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.

  • Eyes On You Eyelet Tie Back Dress

    All eyes on you in this eyelet lace mini dress! It features puff sleeves, a square neck, a ruched bust, an open back with a tie closure, and a bodycon silhouette. Complete the look in lace-up sandals for a picnic date.

    Fit & Features

    • Short puff sleeves, cinched hems
    • Square neckline, ruched bust
    • Open back, tie closure
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4438

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Falling For Eyelet Mini Dress

    Fall for this eyelet mini dress for a cute vibe all summer long! It features a sleeveless, square neck, adjustable spaghetti straps, a flirty tie-front bust, and a form-fitting silhouette. Complete the look in a dainty necklace and wedges.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Tie-front along the bust
    • Form-fitting silhouette
    • Mini-length hem
    • Eyelet knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4435

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Finest Floral Tie-Back Skater Dress

    The florals on this skater dress are oh-so-fine! Create a cute spring look in this sleeveless, boat neckline, adjustable spaghetti straps, a flirty open-back with tie closure, and a ruffled skater silhouette. Complete the look in stud earrings for Easter brunch.

    Fit & Features

    • Sleeveless, boat neckline, adjustable spaghetti straps
    • Open-back, tie closure
    • Ruffled skater silhouette
    • Short hem
    • Floral chiffon-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4432

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Born To Rock Lace-Up Graphic Tunic

    Feel the rockstar vibes in this trendy graphic tunic for all of your jam sessions! It features a sleeveless mock neck, dual side lace-up detail, and a front graphic script that reads, 'Let's Make Some Noise/Born To Be A Rockstar'. Complete the look in lug booties.

    Fit & Features

    • Sleeveless, mock neck
    • Dual side lace-up detail
    • Graphic reads, 'Let's Make Some Noise/Born To Be A Rockstar'
    • Form-fitting bodice
    • Short hem
    • Cotton knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1149

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Love Eyelet Mini Dress

    You'll fall in love with the adorable details of this eyelet mini dress! It features a sweetheart neckline with a ruffled trim, a ruched bust with a tie-front, short puff sleeves, and a mini-length, form-hugging fit. The eyelet knit fabric features a lightweight lining. Style this dress with cute espadrille sandals.

    Fit & Features

    • Sweetheart neckline, ruffled trim
    • Ruched bust, tie-front detail
    • Short puff sleeves, elasticized hems
    • Short, form-fitting silhouette
    • Eyelet knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4433

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunday Girl Eyelet Lace-Up Skater Dress

    This eyelet skater dress is perfect for Sunday brunch! It features adorable short puff sleeves, a square neck, an elasticized waist, an open-back design with lace-up closure, and a flared skirt. Composed of breathable cotton fabric with an inner lining. Finish the look in strappy sandals.

    Fit & Features

    • Short puff sleeves
    • Squareneck
    • Elasticized waist
    • Open-back design, lace-up closure
    • Flared, skater silhouette, short-length hem
    • Eyelet lace cotton fabric, inner lining
    • Fits true to size, no stretch

    Style Number/Barcode: 05102-4428

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shamrock Shake Ruched Mini Dress

    Look like a treat this St. Patrick's Day! This sleeveless mini dress features an on-trend square neck, spaghetti straps, and dual side ruching with adjustable ties, a shamrock pattern, and a bodycon silhouette. Composed of a brushed knit fabric with a moderate stretch. Finish the look in strappy sandals. 

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Dual side ruching, adjustable ties
    • Shamrock pattern
    • Bodycon silhouette
    • Mini hem
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4430

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Eye On The Eyelet Lace Mini Dress

    Keep your eye on this prize! Bring the flirty allure in this eyelet lace mini dress featuring short puff sleeves, a ruffle sweetheart neck with tie, and a babydoll-style bodice on a form-fitting silhouette. Complete the look in lace-up sandals for a cute picnic look.

    Fit & Features

    • Short puff sleeves
    • Ruffle sweetheart neck with tie
    • Babydoll-style bodice
    • Form-fitting silhouette
    • Mini-length hem
    • Eyelet lace knit lined fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 05102-4429

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Breeze Linen Halter Skater Dress

    Feel the breeze this spring! This linen skater dress is perfect for your next daytime soiree featuring a sleeveless halter V-neckline, open-back design, dual tie-back closure, and a flowy, A-line skater silhouette. Composed of linen fabric with an inner knit lining with minimal stretch. Style with strappy heels.

    Fit & Features

    • Sleeveless, halter V-neck
    • Open-back design, dual tie-back closure, lower back elasticized waistband
    • Flowy, A-line skater silhouette
    • Above-the-knee length hem
    • Linen fabric, inner knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4414

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Easy Decision Eyelet Tie-Back Dress

    A sleek and easy piece to dress up or down? Decision made! Keep it trendy in this eyelet lace mini dress designed in a sleeveless scoop neckline, spaghetti straps, tie-back detail, and a bodycon silhouette. Complete the look in basic heels for an outdoor dinner party.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Tie-back detail
    • Eyelet lace-lined fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4422

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sea Breeze Tropical Midi Dress

    Take a sunset stroll in this alluring tropical midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, ruched detailing down one side, and a midi-length, asymmetrical hem creating a high side slit. The all-over palm leaf print will bring major vacay vibes. Style with strappy sandals and a flowy kimono.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Ruching down one side
    • Midi-length, asymmetrical hem, side slit
    • Curve-hugging silhouette
    • Palm leaf print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4421

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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