Casual Dresses

Explore the array of casual dresses perfect for brunch with your besties to stroll around the farmers market on the weekends. Discover a variety of casual fabrics like ribbed knit, denim, mesh, linen, or cotton gauze. Browse the variety of skater dresses, sundresses, t-shirt dresses, and boho-inspired maxis. Look out for off-the-shoulder mini dresses, tropical print shift dresses, and tie-dye ribbed dresses perfect for a laid-back vibe but always with a chic aesthetic.

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STYLE SPOTLIGHT

Cute Work Dresses

Floral Print Dresses

Effortlessly Chic Casual Dresses for Spring and Summer

Refresh your warm-weather wardrobe with stylish and easygoing casual dresses from Windsor. Whether you're heading to brunch, running errands, or meeting friends for a relaxed day out, our collection offers effortless styles that keep you looking put-together with minimal effort.

This season, embrace breezy silhouettes and lightweight fabrics designed for comfort and movement. Choose from flowy midi and maxi dresses in fresh floral prints, playful minis in vibrant hues, and sleek knit dresses perfect for everyday wear. Stay on-trend with tunic and t-shirt dresses featuring stylish necklines, cutouts, and ruching details that elevate your casual looks.

Looking for a dress that easily transitions from day to night? A flattering midi dress in a soft, breathable fabric is your go-to for a chic yet comfortable outfit. Style it with white sneakers for a casual afternoon or swap them for strappy sandals to take your look into the evening.

Long casual dresses are a must-have for those easy summer days. Opt for flowy maxi styles in soft pastels or classic neutrals for an effortlessly polished vibe. Go for classic black for an ultra-versatile look. Pair your casual maxi with a denim jacket and trendy slides for a stylish yet relaxed ensemble.

If you love cozy yet chic styles, these styles are polished yet cozy, perfect for a casual yet refined outfit during transitional weather. Pair it with ankle booties for an effortless spring-to-summer transition.

No matter your plans, finding a versatile dress that fits your personal style has never been easier. From relaxed weekend outings to spontaneous getaways, our selection of everyday dresses is designed to keep up with your plans while keeping you stylish and comfortable. Explore our casual dresses online, in-app, or in-store today!

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!

  • Raise The Bar Ribbed Knit High Slit Midi Dress

    Raise the bar in this knit high slit midi dress boasting a sultry off-the-shoulder neckline and a form-hugging fit. Pair with boots.

    Fit & Features

    • Ribbed knit fabric, plenty of stretch
    • Off-the-shoulder neckline
    • Fold over accent at bust
    • High side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-2081

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Allure Abstract Print Mesh Midi Dress

    Show up and stun in this airy mesh midi dress accented with a trendy abstract print for a bold allure. The dress features a crew neckline, short cap sleeves, and a form-hugging silhouette to highlight your curves.

    Fit & Features

    • Abstract printed sheer mesh fabric with partial knit lining, plenty of stretch
    • Lettuce edge hems
    • Crew neckline
    • Short cap sleeves
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5628

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • So Adorable Drop Waist Bubble Hem Skater Dress

    Adorable and trendy will be your vibe in this soft knit skater dress featuring a mock neckline, tank shoulder straps, ruched side seams to accentuate your curves, and a short ruched bubble hem. Style with platform heels for a cute party look!

    Fit & Features

    • Double-lined brushed knit fabric, plenty of stretch
    • Mock neckline, tank shoulder straps
    • Ruching
    • Drop waist seam
    • Short skater silhouette
    • Ruched bubble hem
    • Runs true to size

    Style Number/Barcode: 05102-5902

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Moment Faux Suede Lattice Cutout Mini Dress

    Fit & Features

    • Faux suede fabric with knit lining, moderate stretch
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Back zipper with hook-eye closure
    • Dual lattice side cutouts at bodice and waist
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5782

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: TAN

    Available Size: XS, S

    Product Badge:
    • Sale
  • Marvelous Blooms Lace-Up Corset Floral Skater Dress

    Stay stunning all night in this floral skater dress at prom, birthdays, or dressy events! With adjustable spaghetti straps and a drawstring sweetheart neckline, this dress offers a perfect fit every time. The underwire bust, flexible boning, and a lace-up back provide support and a flattering silhouette, while the mini-length hem adds a playful touch. Complete the look in chic block heels.

    Fit & Features

    • Floral print, woven fabric, woven lining, no stretch
    • Adjustable spaghetti straps
    • Drawstring sweetheart neckline
    • Side zipper and hook-eye closure
    • Underwire bust
    • Flexible boning, lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3550

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sealed With Charm Ponte Mini Dress

    Seal your style with this charming ponte mini dress featuring an adorable strapless sweetheart neckline with a bow and a bodycon fit. Style with earrings.

