Casual Dresses

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.

  • Stripe Right Mock Neck Mini Dress

    We're crushing on stripes and lovin' the mock neck on this mini. Toss on a leather jacket and a pair of white sneakers, and you're all ready to mingle! 

    Fits & Features

    • Mock Neckline
    • Fitted Long Sleeves
    • Mini Length Silhouette
    • Ribbed Knit With An All Over Stripe Print 
    • Bodycon Fit I Plenty Of Stretch

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0320

    Category Name: Casual Dresses

    Price: $9.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Dream Eyelash Knit Mini Dress

    Look like a total dream babe in this adorable eyelash knit mini! The soft knit fabric has plenty of stretch for a total comfy form hugging fit.

    Fit & Features

    • Off the shoulder neckline
    • Short sleeves
    • Mid-thigh length hem
    • Fuzzy eyelash ribbed knit fabric

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

    Style Number/Barcode: 06005-0196

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • V-Neck Ruched Midi Dress
    Bring some style to the basic midi with this ruched detail dress! It features long fitted sleeves, a notch front V neckline, ruching along the sides, and a mid-length, curve hugging fit. The dress is composed of a stretchy knit fabric.

    Style Number/Barcode: 05102-0319

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rianna One Shoulder Heat Stone Dress

    Special Occasion 

    Light up the night with dazzling heat stones as you wow in our Rianna dress!

    Fit & Features 

    • One Shoulder Neckline
    • Ruched Side Seam 
    • Heat Stones
    • Lined Mesh 
    • Midi Silhouette 
    • Form Hugging Fit 
    • Moderate Stretch 

     Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0268

    Category Name: Casual Dresses

    Price: $24.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Turtleneck Long Sleeve Ribbed Knit Mini Dress

    Bundle up to this ribbed knit mini for those cool nights. This cozy number features a turtleneck, long sleeves, scalloped hem, and mini length silhouette. The ribbed knit construction offers ample stretch. Zipper not included. 

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

    Style Number/Barcode: 05102-0308

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Snap Snap Slay Ribbed Sweater Dress

    Oh snap she came to play! This sexy sweater dress is designed with a mock neckline, long sleeves, and a mid length hem that hits right passed the knee. Dress has a side slit detailing with faux snap buttons that lead down. Composed of a ribbed knit material that offers a form fit with moderate stretch.

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small

    Style Number/Barcode: 06005-0193

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Julissa Knot Front Heat Stone Mini Dress

    Special Occasion 

    Sparkle and glitter like the night sky in our statement Julissa! 

    Fits & Features

    • Plunging V Neckline With Twist Front Design
    • Adjustable Spaghetti Straps
    • Zipper With Hook & Eye Closure At Back
    • Ruching Along The Sides & Center Back
    • Mini Length Silhouette
    • Fully Lined, Mesh Knit Fabric With Heat Stone Embellishments All Over
    • Curve Hugging Fit With Ample Stretch 

     

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

     

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0249

    Category Name: Casual Dresses

    Price: $25.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sophisticated Faux Suede Midi Dress

    Keep it sophisticated in statement faux suede! The mini dress features a sleeveless bodice, a scoop neckline, spaghetti straps, vertical princess seams that create an hourglass illusion and a midi length silhouette with a side slit. The back features a sexy keyhole accent to show off more than a hint of skin! Dress is composed of a faux suede fabric that offers a form hugging fit with slight stretch.

     

    Style Number/Barcode: 05101-0276

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Miss Me Mini Dress

    Get tied to this cute mini! It features a plunging V neckline with a tie front accent, fitted long sleeves, a sexy mid-drift cut out and a mini length silhouette. Dress is composed of a ribbed knit fabric that offers a curve hugging fit with a moderate stretch.

    Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0307

    Category Name: Casual Dresses

    Price: $13.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Danya Scuba Floral A-Line Dress

    Special Occasion

    Sway and sashay your way around the dance floor with our beautiful Danya! Her delicate floral prints add a flirty feminine touch.

    Fits & Features

    • Spaghetti Straps 
    • Plunging V Neckline I Princess Seams 
    • Zipper With Hook & Eye Closure At The Back 
    • A-Line, Floor Length Hem I High Slit At The Front
    • Smooth Scuba Knit Fabric With Floral Prints Throughout 
    • Form-Hugging Fit I Moderate Stretch

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-0355

    Category Name: Casual Dresses

    Price: $19.97 $56.90

    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 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
  • 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
  • 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
  • Plaid Knit Mini Dress
    Pretty plaid is the way to go! This knit mini dress features a sleeveless bodice, spaghetti straps, a scoop neck, a square back, and a short, curve hugging fit. The dress offers plenty of stretch and includes a knit lining.

    Style Number/Barcode: 05102-0302

    Category Name: Casual Dresses

    Price: $12.97 $31.90

    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
  • Rock On Distressed Tunic Top
    Hey, wild child! Show off your spirited side in this distressed tunic top (or be bold and make it a mini!). Top features a crew neck, short sleeves, shredded V detail at chest and hem, and a large "Rock On" contrast graphic. Top is cut for a slim fit and made from an ultra-soft rayon knit with moderate stretch.

    Style Number/Barcode: 06002-0188

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Spot On A-Line Midi Dress

    Throw on a cozy knit sweater, add a pair of boots, and your outfit will be looking spot on! Showcasing a smudge spot print, the sleeveless bodice features adjustable shoulder straps and a v-neckline. Decorative buttons trail down the front, leading to a center split. Linen crafted, this dress features an A-line silhouette and offers little to no stretch. Zipper at center back. 

     Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0301

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    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
  • Katelyn Ruched Midi Dress

    Chic and fab, the Katelyn ruched midi dress is a new go-to. She features a sleeveless bodice, a Y neck with halter straps, a knot detail, and a front keyhole cut out, and a square back with a zipper closure. Her high waist band leads to a curve hugging skirt with ruched side details and a mid-length hem. The dress is composed of a stretchy knit fabric with a pretty sheen.

    Model is 5'8" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small. 

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0238

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • 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
  • 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
  • Vacay Vibes Crochet Knit Maxi Dress

    Channel those vacay vibes with a maxi dress that brings those resort vibes! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a lower back keyhole with tie-back straps, and a maxi length silhouette. The dress is composed of a lined gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Lower back keyhole with tie-back straps
    • Maxi length silhouette
    • Lined gauze knit fabric
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0297

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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