Casual Dresses

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STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

Discover New Skater Dress Styles

Everyday Ease: Casual Dresses for Cool-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.

Laid-Back & Versatile

Knit, ribbed, and sweater dresses bring comfort and style to crisp fall 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 burgundy 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!

  • Charming Appeal Puff Sleeve Eyelet Knit Skater Dress

    The sweet eyelet design and adorable details give this puff sleeve skater dress a charming appeal! Made with an airy sheer eyelet knit fabric with a partial knit lining, this short dress is perfect for your spring and summer weekend outings. It features a square neckline with chic ruching at the bust, sheer short puff sleeves with a dainty ruffled trim, a sheer corset-style bodice to create a cinched look, and a fit-and-flare skater silhouette for a flirty vibe. Complete your outfit with hoop earrings!

    Fit & Features

    • Sheer eyelet knit fabric, partial knit lining, plenty of stretch
    • Square neckline with ruched bust
    • Sheer short puff sleeves, ruffled trim, elastic cinched hems
    • Sheer corset-style bodice, stretchy high waist seam
    • Fit and flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5427

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Main Style Ribbed Knit Tank Mini Dress

    This adorable tank mini dress will be your new main style to create the cutest everyday looks! Designed with a stretchy ribbed knit fabric for comfortable wear, it features a sleeveless scoop neck and back, thin tank shoulder straps, and a bodycon silhouette to flaunt your figure. Pair this short dress with a denim jacket and sneakers for a coffee date with friends.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Scoop neck and back
    • Thin tank straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1975

    Category Name: Casual Dresses

    Price: $8.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Allure One-Shoulder Cutout Waist Knit Midi Dress

    Bring the bold allure to your summer 'fits with this sultry cutout waist midi dress! Made with a lined stretchy ribbed knit fabric, the mid-length dress features a sleeveless one-shoulder neckline and a tank strap with a trendy twisted-back design. The asymmetric goes around the waist, accented with a chic O-ring cutout at the front. The midi-length hem is detailed with a high-cut side slit along the figure-flaunting bodycon silhouette. Style with lace-up sandals for a weekend getaway!

    Fit & Features

    • Stretchy ribbed knit fabric, knit lining
    • One-shoulder neckline, tank strap with twisted-back design
    • Asymmetric waist cutout
    • Front O-ring cutout
    • High side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5697

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Beauty Chiffon A-Line Midi Dress

    Create a truly beautiful look for spring and summer weddings in this floral chiffon midi dress! The airy chiffon fabric showcases a blooming floral print and includes a stretchy knit lining for coverage. The tea-length dress is shaped with a sleeveless square neckline and adjustable spaghetti straps for a perfect customized fit. Smocking at the back provides added stretch and features a secure zipper closure. The fitted high waist seam flows out to a classic A-line silhouette with a front slit for extra movement. Style this pretty midi dress with sleek hoops and block heels.

    Fit & Features

    • Sheer chiffon fabric with stretchy knit lining, floral print
    • Sleeveless square neckline, no-slip strip, adjustable spaghetti straps
    • Stretchy smocked back, zipper with hook and eye closure
    • High waist seam, front slit
    • A-line silhouette
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05101-2356

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamiest Summer Smocked Floral Chiffon Midi Dress

    Have the dreamiest summer romance in this floral chiffon midi dress perfect for dates and parties! This dress features a square neckline, adjustable spaghetti straps, and a stretchy smocked bodycon silhouette for a comfortable and flattering fit. The tiered ruffled midi-length hem adds a touch of femininity, while the floral print on chiffon fabric gives the prettiest look. Style this floral dress with earrings and block heels.

    Fit & Features

    • Floral print, chiffon fabric
    • Adjustable spaghetti straps
    • Square neckline
    • Stretchy smocked bodycon silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-2985

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adorable Intent Sleeveless Bow Bodycon Mini Dress

    Keep up with the adorable coquette trend in this sleeveless mini dress! Adorned with charming shoulder straps and playful bows, this dress will hug your curves in all the right places and flatter your figure with its bodycon fit and mini-length hem. Complete the look with strappy sandals.

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Shoulder straps with bows
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5818

    Category Name: Casual Dresses

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dot to Trot Polka Dot Mini Dress

    Playful yet polished, this polka dot mini dress hugs in all the right places. With its sweetheart neckline and curve-hugging fit, it’s a flirty staple for last-minute plans or casual brunches!

