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.

  • Destination Vacay Tropical Floral Mini Dress

    Jet set to your destination vacay in this tropical floral print mini dress, perfect for sunset happy hour. Designed with a square neck, adjustable spaghetti straps, and a short fitted silhouette, style with gold hoops and slide-on sandals.

    Fit & Features

    • Scuba knit fabric, stretchy knit lining
    • Tropical floral print
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Back zipper closure
    • Mini-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6077

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • Lovely Day Eyelet A-Line Midi Dress

    It'll be love at first wear in this strapless midi dress, perfect for shower celebrations, brunch, or parties! The intricate eyelet detailing adds a touch of romance while the flattering A-line silhouette accentuates your figure.

    Fit & Features

    • Eyelet woven fabric, woven lining
    • Strapless stretchy smocked neckline
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6078

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sweet Flirt Floral Mini Tube Dress

    Bring the sweet flirty vibes to your weekend plans in this cute mini tube dress with a dainty floral print on lined chiffon fabric. The strapless smocked bodice leads to a V-shaped waist, tiered ruffled design, and flowy skater silhouette.

    Fit & Features

    • Woven chiffon fabric with stretchy knit lining, dainty floral print
    • Strapless straight-across neckline
    • Stretchy smocked bodice
    • V-shaped waist
    • Tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4077

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • On Vacay V-Neck Floral Maxi Dress

    Look a daydream come true in this floral maxi dress while on vacay! Designed with a bold floral print on a sultry form-hugging silhouette.

    Fit & Features

    • Floral print, mesh-lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4076

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Ready To Bloom Strapless Lace-Up Floral Maxi Dress

    With the warmer months ahead it's time to bloom in this floral maxi dress perf for vacations and weekend getaways! The dress boasts an eye-catching lace-up back and a mermaid silhouette that accentuates your natural curves.

    Fit & Features

    • Floral print, knit fabric lined with stretchy knit
    • Lace-up back
    • Mermaid silhouette
    • Ruffled maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4080

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Paradise Beauty Floral Mesh Maxi Dress

    A beautiful floral mesh maxi dress for your escape to paradise! The dress boasts a flattering V-neckline and a form-hugging fit that flares into a flowy maxi-length hem. Pair with earrings and a bracelet.

    Fit & Features

    • Floral print, mesh lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging fit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4075

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

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  • Major Energy Strapless Floral Mesh Maxi Dress

    Bring major energy in this strapless floral mesh maxi dress design to flaunt your figure in a bodycon fit and show some skin with a high-side slit. Pair with mules.

    Fit & Features

    • Floral print, mesh fabric, soft and stretchy knit lining
    • Strapless neckline
    • High-side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-001515

    Category Name: Casual Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PLUM-2

    Available Size: XS, S, M, L, XL

    Product Badge:
    • Sale
  • Showstopper Cutout Ruffle Slit Maxi Dress

    Serve major allure in this sleeveless maxi dress while on vacay or weekend getaway! The maxi dress delivers a sultry design with a twist plunge V-neckline, cutout bodice, and a high front slit with a ruffled trim.

    Fit & Features

    • Slinky knit fabric, short knit lining
    • Plunge twist V-neckline
    • Shoulder straps, one metal accent piece
    • Cutout bodice
    • High front slit with ruffle trim
    • Bodycon maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4070

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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  • Breath Of Fresh Air Smocked Maxi Tube Dress

    Step out looking like a breath of fresh air in this maxi tube dress on vacay or weekend plans! The strapless, stretchy, smocked bodice ensures a perfect and comfortable fit that flatters your figure while the flowy, maxi-length hem creates an effortless look.

    Fit & Features

    • Woven fabric, bust knit lining
    • Strapless V-wired neckline
    • Stretchy smocked bodice
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6076

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Trend Moment Lace-Up Bodycon Midi Dress

    Have your trending moment in this midi dress! It's designed to hug your curves in a bodycon silhouette while the front lace-up adds a playful touch to your day or night look.

    Fit & Features

    • Knit fabric with moderate stretch
    • Square neckline
    • Lace-up front bust
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6072

    Category Name: Casual Dresses

    Price: $9.97

    Availability: Out of Stock

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  • Sunset Beauty Tropical Print Maxi Dress

    Show off your beauty at sunset happy hour in this tropical print maxi dress designed with sheer mesh fabric and a mini-length lining. The high-cut side slit adds an alluring detail to turn heads.

    Fit & Features

    • Sheer knit fabric with mini-length knit lining, high stretch
    • Tropical print
    • Sleeveless cowl neckline
    • Spaghetti straps, cross-back design
    • High side slit
    • Maxi-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6074

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Ocean View Tropical Floral Satin Mini Dress

    Enjoy a dinner with an ocean view in this tropical floral satin mini dress! With a flattering strapless neckline and flowy A-line silhouette, this dress will have you feeling vibrant and luxe.

