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!

  • Cup Of Tea Striped Halter Midi Dress With Pockets

    Look cute spilling the tea in this striped midi dress boasting a flattering A-line fit adorned with hidden side pockets perfect for keeping your hands warm!

    Fit & Features

    • Striped print, cotton-blend woven fabric, woven lining
    • Halter plunge neck with ties
    • Back zipper closure
    • Hidden side pockets
    • A-line fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000033

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetest Soul Strapless Floral Flare Midi Dress

    A floral midi dress that'll capture your sweet essence! Designed with a strapless sweetheart neckline, this dress boasts a form-hugging fit and a trendy flare hem for effortless style.

    Fit & Features

    • Ditsy floral print lined with stretchy knit
    • Strapless sweetheart neckline, padded bra cups
    • Form-hugging fit
    • Flare midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000036

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destination Paradise V-Neck Floral Maxi Dress

    The perfect floral maxi dress for your next getaway! Designed in a sleeveless silhouette, this dress features a flattering V-neckline, sleek spaghetti straps, and a form-hugging fit with a flowy floor-length hem. Complete the look with earrings.

    Fit & Features

    • Floral print, mesh lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging fit
    • Flowy floor-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3915

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paradise Beauty Floral Mesh Maxi Dress

    A beautiful floral mesh maxi dress for your escape to paradise! The dress boasts a flattering V-neckline and a form-hugging fit that flares into a flowy maxi-length hem. Pair with earrings and a bracelet.

    Fit & Features

    • Floral print, mesh lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging fit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4075

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Suits You Perfectly Vest Pleated Skater Dress

    From the office to lunch with the girls, this sleeveless skater dress will get you noticed with the unique vest top and pleated mini-length hem! Style with pumps and a purse.

    Fit & Features

    • Woven fabric
    • Button-down vest top
    • Skater silhouette
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000039

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Vibes V-Neck Floral Mesh Maxi Dress

    An effortless and dreamy floral mesh maxi dress to slip into for date night or dinners on vacay! The sleeveless dress is designed with a flattering V-neckline, delicate adjustable spaghetti straps, and a form-hugging fit that leads to the flowy floor-length hem. Pair with a hair accessory.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • V-neckline, adjustable spaghetti straps
    • Form-hugging fit
    • Flowy floor-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4012

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stroll The Gardens Floral Corset Lace Skater Dress

    Stroll the gardens looking so pretty in this floral corset skater dress featuring delicate lace trim and a flattering flowy short-length hem that'll give you a dreamy feel. Pair with earrings and heels.

    Fit & Features

    • Floral pattern, woven fabric, woven lining with lace trim
    • Adjustable shoulder straps, sweetheart neckline
    • Corset bodice, underwire bust, flexible boning, lace trim
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Flowy short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3719

    Category Name: Casual Dresses

    Price: $9.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Forward Strappy Back Skater Dress

    Spring forward in the cutest skater dress showcasing a head-turning strappy tie-back and a flattering ruffled mini-length hem that'll swoon everyone!

    Fit & Features

    • Woven fabric with woven lining
    • Square neckline with bust tie
    • Spaghetti straps
    • Strappy tie-back design
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3687

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Petals In Motion Floral Ruffled Mini Dress

    This is what you wear when the invite says “cute but effortless.” A floral ruffled mini dress with a flouncy fit that brings movement, charm, and just enough drama for every plan on your calendar.

    Fit & Features

    • Lightweight woven fabrication
    • Sleeveless square neckline, adjustable straps
    • Open back design with tie-back accent
    • Floral pattern
    • Tiered ruffled hem
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000041

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

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

  • Sweet Spice Corset Lace-Up Floral Midi Dress

    Sweet and spice combine on this floral midi dress designed with a stylish lace-up back, corset bodice, and a flirty front slit for movement. Complete the look with mules.

    Fit & Features

    • Ditsy floral print, smooth woven fabric, woven lining
    • Sleeveless sweetheart neckline with tie
    • Shoulder straps, side zipper and hook-eye closure
    • Lace-up back design
    • Underwire bust, corset bodice
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3819

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Lovin' Crochet Knit Mini Dress

    You'll love the summer vibes this crochet knit mini dress brings to your happy hour look. Designed with a strapless neckline and sultry side slit, the bodycon fit will flaunt your stunning curves.

    Fit & Features

    • Sheer crochet knit fabric with knit lining, moderate stretch
    • Strapless straight-across neckline
    • Ruched side seam, adjustable drawstring, side slit
    • Mini-length asymmetric hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000046

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetheart Status Tube Midi Dress

    She’s sculpted, strapless, and made to serve. This textured midi dress brings the heat with a sweetheart neckline, front cutout, and curve-hugging fit—perfect for date nights, rooftop vibes, or that one party everyone’s posting about.

    Fit & Features

    • Texture knit fabric, smooth knit stretchy lining
    • Strapless sweetheart tube neckline with notch cutout
    • Mini bust cutout
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000047

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunday Soiree Strapless Floral Midi Dress

    Enter a cute bliss in this strapless floral midi dress for a Sunday soiree! The dress boasts a form-hugging fit with a chic flared hem perfect for styling with strappy sandals.

    Fit & Features

    • Floral print, rib knit fabric lined with stretchy knit
    • Strapless neckline
    • Form-hugging fit
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000045

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Confident Moves Crew Neck Ruffled Mini Dress

    Get ready to make confident moves in this sleeveless mini dress perfect for office days and after work play! Featuring a crew neckline and bodycon fit, this dress will have you feeling fabulous. The tiered ruffled mini-length hem adds a playful touch that will have heads turning. Complete the look in stiletto pumps and a blazer.

    Fit & Features

    • Smooth double-lined knit fabric, moderate stretch
    • Crew neck
    • Bodycon fit
    • Tiered ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5792

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Days Smocked Strapless Mini Dress

    This dress is soft, sunny, and made for days that turn into plans. The smocked strapless bodice hugs just right, while the flowy skirt keeps things light and easy.

    Fit & Features

    • Poplin woven fabric
    • Strapless tube neckline
    • Smocked bodice for stretch
    • Skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000048

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Flirty Girlie Bow Pleated Skirt Romper

    Feel like a dream in this modern sleeveless romper with a front bow inset and pleated skirt overlay that boasts a flirty silhouette. Complete the look with boots.

    Fit & Features

    • Smooth knit fabric
    • Square neckline, wide shoulder straps
    • Front bow inset
    • Pleated skirt overlay, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-1267

    Category Name: Casual Dresses

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Mode Halter Cutout Maxi Dress

    Amp up the sultry vibes of your summer 'fits with this sleek knit maxi dress featuring a halter square neck, an asymmetric waist cutout, and a curve-hugging silhouette.

    Fit & Features

    • Smooth knit fabric with knit lining, high stretch
    • Sleeveless square neckline
    • Tie-back halter spaghetti straps, partially open back
    • Asymmetric side cutout
    • Ruching
    • Maxi-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000051

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Mode Tropical Print One-Shoulder Maxi Dress

    You'll be on vacay mode in this sultry tropical print maxi dress featuring a one-shoulder neckline with a chic O-ring accent and an alluring bust cutout. The floor-length fitted silhouette will flaunt your stunning curves.

    Fit & Features

    • Mesh fabric, high stretch, knit lining
    • Tropical print
    • Sleeveless one-shoulder neckline, O-ring accent
    • Asymmetric bust cutout
    • Asymmetric back strap
    • Maxi-length hem, form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000050

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feeling Flirtatious Floral Button Skater Dress

    With a pretty floral pattern and button accents, this skater dress exudes flirtatious romance vibes! The mini-length dress boasts a flattering V-neckline, a lace-up back that turns heads, and a twirl-worthy skater silhouette. Pair with sneakers for a casual look.

    Fit & Features

    • Burnout floral pattern, woven fabric lined with stretchy knit
    • V-neckline, adjustable spaghetti straps
    • Lace-up back
    • Faux button front accents
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3229

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold And Beautiful Rosette Halter Cutout Maxi Dress

    Step out like a bold beauty in this printed maxi dress for brunch, shower celebrations, or parties! This stunning maxi features an elegant halter neckline adorned with rosette detail, flirty cutouts that flatter your silhouette, and a flowing skirt that moves gracefully with every step.

    Fit & Features

    • Abstract print, woven fabric
    • Halter neckline with rosette detail, bust knit lining
    • Side cutout accents
    • Flowy ruffled maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000054

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tan Lines Cutout Bodycon Mini Dress

    Flaunt your figure in this sultry strapless mini dress on vacay or a bach weekend! Designed with cutout accents and stylish hoop inserts, it creates an alluring silhouette that demands attention along the bodycon silhouette.

    Fit & Features

    • Texture knit stretchy fabric, sewn-in knit lining
    • Strapless sweetheart neckline
    • Front cutouts and hoop inserts
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000170

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunshine Bliss Ditsy Floral Lace Corset Skater Dress

    An adorable ditsy floral short dress for brunch, day dates, or celebration! The skater dress showcases a femme allure with a lace trim corset bodice designed to snatch your figure while the back bow tie and drop waist seam accentuate your figure. Pair with a ring set.

    Fit & Features

    • Ditsy floral print, woven fabric, woven lining with lace trim
    • Lace trim sweetheart neckline
    • Adjustable shoulder straps, back zipper closure
    • Corset lace trim bodice, underwire bust, flexible boning
    • Drop waist seam, skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3770

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wanting More Strapless Lace Knit Maxi Dress

    Leave everyone wanting more when you're in this lace knit maxi dress! Perfect for any summer plans, this dress flaunts a sleek strapless neckline and form-hugging fit that flares out into a long hem.

    Fit & Features

    • Lace knit fabric, lined
    • Strapless neckline
    • Form-hugging fit
    • Flared maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000057

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Make Your Debut Strapless Abstract Mesh Maxi Dress

    Make your effortless debut in this abstract mesh maxi dress that hugs your curves in a flattering bodycon silhouette with a long-length hem. Pair with stiletto mules.

    Fit & Features

    • Abstract print, mesh fabric, soft and stretchy knit lining
    • Strapless neckline
    • Bodycon silhouette
    • Long-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4148

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free