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.

  • Darling Babe Striped Drop Waist Skater Dress

    So darling, this striped woven skater dress is effortless perfection. The sleeveless square neckline is accented with a mini bow detail, and the drop waist design leads to a pleated fit-and-flare silhouette.

    Fit & Features

    • Striped woven fabric
    • Sleeveless square neckline, eyelet trim, mini bow detail
    • Tank shoulder straps
    • Square back, zipper closure
    • V-shaped drop waist
    • Short pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000145

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Off-Duty Icon Mock Neck Mini Dress

    A sleek mock neck and bodycon ruched silhouette keep your fit snatched from every angle, while the abstract print brings chic energy to your next date night or rooftop dinner.

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Mock neck
    • Ruched bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000188

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine Cutie Strapless Ruffle Eyelet Mini Dress

    Created for the cuties, this eyelet mini dress is a cute look for shower celebrations or casual parties! Designed to hug your form for a flattering fit, the strapless neckline and ruffled mini hem add a flirty and playful touch.

    Fit & Features

    • Eyelet fabric, stretchy knit lining
    • Strapless neckline
    • Form-hugging fit
    • Ruffled layer mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000187

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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  • Once Upon This Corset Skater Dress

    Whimsy in every stitch. With lace trims, corset details, and a floaty mini hem, this skater dress feels like it was made for fairy tales, flower fields, and falling in love (again).

    Fit & Features

    • Cotton-blend woven fabric
    • Multiple petticoat tulle and lace trim woven linings
    • Strapless lace trim drawstring tie square neckline
    • Hidden side zipper and hook-eye closure
    • Corset bodice, flexible boning, lace and pleated trims, back lace-up placket
    • Drop waist seam, voluminous skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000229

    Category Name: Casual Dresses

    Price: $69.90

    Availability: Out of Stock

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  • Casual Fave Flowy V-Neck Midi Dress

    This breezy lightweight midi dress will be your new casual fave for weekend plans. Designed with a sleeveless V-neck, low back, and mid-length flowy fit, style with a layered necklace and strappy sandals.

    Fit & Features

    • Gauze woven fabric, mini-length stretchy knit lining
    • Sleeveless V-neckline
    • Adjustable spaghetti straps, low back
    • Hidden side pockets
    • High side slit
    • Midi-length flowy silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000185

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

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  • Gorgeous Vibe Floral Bodycon Mini Dress

    Radiate a gorgeous vibe in this bold floral print mini dress designed with a strapless neckline and bodycon silhouette to flaunt your curves.

    Fit & Features

    • Smooth knit fabric with knit lining, high stretch
    • Large floral print
    • Strapless straight neckline, no-slip strip
    • Mini-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000147

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Bubbly and Booked Striped Collar Dress

    For the girl with plans, lattes, and an effortless look. This striped dress keeps it crisp with a collar button-down design and a bubble hem that adds a little bounce to every step.

    Fit & Features

    • Striped print, cotton fabric, sewn-in woven lining
    • Collared neckline
    • Button-down closures
    • Belted waist
    • Bubble short hem
    • Runs true to size

    Style Number/Barcode: 05102-000182

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Hot Glow Denim Western Mini Dress

    Bold lines, bold moves. This strapless bodycon mini dress features standout topstitch detailing and a daring front cutout that sculpts your curves and keeps all eyes on you.

    Fit & Features

    • Denim fabric, slight stretch, Western flame stitched design
    • Strapless sweetheart wired neckline, padded bra cups
    • Front keyhole cutout
    • Back zipper and hidden button-up closures
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000181

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Bloom Flocked Floral Mesh Maxi Dress

    This dress is giving sultry garden goddess. The strapless neckline and body-hugging mesh silhouette keep it sleek, while the flocked floral detail adds just the right amount of romance. Perfect for whenever you want to turn a subtle moment into the moment.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Flocked floral print pattern
    • Strapless straight-across neckline
    • Back zipper closure
    • Ruching
    • Fitted silhouette, midi-length flared hem
    • Runs true to size

    Style Number/Barcode: 05101-000180

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • So Sweet Floral And Plaid Patchwork Mini Dress

    Create the perfect weekend look in this oh-so-sweet mini dress designed with a floral and plaid patchwork pattern. The crochet bust trim and tie-front detail are dainty details you'll adore.

    Fit & Features

    • Woven fabric, no stretch
    • Ditsy floral and plaid patchwork pattern
    • Sleeveless sweetheart neckline, crochet trim and tie-front detail, ruched bust
    • Adjustable spaghetti straps
    • Hidden back zipper, hook-eye closure
    • Mini-length hem, fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000178

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Ruffle Repeat Lace Tube Mini Dress

    She’s sleek up top, party on the bottom—aka your new go-to for nights that need a little extra twirl. The strapless neckline and tiered ruffles make it an easy yes for going out.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Strapless tube neckline
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000171

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • That Girl Energy Cutout Tube Midi Dress

    Steal the scene and leave them speechless. This sleek strapless midi hugs your curves with a smooth, sculpted fit perfect for date nights, parties, or whenever you’re feeling that girl energy.