    Fit & Features

    • Ponte knit fabric, plenty of stretch
    • Strapless sweetheart neckline
    • Bow tie front accent 
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5897

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: L

    Product Badge:
    • Sale
  • Romance Dreamer Sweetheart A-Line Lace Mini Dress

    Embrace your romantic side in this lace mini dress to add a whimsical allure to parties, birthdays, and dates! The sweetheart neckline and adjustable spaghetti straps flatter and give you a perfect fit, while the corset-trim fitted bodice and A-line silhouette provide a lovely silhouette along the ruffled mini-length hem. Complete the look with platform heels and a purse.

    Fit & Features

    • Delicate lace fabric line with stretchy knit
    • Adjustable spagehtti straps
    • Corset trim fitted bodice
    • Ruffled mini-length hem
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3302

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy Chicness Lace Trim Plaid Bodycon Dress

    This plaid mini dress features a lace rose trim square neckline, spaghetti strap ties, and a flattering bodycon silhouette perfect for casual plans. 

    Fit & Features

    • Plaid print, knit fabric with minimal stretch
    • Lace rose trim square neckline
    • Spaghetti strap ties
    • Back zipper closure
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5836

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightful Impact Corset Slit Chiffon Midi Dress

    A sleeveless chiffon midi dress boasts a sweetheart tie neckline, a corset-inspired bodice with a lace-up back, and a front slit for a stylish flair. Perfect for styling with heels for a dressy occasion.

    Fit & Features

    • Burnout pattern, chiffon fabric lined with stretchy knit
    • Sweetheart tie neckline, shoulder straps
    • Underwire bust, side zipper and hook-eye closure
    • Corset bodice, lace-up back
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3591

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

  • Blooming Bouquet Sleeveless Floral Mesh Mini Dress

    Get ready to bloom in this floral mesh mini dress at a girl's brunch or evening soiree! The sleeveless crew neckline and bodycon silhouette highlight your curves, while the bold floral print and mesh fabric add a touch of feminine charm. Complete the look in simple stiletto heels.

    Fit & Features

    • Blooming floral print
    • Sheer mesh fabric with knit lining, plenty of stretch
    • Crew neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5612

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stripes In Style Off The Shoulder Mini Dress

    Stay stylish in this trendy off-the-shoulder mini dress showcasing a classic striped pattern and a form-hugging fit. Pair with knee-high boots.

    Fit & Features

    • Ribbed knit fabrication
    • Off-the-shoulder neckline
    • Long dolman sleeves
    • Stripes
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-5885

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Memorable Vibe Strapless Plaid Pleated Mini Dress

    A strapless plaid mini dress features a form-hugging fit with a sassy pleated hem. Perfect for back-to-school styling.

    Fit & Features

    • Plaid print, woven fabric, slight stretch
    • Strapless folded neckline
    • Back zipper closure
    • Form-hugging fit
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5862

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Silhouette Square Neck Tank Midi Dress

    Effortlessly chic and oh-so-flattering, this sleeveless midi dress will become your new favorite go-to. This bodycon dress has a sleeveless square neckline and tank straps and hugs your curves in all the right places. The midi-length hem adds a touch of sophistication, while the rib knit fabric lining ensures comfort all day long. Complete the look in a layered necklace for any occasion!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, stretchy
    • Bodycon fit
    • Midi-length 
    • Runs true to size

    Style Number/Barcode: 05102-5587

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemian Chic Lace Off-The-Shoulder Skater Dress

    Channel that bohemian chic aesthetic in this airy sheer lace skater dress featuring an off-the-shoulder straight neckline with a fold-over design and sheer long fitted sleeves. The trendy V-shaped drop waist seam leads to a short uneven hem with a flowy skater silhouette.

    Fit & Features

    • Sheer lace fabric with partial knit lining, plenty of stretch
    • Off-the-shoulder straight neckline with fold-over design
    • Sheer long fitted sleeves
    • V-shaped drop waist seam
    • Short uneven hem
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3714

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Ray Of Beauty Lace-Up Corset Skater Dress

    You'll be a ray of beauty in this chic lace-up corset skater dress! Designed with a lightweight woven fabric with a stretchy knit lining, this adorable short dress captures the summer season. It features an alluring sleeveless corset-style bodice with a ruched sweetheart neckline and a tie-front detail at the bust. The thin adjustable tank straps lead to a lace-up strappy back design to find your perfect fit. The angled high waist seam flows out to a fit-and-flare skater silhouette with pleating for a flirtatious vibe. Complete the look with platform heels!

