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.

  • Sweet Days Smocked Strapless Mini Dress

    This dress is soft, sunny, and made for days that turn into plans. The smocked strapless bodice hugs just right, while the flowy skirt keeps things light and easy.

    Fit & Features

    • Poplin woven fabric
    • Strapless tube neckline
    • Smocked bodice for stretch
    • Skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000048

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Chic Vibes Only Strapless Drop Waist Romper

    Show off chic vibes only in this strapless drop waist romper designed with a tiered mini-length overlay with a short side slit. Perf for pairing with mules for happy hour!

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Strapless straight neckline
    • Drop waist design
    • Ruching
    • Tiered mini-length overlay, small bow detail, short side slit
    • Fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000023

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sunday Soiree Strapless Floral Midi Dress

    Enter a cute bliss in this strapless floral midi dress for a Sunday soiree! The dress boasts a form-hugging fit with a chic flared hem perfect for styling with strappy sandals.

    Fit & Features

    • Floral print, rib knit fabric lined with stretchy knit
    • Strapless neckline
    • Form-hugging fit
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000045

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sweetheart Status Tube Midi Dress

    She’s sculpted, strapless, and made to serve. This textured midi dress brings the heat with a sweetheart neckline, front cutout, and curve-hugging fit—perfect for date nights, rooftop vibes, or that one party everyone’s posting about.

    Fit & Features

    • Texture knit fabric, smooth knit stretchy lining
    • Strapless sweetheart tube neckline with notch cutout
    • Mini bust cutout
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000047

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Lovin' Crochet Knit Mini Dress

    You'll love the summer vibes this crochet knit mini dress brings to your happy hour look. Designed with a strapless neckline and sultry side slit, the bodycon fit will flaunt your stunning curves.

    Fit & Features

    • Sheer crochet knit fabric with knit lining, moderate stretch
    • Strapless straight-across neckline
    • Ruched side seam, adjustable drawstring, side slit
    • Mini-length asymmetric hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000046

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sun Rays Tropical V-Neck Babydoll Mini Dress

    Flaunt beachy perfection in this tropical babydoll dress with a strappy tie-back that turns heads with every wear! Style with sandals for a cute vacation look.

    Fit & Features

    • Tropical print, woven fabric, bust knit lining
    • V-neckline, twisted bust
    • Spaghetti straps
    • Strappy tie-back design
    • Babydoll silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000042

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

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  • Petals In Motion Floral Ruffled Mini Dress

    This is what you wear when the invite says “cute but effortless.” A floral ruffled mini dress with a flouncy fit that brings movement, charm, and just enough drama for every plan on your calendar.

    Fit & Features

    • Lightweight woven fabrication
    • Sleeveless square neckline, adjustable straps
    • Open back design with tie-back accent
    • Floral pattern
    • Tiered ruffled hem
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000041

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Suits You Perfectly Vest Pleated Skater Dress

    From the office to lunch with the girls, this sleeveless skater dress will get you noticed with the unique vest top and pleated mini-length hem! Style with pumps and a purse.

    Fit & Features

    • Woven fabric
    • Button-down vest top
    • Skater silhouette
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000039

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sleek Fit Strapless High Slit Maxi Dress

    Show off a sleek fit in this chic smooth knit maxi dress featuring a strapless neckline and high-cut side slit. The form-hugging silhouette will flaunt your gorgeous figure.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Strapless straight neckline
    • Ruched high front slit
    • Maxi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000684

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: GREEN-2, PINK

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Casually Sultry Strapless Bodycon Midi Dress

    Strut looking casually sultry in this strapless midi dress that accentuates your curves and can easily be dressed up or down!

    Fit & Features

    • Brushed knit double-lined stretchy knit fabric
    • Strapless neckline
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem, side slit
    • Runs true to size

    Style Number/Barcode: 05102-000034

    Category Name: Casual Dresses

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Soul Strapless Floral Flare Midi Dress

    A floral midi dress that'll capture your sweet essence! Designed with a strapless sweetheart neckline, this dress boasts a form-hugging fit and a trendy flare hem for effortless style.

    Fit & Features

    • Ditsy floral print lined with stretchy knit
    • Strapless sweetheart neckline, padded bra cups
    • Form-hugging fit
    • Flare midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000036

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cup Of Tea Striped Halter Midi Dress With Pockets

    Look cute spilling the tea in this striped midi dress boasting a flattering A-line fit adorned with hidden side pockets perfect for keeping your hands warm!

    Fit & Features

    • Striped print, cotton-blend woven fabric, woven lining
    • Halter plunge neck with ties
    • Back zipper closure
    • Hidden side pockets
    • A-line fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000033

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Vacay Scandal Tropical Cutout Maxi Dress

    Booked the trip? Now bring the drama in this tropical maxi dress! With metal hardware and skin-baring cutouts, this maxi is not for blending in—it's bold, body-hugging, and built for after-hours.

