Casual Dresses

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Cute Sweater 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!

  • Soft Glow Bodycon Mini Dress

    Cute, simple, and effortlessly flattering. This ribbed knit bodycon mini dress hugs in all the right places with a clean square neckline and delicate straps, making it the perfect dress for day dates, brunch, or a casual night out.

    Fit & Features

    • Rib knit fabric, sewn-in lining
    • Square neckline
    • Spaghetti straps
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000560

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

  • Styled Up Off-Shoulder Mini Dress

    Easy, confident, and styled without overthinking. This off-the-shoulder blouson mini dress drapes up top with a fitted bottom that keeps the silhouette clean and pulled together for any plans that pop up.

    Fit & Features

    • Soft knit fabric with comfortable stretch
    • Relaxed blouson top with a fitted mini skirt
    • Off shoulder neckline
    • Relaxed short sleeves
    • Runs true to size

    Style Number/Barcode: 05102-000563

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: BROWN, YELLOW

    Available Size: XS, S, M, L

  • Spring Muse Floral Midi Dress

    Soft florals and a sleek silhouette make this one an instant favorite. This strapless floral eyelet bodycon midi dress hugs your curves and adds a polished look for brunch, garden parties, and getaways.

    Fit & Features

    • Ditsy floral print, eyelet knit fabric, soft lining
    • Strapless tube neckline
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000570

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Talker Floral Eyelet Midi Tube Dress

    Soft, fitted, and low-key stealing attention. This floral print eyelet midi tube dress hugs in all the right places with a stretchy feel that’s made for brunch plans, day dates, and everything after.

    Fit & Features

    • Eyelet knit fabric with sewn-in knit lining, high stretch
    • Floral print
    • Strapless elasticized straight-across neckline
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000569

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, L

    Product Badge:
    • Sale
  • Island Plans Tropical Tube Mini Dress

    Booked, busy, and already packing this. This floral print mini dress hugs you in all the right places and was made for beach stays, resort destinations, and tropical escapes!

    Fit & Features

    • Slinky knit-lined stretchy fabric
    • Tube strapless neckline
    • Statement floral print
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000571

    Category Name: Casual Dresses

    Price: $35.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Pearls Before Midnight Denim Mini Dress

    A little country, a little glamorous, and fully committed to being overdressed. This denim skater mini dress brings together pearl embellishments, a fitted bodice, and flirty volume for the kind of outfit that owns the room before you even say hi.

    Fit & Features

    • Denim fabric, bust lining
    • Sweetheart neckline, adjustable spaghetti straps
    • Button front accents. back zipper and hook-eye closure
    • Skater silhouette
    • Faux pearl embellishments
    • Pleated side mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000568

    Category Name: Casual Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S, M, L

  • Styled Chic Button Halter Neck Mini Dress

    Serving sculpted and styled without trying too hard. This halter neck mini dress hugs your curves with a sleek ribbed feel and subtle button detail that keeps it chic from every angle.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Sleeveless V-neckline
    • Varied button accents
    • Halter strap, partially open back
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000316

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Postcard From Paradise Maxi Dress

    Mentally already sipping something fruity by the water. This flowy maxi dress brings vacation dressing to life with a citrus postcard print, flirty front tie detail, and lace-up back that looks good from every angle.

    Fit & Features

    • Multi-printed design, woven fabric
    • V-neckline with trim and tie bust
    • Spaghetti straps
    • Lace-up tassel back
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000572

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Sweet Charm Flower Strap Crochet Mini Dress

    Serving shape with a side of charm. This crochet mini dress hugs your curves while the flower strap detail brings just enough sweetness—wear it when you want compliments without trying.

    Fit & Features

    • Crochet knit fabric with knit lining, moderate stretch
    • Lettuce edge trims
    • Sleeveless V-neckline
    • Adjustable spaghetti straps, front flower accents
    • Mini-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000318

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Getaway Ready Floral Print Maxi Dress

    Out of office and not checking. This floral hem print maxi dress features a plunge halter neck, front slit, and a cross strap back that brings the drama from every angle. Perfect for packing with you on vacations, honeymoons, or weekend escapes!

    Fit & Features

    • Smooth knit stretchy fabric, knit lining
    • Halter plunge neckline, hardware insert, adjustable cross back straps
    • Open back design
    • Cutout bosdice
    • Flowy maxi-length silhouette with floral hem print
    • Runs true to size

    Style Number/Barcode: 05102-000576

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling Detail Strapless Midi Dress

    Clean lines, zero effort, maximum compliments. This strapless midi dress hugs in all the right places with a textured knit feel that makes dinner plans, celebrations, and last-minute invites look very handled.

    Fit & Features

    • Textured knit-lined fabric
    • Strapless neckline
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000578

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Brunch Booked Floral Mini Dress

    Serving vacation mood before you've even packed a bag. This floral tube mini dress features a flattering A-line fit that feels effortless for brunch, parties, and every warm-weather plan that pops up.

    Fit & Features

    • Floral print, lined knit fabric
    • Strapless tube neckline
    • A-line mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000581

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Flirty Fit Lace Ruffle Romper

    The one that instantly upgrades whatever’s on your calendar. A lace cutout ruffle romper with a flirty fit that’s made for parties, birthdays, and last-minute invites you’re definitely saying yes to.