    Fit & Features

    • Polka dot print, mesh-lined fabric
    • Sweetheart neckline
    • Spaghetti straps
    • Curve-hugging fit
    • Flowy mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000314

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: L

  • Getaway Girl Halter Open Back Tropical Mini Dress

    Getaway to paradise in this tropical mini dress! Featuring a sultry cowl halter neckline and an open back with dual spaghetti strap ties, this dress will show plenty of skin on vacay while the bodycon silhouette and mini-length hem flatter your figure. Complete the look with doorknocker earrings and heels.

    Fit & Features

    • Tropical print, mesh fabric lined with stretchy knit
    • Halter cowl neckline
    • Open back with dual spaghetti strap ties
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5795

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Vibe Tie-Back Flowy Floral Woven Maxi Dress

    Give off a charming vibe at summer parties in this simply stunning floral woven maxi dress! The breezy lightweight woven fabric is detailed with a gorgeous floral print pattern and includes a mini-length lining for coverage. The sleeveless bodice is shaped with a sweetheart neckline, a dainty tie-front bust design for a cute detail, and spaghetti straps leading to an open back with a cross-back strappy design and a customized tie closure. The fitted high waist flows out to a maxi-length hem with an effortlessly chic A-line silhouette. Style with hoop earrings and slip-on sandals.

    Fit & Features

    • Floral print
    • Lightweight woven fabric, mini-length woven lining, no stretch
    • Sweetheart neckline with tie-front bust, spaghetti straps
    • Open back, cross-back strappy design, tie closure
    • High waist seam
    • Flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3048

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Blossom Sweetheart Floral Mesh Mini Dress

    Your amount of admirers will blossom when they see you in this sultry floral mesh mini dress! This flirty mini dress features a sweetheart neckline and padded bra cups for a flattering fit. Its adjustable spaghetti straps and ruched seams ensure the perfect bodycon silhouette. Complete the look in block heels.

    Fit & Features

    • Floral print, mesh fabric, sewn-in knit lining, moderate stretch
    • Sweetheart neckline
    • Adjustable spaghetti straps, padded bra cups
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5478

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Ditsy Floral Eyelet Strapless Mini Dress

    Keep your summer date 'fits flirty and stylish with this floral eyelet strapless mini dress! The airy lightweight eyelet knit fabric is detailed with a sweet ditsy floral print and features a brushed knit lining for coverage. The mini-length dress is shaped with a strapless straight-across elasticized neckline for added stretch and a bodycon silhouette to highlight your curves. Pair with platform sandals and hoop earrings.

    Fit & Features

    • Ditsy floral print
    • Stretchy eyelet knit fabric with knit lining
    • Strapless straight neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5799

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty In Italy Halter Button Striped Mini Dress

    Look pretty strolling the streets of Italy in this striped mini dress for a darling allure! With a halter V-neckline and tie-front bust, this dress is perfect for showing off your curves. The front button-down closures add a flirty touch, while the mini-length hem keeps stylish. Complete the look in trendy sandals and sunglasses!

    Fit & Features

    • Striped pattern, linen blend fabric, no stretch
    • Halter V-neckline with tie closure
    • Tie-front bust, button-down closures
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5741

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Natural Attraction Ditsy Floral Mini Dress

    You're sure to have a natural attraction to this ditsy floral mini dress - perfect for a casual birthday or afternoon tea! It features a sleeveless scoop neck, spaghetti straps, a flirty tie front, and ruched bust, and a bodycon silhouette. Style with lace-up heels for a statement finish!

    Fit & Features

    • Sleeveless scoop neck
    • Spaghetti straps
    • Tie front and ruched bust
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy floral print, smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4938

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Meadow Vibes Floral Eyelet Lace Mini Dress

    Give your closet a dreamy meadow vibe with this floral mini dress - an adorable option for brunch and day dates! Featuring puff short sleeves, a sweetheart neck, front bust tie, and side ruched seam to accentuate your curves along the bodycon silhouette. The dress is composed of a ditsy daisy print on eyelet lace fabric with a stretchy knit lining. Complete the look in strappy sandals.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck, front bust tie
    • Side ruched seams, bodycon silhouette
    • Mini-length hem
    • Ditsy daisy print
    • Eyelet lace, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4945

    Category Name: Casual Dresses

    Price: $5.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Truly Charming Sleeveless A-Line Mini Dress

    Unlock a truly charming style in this sleeveless mini dress at BBQs to summer picnics! Features a square neckline and adjustable spaghetti straps for the perfect fit. Its A-line silhouette flatters every figure, and the mini-length hem adds flirtatiousness. Complete the look with sunglasses and wedges.

