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!

  • Such A Cutie Halter Ruffle Mini Dress

    Make this halter mini dress a staple this season! The form-hugging silhouette accentuates your curves in all the right places, while the playful ruffled hem adds flirty movement. Style with strappy heels.

    Fit & Features

    • Texture knit fabric, moderate stretch
    • Cowl neckline
    • Spaghetti straps with hoop inserts
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000132

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Appeal Mock Neck Bodycon Mini Dress

    A must-have basic for the upcoming season! This dress features fitted long sleeves, a mock neck, a flattering bodycon silhouette, and a mini-length hem. It's composed of a cotton-blend knit fabric with a moderate stretch for comfort. Complete the look in strappy heels for a birthday brunch!

    Fit & Features

    • Fitted long sleeves
    • Mock neck
    • Bodycon silhouette
    • Mini-length hem
    • Cotton-blend knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5153

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Duo Strapless Skater Mini Dress

    A charming strapless skater dress you'll adore for brunch or family gatherings! Pair with the matching bolero for a complete look.

    Fit & Features

    • Soft rib knit stretchy fabric
    • Strapless neckline, non-slip grip lining
    • Skater silhouette
    • Flair mini-length hem
    • Runs true to size

     

    Shop The Matching Bolero: Charming Duo Long Sleeve Bolero

    Style Number/Barcode: 06005-2235

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tea Time Corset Lace-Up Floral Skater Dress

    It's time to spill the tea at the garden party in this chic floral skater dress with a pretty corset bodice that snatches your waist and a lace-up back that turns heads!

    Fit & Features

    • Floral print, poplin woven lined lace trim fabric
    • Square neckline, lace trim, underwire bust, wide shoulder straps
    • Corset bodice, flexible boning, lace trim, lace-up back
    • Drop waist seam
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3923

    Category Name: Casual Dresses

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Laced In Chic Lace-Up Skater Dress

    Chic and charming, this lace skater dress boasts a flirty lace-up back that'll capture all the attention at parties!

    Fit & Features

    • Lace fabric, mesh lining, stretchy knit lining
    • V-neckline
    • Spaghetti straps
    • Lace-up back
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3521

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Retro Vision Halter Striped Crochet Midi Dress

    The perfect blend of modern and retro! This halter striped crochet midi dress can easily be styled with sandals for the day and heels for night.

    Fit & Features

    • Striped design, crochet fabric, short stretchy knit lining
    • Halter neckline, spaghetti strap tie
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2264

    Category Name: Casual Dresses

    Price: $8.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Look Eyelet Knit Skater Dress

    Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette.

    Fit & Features

    • Eyelet knit fabric with knit lining
    • Sleeveless square neckline, underbust seam
    • Adjustable spaghetti straps
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6001

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool Breeze Cutout Striped Knit Mini Dress

    As the temps rise so will your style in this striped knit mini dress with a flirty cutout back and bodycon fit perfect for layering with a denim jacket on cooler nights.

    Fit & Features

    • Striped pattern, knit fabric
    • Scoop neckline
    • Wide shoulder straps
    • Cutout back
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2268

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dream Of Me Corset Lace-Up Floral Midi Dress

    Dreamy days call for this floral midi dress that makes your cottagecore romance a reality! With a gorgeous corset bodice, lace-up back, and voluminous A-silhouette, this dress is stunning for bridal showers or garden parties.

    Fit & Features

    • Delicate floral print, woven fabric, tulle and woven linings
    • V-neckline, adjustable spaghetti straps
    • Hidden side zipper and hook-eye closure
    • Corset bodice, flexible boning, lace-up back
    • Voluminous A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3795

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Kissed By Blooms Corset Skater Floral Dress

    Blossom so cute in this skater floral dress boasting a corset bodice that flaunts your femme figure and a trendy lace-up back for added allure!

    Fit & Features

    • Floral print, woven fabric, tulle and woven linings
    • Sweetheart neckline
    • Adjustable spaghetti straps, side zipper and hook-eye closure
    • Lace-up smocked stretchy back
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3769

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Admired Cutie Floral A-Line Midi Dress

    Catch every eye when you breeze by in this floral midi dress with flirty details like a corset-inspired bodice and a flowy A-line silhouette!

    Fit & Features

    • Ditsy floral print, woven fabric lined with tulle and stretchy knit
    • Sweetheart neckline with bust tie
    • Lace trim wide shoulder straps
    • Back zipper and hook-eye closure, stretchy smocked back
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4053

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beauty In The Detail Tie Back Floral Skater Dress

    There's beauty in every detail on this floral skater dress from the flirty crisscross straps and tie-back design to the ruffled mini-length hem! 

    Fit & Features

    • Floral print, woven fabric
    • Square neckline
    • Adjustable spaghetti straps
    • Crisscross, tie-back design
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3992

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Beauty Puff Sleeve Floral Chiffon Midi Dress

    This breezy floral chiffon midi dress will forever be a beautiful style for bridal showers, parties, and brunches! The airy sheer chiffon fabric is accented with a dainty floral print for a soft feminine vibe and includes a knit lining for coverage. The mid-length dress features a ruched square neckline detailed with a keyhole cutout and tie-front design, adorable short puff sleeves with elastic cinched hems, fitted high waist seams, and a chic high front slit for added movement on the flowy A-line silhouette. Complete the look with heels.

