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!

  • Sweet Intentions Flower Strapless Mini Dress

    Soft details, confident energy. This strapless mini dress pairs a sweetheart neckline with a subtle cutout and floral accent for a look that feels romantic but never too precious.

    Fit & Features

    • Smooth knit fabric with knit lining, high stretch
    • Strapless sweetheart neckline, no-slip strip
    • Front cutout with floral trim detail
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000412

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Desert After Dark Denim Mini Dress

    Serving curves with a little edge. This denim halter mini dress features a plunging grommet V neckline and corset-inspired seams that sculpt your shape and keep all eyes exactly where you want them.

    Fit & Features

    • Denim fabric with color fade effect
    • Halter neckline with grommet embellishments
    • Corset seam construction
    • Open back with zipper closure
    • Bodycon mini silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000415

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Weekend Wandering Open Back Maxi Dress

    Light, airy, and made for unhurried afternoons that turn into early evenings. This gauze maxi drapes effortlessly, skims the body just right, perfect for shower celebrations, vacation, or a brunch.

    Fit & Features

    • Soft gauze fabric with lightweight drape, knit lining
    • V-neckline with cutout detail
    • Spaghetti straps
    • Open back with tie, zipper and hook-eye closure
    • Fitted waist flowing into a relaxed maxi skirt
    • Runs true to size

    Style Number/Barcode: 05102-000416

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Plans Chevron Crochet Maxi Dress

    This chevron crochet knit maxi dress features a flattering V-neck and lace-up back that feels equal parts stylish and unforgettable—perfect for beachside restaurants or warm nights out.

    Fit & Features

    • Chevron striped pattern
    • Crochet knit lined fabric
    • V-neck, spaghetti straps
    • Lace-up back
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000418

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: L

    Product Badge:
    • Sale
  • Undeniable Allure Halter Cutout Mini Dress

    She doesn’t enter quietly—she arrives undeniable. A plunging halter cutout mini dress with bold metal hardware and a body-hugging fit that was made for rooftop nights, vacation dinners, and any plan that deserves extra.

    Fit & Features

    • Textured knit fabric, high stretch
    • Sleeveless plunging V-neckline
    • Dual circular metal hardware accents, waist cutouts
    • Tie-back halter straps
    • Open back, lower tie-back spaghetti straps
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000417

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Island After Hours One Shoulder Maxi Dress

    This is what you pack when the itinerary says “sunset drinks,” and you plan on being the view. The one-shoulder neckline with hardware detail gives elevates the look, while the tropical floral print and front slit keep it flowy, flirty, and very camera-ready.

    Fit & Features

    • Tropical floral print knit fabric
    • One-shoulder neckline
    • Statement hardware strap detail
    • Front slit with ruffle accent
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05102-000419

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, L, XL

    Product Badge:
    • Sale
  • Invite Only Rhinestone Floral Dress

    You weren’t planning on being the best dressed—but here we are. This strapless mini dress with a rhinestone floral detail brings just enough shine for every invite on your calendar.

    Fit & Features

    • Mesh-lined fabric
    • Strapless tube neckline
    • Side rhinestone floral embellishment
    • A-line mini silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000423

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: S, M, L

  • Majorly Chic Ribbed Knit Mock Neck Midi Dress

    Meet the midi dress that makes minimal feel major. The mock neck and keyhole detail bring a chic vibe, while the ribbed knit stretch keeps it comfy enough from brunch meet-ups to dinner dates.

    Fit & Features

    • Ribbed hacci knit fabric with knit lining, high stretch
    • Sleeveless mock neckline
    • Keyhole cutout at the bust
    • Angled seams under the bust
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000422

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Golden Hour Energy Tube Mini Dress

    This dress feels like golden hour bottled up. The abstract mesh, bold cutouts, and flowing sash bring a confident, getaway-ready vibe made for warm nights!

    Fit & Features

    • Stretch mesh-lined fabric with an abstract printed design
    • Strapless tube neckline
    • Front cutout detail for a bold silhouette
    • Attached sash detail
    • Mini length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-000421

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Glow Strapless Maxi Dress

    Serving sunkissed confidence with every step. The strapless lace maxi dress contours through the bodice, highlights the neckline with hardware detail, and falls into a sleek, elongating shape that feels equal parts elevated and effortless.

    Fit & Features 

    • Striped design, lace-lined fabric
    • Strapless sweetheart neckline, hardware insert, non-slip grip lining
    • Form-hugging
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000425

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: S, L

  • Sunset Swirl Lace-Up Maxi Dress

    Serve vacation glow from every angle in this striped maxi dress. This dress hugs your curves while the crisscross lace-up back and flared mermaid hem bring the drama for cocktails and dinners with a view.

    Fit & Features

    • Striped pattern, crochet knit lined fabric
    • V-neckline with tie front detail
    • Spaghetti straps shape the strappy lace-up back
    • Mermaid flared maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000426

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: PINK

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

  • Vacay Sparkle Tropical Sequin Mini Dress

    Booked the trip and packed the drama. This tropical floral sequin tube bodycon mini dress hugs close with a glossy, light-catching finish that was made for sunset cocktails and flash photography.

    Fit & Features

    • Tropical floral, sequin mesh fabric, sewn-in lining
    • Tube strapless neckline, non-slip grip lining
    • Side zipper and hook-eye closure
    • Bodycon mini fit
    • Runs true to size

    Style Number/Barcode: 05102-000427

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Plans In Bloom Floral Chiffon Babydoll Dress

    RSVP yes, figure out the details later. This floral chiffon babydoll dress is light, flirty, and effortless with its ruched sweetheart neckline and open tie-back—basically your go-to when the group chat says brunch, birthday, or both.