    Fit & Features

    • Tropical floral print, satin fabric, stretchy knit lining
    • Strapless neckline
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6075

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Effortless Look Ruffle Skater Dress

    You'll love the effortlessly pretty look this flowy skater dress brings to your summer plans. It features a V-neckline, an open cross-back design, and a babydoll skater silhouette with a short ruffled hem.

    Fit & Features

    • Gauze woven fabric, woven lining
    • Sleeveless V-neckline
    • Spaghetti straps
    • Open cross-back design, tie closure, lower back cutout
    • Short ruffled hem
    • Babydoll skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6071

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • 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:
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  • Spring Fling Corset Tie A-Line Midi Dress

    Unleash your inner romantic in this midi dress at showers, graduations, or brunch! The tie bust corset bodice and lace-up back create a flattering silhouette, while the midi-length hem and textured fabric add a touch of playfulness.

    Fit & Features

    • Texture woven fabric, woven lining
    • Sweetheart neckline, wide shoulder straps
    • Dual tie front corset bodice, lace-up back
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6068

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Breeze By Strapless Striped A-Line Midi Dress

    Breeze by like a breath of fresh air in this striped midi dress! It's adorned with hidden side pockets to keep your hands warm and has a flattering A-line silhouette.

    Fit & Features

    • Striped print, woven fabric, woven lining
    • Strapless neckline
    • Stretchy smocked bodice
    • Hidden side pockets
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6069

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Dinner Downtown Sleeveless Ruched Midi Dress

    The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch.

    Fit & Features

    • Smooth knit fabric, stretchy knit lining
    • Sleeveless crew neck
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6066

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

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  • Flirty Girlie Bow Pleated Skirt Romper

    Feel like a dream in this modern sleeveless romper with a front bow inset and pleated skirt overlay that boasts a flirty silhouette. Complete the look with boots.

    Fit & Features

    • Smooth knit fabric
    • Square neckline, wide shoulder straps
    • Front bow inset
    • Pleated skirt overlay, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-1267

    Category Name: Casual Dresses

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Remarkable Allure Long Sleeve Mini Dress

    You'll look all kinds of alluring in this long sleeve mini dress in a sultry bodycon fit perfect for dressing up or down.

    Fit & Features

    • Stretchy knit fabric
    • Fitted long sleeves
    • Square neckline
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6063

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Lively Elegance Smocked Floral Babydoll Dress

    You'll fall in love with this breezy floral babydoll dress, so adorable for weekend parties and graduations! With its stretchy smocked bodice and adjustable straps, you'll get the perfect fit. The chiffon fabric and pretty floral print add a touch of elegance to the playful babydoll silhouette and ruffled short-length hem.

    Fit & Features

    • Floral printed chiffon fabric, stretchy knit lining
    • Square neckline
    • Stretchy smocked bodice
    • Adjustable spaghetti straps
    • Babydoll silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6062

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Vacay Escape Halter Bodycon Crochet Midi Dress

    Escape on vacay in this must-have halter crochet midi dress perfect for enjoying a sunset dinner and drinks!

    Fit & Features

    • Crochet fabric, stretchy knit lining
    • Halter neckline, tie-back
    • Front bust tie with keyhole accent
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6060

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flawless Beauty Cutout A-Line Midi Dress

    Step out in this A-line midi dress for a flawless look all spring to summer! Designed with a sleek sweetheart neckline and underbust cutout, this dress makes a delightful impression.

    Fit & Features

    • Woven fabric
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Underbust cutout, back zipper closure
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6064

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Looking Like A Daydream Eyelet Lace Dress

    Look like a daydream in this adorable eyelet lace mini dress for your next date. Designed with short puff sleeves and a bodycon silhouette with a ruffled hem, you'll bring flirty vibes.

    Fit & Features

    • Eyelet lace fabric with knit lining, moderate stretch
    • Sweetheart neckline, ruched bust
    • Short puff sleeves, ruffle trim
    • Bodycon silhouette
    • Mini-length tiered ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-6059

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Vacay Vibe Tropical Floral Halter Maxi Dress

    You'll be a total vibe on your summertime vacay in this tropical floral print maxi dress. The plunging halter neckline, ruched side seams, and curve-hugging fit are all alluring details you'll love.

    Fit & Features

    • Knit fabric with knit bust lining, high stretch
    • Tropical floral print
    • Sleeveless plunge V-neckline
    • Tie-back halter straps, partially open back
    • Ruched side seams
    • Maxi-length hem, curve-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-6056

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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