    Fit & Features

    • Tropical print, mesh fabric, smooth stretchy knit lining
    • Halter neckline with hardware accents, spaghetti strap tie
    • Bandeau-style cutout bodice with center metal U-ring
    • Ruched high waist with hardware accent
    • High front slit on a body-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000032

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Savor The Moment Halter Cutout Maxi Dress

    Step into the spotlight in this halter maxi dress on vacation or for some summer fun! Featuring a striking halter neckline adorned with elegant hardware and a shimmering stone insert, this bodycon dress offers a bold cutout design that highlights your figure.

    Fit & Features

    • Smooth knit stretchy fabric
    • Halter neckline with tie closure
    • Hardware and stone insert
    • Cutout accents
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000030

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cute But Chill A-Line Mini Dress

    Looks like a serve, feels like a chill day 'fit. This nylon mini dress comes through with a flattering silhouette and hidden shorts, so you can dance, lounge, or do your thing without a second thought.

    Fit & Features

    • Smooth nylon fabric, moderate stretch
    • Sleeveless square neckline
    • Spaghetti straps
    • Short front slit
    • Mini-length hem, hidden shorts
    • Fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000031

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Out Of Town Striped Mini Dress

    Head out of town in this stylish striped mini dress for an effortlessly cute look everywhere! Designed with a trendy twisted bust and a bodycon mini-length silhouette that perfectly flaunts your figure. Style with sandals!

    Fit & Features

    • Striped pattern, stretchy knit fabric
    • Twist sweetheart strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000029

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Coastal Chic Linen Halter Maxi Dress

    Meet your vacay soulmate. This breezy maxi serves minimal effort with major impact thanks to its sleek halter neckline, open tie back, and flowy fit made for golden hour strolls or rooftop cocktails.

    Fit & Features

    • Linen-blend woven fabric
    • High halter neckline, spaghetti strap tie
    • Open back with spaghetti strap tie, lower zipper and hook-eye closure
    • High side slit
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000026

    Category Name: Casual Dresses

    Price: $11.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Breezy As Can Be Strapless Ruffled Midi Dress

    This midi dress will be your go-to choice from shower celebrations to sunset dinners. Cascading ruffles create a feminine silhouette that flows with your movements, while the midi hem lets you show off your shoes.

    Fit & Features

    • Gauze woven fabric, woven lining
    • Strapless smocked stretchy bodice
    • Ruffled cascading silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000027

    Category Name: Casual Dresses

    Price: $15.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Lovely Day Tie Back Ruffle Skater Dress

    Perfect for any occasion, this skater dress will make you stand out in style! The tie back adds a touch of charm while the ruffled details bring a playful and flirty vibe to the mini-length hem.

    Fit & Features

    • Woven fabric, woven lining
    • Square neckline, spaghetti straps
    • Tie-back design
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000025

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Golden Hour Tropical Floral Mesh Midi Dress

    Make it your moment to glow in this tropical floral midi dress during golden hour! Featuring a strapless neckline and ruched side seams, this dress flatters your silhouette with a form-hugging fit that leads to a flowy sheer hem.

    Fit & Features

    • Tropical floral print, mesh fabric, sewn-in brushed knit lining
    • Strapless neckline
    • Side ruched seams
    • Form-hugging silhouette
    • Sheer flowy midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000024

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Twist Tie-Back Striped Midi Dress

    A chic twist on a classic sundress. This head-turning midi dress is designed with an open tie-back with button accents and hidden side pockets that keep your hands warm!

    Fit & Features

    • Striped print, woven fabric, woven lining
    • V-neckline
    • Spaghetti straps
    • Open tie-back design, lower button accents
    • Hidden side pockets
    • A-line silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000022

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Update Convertible Ruched Long Dress

    The perfect sleeveless long dress to update your chic wardrobe! The dress features a convertible neckline allowing for versatile styling like a halter or an off-the-shoulder look atop the form-hugging slim silhouette. Pair with earrings.

    Fit & Features

    • Smooth knit fabric
    • Convertible neckline
    • Halter or off-the-shoulder
    • Form-hugging slim silhouette
    • Long length hem
    • Runs true to size

    Style Number/Barcode: 05102-000023

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Coastal Cute Striped Bodycon Mini Dress

    An effortless striped mini dress for days spent by the coast or in the city! With a flattering strapless neckline and bodycon silhouette, this dress is perfect for layering.

    Fit & Features

    • Striped print, stretchy knit fabric
    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000017

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Effortless Days Strapless Bodycon Midi Dress

    A trendy babe like you needs this effortless strapless bodycon midi dress for easy styling! 

    Fit & Features

    • Double-lined rib knit stretchy fabric
    • Strapless neckline
    • Bodycon fit
    • Flowy midi-length hem
    • Extra glitter for maximum sparkle - may have some natural fallout
    • Runs true to size

    Style Number/Barcode: 05102-000021

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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