    Fit & Features

    • Chiffon fabric with lining
    • Floral print
    • Sleeveless sweetheart neckline, ruched bust
    • Adjustable spaghetti straps
    • Open back, tie-back design
    • Mini-length babydoll silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000878

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Back It Up Denim Halter Mini Dress

    Classic denim, unexpected angles. This halter mini dress brings a sleek, body-con fit with an open back moment that feels equal parts polished and playful—perfect for day plans, concerts, or festivals.

    Fit & Features

    • Light wash denim fabric
    • Halter collar neckline
    • Button front
    • Open back with 8 patchwork detail
    • Bodycon silhouette
    • Classic jean styling, mini-length micro hem
    • Runs true to size

    Style Number/Barcode: 05102-000429

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, DENIM

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Seaside Glamour Crochet Strapless Mini Dress

    Serving seaside glamour. This seashell crochet mini dress hugs in all the right places, with a strapless sweetheart neckline and textured crochet knit, ready for beach clubs, sunset dinners, and every vacation photo moment.

    Fit & Features

    • Sheer crochet knit fabric with lining
    • Seashell embellishments
    • Strapless sweetheart neckline, padded bust
    • Back zipper closure
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000430

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Sweet Plans Ahead Ditsy Floral Print Skater Dress

    This dress gets compliments before you even say hi. The ditsy floral print, smocked bodice, and tiered ruffle skater silhouette make it the easiest pick for brunch dates, garden parties, and every cute plan on your calendar.

    Fit & Features

    • Woven gauze fabric with ditsy floral print
    • Sleeveless V-neckline
    • Halter tie-back straps, partially open back
    • Stretchy smocked bodice
    • Lace inserts, tiered ruffled design
    • Mini-length hem with lace trim, skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000432

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: L, XL

    Product Badge:
    • Sale
  • Mood Set Strapless Ruffled Mini Dress

    Soft, sheer, and made for late plans. This strapless mini dress hugs through the bodice and flows into a tiered skirt that moves with you, giving effortless drama for nights out, date plans, and anywhere compliments are guaranteed.

    Fit & Features

    • Burnout velvet pattern, mesh-lined fabric
    • Strapless tube neckline
    • Form-hugging bodice
    • Tiered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000884

    Category Name: Casual Dresses

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City Girl Denim Halter Mini Dress

    Denim, but make it the main character. This halter mini dress features a sharp collar, flattering V-neckline, and curve-hugging seams that flatter your figure, giving you an effortless look this season.

    Fit & Features

    • Denim fabric with stretch
    • Collared V-neckline, sleeveless design
    • Open back, zipper and hook-eye closure
    • Curve-contouring seams, front pockets
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000431

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S

  • Written In Roses Strapless Midi Dress

    This one doesn’t rush—it lingers. A strapless silhouette with a fluid floral print and front slit that moves easily, feels confident, and looks unforgettable from every angle.

    Fit & Features

    • Floral print, mesh-lined stretchy fabric
    • Strapless neckline
    • Front slit for movement
    • Curve-hugging midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000433

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED

    Available Size: XS

    Product Badge:
    • Sale
  • Café Plans Polka Dot Halter Mini Dress

    Easy, breezy, and perfectly on schedule for an afternoon out. This polka dot halter mini feels light, moves with you, and looks chic for brunches, iced coffees, and spontaneous photo ops.

    Fit & Features

    • Polka dot print chiffon fabric with woven lining
    • Halter neckline with open back detail
    • Back zipper and hook-eye closure
    • Fitted bodice with subtle shaping seams
    • A-line mini skirt with godet flare panels
    • Runs true to size

    Style Number/Barcode: 05102-000435

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Soft Drama Off Shoulder Side Tie Mini Dress

    This mini dress mixes soft draping with curve-hugging ruching for a look that reads chic without trying too hard. The off-the-shoulder neckline and dramatic side tie keep things flirty, polished, and ready for whatever the night turns into.

    Fit & Features

    • Smooth knit stretch fabric
    • Off-the-shoulder foldover neckline
    • Long fitted sleeves with slight flare at the wrists
    • Ruched bodice and sides for a contoured silhouette
    • Side tie accent with extended drape detail
    • Bodycon silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000434

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bloom Mood Floral Midi Dress

    Soft, romantic, and ready for compliments. This floral midi dress features a strapless neckline and textured knit eyelet fabric that hugs your shape while keeping the vibe perfect for brunch dates, showers, or sunny day plans.

    Fit & Features

    • Ditsy floral print, eyelet mesh-lined fabric
    • Strapless neckline
    • Bodycon fit
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000436

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lowkey Bold Studded Denim Bodycon Dress

    Confident from every angle, this denim mini doesn’t wait for an invite. The halter neckline, body-hugging fit, and subtle stud details make it an easy yes for nights out, concerts, or festivals.

    Fit & Features

    • Denim fabric with vintage-inspired wash
    • Halter sweetheart neckline with studded trim
    • Front zipper closure
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000440

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK, DENIM

    Available Size: XS

    Product Badge:
    • Sale
  • Amalfi Mood Halter Skater Dress

    Serving sunshine in dress form. This citrus print halter mini dress features a sweetheart neckline and breezy A-line skirt, making it the perfect pick for vacations, brunch, and sunny day plans.

    Fit & Features

    • Citrus multi-print, woven fabric with woven lining
    • Sweetheart halter neckline
    • Padded bra cups, non-slip grip lining
    • Back zipper and hook-eye closure
    • A-line fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000438

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free