    Fit & Features

    • Brushed knit soft fabric, knit lining, moderate stretch
    • Strapless tube neckline
    • Cutout back, lower ruched seam
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000176

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Twirl Season One-Shoulder Skater Mini Dress

    A little flirty, a little playful. This dress boasts a flattering skater silhouette and an off-shoulder neckline, making it made for cute date nights and celebrations!

    Fit & Features

    • Sweater knit fabric, moderate stretch
    • Asymmetrical one-shoulder neckline
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000079

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Brunch Plans Cherry Halter Skater Dress

    Turn heads effortlessly in this adorable cherry mini dress for brunch or celebrations! Its flattering halter neckline and playful skater silhouette create a perfect balance of flirty and fun for your summer wardrobe.

    Fit & Features

    • Cherry embroidered pattern
    • Gauze cotton fabric, multiple woven and tulle linings
    • Plunge halter neckline, tie closure
    • Back zipper and hook-eye closure
    • Drop waist seam
    • Skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000175

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Barely Blushing Floral Mini Dress

    Soft girl, but make it sultry. This floral mini dress clings in all the right ways, with delicate straps and a dreamy texture that feels flirty but effortless!

    Fit & Features

    • Floral print, burnout texture, mesh fabric, stretchy knit lining
    • Scoop neckline
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000165

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Belt It Babe Strapless Denim Mini Dress

    This denim tube dress understood the assignment—snatched waist, pleats for drama, and grommets for edge. The belted fit hugs you just right, and the mini hem? Major moment.

    Fit & Features

    • Denim fabric
    • Strapless tube neckline with grommet trim
    • Fitted bodice with seam detail
    • Adjustable belted waist
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000171

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Beach Goddess Crochet Lace-Up Maxi Dress

    She’s giving beach goddess vibes from brunch to golden hour cocktails. This crochet maxi hugs your curves with a bodycon fit and an open lace-up back that’s totally Insta-worthy.

    Fit & Features

    • Crochet lined fabric
    • V-neckline
    • Spaghetti straps
    • Open lace-up back design
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000072

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Tan Lines Cutout Bodycon Mini Dress

    Flaunt your figure in this sultry strapless mini dress on vacay or a bach weekend! Designed with cutout accents and stylish hoop inserts, it creates an alluring silhouette that demands attention along the bodycon silhouette.

    Fit & Features

    • Texture knit stretchy fabric, sewn-in knit lining
    • Strapless sweetheart neckline
    • Front cutouts and hoop inserts
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000170

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sweetly Sultry Floral Bodycon Midi Dress

    So sweet and sultry in every way, this floral midi dress flaunts a sleek, flattering strapless neckline and bodycon fit perfect for shower celebrations or casual events.

    Fit & Features

    • Floral print, eyelet fabric, sewn-in knit lining
    • Strapless neckline
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000169

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twist Of Fate Strapless Ruffled Maxi Dress

    Because you didn’t plan to look this good... it just happened. Make your way in this breezy maxi dress designed with effortless, dreamy details from the twisted strapless bust to strappy open back and flowy ruffled silhouette. 

    Fit & Features

    • Satin woven fabric, woven lining
    • Strapless sweetheart neckline
    • Twisted bust, keyhole cutout accent
    • Strappy open back
    • Ruffled silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000168

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On Island Time Strapless Floral Romper

    This strapless romper exudes carefree vibes, perfect for vacations! The strapless neckline and form-hugging fit accentuate your curves, while the statement floral print adds a touch of tropical essence.

    Fit & Features

    • Stretchy knit fabric, statement floral print
    • Strapless neckline
    • Form-hugging fit
    • Ruffled hem, fitted knit shorts
    • Runs true to size

    Style Number/Barcode: 06503-000053

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Serving Curves Keyhole Maxi Dress

    Serving curves and confidence—this dress eats every time. The keyhole cutout and body-hugging silhouette? A certified head-turner for nights that don’t end early.

    Fit & Features

    • Stretchy textured knit fabric
    • Scoop neckline with spaghetti straps
    • Front keyhole cutout at bust
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000166

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cutest Plans Floral Eyelet Corset Skater Dress

    Your group chat is already asking where you got it. This floral eyelet corset skater dress cinches you in with a sculpted bodice and flares out into the cutest twirl-ready silhouette for brunch dates, garden parties, and every camera roll moment in between.

    Fit & Features

    • Floral eyelet woven fabric, tulle and knit linings
    • Sleeveless sweetheart neckline, ruched bust, small cutout, tie-front detail
    • Underwire bust support
    • Tie-shoulder straps, side zipper and hook-eye closure
    • Corset bodice with boning, V-shaped waist, ruffled trim
    • Lace-up back design, short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000130

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Weekend Chic Sleeveless Midi Dress

    Elevate your weekend look with this sleeveless midi dress with a sleek boat neckline, flirty low-cut back, and a flattering flowy silhouette. Dress it up with strappy sandals!

    Fit & Features

    • Woven fabric
    • Boat neckline
    • Low-cut back
    • Drop waist seam
    • Flowy silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000164

    Category Name: Casual Dresses

    Price: $19.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free