    Fit & Features

    • Floral print
    • Sheer chiffon fabric with stretchy knit lining
    • Ruched square neckline, keyhole cutout with tie-front
    • Short puff sleeves, back zipper with hook and eye closure
    • High front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3033

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Prettiest Darling Puff Sleeve Floral Skater Dress

    A pretty floral skater dress like this is everything this season! Designed with a dainty rose floral print, this mini dress features adorable puff sleeves and a tie bust that shapes the flattering a-line silhouette. Pair with boots.

    Fit & Features

    • Dainty rose print, woven fabric lined with stretchy knit
    • Puff short sleeves
    • Sweetheart neckline with bust tie
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3471

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take Me There V-Neck Slit Bodycon Midi Dress

    A perfectly flattering bodycon midi dress for any of your upcoming social plans!

    Fit & Features

    • Stretchy rib knit fabric
    • V-neckline
    • Spaghetti straps
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2286

    Category Name: Casual Dresses

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easily Stunning Cutout Striped Midi Dress

    This cutout striped midi dress was made for a laidback babe like you! With a bodycon fit and dual side slits for effortless allure, this dress is perfect for vacation or strolling the beach.

    Fit & Features

    • Striped print, stretchy knit fabric
    • V-neckline with cutout
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Dual side slits
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2290

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Girl Short Sleeve Bodycon Slit Mini Dress

    Enter a chic girl era in this sultry LBD designed in a flattering bodycon silhouette that flaunts your curves and a flirty front slit along the mini-length hem. 

    Fit & Features

    • Smooth knit stretchy fabric
    • Short sleeves
    • Square neck
    • Bodycon silhouette
    • Front slit accent
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5961

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Idea Of Bliss Corset Lace-Up Floral Skater Dress

    Bold and pretty blooms dance across this dreamy floral skater dress perfect for sunshine dressing! The dress boasts an adorable corset bodice with lace trim and a back lace-up that turns heads while the voluminous skater silhouette has a romantic lace trim lining.

    Fit & Features

    • Floral print, woven fabric, multiple linings with lace trim
    • Strapless neckline with bow, flexible boning
    • Side zipper and hook-eye closure
    • Corset bodice, lace trim, lace-up back
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3793

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Caught Your Eye Strapless Lace-Up Skater Dress

    Catch every eye in this eyelet skater dress with a flirty lace-up bust and a flowy mini-length hem perfect for twirling at parties!

    Fit & Features

    • Eyelet cotton fabric with woven cotton lining
    • Strapless neckline, lace-up bust, padded bra cups
    • Skater silhouette
    • Flowy mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4009

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playful And Pretty Corset Lace-Up Midi Dress

    Playful and pretty, this corset midi dress has a timeless silhouette. It has a unique lace-up back, a flattering A-line fit, and convenient side pockets that warm your hands.

    Fit & Features

    • Woven poplin lined fabric lined with stretchy knit
    • Sweetheart neckline with bust tie
    • Adjustable shoulder straps
    • Lace-up back, side zipper and hook-eye closure
    • A-line silhouette, front slit, side pockets
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3968

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Summer Vibe Polka Dot Satin Mini Dress

    This polka dot satin mini dress will bring that sweet summer vibe featuring a dainty lace trim, halter V-neckline, and a short A-line silhouette. Style with sneakers for a casual look.

    Fit & Features

    • Satin woven fabric, sheer lace trim
    • Polka dot print
    • Sleeveless V-neckline
    • Halter straps with tie-back design, open back
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000156

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Afterglow Knit Maxi Dress

    Booked the trip and get to wear this maxi dress. This long sleeve maxi dress brings that getaway glow with its open back and side slit made for sunset dinners and cocktails.

    Fit & Features

    • Texture knit fabric, smooth knit lining
    • Plunge V-neckline, hardware insert
    • Long bell sleeves
    • Cutout bodice, open back
    • High side slit
    • Form-hugging, maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000155

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Weekend Chic Sleeveless Midi Dress

    Elevate your weekend look with this sleeveless midi dress with a sleek boat neckline, flirty low-cut back, and a flattering flowy silhouette. Dress it up with strappy sandals!

    Fit & Features

    • Woven fabric
    • Boat neckline
    • Low-cut back
    • Drop waist seam
    • Flowy silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000164

    Category Name: Casual Dresses

    Price: $19.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Compelling Romantic Off-The-Shoulder Pleated Maxi Dress

    Make a toast to looking lovely in this off-the-shoulder pleated maxi dress as the bride-to-be or party guest! With a flowy silhouette and flattering drop waist seam, you'll look and feel so dreamy.

    Fit & Features

    • Smooth knit stretch fabric
    • Folded off-the-shoulder neckline
    • Drop waist seam
    • Pleated flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3867

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free