Casual Dresses

Loading...

Casual Dresses Made for Everyday Fall Plans

Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.

Easy Prints, Textures & Layers for the Season

Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.

What Makes a Dress Casual?

A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.

How Do You Transition a Casual Dress From Summer to Fall?

Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.

Which Fabrics Work Best for Everyday Dresses?

Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.

How Can You Style One Casual Dress for Different Plans?

Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.

  • Take The Plunge Floral Maxi Dress
    Add a hint of island-inspired chic to your wardrobe with this gauzy sleeveless maxi dress. Dress features a deep V at front and back, a shirred banded waist, and an all-over floral print. Dress is composed of a rayon fabric and has plenty of stretch in the waist and moderate stretch throughout the rest.

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

    Style Number/Barcode: 05102-4050

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Va Va Venom Knit Dress

    You don't bite, but you're ready to pounce! Channel your wild side in this bold mini. Dress slips on, has a curve-hugging fit, and features spaghetti straps and a scoop neck. Dress is made from a ultra-soft brushed knit fabric 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: 05102-0169

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Girl Mini Dress

    Show us your sweet side with this eyelet-detailed mini dress! It features a V neckline, ruffled cap sleeves, single-button closure with keyhole at back, an empire waist, and a short A-line skirt with pockets leading to a wavy hemline. Dress is lined, made from cotton, includes a linen short underlay. 

    Style Number/Barcode: 05102-0310

    Category Name: Casual Dresses

    Price: $16.97 $47.60

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lovely Little Linen Skater Dress

    Leave a flirty impression in this lovely little linen skater dress! It features long fitted sleeves with ruffled elastic cuffs, a deep V neckline with a ruffle trim, a hidden back zipper and hook and eye closure, ruffle detail seams, and a flowy skater skirt. The dress is composed of a lightweight linen fabric with a woven lining and has no stretch.

    Style Number/Barcode: 05102-0300

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Beauty Eyelet Mini Dress
    Showcase your effortless beauty in this beyond gorgeous eyelet mini dress! It features a square neck and back, short sleeves with ruffle detailing, a hidden back zipper and hook and eye closure, mini side cut outs at the waist seam, and a short, mid-thigh length. The dress is composed of a woven fabric with a full lining and has no stretch.

    Style Number/Barcode: 05102-0150

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunset Beauty Tropical Print Maxi Dress

    Show off your beauty at sunset happy hour in this tropical print maxi dress designed with sheer mesh fabric and a mini-length lining. The high-cut side slit adds an alluring detail to turn heads.

    Fit & Features

    • Sheer knit fabric with mini-length knit lining, high stretch
    • Tropical print
    • Sleeveless cowl neckline
    • Spaghetti straps, cross-back design
    • High side slit
    • Maxi-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6074

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Solid Stunner Ruched Tube Dress
    We'll keep it brief: this mini is made for for your next night out! Tube-style dress features a curve-hugging cut, strapless neckline, and all-over strategic ruching detail. Don't forget to pair it with the matching duster! Dress slips on and is made from a smooth, solid woven material with moderate stretch.

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0165

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    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 red toned midi dress has a skinny stripe pattern and is composed of a soft knit material that offers maximum stretch. 

    Style Number/Barcode: 05102-3994

    Category Name: Casual Dresses

    Price: $9.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Plus Thrill Of Knit Ribbed Dress

    Toe the perfect line between casually chic and sultry-on-trend in this off-the-shoulder mini. Dress features all-over medium-width ribbing, a scoop neck, decorative wood-like buttons and a full lining. Dress is made from a soft, heavier-weight cotton blend with a fair amount of stretch. 

    Style Number/Barcode: 15102-0035

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ruffle Ride Skater Dress

    Keep it cool in this breezy-beautiful skater dress! It features adjustable spaghetti straps, a seamed V neck bodice, tiers of ruffle trim at the bust, waist, thigh and hem, and an A-line skirt with back zip. Dress is fully lined and made from a lightweight Tencel-blend with natural crinkle-effect and little to no stretch.

    Style Number/Barcode: 05102-0329

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Chic Midi Dress

    Get a total casual chic vibe with this adorable daytime LBD! It features a V neckline, short sleeves, and a mid-length, curve hugging fit. The dress is composed of a ribbed knit fabric that offers plenty of stretch.

    Style Number/Barcode: 05102-0197

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Flirt Floral Mini Tube Dress

    Bring the sweet flirty vibes to your weekend plans in this cute mini tube dress with a dainty floral print on lined chiffon fabric. The strapless smocked bodice leads to a V-shaped waist, tiered ruffled design, and flowy skater silhouette.

