Casual Dresses

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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.

  • Edge of Allure Cutout Mini Dress

    The kind of dress that doesn’t wait for an occasion. This one-shoulder mini dress hugs your curves with asymmetric ruching and a daring side cutout—perfect for owning the night (and every entrance).

    Fit & Features

    • Smooth knit stretchy fabric
    • One-shoulder neckline
    • Side cutout waist accent
    • Bodycon fit
    • Asymmetrical mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000239

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Autumn Attitude Strapless Pleated Plaid Mini Dress

    Embrace the new season in this plaid mini dress featuring a strapless neckline, form-hugging silhouette, and a flirty pleated mini-length hem. Perfect for back-to-school and styling with flats.

    Fit & Features

    • Plaid pattern, knit fabric, moderate stretch
    • Strapless folded neckline
    • Form-hugging silhouette
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5863

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Blue Crush Denim Halter Skater Dress

    Meet your new denim obsession. This square neck halter mini dress serves curve-hugging confidence with belted detailing and flirty side cutouts made for catching glances.

    Fit & Features

    • Stretch denim fabric, knit panty lining
    • Adjustable belted halter square neckline, foldover accent
    • Back zipper and hook-eye closure
    • Side waist cutouts
    • Front seam detailing
    • Skater short-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000241

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Alluring Sensation Halter Open Back Maxi Dress

    Wherever your summer takes you, this maxi dress will look sensational against any tropical or beach background! This dress features a striking cowl halter neckline, a sleek hoop insert, and a captivating form-hugging silhouette, while the open back adds a daring touch.

    Fit & Features

    • Slinky knit stretchy fabric
    • Cowl halter neckline, hoop insert, tie back
    • Open back
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000124

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Getaway Bound Lace-Up Print A-Line Dress

    With an Italian-inspired print, this A-line dress is perfect for packing with you! This dress is designed in a flattering A-line mini silhouette with a stylish lace-up front and a chic cutout back that turns heads.

    Fit & Features

    • Multi-printed, woven fabric, woven lining
    • V-neckline with lace-up bust
    • Adjustable spaghetti straps
    • Cutout back
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000659

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: MULTI-2

    Available Size: XS, S, M, L

  • Thriving Blooms Corset Floral Slit Midi Dress

    Thrive with sweet energy in this floral midi dress perfect for brunches or dates! With a corset bodice that snatches your waist and a flirty front slit, this a-line dress will captive everyone. Pair with a necklace.

    Fit & Features

    • Ditsy floral print, woven fabric
    • Wide shoulder straps, sweetheart neckline
    • Corset bodice
    • Side pockets
    • A-line silhouette, front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4051

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sun And Spritz Tropical Cutout Maxi Dress

    Just add sun and a spritz—this tropical print maxi is made for main character getaways. With side cutouts and breezy vibes, it’s giving effortlessly hot in every snap.

    Fit & Features

    • Lightweight woven fabric with tropical print, bust lining
    • Square neck
    • Cutout sides on the bodice
    • Fitted bodice with trim detailing
    • Bust tie, tank shoulder straps, back zipper and hook-eye closure
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000246

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Elevated Edge Denim Corset Midi Dress

    Effortlessly sculpted with just the right edge. This denim corset midi dress defines your shape with a structured bodice and a sleek strapless neckline that feels elevated, confident, and ready for plans that don’t end early.

    Fit & Features

    • Strapless sweetheart neckline
    • Corset-inspired bodice with seamed detailing
    • Back zipper and hook-eye closure
    • Back slit for ease of movement
    • Midi-length silhouette, bodycon silhouette
    • Denim fabric with moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-000250

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetheart Strings Lace-Up Denim Dress

    This lace-up skater dress brings the perfect mix of sweet-meets-spicy with its sweetheart neckline, flirty pleated skirt, and strappy open-back moment that’s basically engineered for compliments. 

    Fit & Features

    • Dark wash denim fabric
    • Sweetheart neckline with front lace-up detail, grommet insets
    • Adjustable spaghetti straps
    • Open crisscross lace-up back
    • Fitted bodice with pleated skater skirt
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-000248

    Category Name: Casual Dresses

    Price: $11.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Flattering Look A-Line Ruffled Mini Dress

    This A-line mini dress gives you a flattering look for every social event on your calendar! The V-neckline adds a touch of elegance to this fun, versatile piece. Perfect for a variety of occasions, this dress will keep you looking stylish. Complete the look with dainty earrings.

    Fit & Features

    • Soft model-blend knit fabric, lined, moderate stretch
    • V-neckline
    • A-Line silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5769

    Category Name: Casual Dresses

    Price: $7.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Time To Vacay Halter Lace-Up Maxi Dress

    Your next vacay fit is here - say aloha to this knit maxi dress designed to showcase your curves in a bodycon fit and bare some skin with the alluring lace-up back.

    Fit & Features

    • Texture knit fabric, knit lining, moderate stretch
    • High halter neckline
    • Spaghetti straps
    • Lace-up back
    • Bodycon fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000053

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Rustic Charm Faux Suede A-Line Mini Dress

    Channel all the cozy fall feels with a sleek twist. This faux suede mini dress features a button-front design and a daring open back, accented by a statement buckle strap. Perfect for layering under a trench or pairing with knee-high boots for an effortlessly chic allure.

    Fit & Features

    • Smooth faux suede fabric, sewn-in knit lining
    • Sleeveless crew neck
    • Adjustable buckle strap and cutout design
    • Front button accents
    • A-line fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000258

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sunny Days Floral Halter Skater Dress

    Sunny days call for this cute floral skater dress featuring tie-back straps and a breezy fit-and-flare silhouette!

    Fit & Features

    • Rayon woven fabric
    • Floral print
    • Sleeveless V-neckline
    • Tie-back halter straps
    • Open back, lower tie-back design
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5874

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Love Spell Lace Skater Dress

    Flirty with a touch of vintage romance. This lace corset mini flatters every curve with a sweetheart neckline and flared skater skirt—made for date nights, parties, or whenever you want all eyes on you.

    Fit & Features

    • Lace-lined fabric, flocked velvet trims, attached panty lining
    • Strapless sweetheart neckline, bust lining
    • Corset-inspired sheer bodice, flexible boning
    • Back zipper and hook-eye closure
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000263

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Party Chic Lace Floral Maxi Dress

    Giving flirty fairytale but make it chic. This lace-trimmed maxi dress hugs like a dream and serves up soft-girl glam with a sultry high side slit. Perfect for garden parties, shower celebrations, and dressy dates.

    Fit & Features

    • Floral print, mesh-lined fabric
    • Lace sweetheart neckline and shoulder straps
    • Back zipper closure
    • High side slit
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000264

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spice Things Up V-Neck Cutout Skater Dress

    Casual gets a sultry upgrade with this short skater dress perfect for showers and birthdays! This flirty skater dress boasts flowy sleeves, a front and back V-neckline, and a cutout bodice for an alluring look. The gauze fabric adds breezy comfort while the skater silhouette and short length keep you on-trend. Complete the look in strappy wedges.

    Fit & Features

    • Gauze woven fabric lined with stretchy knit
    • V-Neckline front and back
    • Cutout bodice, elasticized straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5419

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • The Drama Edit Ruffle Mini Dress

    Turn the charm all the way up in this halter mini dress that serves effortless allure. Designed with a flirty open back and tiered ruffle hem, it’s your go-to for nights that deserve a little drama.

    Fit & Features

    • Stretchy knit fabric
    • Cowl halter neckline
    • Open tie back
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000270

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Laced In Denim Strapless Mini Dress

    Meet the denim moment everyone’s talking about. This strapless corset mini cinches you in all the right places with lace-up sides and a structured bodice that gives instant shape. It’s flirty, bold, and begging to be admired at concerts or nights out.

    Fit & Features

    • Denim fabric with slight stretch
    • Strapless neckline
    • Corset-seamed bodice, back zipper and hook-eye closure
    • Rhinestone-embellished lace-up side plackets
    • Curved drop waist seam
    • Skater silhouette, frayed edge trim, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000273

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Game Set Slay Sweater Dress

    She’s giving preppy with a playful twist. This sleeveless sweater dress hugs in all the right places with contrast trim and a flared mini-length hem that makes it a serve for every season!

    Fit & Features

    • Rib knit stretchy fabric
    • Square neckline and tank shoulder straps, contrast trim
    • Skater silhouette
    • Pleated, flare mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2219

    Category Name: Casual Dresses

    Price: $21.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • After Hours Pinstripe Lace Mini Dress

    When the city lights come on, this dress takes over. The after-hours pinstripe lace mini serves sultry vibes with its corset fit, lace peekaboo, and flirty ruffle hem that’s made for late-night adventures.

    Fit & Features

    • Woven knit fabrication
    • Pinstripe pattern
    • Sleeveless sweetheart neckline
    • Sheer lace panel front detail
    • Tiered ruffled hemline
    • Mini length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000276

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightful Charm Halter A-Line Midi Dress

    Step out looking delightful in this charming sleeveless midi dress for parties or showers! The halter pleated neckline and open back add a flirty touch, while the beaded tie waist cinches your waist for a flattering A-line silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Woven fabric, no stretch
    • Halter pleated neckline
    • Open back, zipper and hook-eye closure
    • Beaded tie waist
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5648

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Floral Instinct Tie Back Maxi Dress

    Romantic with a wild streak. This halter maxi dress mixes abstract rose and animal prints with a lace-trim bust and open tie back—perfect for day or night out plans.

    Fit & Features

    • Abstract animal rose print, mesh-lined fabric, moderate stretch
    • Halter plunge neckline, tie closure
    • Lace bust
    • Open tie back design
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000279

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Easy Elegance A-Line Maxi Dress

    Chic, minimal, and made for any moment. This strapless maxi dress keeps it effortless with a fitted bodice and flowy skirt that moves with you—perfect for everything from beach strolls to brunch dates.

    Fit & Features

    • Smooth knit stretch fabric
    • Strapless tube neckline
    • Fitted bodice
    • Side pockets
    • A-line silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000281

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Happy Hour Ruffled Skater Dress

    This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag.

    Fit & Features

    • Sleeveless V-neckline
    • Halter tie-back straps, open back
    • Stretchy smocked high waist
    • Short skater skirt, tiered ruffled design
    • Fit and flare silhouette
    • Twill fabric, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-5531

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free