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.

  • Sophisticated Vibe Double-Breasted Longline Vest

    Redefine business casual in this longline vest, perfect for polishing your everyday look! This vest has a lapel collar neckline, double-breasted buttons, and a belted waist, It's a chic layer to have in your closet.

    Fit & Features

    • Woven fabric, sewn-in knit lining
    • Lapel collar neckline
    • Double-breasted button closures
    • Belted waist
    • Longline hem
    • Runs true to size

    Style Number/Barcode: 06204-000004

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

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  • All Eyes On You High Slit Maxi Dress

    Giving "I didn’t come to play, I came to slay" energy. With a draped neckline, leggy side slit, and flattering ruching—this dress is a total scene-stealer from cocktail hour to afterparty.

    Fit & Features

    • Soft knit fabric with stretch, full knit lining
    • Draped cowl neckline with adjustable spaghetti straps
    • Side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000059

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Beauty So Bold Floral Mesh Maxi Dress

    Stroll like a bold beauty in this floral mesh maxi dress for any occasion! Its strapless design and curve-hugging fit accentuate your natural beauty, while the flowing maxi hem adds elegant movement.

    Fit & Features

    • Bold floral print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000058

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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  • Wanting More Strapless Lace Knit Maxi Dress

    Leave everyone wanting more when you're in this lace knit maxi dress! Perfect for any summer plans, this dress flaunts a sleek strapless neckline and form-hugging fit that flares out into a long hem.

    Fit & Features

    • Lace knit fabric, lined
    • Strapless neckline
    • Form-hugging fit
    • Flared maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000057

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • Romantic Flair Floral Lace-Up Maxi Dress

    Bring the romantic flair in this gorgeous floral print maxi dress with a form-hugging silhouette to highlight your curves. The alluring open lace-up back will turn heads and capture all the attention.

    Fit & Features

    • Knit fabric, high stretch
    • Floral print
    • Sleeveless V-neckline
    • Open back, cross-back lace-up design
    • Maxi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000055

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Courtside Style Cutout Pleated Skater Dress

    Look cute courtside in this stylish tennis-inspired skater dress! Featuring a trendy cutout back and a flattering skater silhouette, this pleated dress combines playful charm with modern flair.

    Fit & Features

    • Attached panty lining
    • Scoop neckline, tank shoulder straps
    • Double-lined soft knit bodice
    • Cutout back design
    • Woven pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000055

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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  • Beachy Breeze Strapless Slit Maxi Dress

    Enjoy a sunset dinner by the beach in this chic strapless maxi dress showcasing a high slit for effortless movement and a flattering bodycon silhouette.

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Strapless sweetheart neckline, twist accent
    • Bodycon silhouette
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000052

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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  • Eyes On You Lace-Up Slit Maxi Dress

    Not just a dress—this is the moment. From date nights to rooftop dinner parties, this linen maxi dress boasts a cutout bodice and leg-baring slit that does all the flirting for you!

    Fit & Features

    • Gauze linen-blend woven fabric, stretchy knit lining
    • Halter neckline, spaghetti strap ties
    • Lace-up back
    • Cutout accents
    • High front slit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000053

    Category Name: Casual Dresses

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

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  • Bold And Beautiful Rosette Halter Cutout Maxi Dress

    Step out like a bold beauty in this printed maxi dress for brunch, shower celebrations, or parties! This stunning maxi features an elegant halter neckline adorned with rosette detail, flirty cutouts that flatter your silhouette, and a flowing skirt that moves gracefully with every step.

    Fit & Features

    • Abstract print, woven fabric
    • Halter neckline with rosette detail, bust knit lining
    • Side cutout accents
    • Flowy ruffled maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000054

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

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  • Vacay Muse Floral Mesh Maxi Dress

    You'll be a gorgeous vacay muse in this curve-flaunting maxi dress designed with a large floral print on airy mesh fabric. Perf for pairing with wedges!

    Fit & Features

    • Sheer mesh fabric, full-length knit lining, high stretch
    • Large floral print
    • Sleeveless V-neckline
    • Spaghetti straps
    • Maxi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000056

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Vacay Mode Tropical Print One-Shoulder Maxi Dress

    You'll be on vacay mode in this sultry tropical print maxi dress featuring a one-shoulder neckline with a chic O-ring accent and an alluring bust cutout. The floor-length fitted silhouette will flaunt your stunning curves.

    Fit & Features

    • Mesh fabric, high stretch, knit lining
    • Tropical print
    • Sleeveless one-shoulder neckline, O-ring accent
    • Asymmetric bust cutout
    • Asymmetric back strap
    • Maxi-length hem, form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000050

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sultry Mode Halter Cutout Maxi Dress

    Amp up the sultry vibes of your summer 'fits with this sleek knit maxi dress featuring a halter square neck, an asymmetric waist cutout, and a curve-hugging silhouette.

    Fit & Features

    • Smooth knit fabric with knit lining, high stretch
    • Sleeveless square neckline
    • Tie-back halter spaghetti straps, partially open back
    • Asymmetric side cutout
    • Ruching
    • Maxi-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000051

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

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  • Stylishly Sweet Smocked Tube Skater Dress

    Stylishly sweet, this smocked tube skater dress is perfect for weekend brunch! It features a strapless straight neckline, a V-shaped waist, and a short A-line silhouette for that flirty flair.

    Fit & Features

    • Poplin cotton-blend woven fabric, stretchy knit lining
    • Strapless straight-across neckline
    • Stretchy smocked bodice
    • V-shaped waist
    • Pleating
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000049

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • 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

    Product Badge:
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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:
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  • 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

    Product Badge:
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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

    Product Badge:
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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

    Product Badge:
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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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