Casual Dresses

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STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

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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!

  • Sweet Style Bow Detail Polka Dot Mesh Mini Dress

    Show off the sweetest style on summer dates in this bow detail polka dot mini dress! Designed with an airy sheer mesh fabric with a knit lining for coverage, this mini-length dress is accented with an adorable polka dot pattern for the cutest vibe. It features a sleeveless V-neck and back design with a dainty eyelet trim, tank shoulder straps, a mini bow detail at the bust for a sweet touch, tie-back spaghetti straps, and a flirty flowy A-line silhouette. Pair with strappy mules.

    Fit & Features

    • Polka dot printed sheer mesh fabric with knit lining
    • Plenty of stretch
    • V-neck and back, tank shoulder straps
    • Mini bow detail, eyelet trim
    • Tie-back straps
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5828

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Lace Off-The-Shoulder Drop Waist Romper

    Look like a daydream in this boho lace romper designed with a ruffled off-the-shoulder neckline and a flattering skater silhouette.

    Fit & Features

    • Sheer lace fabric with knit lining, moderate stretch
    • Off-the-shoulder straight neckline, ruffled overlay
    • V-shaped drop waist
    • Flowy shorts, skater silhouette
    • Romper in size small is 25" shoulder to hem with an 8.5" front rise and a 3" inseam
    • Runs true to size

    Style Number/Barcode: 06503-1228

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ahead Of The Curve Crew Neck Bodycon Mini Dress

    A sleeveless mini dress that's ahead of the curve in every way! With a flattering bodycon fit and a mini-length hem, this dress will accentuate your curves in all the right places. The crew neckline and side ruched seam add unique details to this stylish dress. Complete the look with a crop jacket and sandals for any plans!

    Fit & Features

    • Slinky knit fabric lined with stretchy knit
    • Crew neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5753

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sleek Strappy Back Maxi Dress

    A dress that does the flirting for you—sleek, slinky, and unforgettable. With a curve-loving fit and sultry strappy back, it’s your go-to for nights that demand a little drama.

    Fit & Features

    • Slinky knit fabric, high stretch
    • Sleeveless V-neckline
    • Dual bungee spaghetti straps
    • Open back, cross-back strappy design
    • Maxi-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000368

    Category Name: Casual Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L, XL

  • Looking Back Strapless Strappy Mini Dress

    Make everyone look back at you in this sassy rib knit mini dress! Perfect for summer BBQs or pool parties, this dress boasts a flattering strapless neckline and bust cutout, a strappy back design, and a bodycon fit. Complete the look in sandals and sunnies!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Strappy back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5767

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whimsical Appeal Puff Sleeve Chiffon Skater Dress

    Swiss dots add whimsical appeal to this charming chiffon skater dress perfect for birthdays, graduations, or showers! With sheer puff sleeves, a sweetheart neckline, and a tiered ruffled skater silhouette, this dress is both playful and flattering. Its short-length hem adds a touch of flirty charm. Complete the look in mules and a trendy purse!

    Fit & Features

    • Swiss dot chiffon fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2999

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Day Dream Lace Up Eyelet Skater Dress

    Make your garden party daydream come true in this floral eyelet skater dress! This playful skater dress features a sweetheart neckline, spaghetti straps, and a lace-up back for a flirty touch. Its skater silhouette and short-length hem make it perfect for twirling! Complete the look with teardrop earrings and a bracelet.

    Fit & Features

    • Floral print, eyelet woven lined fabric, no stretch
    • Sweetheart neckline
    • Spaghetti straps
    • Lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3197

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Day Sleeveless Mermaid Denim Midi Dress

    Look cute and casual wherever you go in this denim midi dress! Featuring spaghetti straps, a sweetheart neckline, a flattering mermaid silhouette, and a flared midi-length hem, this dress will have you looking and feeling amazing. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Denim fabric, minimal stretch
    • Spaghetti straps
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5567

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Silhouette Rosette Ruffled Knit Mini Dress

    The knit mini dress features a sleeveless scoop neckline accented with a dainty rosette detail for an adorable touch. The tiered ruffled mini-length hem and bodycon fit add a flirty feel while highlighting your curves.

    Fit & Features

    • Ribbed knit fabric with knit lining, plenty of stretch
    • Scoop neckline with rosette detail
    • Spaghetti straps
    • Tiered ruffled mini-length hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5846

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Blooms Floral Ruffle Chiffon Skater Dress

    Let this tropical floral skater dress bloom into your summer lineup! With a sweetheart neckline featuring delicate ruffle trim, adjustable spaghetti straps and padded bra cups, this skater silhouette will flatter your figure. The mini-length hem adds a flirty touch to this tropical floral printed chiffon dress. Complete the look with a crossbody purse and sandals!

    Fit & Features

    • Tropical floral print
    • Chiffon fabric with woven lining, no stretch
    • Sweetheart ruffle trim neckline
    • Padded bra cups
    • Adjustable spaghetti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3204

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Design Cutout Bodycon Knit Midi Dress

    This bodycon midi dress features a sultry lower back cutout and back slit accent for a chic allure. The curve-hugging dress is made with a lined, soft, brushed knit fabric offering plenty of stretch for comfortable wear.

    Fit & Features

    • Lined brushed knit fabric, plenty of stretch
    • Square neckline
    • Tank shoulder straps
    • Lower back cutout
    • Back slit
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5595

    Category Name: Casual Dresses

    Price: $14.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemain Charm Halter Open Back Tie Dye Maxi Dress

    Meet the bohemian charm of this tie dye maxi dress for summer soirees and parties! Featuring a halter cowl neckline and an alluring open back with tie closure, this dress exudes sensuality. The side ruched seams and form-hugging fit accentuate your curves, while the front slit and sheer maxi-length hem add a chic touch! Complete the look with earrings and a clutch.

    Fit & Features

    • Tie dye print, stretchy mesh fabric, sewn-in knit lining
    • Halter cowl neckline
    • Open back with tie closure
    • Form-hugging fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3445

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crusin' The Tropics Lace-Up Tropical Mini Dress

    Cruise the tropics in this stylish tropical mini dress! Designed with a tropical palm print on knit fabric, this dress is sure to stand out on the island and boat. Featuring a V-neckline and spaghetti straps, a lace-up back that lets you customize the style, and a flattering bodycon fit. Complete the look with sunglasses.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, sewn-in lining
    • Spaghetti straps
    • V-neckline
    • Lace-up back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5549

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Charmer Ribbon Bow Bodycon Mini Dress

    Show off your cute charm in this bodycon mini dress on day dates or weekend brunch! Designed with a double-lined brushed knit fabric, this mini-length dress offers plenty of stretch for comfortable wear. It features a sleeveless square neckline with a dainty sheer eyelet lace trim and ribbon bow detail, spaghetti straps, and ruching down the side seams to accentuate your curves along the bodycon silhouette. Complete your coquette-inspired look with pearl earrings and strappy mules!

    Fit & Features

    • Stretchy double-lined brushed knit fabric
    • Square neckline
    • Sheer eyelet lace trim, ribbon bow detail
    • Spaghetti straps
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5735

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Class Act Cowl Neck Polka Dot Midi Dress

    A sleeveless polka dot midi dress features a flattering cowl neckline, spaghetti straps, and a flowy silhouette with a front slit. Perfect for styling with stiletto heels for any occasion.

    Fit & Features

    • Polka dot print, mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Cowl neckline
    • Front slit
    • Flowy midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5849

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine On My Mind Strapless Tropical Skater Dress

    This tropical skater dress will inspire sunshine on your mind! Perfect for vacations or a beach day, this strapless dress features a stretchy waist leading to the skater silhouette and a flirty ruffled mini-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Tropical palm print, gauze woven fabric, bust lining
    • Strapless neckline
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5744

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made To Amaze Strapless Marble Bodycon Midi Dress

    Everyone will admire your style in this strapless marble bodycon midi dress at the art show downtown! Made from a mesh fabric boasting a gorgeous marble print, you'll be sure to amaze. With a strapless neckline and side ruched seams, this dress hugs your curves in all the right places for a bodycon fit along the midi-length hem. Complete the look with stiletto heels.

    Fit & Features

    • Marble print, stretchy mesh fabric, sewn-in knit lining
    • Strapless neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5576

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Must-Have Tie Back A-Line Mini Dress

    A must-have tie back A-line mini dress for casual nights out! Featuring chic cap sleeves, a square neckline, a sultry open back with tie closure, and a flattering A-line silhouette with a mini-length hem, this dress will elevate your style game. Complete the look in faux suede heels and a purse!

    Fit & Features

    • Slinky knit fabric lined with stretchy knit
    • Open tie-back design
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5681

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fierce Flirt Animal Print Mini Dress

    This animal print mini dress was made for turning heads. With its draped cowl neckline, strappy halter fit, and flouncy layered hem, it’s a party dress with untamed vibes.

    Fit & Features

    • Animal print, mesh-lined stretchy fabric
    • Halter cowl neckline with adjustable belted strap
    • Open back
    • Form-hugging fit
    • Layered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000320

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: GRAY

    Available Size: XS, S, M, L

  • Weekend Plans Ribbed Knit Maxi Dress

    This casual-chic maxi dress is perfect for your upcoming weekend plans. It features a sleeveless one-shoulder neckline for an effortless and trendy vibe, a single tank shoulder strap, an open back with a dual strap design, a fitted, maxi-length silhouette, and a high side slit. Style this dress with hoop earrings.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Single tank shoulder strap
    • Open back, dual strap design
    • Maxi-length hem, form-hugging fit, side slit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4737

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blissful Afternoons Corset A-Line Midi Dress

    Enjoy an afternoon of bliss looking so sweet in this A-line midi dress at showers or semi-formal weddings! The sweetheart neckline and adjustable spaghetti straps accentuate your figure while the corset bodice with built-in padded underwire bust provides support. The flowy A-line silhouette and midi-length hem add elegance to your look. Complete the look in strappy heeled sandals.

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Sweetheart neckline
    • Corset bodice, built-in padded underwire bust
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3309

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute And Fab Sweater Dress

    You'll look so cute and fab in this trendy sleeveless sweater dress. It features a mock neckline, a short, curve-hugging fit, and is composed of a fuzzy eyelash knit fabric. Style this dress with combat booties.

    Fit & Features

    • Sleeveless
    • Ribbed mock neckline
    • Mini-length, form-fitting silhouette
    • Eyelash knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1112

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Done In One Ribbed Knit Bodycon Midi Dress

    Be ready in a flash with this done-in-one bodycon midi dress perfect for styling up or down! Made with stretchy ribbed knit fabric, it's also soft and comfortable to wear all day. It features a flattering scoop neckline and tank shoulder straps for a comfortable and stylish fit. With a bodycon silhouette and midi-length hem, this dress will hug your curves! Complete the look in a crop denim jacket and sandals.

    Fit & Features

    • Ribbed knit fabric, sewn-in knit lining, moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5666

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out Of Office One Shoulder Tropical Maxi Dress

    This tropical maxi dress says it's time for vacation! Switch your email to out of office and enjoy a sunny destination in this sleeveless dress featuring a one-shoulder neckline adorned with a knotted shoulder strap, a flattering mermaid silhouette, and a maxi-length hem. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical palm leaf print, stretchy knit fabric
    • One-shoulder neckline
    • Knotted shoulder strap
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5695

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale