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.

  • Forever Fave Strapless Bodycon Mini Dress

    This curve-flaunting mini dress will be a forever fave for rooftop bars or dressy date nights. The textured knit fabric adds a chic allure to the strapless bodycon silhouette.

    Fit & Features

    • Textured knit fabric, full-length knit lining, high stretch
    • Strapless sweetheart neckline, no-slip strip
    • Padded bust, bust seam outline
    • Back zipper with hook-eye closure
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000190

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Steal The Scene Floral Corset Ruffle Mini Dress

    This floral corset mini dress serves up ruffles, romance, and just the right amount of sass. With its curve-hugging bodice and flirty layered hem, it’s basically a love letter in dress form.

    Fit & Features

    • Flocked floral pattern, mesh-lined fabric
    • Strapless sweetheart neckline, padded bra cups
    • Corset-inspired bodice
    • Back zipper and hook-eye closure
    • Form-hugging fit
    • Tiered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001053

    Category Name: Casual Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: IVORY-2

    Available Size: L

  • All Eyes On You Strapless Maxi Dress

    Effortlessly sleek, this strapless maxi is giving luxe with zero effort. The body-hugging fit and flowy hem make it your go-to for dinner dates or rooftop hotel bars.

    Fit & Features

    • Rib knit stretchy fabric
    • Strapless neckline
    • Bodycon fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000088

    Category Name: Casual Dresses

    Price: $12.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Through The Meadow Floral Corset Dress

    Too sweet to scroll past. This corset floral dress brings all the cottagecore charm with a flirty twist—yes, that oversized bow is doing the most. Perfect for shower celebrations or dressy events!

    Fit & Features

    • Floral print, woven texture fabric, lace trim woven lining
    • Sweetheart lace trim neckline, bust tie
    • Adjustable shoulder straps
    • Corset bodice, flexible boning inserts, lace trim
    • Back bow tie, zipper and hook-eye closure
    • Drop waist seam, skater short-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000269

    Category Name: Casual Dresses

    Price: $9.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sunkissed Curve Knit Midi Dress

    This striped midi dress was made to highlight every curve with a sculpting rib texture, front cutout detail, and side slit. Dress it up with heels for a night out or keep it elevated with sandals for a chic daytime moment.

    Fit & Features

    • Striped print, rib knit fabric
    • Sweetheart neckline, cutout bust accent
    • Adjustable spaghetti straps
    • Bodycon fit
    • Dual side slits
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000084

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Effortlessly Chic Ribbed Knit Skater Dress

    When your outfit says polished but still playful, this is the skater dress. The mock neck and fit-and-flare silhouette keep it chic, flirty, and ready for any plans on your calendar.

    Fit & Features

    • Ribbed sweater knit fabric, moderate stretch
    • Sleeveless mock neckline
    • Tank shoulder straps
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000085

    Category Name: Casual Dresses

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bloom Season Floral Mesh Maxi Tube Dress

    Meet your new obsession for dinner dates and chic soirées. This floral mesh maxi dress hugs in all the right places with a strapless neckline that feels effortlessly elevated.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Floral print
    • Strapless straight-across neckline
    • Ruching
    • Maxi-length hem, back slit
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000252

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Laced In Love Corset Mini Dress

    She’s giving drama, curves, and just the right amount of trouble. This corset mini dress hugs you in all the right places with a flirty ruffle that finishes the look with a wink.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Strapless sweetheart neckline
    • Built-in underwire padded but
    • Corset bodice, flexible boning, back zipper and hook-eye closure
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000256

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Dreamy Romance Floral Lace Skater Dress

    Sweet? Always. Innocent? Rarely. This lace mini gives flirty vintage feels with a neckline made to be noticed and a hem made to be twirled.

    Fit & Features

    • Floral print, lace fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Ruched square neckline
    • Skater silhouette, drop waist seam
    • Flared mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000240

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Whirlwind Romance Floral Abstract Maxi Dress

    This maxi dress is giving goddess in the wild. The sheer mesh and abstract floral print bring soft drama to any scene, whether it's brunch or rooftop party soirees! 

    Fit & Features

    • Abstract floral print, mesh lined fabric
    • Sweetheart neckline, padded bra cups, ruched bust seam
    • Spaghetti straps
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000242

    Category Name: Casual Dresses

    Price: $7.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Vacation Booked Floral Maxi Dress

    Already picturing the dinner plans in this one. This tropical floral maxi dress features a soft cowl neckline and an open back that brings just the right amount of drama for your getaway lineup.

    Fit & Features

    • Tropical floral print, mesh-lined fabric, high stretch
    • Cowl neckline
    • Adjustable spaghetti straps
    • Open strappy back
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000189

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • 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

    Product Badge:
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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

    Product Badge:
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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

    Product Badge:
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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

    Product Badge:
    • Ships Free
  • 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

    Product Badge:
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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:
    • Ships Free
  • 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:
    • Ships Free
  • 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:
    • Ships Free