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.

  • 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

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  • All This Allure Strappy Halter A-Line Skater Dress

    You'll be irresistible in this A-line skater dress on a night out! This stunning dress features a plunging halter neckline and a strappy back, adding a touch of allure to any occasion, while the mini-length hem offers a flirty touch.

    Fit & Features

    • Smooth knit fabric, stretchy knit lining
    • Plunge halter neckline, bar accent, tie straps
    • Strappy back with spaghetti strap tie
    • A-Line skater silhouette
    • Seam detailing, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000697

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cut It Out Babe Midi Dress

    Effortless, but make it extra. With a bold cutout bodice and sleek side slit, this midi dress hugs in all the right places for dates, brunch, or casual plans.

    Fit & Features

    • Stretchy rib knit fabric, contrast trim
    • Square neck, tank shoulder straps
    • Cutout bodice
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000045

    Category Name: Casual Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Obsessed With The Vibe Fringe Lace Mini Dress

    A lace mini dress for when the girls' trip makes it out of the group chat! The playful fringe long sleeves create movement with every gesture, while the strappy open back design reveals just enough skin to turn heads.

    Fit & Features

    • Lace pattern, soft velvet-like fabric, stretchy knit lining
    • Sheer fitted long sleeves with fringe trim
    • V-neckline, keyhole cutout bust tie
    • Strappy open back with tie
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000122

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

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  • Heat Check Abstract Cutout Maxi Dress

    This isn’t just a dress, it’s a moment. With sultry cutouts, strappy details, and a leggy high slit, this curve-hugging mesh maxi brings the heat for nights out, birthdays, and turning heads on vacation!

    Fit & Features

    • Abstract tie-dye print, mesh fabric, sewn-in knit lining
    • One-shoulder neckline, bungee spaghetti strap
    • Side cutout, open back
    • High front slit, adjustable bungee cord strap with toggle
    • Hidden side zipper and hook-eye closure
    • Curve-hugging fit, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000125

    Category Name: Casual Dresses

    Price: $19.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Perfect Collar Short Sleeve Mini Dress

    There's nothing more perfect for warmer temps than this rib knit mini dress for an effortless athleisure vibe! This bodycon dress features a chic collar and short sleeves making it ideal for sunny days while the subtle side slit adds a flirty look.

    Fit & Features

    • Rib knit stretchy fabric
    • Collar V-neckline
    • Short sleeves
    • Bodycon silhouette
    • Side slit accent
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000127

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • Casually Cute Ribbed Knit Strapless Mini Dress

    Casually cute, this strapless mini dress is perfect for styling from coffee dates to happy hour. The A-line fit adds a flirty flair to the short silhouette.

    Fit & Features

    • Ribbed knit fabric with knit lining, high stretch
    • Strapless straight-across neckline
    • Mini-length hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000123

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sweet Memories Tie-Back Babydoll Mini Dress

    Make sweet memories at showers or graduations in this cute babydoll mini dress with a flirty tie-back and flowy hem.

    Fit & Features

    • Woven fabric
    • Sweetheart neckline, wide shoulder straps
    • Tie-back design
    • Babydoll silhouette
    • Flowy mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000120

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

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  • Breezy Fave High Slit Maxi Dress

    Show off effortless style in this breezy gauze maxi dress designed with a smocked waist, high front slit, and flowy A-line silhouette. Perf for summer parties, pair with espadrille sandals.

    Fit & Features

    • Gauze woven fabric, stretchy knit lining
    • Sleeveless V-neckline, spaghetti straps
    • Open cross-back tie-back design
    • Smocked high waist
    • Tiered design, thigh-high front slit
    • Maxi-length hem, flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000121

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Turn Up The Heat One-Shoulder Cutout Midi Dress

    Turn up the heat in this sultry knit midi dress designed with a one-shoulder neckline, front cutouts, sleek O-ring accents, and a high-cut side slit. The bodycon fit will highlight your gorgeous curves.

    Fit & Features

    • Smooth knit fabric with knit lining, high stretch
    • Sleeveless asymmetric one-shoulder neckline, gold metal O-ring accent, tank strap
    • Dual front cutouts under the bust and above the waist, gold metal O-ring accent
    • Ruching
    • Midi-length hem, thigh-high side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000117

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Groovy Gal Striped Cutout Mini Dress

    When your dress is the moment, this one’s got that groovy energy! The bold bell sleeves and plunging neckline were made for concerts, bright lights, and dance floors.

    Fit & Features

    • Striped texture knit fabric, soft stretchy knit lining
    • Plunging V-neckline with half hoop insert
    • Bell long sleeve
    • Side cutouts and open back
    • Bodycon silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000118

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Wow Factor Cutout Maxi Dress

    In this strapless maxi dress, you'll be checking yourself out in every mirror you pass! It boasts a metal square accent with a chic drape, a cutout bodice to show some skin, and a high front slit for effortless movement.

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Strapless sweetheart neckline, metal square accent, drape design
    • Padded bra cups
    • Cutout bodice, back zipper and hook-eye closure
    • High front slit
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000116

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Simply Cute Tie-Front Pleated Mini Dress

    With just the snap of a finger you'll look simply cute in this tie-front pleated mini dress designed to make a statement! 

    Fit & Features

    • Woven fabric, woven lining
    • Square neckline with dual tie-front
    • Spaghetti strap ties, side zipper and hook-eye closure
    • Drop waist seam
    • Fitted silhouette
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000119

    Category Name: Casual Dresses

    Price: $7.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Striking A Pose Halter Cutout Mini Dress

    Stunning textured knit adorns this sultry bodycon mini dress with a high halter neck and cutout side accent that reveals a peak of skin!

    Fit & Features

    • Texture knit fabric, smooth stretchy knit lining
    • High halter neckline, spaghetti strap tie
    • Side cutout
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000114

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Too Hot to Handle Halter Knit Mini Dress

    This halter mini dress hugs you with a bodycon fit and a side sash that brings the drama and accentuates your curves. Pair with sandals for brunch by the beach or vacay!

    Fit & Features

    • Texture knit stretchy fabric, stretchy knit lining
    • Halter neckline with hardware trim, spaghetti strap tie
    • Padded bra cups
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Front wrap sash design
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000115

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Jetset Babe Tropical Print Belted Maxi Dress

    Jetset to somewhere fabulous in this tropical print maxi dress! The flattering belted waist cinches your silhouette while hidden side pockets add convenience. A sultry side slit creates movement for a trendy look.

    Fit & Features

    • Tropical multi-print, woven fabric
    • Strapless neckline
    • Belted waist
    • Hidden side pockets
    • Flowy maxi silhouette, side slit
    • Runs true to size

    Style Number/Barcode: 05102-000112

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sent A Postcard Lace-Up Print Mini Dress

    A chic printed mini dress for your next cute trip! This dress is designed to turn heads with a lace-up back that adjusts to your perfect fit, statement puff sleeves, and a form-hugging fit that showcases your curves.

    Fit & Features

    • Printed design, woven fabric, woven lining
    • Puff short sleeves
    • Sweetheart neckline
    • Lace-up back, lower zipper and hook-eye closure
    • Form-hugging fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000113

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Forever Dreaming Strapless Cutout Ruffle Mini Dress

    Take a trip downtown or somewhere new in this strapless abstract print dress! With a cutout back, form-hugging fit, and ruffled mini hem, it's the ultimate look for summer.

    Fit & Features

    • Abstract print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • Cutout back
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000110

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Dinner By The Sea Tube Crochet Midi Dress

    You'll be a dreamy view in this crochet tube midi dress, enjoying a dinner by the sea. The form-hugging silhouette showcases your figure while the high side slit adds a daring touch of allure with seashell trim creates a captivating coastal-inspired look.

    Fit & Features

    • Crochet knit fabric, short knit stretchy lining
    • Strapless tube neckline
    • Form-hugging fit
    • High side slit, seashell trim
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000109

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Let's Have Some Fun Lace Bodycon Ruffle Mini Dress

    Looking for a flirty, fun vibe? Then you'll adore this lace mini dress designed with a flattering ribbon lace trim V-neckline and a bodycon fit with a ruffled hem.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Lace ribbon trim V-neckline
    • Adjustable spaghetti straps
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000079

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Little Things Striped A-Line Mini Dress

    Show off your cute self in this striped mini dress for any summer occasion! The playful ruffle details add movement and feminine charm, while the flattering A-line silhouette hugs your curves in all the right places.

    Fit & Features

    • Striped print, cotton-blend lined fabric
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Stretchy smocked bodice
    • A-Line silhouette, ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000106

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Meet Me in the Meadow Chiffon Floral Maxi Dress

    Easy, breezy, and made for photoshoots and parties. This strapless chiffon maxi dress with a smocked bodice and floral print gives off-carefree weekend energy with a soft, boho vibe.

    Fit & Features

    • Floral print, chiffon fabric, short woven lining
    • Strapless smocked bodice
    • Flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000107

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Island Time Tropical Floral Mesh Maxi Dress

    Get ready to be on island time in this gorg tropical floral mesh maxi dress perf for vacay. Featuring a strapless neckline and high side slit, style with heels.

    Fit & Features

    • Sheer mesh fabric with full-length knit lining, high stretch
    • Large tropical floral print
    • Strapless straight neckline
    • High-cut side slit
    • Maxi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000102

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Major Head Turner Floral Bodycon Mini Dress

    With a sultry strut and this floral mini dress, you'll be a major head turner on vacation or at parties! 

    Fit & Features

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

    Style Number/Barcode: 05102-000103

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free