    Fit & Features

    • Woven fabric, minimal stretch
    • Square neckline
    • Adjustable spaghetti straps
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5704

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Western Moves Sweetheart Denim Skater Mini Dress

    Show off your Western style in this denim skater mini dress for dancing in the desert at festivals or concerts!

    Fit & Features

    • Denim fabric, stretchy knit lining
    • Sweetheart neckline, underwire bust
    • Adjustable spaghetti straps
    • Back zipper closure
    • Bodycon bodice
    • Skater chiffon lace trim mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6018

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty In Floral Sweetheart Bodycon Mini Dress

    Step out in this flirty floral mini dress for Valentine's Day, dates, and parties! Showcasing a ditsy floral print on soft brushed knit fabric, this dress features a bust tie keyhole, side ruching, and a bodycon fit, to accentuate your figure. Complete the look with a mini purse and heels.

    Fit & Features

    • Ditsy floral print, brushed knit fabric with stretch
    • Spaghetti straps
    • Bust tie keyhole
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5523

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Modern Romance Sleeveless Lace-Up A-Line Midi Dress

    Designed for a modern-day romance, this sleeveless woven midi dress is perfect for day dates! The sweetheart ruched neckline and adjustable straps are flattering, while the lace-up design cinches your waist for a beautiful silhouette. The front slit adds a touch of allure to this A-line midi-length dress. Complete the look in strappy wedges.

    Fit & Features

    • Texture woven fabrication with a woven lining
    • Sweetheart neckline, ruched bust, dainty lace trim
    • Adjustable straps
    • Lace-up waist, stretchy smocked back
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5722

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Seasons Favorite Off-The-Shoulder Midi Dress

    A sweater dress, but elevated. With its foldover neckline and bodycon silhouette, this midi dress is a go-to for chic fall days or nights.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Off-the-shoulder folded neckline, cinched seam
    • Fitted long sleeves
    • Bodycon fit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000162

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • New Arrival
  • Playful Summer Sweetheart Ruffled Eyelet Midi Dress

    Looking for the perfect summer dress? Look no further than this playful sleeveless midi dress! With its flattering sweetheart neckline with a structured bust and adjustable spaghetti straps, this A-line silhouette dress will have you feeling confident and stylish. The ruffled midi-length hem and floral embroidered eyelet woven fabric add a touch of playfulness to this must-have dress! Complete the look with wedge sandals.

    Fit & Features

    • Floral embroidered eyelet woven fabric, stretchy knit lining
    • Sweetheart neckline, padded bust with underwire
    • Adjustable spaghetti straps, back zipper with hook and eye closure
    • High waist seam, A-line silhouette
    • Ruffled midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3015

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovely In Eyelet A-Line Mini Dress

    Make a lovely impression in this eyelet A-line mini dress at bridal showers or brunch with the girls! 

    Fit & Features

    • Eyelet lace fabric, stretchy knit lining
    • Strapless neckline
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5997

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Admiring Style Strapless Ruffle High Low Denim Dress

    Prepare for plenty of admiring stares when you're in this stylish denim strapless dress! This cute and casual dress features a sweetheart neckline and form-hugging fit, accentuating your curves in all the right places. The patchwork seam detailing adds a touch of unique style, while the high-low ruffled hem adds a playful and flirty element. Complete the look in platform shoes and sunnies!

    Fit & Features

    • Denim fabric, slight stretch
    • Strapless sweetheart neckline
    • Back zipper and hook-eye closure
    • Form-hugging fit
    • Ruffle high low hem
    • Runs true to size

    Style Number/Barcode: 05102-5574

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Cute Strapless Tie-Dye Bodycon Mini Dress

    Looking cute is easy with this tie-dye mini dress for summer! This mini-length dress will effortlessly enhance your curves and flatter your figure featuring a trendy strapless neckline and bodycon silhouette. Complete the look with earrings and heels for a party!

    Fit & Features

    • Tie-dye print, mesh fabric lined with stretchy knit
    • Strapless neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5782

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ace The Test Open Tie Back Skater Dress

    This skater dress understood the assignment. Featuring a flattering halter V-neckline and a chic open tie-back design, this mini-length dress will have you feeling confident and cute for any casual occasion!

    Fit & Features

    • Woven fabric
    • Halter V-neckline, spaghetti strap ties
    • Open tie-back design
    • Flowy skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6030

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free