    Fit & Features

    • Woven chiffon fabric with stretchy knit lining, dainty floral print
    • Strapless straight-across neckline
    • Stretchy smocked bodice
    • V-shaped waist
    • Tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4077

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Talk Skater Dress

    This adorable skater dress will definitely sweet talk its way into your closet! It features short flowy sleeves, a plunging V neckline, an open back with a top tie closure with tassel details, a back hidden zipper and hook and eye closure, a high waist seam, a back tie detail, a faux button down front, and a flowy skater skirt. The dress is composed of a woven gauze fabric with a woven lining and has no stretch.

    Style Number/Barcode: 05102-0174

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stun And Snap Mini Dress
    Stun in this snap-worthy LWD (Little White Dress)! The sweater dress features a sleeveless bodice, spaghetti straps, a V neckline, a gold faux snap button front, and a short, curve hugging fit. The black dress is composed of a ribbed knit fabric that offers plenty of stretch.

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06005-0175

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready For My Snap Midi Dress
    Get ready to take all the snaps in this simply stunning midi! The sweater dress features a sleeveless bodice, tank-like shoulder straps, a scoop neckline, double white striped detailing and gold faux snap buttons down each side, and a mid-length fit. The black dress is composed of a ribbed knit fabric with plenty of stretch.

    Style Number/Barcode: 06005-0096

    Category Name: Casual Dresses

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smocked Stunner Mini Dress

    Showcase the stylish stunner you are in this adorable smocked mini dress! It features a sleeveless bodice, thick smocked shoulder straps with ruffle detailing, a sweetheart neckline, a stretchy and smocked bust, a high waist seam with a ruffle trim, and a flowy skirt with a tiered ruffle hem. The dress is composed of a lightweight woven fabric with a woven skirt lining.

    Style Number/Barcode: 05102-0230

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay All Day Mini Dress

    Feel like you're on a vacay all day in this fun tropical printed mini! It features a sleeveless bodice, spaghetti straps, a scoop neckline, and a short, form hugging fit. The dress is composed of a scuba knit fabric that offers moderate stretch and showcases a vibrant print.

    Style Number/Barcode: 05102-0008

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Soft And Sweet Dress

    Show off your soft sweet side baby girl! This off shoulder dress is the perfect ensemble for a day in the sun. Featuring a straight off-shoulder neckline and wooden buttons down the middle, this dress has a form fitting bodice and a ribbed knit material that will offer maximum stretch as well as a soft inner lining. Show off those shoulders girl!

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

    Style Number/Barcode: 05102-4039

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunshine Dream Open Tie Back Floral Maxi Dress

    A floral print adds to the dreamy charm of this flowy maxi dress boasting an open tie back design and ruffled silhouette perfect for beachside strolls or day parties.

    Fit & Features

    • Floral print, woven fabric, short woven lining
    • Sweetheart neckline with bust tie
    •  Spaghetti straps
    • Open tie back design
    • Ruffled flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3912

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smocked And Stylin' Mini Dress

    This adorable floral printed mini is smocked and stylin'! The dress features a sleeveless bodice, tie shoulder spaghetti straps, a square neckline with a bust keyhole cut out, a square back, pleated details, and a stretchy and smocked fit. The dress is composed of a lightweight linen fabric that offers a form hugging fit.

    Style Number/Barcode: 05102-0283

    Category Name: Casual Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Get Sprung On Florals Mini Dress

    Get sprung on this too cute mini dress! It features an off the shoulder neckline with short cuffed sleeves, a trendy tie front with a keyhole cut out, seam detailing, a smocked back, and a short, form hugging fit. The dress is composed of a woven fabric with no stretch.

    Style Number/Barcode: 05102-0099

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Not So Basic Mini Dress

    Sure, you probably have your share of mini dresses. Now it's time for an of-the-moment upgrade! This ultra-chic mini features an off-the-shoulder elasticized neckline, gathered bodice and sleeves, a back zip, banded waist with back smocking, and pencil skirt with gather-drape detail. Dress is made from a mid-weight woven material with little to no stretch.

    Style Number/Barcode: 05101-0165

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral In Love Midi Dress
    Fall in love with this romantic floral midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline created by a knot front detail, a hidden back zipper and hook and eye closure, and an A-line mid-length fit with a front slit. The dress is composed of a lightweight woven fabric.

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0209

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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, 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: 05102-0159

    Category Name: Casual Dresses

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free