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!

  • Crochet In Color Dress
    This cute crochet dress is perfect for a day out! It features a V neckline, padded cups, adjustable spaghetti straps that create an X back, a sheer crochet waist, and a short flared skirt with a full lining. Dress is composed of a combination lace and gauze fabric that offers a relaxed fit with minimal stretch.

    *Also available in Plus.

    Style Number/Barcode: 05102-3959

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Botanical Beauty Midi Dress
    This botanical print dress features a square ruffled neckline, elastic ruffle straps and a straight bodice. The backing of the dress has a hidden zipper and  stretch smock detailing.This piece has a dark toned floral print and is mid-length with a smooth inner lining and a side slit.It is composed of a sheer chiffon-like material that offers a relaxed fit with minimal stretch. On a stroll through the park or a gals brunch date, this dress is bound to have heads turning!

    Model is 5'9" with a 32" bust, a 24" waist, and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0210

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Miss Midi Striped Dress

    Hey there miss midi, we see you! and we are on the same page too, filling our closet with midi dresses this season. This piece features a  v-neckline, attached dark neutral marbled buttons, and adjustable spaghetti straps that lead to a square back. This toned midi dress has a skinny stripe pattern and is composed of a soft knit material that offers maximum stretch. 

    Style Number/Barcode: 05102-3992

    Category Name: Casual Dresses

    Price: $8.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rainbow Wave Maxi Dress

    You love color, so embrace the rainbow! All eyes will be on you in this vibrantly chic maxi dress, which features a multi-hued stripe pattern, spaghetti straps, scoop neck, pockets at either hip, and plenty of stretch. Don't forget to pair it with the matching head wrap! 

    Style Number/Barcode: 05102-0244

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Daring In Denim Mini Dress

    We dare you to be bold in this hot denim mini! The dress features a sleeveless strapless square neckline, double vertical seam detailing down the front and back, and a short, raw hem. The dress is composed of a jean fabric that offers moderate stretch and a curve hugging fit.

    Model is 5'9" with a 33" bust, 24" waist and 35.5 hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0162

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic Chic Shirt Dress

    This classic chic mini shirt dress is everything you need and more. It features a collar, a plunging wrap front V neckline, long sleeves with buttons to cuff, a high waist seam, side ruched detailing, and a short fit. The dress is composed of a woven fabric with no stretch.

    Model is 5'9" with a 33" bust, 24" waist and 35.5 hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0293

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish And Sultry Mini Dress

    You're a stylish girl who likes her look to be a little sultry too! This ribbed knit mini dress features long fitted sleeves, a wired sweetheart neckline with padded cups and a small front cut out, and a short, form hugging fit. The dress offers plenty of stretch.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0103

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Memorable Moments Skater Dress

    Create more memorable moments in this navy blue skater dress! It features a high round neckline, narrow shoulder straps that lead to a sheer lace back panel and a gold zipper, a fitted bodice with a high waist seam, and a short flowy skirt. Dress is composed of an unlined crepe fabric with a moderate stretch. 

    Style Number/Barcode: 05101-8465

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flowy Floral Mini Dress
    This flowy floral dress is the perfect piece to transition into fall! It features a wrap front V neckline, a hidden back zipper and hook and eye closure, long sleeves with smocked cuffs, a faux button down front, a high waist seam, ruched detailing, and a flirty ruffle hem. The printed dress is composed of a sheer chiffon fabric with a stretchy knit lining.

    Style Number/Barcode: 05102-0303

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Live It Up In Linen Midi Dress
    Live it up in this absolutely adorable ditsy floral printed midi! The dress features a sleeveless bodice, tie shoulder spaghetti straps, a sweetheart neckline with pleated detailing and a tie front, and a hidden back zipper and hook and eye closure. The dress is composed of a linen fabric with a shorter woven lining and has no stretch.

    Style Number/Barcode: 05102-0305

    Category Name: Casual Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Courtside Style Cutout Pleated Skater Dress

    Look cute courtside in this stylish tennis-inspired skater dress! Featuring a trendy cutout back and a flattering skater silhouette, this pleated dress combines playful charm with modern flair.

    Fit & Features

    • Attached panty lining
    • Scoop neckline, tank shoulder straps
    • Double-lined soft knit bodice
    • Cutout back design
    • Woven pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000055

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Life's A Beach Mesh Dress
    Hit the pool, bask by the beach, or prep to party in this colorful mesh maxi! Dress features a vibrant tropical print in turquoise, blue, and rust, a strapless neckline, dramatic ruffle trim running from bust to hem, a high front slit, and built-in briefs. Dress bodice is semi-sheer and does not include a top. Maxi is made from a mesh blend material with moderate stretch.

    Style Number/Barcode: 05102-0286

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Such A Beauty Mini Dress

    Girl, you're such a beauty, and this classically chic mini dress will make for the perfect 'fit. It features a sleeveless bodice, a V-neckline with a tie ruched bust detail, adjustable spaghetti straps, a square back with a hidden zipper and hook and eye closure, a trendy waist front cutout with a tie ruched detail, and a flowy skirt with an adorable ruffled mini-length hem. The short dress is composed of a woven fabric with minimal stretch. Style with a cute pair of mules.

    Fit & Features

    • Sleeveless bodice, V-neckline, tie ruched bust
    • Adjustable spaghetti straps
    • Square back, hidden zipper, hook and eye closure
    • Waist front cutout, tie ruched detail
    • Flowy skirt, ruffled mini-length hem
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-0263

    Category Name: Casual Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On Knit Mini Dress
    You're always on it when it comes to style, and this basic knit mini will make for such a cute 'fit. The dress features a sleeveless bodice, tank-like shoulder straps, a square neck and back, and a short, form hugging fit. The dress is composed of a soft knit that offers plenty of stretch.

    Style Number/Barcode: 05102-0095

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mod Mini Belted Dress

    Get retro glam in this sunny, striking mini! Dress has a body con cut and features thick, tank-style straps, a square neckline, seam detail at bust, an attached fabric belt with oversize buckle, and a pencil skirt. Dress is lined, slips on, and is made from a woven crepe material with a fair amount of stretch.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0171

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild Child Bodycon Mini Dress

    Stay fierce in a dress as wild as you! This bodycon features elasticized spaghetti straps and a square neckline. Cut to a flirty mini length, this piece is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Dress also includes a knit lining.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0152

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Key Velvet Bodycon

    The key to a fab holiday look? This black velvet bodycon dress! It has a mock neckline, long fitted sleeves, a keyhole cut out on the front and back, cross straps at the front, and a body-hugging fit. Dress is composed of an unlined, velvet knit fabric with plenty of stretch.

    Style Number/Barcode: 05101-8068

    Category Name: Casual Dresses

    Price: $14.44 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Steal The Scene Skater Dress
    Steal the scene and turn heads in this captivating skater dress! It features a sleeveless bodice, spaghetti straps that lead to an open cross back and lattice details, vertical seams that run down the bust, a high waist seam, and a flowy high low skater skirt. The dress is composed of a crepe fabric that offers moderate stretch.

    Style Number/Barcode: 05101-8831

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Florals And Lace Skater Dress
    Make it a lacy affair in this must have floral mini dress! It features a sleeveless bodice, a V neckline, princess seams and spaghetti straps. The back features an unlined floral lace back that leads to a lower back keyhole. The slim fit bodice leads to a curve hugging mini length silhouette. Dress is composed of a lined crepe fabric that offers a moderate stretch.

    Style Number/Barcode: 05101-0079

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Walk The Mock Neck Mini Dress

    Talk the talk and walk the walk in this must have mini dress! It features a sleek, form hugging silhouette with a mock neck, long sleeves with thumb-hole slits, and a mini length. Brushed knit offers plenty of stretch.

    Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small

    Style Number/Barcode: 05102-0123

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendsetter In Tie Dye Mini Dress

    Be a total trendsetter in this fun tie dye mini dress! It features a sleeveless bodice, tank-like shoulder straps, a scoop neckline, a tie front accent, and a short, curve hugging fit. The dress is composed of a stretchy knit fabric.

    Style Number/Barcode: 05102-0227

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Such A Babe Button Down Midi Dress

    Yes babe, you'll totally work it in this chic button down midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a square neck and back, lined and padded cups, flattering horizontal seam detailing along the bust, a hidden back zipper closure, a high rise paper bag waist with a tie front belt, faux button detailing, and a mid-length skirt that offers a form hugging fit. The top is composed of a ribbed linen fabric and the skirt is made from a stretchy knit.

    Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0245

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Unforgettably Sweet Floral Bodycon Ruffle Mini Dress

    Create an alluring look in this floral mini dress in a bodycon fit with a flirty ruffled hem. Perfect for shower celebrations and graduations!

    Fit & Features

    • Floral print, lace-lined fabric
    • Strapless neckline
    • Bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5985

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vixen Side Stripe Mini Dress

    Channel the look of your fave '90s-era cool girls in this of-the-moment mini. Dress features spaghetti straps, a square neckline, and stripes running vertically from bust to hem at either side. Dress slips on and  is made from an ultra-soft woven material with moderate stretch.

    Style Number/Barcode: 05102-0044

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance