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!

  • Flawlessly Chic Strapless High Slit Maxi Dress

    You'll look flawlessly chic in this textured knit maxi dress featuring a strapless neckline and high-cut side slit. Style with stiletto heels for a rooftop bar!

    Fit & Features

    • Sheer knit fabric, textured pattern, full-length lining
    • Strapless straight neckline
    • Back zipper closure
    • High side slit
    • Maxi-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000141

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Glow Tube Floral Mini Dress

    Sun, skin, and this dress—name a hotter trio. With bold blooms and a sleek bodycon fit, this strapless mini is your go-to for nights out or island dreams.

    Fit & Features

    • Floral print, knit fabric, moderate stretch
    • Tube strapless neckline
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000194

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fairytale Daze Strappy Back Chiffon Skater Dress

    This stunning skater dress is the perfect blend of effortless and ethereal. It is designed with flirty ruffles and a strappy tie-back that turns heads at parties!

    Fit & Features

    • Chiffon fabric, woven lining
    • V-neckline, spaghetti straps
    • Strappy tie-back, lower zipper and hook-eye closure
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4097

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On Island Time Strapless Floral Romper

    This strapless romper exudes carefree vibes, perfect for vacations! The strapless neckline and form-hugging fit accentuate your curves, while the statement floral print adds a touch of tropical essence.

    Fit & Features

    • Stretchy knit fabric, statement floral print
    • Strapless neckline
    • Form-hugging fit
    • Ruffled hem, fitted knit shorts
    • Runs true to size

    Style Number/Barcode: 06503-000053

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Whimsical Glam Bow and Lace Mini Dress

    This whimsical bow and lace mini dress features adorable cap sleeves and a square neckline that leads to the lace-up back that makes every head turn. Complete the look with statememt flats.

    Fit & Features

    • Lined rayon knit fabric with plenty of stretch
    • Square neckline with lace trim inset and mini bow detail
    • Cap sleeves
    • Open back with lace-up bungee strap design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5839

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Muse Floral Mesh Maxi Dress

    You'll be a gorgeous vacay muse in this curve-flaunting maxi dress designed with a large floral print on airy mesh fabric. Perf for pairing with wedges!

    Fit & Features

    • Sheer mesh fabric, full-length knit lining, high stretch
    • Large floral print
    • Sleeveless V-neckline
    • Spaghetti straps
    • Maxi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000056

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catch Flights Tropical Lace-Up Slit Maxi Dress

    Booked the trip just for the outfit? Valid. This lace-up back maxi brings the heat with a tropical print and a leg-baring high slit that knows how to make an entrance.

    Fit & Features

    • Smooth knit stretchy fabric, tropical print, soft knit stretch lining
    • Square neckline with spaghetti straps
    • Bodycon silhouette
    • Lace-up open back with tie closure
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000005

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Always Bodycon Ruffle Mini Dress

    You'll always be remembered as stunning in this mini dress, perfect for brunch or casual parties and plans! The flattering scoop neckline with a delicate rose accent adds a touch of romance, while the bodycon fit showcases your curves and is finished with a flirty ruffled hem.

    Fit & Features

    • Stretchy knit fabric, knit lining
    • Scoop neckline with a rose accent
    • Spaghetti straps
    • Bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000152

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feeling Pretty Cute Floral Skater Short Dress

    Nothing comes as close to cute as this floral skater dress! Perfect for shower celebrations or afternoon teas, this short dress boasts a pretty corset-inspired bodice and a voluminous hem.

    Fit & Features

    • Floral print, cotton woven fabric, tulle and woven linings
    • Square neckline, bust tie
    • Wide shoulder straps
    • Back zipper and hook-eye closure
    • Corset-inspired bodice, pleating
    • Skater silhouette, short-length hem, pleated trim
    • Runs true to size

    Style Number/Barcode: 05101-4037

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Back At It Twist Back Midi Dress

    You didn’t plan to stand out, but here we are. This sleeveless midi dress hugs in all the right places with a twist cutout back and side slit that catches every eye.

    Fit & Features

    • Soft rib knit fabric, smooth knit lining
    • Square neckline
    • Tank shoulder straps
    • Twist cutout back
    • Side slit
    • Form-hugging, midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000201

    Category Name: Casual Dresses

    Price: $28.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Exceptional Cutie Striped Cutout Midi Dress

    Strut like an exceptional cutie in this striped midi dress all season long! This strapless dress features a cutout bodice that adds a touch of playful sass, while the bodycon silhouette and midi-length hem hug your curves in all the right places.

    Fit & Features

    • Striped pattern, stretchy knit fabric
    • Strapless neckline
    • Cutout bodice
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2296

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold New Look Corset Lace-Up Linen Skater Dress

    Make a bold impression in this corset linen skater dress all season long! The sweetheart neckline with a bust tie and adjustable straps provides a flattering fit while the flexible boning supports your shape. The strappy lace-up back adds a touch of playfulness to the skater silhouette and short-length hem. Complete the look in wedge sandals and a handbag.

    Fit & Features

    • Linen blend fabric lined with stretchy knit
    • Sweetheart neckline with bust tie
    • Adjustable straps, side zipper and hook-eye closure
    • Strappy lace-up back
    • Flexible boning
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3256

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Favorite Staple Striped Cutout Mini Dress

    Slip into this striped mini dress with a flirty cutout and bodycon fit - it'll be your favorite staple all season long!

    Fit & Features

    • Striped pattern, stretchy rib knit fabric
    • Strapless neckline
    • Cutout accent
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000015

    Category Name: Casual Dresses

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dinner With A View Abstract Open Back Maxi Dress

    You'll be a gorgeous view at dinner in this abstract maxi dress!  The cowl halter neckline with hoop insert adds a touch of elegance, while the open back design highlights your figure.

    Fit & Features

    • Abstract print, mesh fabric lined with stretchy knit
    • Cowl halter neckline, hoop insert, tie straps
    • Open back
    • Form-hugging silhouette
    • Floor-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000114

    Category Name: Casual Dresses

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Toasty Sweetheart V-Neck Bodycon Knit Midi Dress

    This sleeveless ribbed knit midi dress features a striking V-neckline and bodycon fit with a front slit detail for movement. Perfect for layering with a jacket and heels.

    Fit & Features

    • Stretchy ribbed knit fabric
    • V-neckline
    • Spaghetti straps
    • Front slit
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-2221

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City Lights Corset Denim Mini Dress

    Meet your after-dark essential—flirty, fitted, and ready for the spotlight. This lace up denim mini is the ultimate cool-girl piece to take you from golden hour snaps to rooftop cocktails.

    Fit & Features

    • Structured denim fabrication, knit panty lining
    • Strapless sweetheart neckline
    • Back zipper and hook-eye closure
    • Corset-like bodice
    • Lace up corset front detail
    • Flared skater hem, mini length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000213

    Category Name: Casual Dresses

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Beauty Abstract Print Mesh Skater Dress

    How to look effortlessly captivating without even trying? Start right here. Soft, stretchy mesh and the trendy abstract print make this ruffle skater dress an easy yes for nights out, brunch plans, or any moment worth catching on camera.

    Fit & Features

    • Spaghetti straps with a soft V-neckline
    • Ruched bodice panels contour the waist with a smoothing effect
    • Drop-waist seam creates a lengthened torso appearance
    • Tiered skater skirt with fluid movement
    • Sheer mesh fabric with knit lining and high stretch
    • Abstract print
    • Runs true to size

    Style Number/Barcode: 05102-000215

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

  • No Rules Leopard Long Sleeve Mini Dress

    A little wild, a lot confident. This mini dress brings fierce animal print, gold stud accents, and a body-hugging fit that’s made to turn heads—because blending in was never the plan.

    Fit & Features

    • Leopard print, mesh-lined stretchy fabric
    • Crew neck
    • Fitted long sleeves
    • Studded embellishments
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000218

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy Summer Strapless Tiered Midi Dress

    This flowy gauze midi dress is perfect for those breezy summer vibes, featuring a strapless smocked bodice and tiered A-line silhouette. Style with mules for sunset happy hour!

    Fit & Features

    • Gauze woven fabric
    • Strapless straight-across neckline
    • Smocked bodice
    • Empire waist seam
    • Midi-length hem, tiered design
    • Flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000144

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paisley and Playful Halter Skater Dress

    Flirty, floaty, and made for dancing under the sun. With a smocked bust and ruffled skater fit, this halter mini dress is your go-to for festivals, vacays, or just looking way too good for no reason.

    Fit & Features

    • Paisley print, woven fabric, bust lining
    • Halter V-neckline, spaghetti strap tie
    • Stretchy smocked bust
    • Open tie-back detail
    • Flowy skater silhouette
    • Ruffled trim short hem
    • Runs true to size

    Style Number/Barcode: 05102-000065

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Adorably Chic Lace Trim Plaid Mini Dress

    This adorable plaid mini dress features sheer lace trims at the neckline and hem and a center bow detail to add a chic touch of femininity. The bodycon silhouette will hug your gorgeous curves, a perfect option for date night.

    Fit & Features

    • Plaid printed woven fabric with sheer lace trims, moderate stretch
    • Square neckline with small bow detail
    • Spaghetti strap
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5838

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Influence Strapless Bodycon Midi Dress

    Achieve a stylish rep in this strapless midi dress wherever you go! With a flattering bodycon fit and trendy stone metal insert, this dress will enhance your natural silhouette and captivate any room you enter.

    Fit & Features

    • Stretchy knit fabric
    • Strapless neckline, stone metal insert
    • bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000062

    Category Name: Casual Dresses

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destination Paradise Tropical Slit Maxi Dress

    Make a statement in this tropical maxi dress on your next visit to paradise! This stunning strapless maxi dress features an alluring side cutout and flirty side slit that creates movement with every step.

    Fit & Features

    • Tropical print, smooth knit stretchy fabric
    • Strapless neckline
    • Side cutout with adjustable drawstring
    • High side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000138

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic On Vacay Geometric Print Maxi Tube Dress

    You'll be chic on vacay in this trendy maxi tube dress designed with a lightweight woven fabric with a bold geometric print. The strapless bodice features a V-shaped front overlay with a fringe trim, leading to a long-length fitted silhouette with a thigh-high side slit to show off some leg.

    Fit & Features

    • Woven fabric with woven lining, no stretch
    • Geometric print
    • Strapless straight-across neckline, no-slip strip
    • V-shaped front overlay, fringe trim
    • Tie-back design, lower open back, hidden zipper with hook-eye closure
    • High-cut side slit
    • Maxi-length fitted silhouette

    Style Number/Barcode: 05102-000142

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free