    Fit & Features

    • Cotton woven fabric, stretchy knit lining
    • Corset-style bodice, ruched sweetheart neckline, tie-front bust
    • Thin adjustable tank straps
    • Lace-up strappy back, tie closure
    • Side zipper with hook and eye closure
    • Fit-and-flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3641

    Category Name: Casual Dresses

    Price: $11.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Flirt Sweetheart Lace Trim Skater Dress

    This sleeveless chiffon skater dress features a lace trim sweetheart neckline and bodice for flirty flair while the drop waist seam accentuates your curves along the mini-length skater silhouette. Perfect for a dressy brunch or party.

    Fit & Features

    • Sheer chiffon woven fabric with stretchy knit lining
    • Lace trim sweetheart neckline with bow detail, bust underwire
    • Adjustable lace trim shoulder straps
    • Partially smocked back with zipper and hook-eye closure
    • Lace trim bodice, drop waist seam
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3461

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Definite Beauty V-Neck A-Line Mini Dress

    Everyone will watch as you walk in wearing this sleeveless mini dress to the school dance or party! Made from smooth lined knit fabric, it's perfect for any occasion.  With its flattering V-neckline and shoulder straps, this dress offers a stunning A-line silhouette and a mini-length hem. Compliment your look with statement heels and a clutch.

    Fit & Features

    • Smooth lined knit fabric
    • V-neckline
    • Shoulder straps
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5844

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glitzy Look Glitter Strapless Skater Dress

    Channel all the glitz and glam in this adorable glitter knit skater dress featuring a strapless straight neckline, ruched side seams, and a subtle drop waist. The pleated skater silhouette flares out to a trendy uneven mini-length hem. Style with metallic heels for a school dance or party!

    Fit & Features

    • Stretchy glitter knit fabric
    • Strapless straight neckline
    • Ruched side seams
    • Subtle drop waist
    • Pleated skater silhouette
    • Uneven mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3512

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: M, L

  • Elevated Vibes Ribbed Knit High Slit Maxi Dress

    This ribbed knit high slit maxi dress will bring elevated vibes to your casual basics! Crafted from a stretchy ribbed knit fabric, this maxi dress features a scoop neckline, long fitted sleeves, a long-length hem with a thigh-high side slit, and a bodycon silhouette that will hug your curves. Style with a faux leather jacket and knee-high boots for a casual-chic date night look!

    Fit & Features

    • Scoop neckline
    • Long fitted sleeves
    • Long-length hem
    • Thigh-high side slit
    • Bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5342

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Look Long Sleeve Abstract Mini Dress

    An abstract print mesh mini dress features sheer fitted long sleeves, a boat neckline, and a flattering bodycon silhouette. Perfect for a party or gallery opening.

    Fit & Features

    • Abstract print, sheer mesh fabric, slip knit lining
    • Fitted long sleeves
    • Boat neckline
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5850

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Chic Style Long Sleeve Ribbed Knit Midi Dress

    The perfect blend of casual and chic, this ribbed knit midi dress features a V-neckline, long fitted sleeves, and a form-hugging silhouette. Style with hoop earrings and sneakers for a cute everyday look.

    Fit & Features

    • Hacci ribbed knit fabric, plenty of stretch
    • V-neckline
    • Long fitted sleeves
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5920

    Category Name: Casual Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: SAGE

    Available Size: XS, S, M, L

  • Read All About It Newspaper Bodycon Mini Dress

    Extra, extra read all about how fine you'll look in this newspaper print mini dress! This dress features a sweetheart neckline with lace trim and adjustable spaghetti straps for a perfect fit. The built-in padded underwire bust ensures support while the bodycon fit and mini-length hem create a flattering silhouette. Complete the look in a crop denim jacket.

    Fit & Features

    • Newspaper print, knit fabric with stretchy lining
    • Adjustable spaghetti straps
    • Sweetheart neckline with lace trim
    • Back zipper and hook-eye closure
    • Built-in padded underwire bust
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5578

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fab Trendsetter Leopard Print Drop Waist Mini Dress

    Fab trendsetter will be your vibe in this leopard print mini dress featuring an off-the-shoulder neckline with short sleeves, a drop waist seam, and an asymmetric tiered mini-length hem with an A-line fit. Style with knee-high boots!

    Fit & Features

    • Leopard-printed brushed knit fabric, plenty of stretch
    • Off-the-shoulder neckline, short sleeves
    • Drop waist seam
    • Asymmetric tiered mini-length hem
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5904

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Fave Open Back Long Sleeve Knit Mini Dress

    This trendy ribbed knit mini dress features a crew neckline, long fitted sleeves, and a bold lower open back with a tie-back strap design. The short bodycon silhouette will highlight your curves and is perf for pairing with knee-high boots.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Crew neckline
    • Long fitted sleeves
    • Open lower back with tie-back straps
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5950

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Sale