    Fit & Features

    • Sheer lace fabric with knit lining, moderate stretch
    • Sleeveless plunging V-neckline, bar strap accent
    • Halter tie-back spaghetti straps
    • Open back, lower tie-back spaghetti straps
    • Drop waist
    • Tiered ruffled mini-length overlay, skater silhouette, hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000252

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: OFF, WHITE

    Available Size: XS, S, M, L

  • One More Pic Button Denim Dress

    Serving attitude with every button. This denim mini dress hugs in all the right places with a lace-up back that makes the exit just as good as the entrance.

    Fit & Features

    • Denim fabric, vintage-inspired wash, high stretch
    • Sleeveless baot neckline
    • Front button-up closures
    • Tailored seams
    • Cutout lace-up strappy back
    • A-line mini silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000586

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S, M, L

  • She's Bold Abstract Floral Midi Tube Dress

    She’s bold, effortless, and fully booked. This abstract floral print midi tube dress hugs your curves with a smooth stretch fit—perfect for when you want your outfit to do all the talking.

    Fit & Features

    • Sleek knit fabric, high stretch
    • Abstract floral print
    • Strapless straight-across neckline
    • Ruched detailing
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000585

    Category Name: Casual Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: ORANGE

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

  • Extra Flirty Ruffle Mini Dress

    This is the mini dress you wear when you want something a little extra. The plunging halter neckline, open back, and ruched drop waist hugs your curves, while the tiered ruffle skirt keeps it flirty for parties, birthdays, and spontaneous nights out.

    Fit & Features

    • Smooth knit fabric with high stretch
    • Sleeveless plunging V-neckline
    • Tie-back halter straps, open back
    • Ruched drop waist
    • Tiered ruffled design
    • Mini-length hem, A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000811

    Category Name: Casual Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: NAVY, WHITE, WINE

    Available Size: XS, S, M, L

  • Spice Done Right Mesh Midi Dress

    Too good to save for just one occasion. This mesh midi dress hugs every curve with ruched detailing and a strapless neckline that makes the whole dress feel a little extra in the best way.

    Fit & Features

    • Mesh-lined fabric
    • Strapless sweetheart neckline
    • Back zipper closure
    • Bodycon silhouette, ruched detail
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000588

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: ORANGE

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

  • Salt Air Striped Knit Cutout Maxi Dress

    Vacation photos are optional, but compliments won't be. This striped knit cutout maxi dress hugs your curves with statement O-ring details and a leg-baring slit that was made for turning heads.

    Fit & Features

    • Abstract striped textured knit fabric, moderate stretch
    • Sleeveless sweetheart neckline
    • O-ring halter design, tie-back halter spaghetti straps
    • Waist cutout with O-ring design
    • Open back, bar strap with hook-eye closure, lower back zipper closure
    • Maxi-length hem, high-cut side slit, bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000590

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Twice As Nice Halter Ruffle Mini Dress

    Date night just found its favorite dress. This halter mini dress serves a plunging neckline and a tiered ruffle skirt that moves with you from cocktails to the dancefloor.

    Fit & Features

    • Lace-lined fabric
    • Plunge halter neckline
    • Open back
    • Form-hugging fit
    • Tiered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000816

    Category Name: Casual Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, L

  • Coast To Cocktails Striped Maxi Dress

    The dress that belongs in your vacation photo dump. With a plunging halter neckline, textured striped knit, and an open tie-back design, this maxi dress was made for ocean views, dinner reservations, and weekend escapes.

    Fit & Features

    • Striped pattern, sheer texture crochet knit fabric
    • Halter neckline, tie straps
    • Open tie-back
    • High side slit
    • Curve-hugging, long hem
    • Runs true to size

    Style Number/Barcode: 05102-000591

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Daydream Detour Paisley Maxi Dress

    Easy, floaty, and somehow always the prettiest thing in your closet. This floral paisley maxi dress features a flowy silhouette, lace trim details, and an open tie back that feels made for brunch, weekend markets, and sunny day plans.

    Fit & Features

    • Floral paisley print, woven fabric, short woven lining
    • V-neckline, spaghetti straps
    • Open tie-back
    • Center front button-up closures
    • Flowy maxi silhouette, sheer lace trim
    • Runs true to size

    Style Number/Barcode: 05102-000592

    Category Name: Casual Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

  • Center Of Attention Floral Maxi Dress

    This is the dress that gets the double-take. Designed with a curve-hugging mermaid silhouette and oversized floral print, it brings major romance with a little bit of drama.

    Fit & Features

    • Statement floral print, lined mesh fabric, high stretch
    • Strapless tube neckline
    • Curve-hugging, mermaid fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000593

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BURGUNDY

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

    Product Badge:
    • New Arrival
  • Weekend Away Strapless Maxi Dress

    This chevron maxi dress hugs in all the right places with a sleek strapless neckline and leg-baring side slit that was practically made for resort dinners, sunset cocktails, and strolling the beachside town.

    Fit & Features

    • Chevron pattern, crochet fabric, smooth knit lining
    • Strapless neckline
    • Side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000595

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Island Intentions Satin Mini Dress

    The dress to pack in your suitcase. Designed with a tropical-inspired print, beaded straps, and a lace-up open back, this satin mini dress was made for oceanfront dinners and resort cocktails.

    Fit & Features

    • Silky satin woven fabric, smooth woven lining
    • Subtle tropical print
    • Square neckline
    • Beaded spaghetti straps
    • Lace-up open back
    • Curve-hugging, mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000596

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L