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.

  • Cute Agenda Long Sleeve Mini Dress

    For the girl with a busy social calendar—this long sleeve mini dress is polished yet practical, featuring a sleek turtleneck, flattering knotted design, and a body-hugging fit that takes you from latte runs to casual dinners downtown.

    Fit & Features

    • Smooth knit-lined stretch fabric
    • Fitted long sleeves
    • Turtle neckline
    • Front knotted design
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000922

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BROWN-2

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Flirty Energy Ruffle Skater Dress

    Playful yet sultry, this ruffle skater dress brings flirty energy with every move. The strappy open back and layered ruffled hem make it the perfect go-to for nights out or weekend plans.

    Fit & Features

    • Knit fabric
    • Sleeveless plunging V-neckline, bar strap detail
    • Tie-back halter spaghetti straps
    • Open back, lower tie-back spaghetti straps
    • Drop waist, tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000284

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easy Elegance A-Line Maxi Dress

    Chic, minimal, and made for any moment. This strapless maxi dress keeps it effortless with a fitted bodice and flowy skirt that moves with you—perfect for everything from beach strolls to brunch dates.

    Fit & Features

    • Smooth knit stretch fabric
    • Strapless tube neckline
    • Fitted bodice
    • Side pockets
    • A-line silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000281

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Instinct Tie Back Maxi Dress

    Romantic with a wild streak. This halter maxi dress mixes abstract rose and animal prints with a lace-trim bust and open tie back—perfect for day or night out plans.

    Fit & Features

    • Abstract animal rose print, mesh-lined fabric, moderate stretch
    • Halter plunge neckline, tie closure
    • Lace bust
    • Open tie back design
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000279

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fall Into Bloom Floral Maxi Dress

    Romantic drama, unlocked—this floral maxi dress hugs in all the right places before flowing into a dreamy silhouette. With strappy back details and bold blooms, it’s perfect for autumn weddings, cocktail nights, or a dressy birthday event.

    Fit & Features

    • Floral print, mesh-lined fabric
    • V-neckline
    • Spaghetti straps
    • Lace-up strappy open back
    • Curve-hugging silhouette
    • Floor-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000633

    Category Name: Casual Dresses

    Price: $7.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Untamed Allure Animal Print Cutout Maxi Dress

    For the nights you want all eyes on you. This sultry animal print cutout maxi dress hugs every curve and serves bold, untamed allure to keep you as the main focus.

    Fit & Features

    • Sheer mesh fabric with mini-length brushed knit lining, high stretch
    • Animal print
    • Sleeveless plunging halter neckline
    • Open back and sides, beaded accents, tie-back straps
    • Maxi-length hem, high-cut side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000278

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Quiet Luxe Off-The-Shoulder Maxi Dress

    Minimal effort, maximum impact. This off-the-shoulder maxi brings that sleek, sculpted vibe with a foldover neckline and curve-hugging silhouette that’s equal parts timeless and sultry.

    Fit & Features

    • Soft rib knit stretchy fabric
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves
    • Bodycon fit
    • Center back slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000183

    Category Name: Casual Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • After Hours Pinstripe Lace Mini Dress

    When the city lights come on, this dress takes over. The after-hours pinstripe lace mini serves sultry vibes with its corset fit, lace peekaboo, and flirty ruffle hem that’s made for late-night adventures.

    Fit & Features

    • Woven knit fabrication
    • Pinstripe pattern
    • Sleeveless sweetheart neckline
    • Sheer lace panel front detail
    • Tiered ruffled hemline
    • Mini length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000276

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Can’t Stop Staring Bodycon Midi Dress

    This sleek knit midi dress is giving heartbreaker energy! The ruched bodycon fit hugs in all the right places—perfect for date nights, girls’ nights, and spotlight-stealing entrances.

    Fit & Features

    • Smooth, stretchy knit fabric, knit lining
    • Sleeveless V-neckline, padded bra cups
    • Adjustable spaghetti straps
    • Ruching
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000153

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seasons Favorite Off-The-Shoulder Midi Dress

    A sweater dress, but elevated. With its foldover neckline and bodycon silhouette, this midi dress is a go-to for chic fall days or nights.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Off-the-shoulder folded neckline, cinched seam
    • Fitted long sleeves
    • Bodycon fit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000162

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Knit to Stun Open Back Mini Dress

    Keep your look playful and unexpected. This sweater mini dress keeps it sleek in the front, daring in the back. The cable knit keeps it cozy while the open back brings a hint of drama. perfect for fall slays.

    Fit & Features

    • Soft cable knit fabric with stretch
    • Mock neckline
    • Fitted long sleeves
    • Open back cutout design
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000460

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: RAISIN

    Available Size: XS, S, M, L

  • Wrapped Up Cute Off-The-Shoulder Dress

    Serving soft girl vibes with a flirty edge, this off-the-shoulder sweater dress hugs just right. Perfect for latte runs, weekend plans, or anytime you want cozy and cute in one move.

    Fit & Features

    • Soft cable knit fabric with stretch
    • Off-the-shoulder folded neckline
    • Fitted long sleeves
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000153

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: TAUPE, BROWN, BURGUNDY

    Available Size: S, M, L

    Product Badge:
    • Best Seller
  • Sunkissed and Stunned Halter Striped Maxi Dress

    This striped knit maxi brings the heat with a flirty open back, high front slit, and sheer vibes made for beach strolls or rooftop sips.

    Fit & Features

    • Striped texture knit design, sheer fabric
    • Halter plunge neckline, tie straps
    • Open back with tie strap
    • High front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000137

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Buttoned Up Charm Off-The-Shoulder Mini Dress

    Sophisticated with a sultry twist, this rib knit mini serves clean lines and gold button details that pop. Perfect for lunch dates, weekend looks, or when you want polished but playful.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Button front accents
    • Faux front pockets
    • Bodycon fit, mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000155

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Allure Cable Knit Mini Dress

    Chic meets snuggly. This off-the-shoulder sweater dress hugs your curves with cable-knit texture while keeping things flirty and polished—perfect for autumn plans, latte runs, or cozy dinners out.

    Fit & Features

    • Cable knit fabric, moderate stretch
    • Folded off-the-shoulder neckline
    • Fitted long sleeves
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000157

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paint The Night Abstract Open Back Midi Dress

    It’s giving art, elegance, and effortless wow. This slinky slip dress was made to glide through gallery nights, rooftop drinks, and every “who is she?” moment in between.

    Fit & Features

    • Abstract print, woven fabric
    • V-neckline
    • Spaghetti straps
    • Open strappy back
    • Curve-hugging silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000615

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt Alert Strapless Ruffle Mini Dress

    Bring the playful drama—this strapless mini dress hugs in all the right places with ruched detail and finishes with a flirty ruffle hem. Perfect for nights when you want your dress to do all the talking.

    Fit & Features

    • Smooth knit stretch fabric
    • Tube strapless neckline
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000274

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Darling Chiffon Ruffle Mini Dress

    Serving darling vibes on repeat. This floral mini dress is your go-to for twirling through summer plans, from picnics to shower celebrations—basically, anytime you wanna feel effortlessly pretty.

    Fit & Features

    • Floral print, chiffon lined fabric
    • V-neckline, ruffle trim
    • Adjustable spaghetti straps
    • Side zipper and hook-eye closure
    • Ruffled trim throughout
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000592

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Laced In Denim Strapless Mini Dress

    Meet the denim moment everyone’s talking about. This strapless corset mini cinches you in all the right places with lace-up sides and a structured bodice that gives instant shape. It’s flirty, bold, and begging to be admired at concerts or nights out.

    Fit & Features

    • Denim fabric with slight stretch
    • Strapless neckline
    • Corset-seamed bodice, back zipper and hook-eye closure
    • Rhinestone-embellished lace-up side plackets
    • Curved drop waist seam
    • Skater silhouette, frayed edge trim, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000273

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Girl Era Strapless Ponte Mini Dress

    This strapless mini dress is giving timeless cute with a flirty edge. Just add hoops and your fave platform shoes.

    Fit & Features

    • Ponte fabric, stretch lining
    • Strapless tube neckline
    • A-Line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000271

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Untamed Denim Strapless Mini Dress

    Bold, fitted, and a stunner. This strapless lace-up denim mini dress is the perfect piece for when you want to keep it casual but still turn heads.

    Fit & Features

    • Denim fabric
    • Strapless neckline
    • Back zipper closure
    • Front lace-up placket
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000272

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Drama Edit Ruffle Mini Dress

    Turn the charm all the way up in this halter mini dress that serves effortless allure. Designed with a flirty open back and tiered ruffle hem, it’s your go-to for nights that deserve a little drama.

    Fit & Features

    • Stretchy knit fabric
    • Cowl halter neckline
    • Open tie back
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000270

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Born to Be Bold Lace Leopard Maxi Dress

    This curve-hugging maxi brings the heat with sultry lace, sheer mesh, and sky-high slits—made for nights when playing it safe isn't on the mood board!

    Fit & Features

    • Leopard print, mesh fabric, stretchy knit lining
    • Lace sweetheart neckline, lace bust, lace shoulder straps
    • High side slits
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000265

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soft Curves Ahead Cap Sleeve Maxi Dress

    It’s giving sleek, sculpted, and effortlessly romantic. With a knotted bust, cap sleeves, and a chic back slit, this maxi is your low-key way to steal the spotlight at brunch, cocktail receptions, or date night!

    Fit & Features

    • Slinky knit fabric, soft knit stretchy lining
    • Cap sleeves
    • Sweetheart knotted neckline
    • Form-hugging silhouette
    • Center back slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000268

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale