Casual Dresses

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Everyday Ease: Casual Dresses for Transitional-Weather Plans

From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.

Laid-Back & Versatile

Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.

Chic from Day to Night

Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in nuetral or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.

Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.

What Makes a Dress Casual?

Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.

Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.

How Do I Style a Dress Casually?

Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.

For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!

  • 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:
    • 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:
    • Ships Free
  • Inspired Art Abstract Bodycon Mini Dress

    Bring a little extra artsy glamour to any plans in this abstract bodycon mini dress sure to inspire many compliments! 

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Adjustable spaghetti straps
    • Square neckline, padded bra cups
    • Front ruched drawstring
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-5952

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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:
    • Ships Free
  • Bold Stunner Floral Mesh Strapless Maxi Dress

    Turn heads your next vacay in this bold floral mesh maxi dress made to impress. The long bodycon silhouette will flaunt your gorgeous curves.

    Fit & Features

    • Sheer mesh fabric with full-length brushed knit lining, high stretch
    • Large floral print
    • Strapless straight neckline
    • Maxi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4149

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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:
    • Ships Free
  • 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:
    • Ships Free
  • The Best Yet Sleeveless Crew Neck Slit Maxi Dress

    The best has come with this stylish basic maxi dress perfect for dressing up or down for any occasion! Crafted from a soft knit fabric, you'll adore this sleeveless dress for its comfort and versatility. The crew neckline gives off a classic vibe while the bodycon silhouette flaunts your curves down to the maxi-length hem with a flirty side slit for movement. Complete the look with a jacket, heels, and a crossbody bag!

    Fit & Features

    • Soft knit fabric, short lining, plenty of stretch
    • Sleeveless crew neckline
    • Tank straps
    • Side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5588

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: 05102-000291

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Falling In Love V-Neck Lace A-Line Mini Dress

    Fall in love with how you'll look in this lace a-line mini dress for every romantic spree! 

    Fit & Features

    • Lace-lined fabric
    • V-neckline with ribbon bow trim
    • Adjustable spaghetti straps
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000017

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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

    Product Badge:
    • Ships Free
  • Ready To Bloom Strapless Lace-Up Floral Maxi Dress

    With the warmer months ahead it's time to bloom in this floral maxi dress perf for vacations and weekend getaways! The dress boasts an eye-catching lace-up back and a mermaid silhouette that accentuates your natural curves.

    Fit & Features

    • Floral print, knit fabric lined with stretchy knit
    • Lace-up back
    • Mermaid silhouette
    • Ruffled maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4080

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Charm Striped Knit Strapless Midi Dress

    Show up with that chic charm in this striped knit midi dress designed with a strapless straight neckline and a curve-hugging bodycon fit.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Striped print
    • Strapless straight neckline
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2222

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetest Poise Button Bodycon Midi Dress

    Polished and poised, this sweet sleeveless midi dress will elevate your everyday style with chic button accents and a bodycon fit.

    Fit & Features

    • Stretchy rib knit fabric
    • Square neckline
    • Wide shoulder straps
    • Button accents, front faux pockets
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2261

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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:
    • Ships Free
  • 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

    Product Badge:
    • Ships Free
  • So Effortless Tie-Front Ruffled Skater Dress

    Make your weekend outfits so effortless with this adorable tie-front skater dress. The lightweight gauze fabric paired with the ruffled skater silhouette creates that breezy, flowy fit you'll love.

    Fit & Features

    • Gauze woven fabric with smooth woven fabric, no stretch
    • Sleeveless V-neckline, padded bust, bust tie accent, keyhole cutout
    • Adjustable spaghetti straps
    • Partially smocked back
    • High waist seam
    • Short skater silhouette, tiered ruffled design
    • Runs true to size

    Style Number/Barcode: 05102-6027

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Boho Bell Sleeve Knit Mini Dress

    Live out those dreamy boho vibes in this breezy knit mini dress featuring a plunging V-neck with beaded bust tie accents, sheer long bell sleeves, and an open back with a tie-back design.

    Fit & Features

    • Sheer textured knit fabric, partial knit lining
    • Plunging V-neckline, dual bust ties with beaded detailing
    • Sheer long bell sleeves
    • Open back, tie-back spaghetti straps
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000129

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romantic Sunny Days Crew Neck Poplin Midi Dress

    This sleeveless midi dress was made for romantic sunny days! It features a classic crew neck and a flattering drop waist seam that accentuates your figure along the A-line silhouette. 

    Fit & Features

    • Stretchy rib knit fabric, poplin woven fabric, stretchy knit lining
    • Crew neck
    • Drop waist seam
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000136

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Serve Abstract Print Mesh Bodycon Mini Dress

    Show off a sultry serve in this abstract print mesh mini dress designed with a strapless neckline and a bodycon fit to flaunt your curves.

    Fit & Features

    • Sheer mesh fabric, full-length knit lining, high stretch
    • Abstract print
    • Strapless straight-across neckline
    • Ruching
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000133

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free