must for weekend brunch! It features a sleeveless V-neckline with halter spaghetti straps, an open-back design, and a short skater skirt with a fit and flare silhouette. The lightweight knit fabric features an all-over floral eyelet pattern. Complete your look with a denim jacket and sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Halter spaghetti straps, tie-back closure
    • Open-back design
    • Fit and flare silhouette
    • Skater style-short skirt
    • Floral eyelet knit fabric, lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4420

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sway With Me Chiffon Dot Tiered Dress

    Sashay all day! Look adorbs in this chiffon sleeveless dress featuring a square neck, tie-straps, and a flowy tiered design on a short-length hem. Complete the look in a cute boater hat.

    Fit & Features

    • Sleeveless, square neck, tie-straps
    • Flowy tiered design
    • Short-length hem
    • Chiffon dot fabric, inner knit lining
    • Fits true to size

    Style Number/Barcode: 05101-1513

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Easy Breezy Eyelet Skater Dress

    Easy, breezy, and flirty! This eyelet skater dress is perfect for your next spring fling. It features a sleeveless, square neck, spaghetti straps, high waist seam, and a trendy open-back with twist detail on the flared short silhouette. The dress is composed of a lined lightweight woven knit fabric that offers a flattering form hugging fit with a moderate stretch. Complete the look in espadrille sandals.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • High waist seam
    • Open-back with twist detail
    • Flared short silhouette
    • Eyelet pattern
    • Lined lightweight woven knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4415

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Crush Floral Skater Dress

    Take your summer crush by surprise when they see you in this flirty floral skater dress! It features a sleeveless, v-neck, ruffled trim shoulder straps, a low-cut back with zipper closure, and a tiered, flowy hem with ruffles. Complete the look in sandals for a day date.

    Fit & Features

    • Sleeveless, v-neck, ruffled trim shoulder straps
    • Low-cut back, zipper closure
    • Skater silhouette
    • Tiered, flowy hem with ruffles
    • Ditsy floral print
    • Chiffon fabric, inner lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4417

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy-Chic Style Halter Midi Dress

    Showcase your trendy-chic status in this of-the-moment midi dress! It features a sleeveless halter neckline, spaghetti straps that lead to a cross-back lace-up strappy design, a sleek front O-ring accent, a midi-length, curve-hugging silhouette, and an all-over geometric striped pattern. Style this dress with heeled mules.

    Fit & Features

    • Sleeveless halter neckline, spaghetti straps
    • Open back, strappy cross-back lace-up design, tie closure
    • Front O-ring detail
    • Midi-length, form-fitting silhouette
    • Geometric striped pattern
    • Knit fabric, partial front knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4411

    Category Name: Casual Dresses

    Price: $4.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destination Dinner Paisley Halter Mini Dress

    Dinner plans? You're gonna need this perfect halter mini dress! It features a sleeveless bodice on an open-back with dual tie-back closure, a front slit accent, bodycon silhouette, and a paisley pattern throughout. Complete the look in lace-up heels.

    Fit & Features

    • Sleeveless, halter neckline
    • Dual tie-back closure
    • Front slit accent
    • Bodycon silhouette
    • Mini-length hem
    • Paisley pattern
    • Knit fabric, partial front knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4410

    Category Name: Casual Dresses

    Price: $4.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feeling Preppy Collared Mini Dress

    Your current mood? Preppy and ready for anything with this cute mini dress featuring short sleeves, a collared V-neck, and a bodycon silhouette on rib-knit fabric. Complete the look in trendy boots.

    Fit & Features

    • Short sleeves
    • Collared V-neckline
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4412

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shift In Seasons Floral Skater Dress

    The sun rises with the shifting seasons and this flirty floral skater dress is ready to make an appearance! Featuring a sleeveless, square neckline, spaghetti straps, a smocked bodice, and a flowy, short skirt. Complete the look in sleek hoop earrings.

    Fit & Features

    • Sleeveless, square neckline, spaghetti straps
    • Smocked bodice
    • Skater short silhouette
    • Floral print
    • Swiss dot chiffon, inner knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1507

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love Story Scoop Neck Mini Dress

    It's a love story so baby, just say yes to this floral mini dress! It features a sleeveless, scoop neck, spaghetti straps, a bust tie-front detail, and a bodycon silhouette on rib-knit fabric. Complete the look in cute sandals for a lunch date.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Bust tie-front detail
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy floral pattern
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4402

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fresh Perspective Eyelet Lace Skater Dress

    This eyelet lace cotton skater dress will give you a fresh perspective for creating a spring wardrobe! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a flattering fit and flare short-length silhouette. Complete the look in cute sandals for brunch or wine tasting!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back design
    • Fit and flare, skater silhouette
    • Short-length hem
    • Eyelet lace cotton fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4886

    Category Name: Casual Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Burst Ruffled Short Dress

    Bring a burst of florals with a short dress that will have you brunch ready! The dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, and a cutout at the midriff. The smocked waist leads to a flowy skater silhouette with tiered ruffles. The dress is composed of a lined chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Cutout at midriff, smocked waistband
    • Floral print
    • Skater silhouetted, tiered ruffles
    • Lined chiffon fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05101-1505

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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