Casual Dresses

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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.

  • Abstract Affair Mesh Mock Neck Dress

    Art meets attitude. This abstract mesh dress brings the heat with its sheer long sleeves, curve-hugging silhouette, and daring open back. It’s bold, lightweight, and made for the nights you want all eyes on you.

    Fit & Features

    • Abstract floral print, mesh-lined stretch fabric
    • Mock neckline, button closures
    • Sheer fitted long sleeves
    • Open back design
    • A-line mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000349

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lace Up and Take Over Mini Dress

    This lace corset mini is equal parts sweet and daring — with a deep V neckline, faux leather lace-up bodice, and tiered lace skirt that moves like you already own the room. It’s that perfect mix of romantic texture and confident structure.

    Fit & Features

    • Lace-lined bodice with plunging V-neckline
    • Sleeveless design, adjustable shoulder straps
    • Faux leather corset waist with grommet lace-up front
    • Back zipper and hook-eye closure
    • Drop-waist seam
    • Tiered lace-lined mini skirt
    • Runs true to size

    Style Number/Barcode: 05102-000352

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild Plans Animal Print Mesh Halter Mini Dress

    Wild plans call for a dress that knows exactly what it’s doing. This animal print mesh halter mini dress hugs through the waist with ruched shaping and flares out with playful tiers that move with you from dinner reservations to wherever the night decides to go.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Animal print
    • Sleeveless halter neckline with tie-back straps, partially open back
    • Metal hardware accent, keyhole bust cutout
    • Ruched drop waist
    • Tiered ruffled design, mini-length A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-000350

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Late Arrival Abstract Maxi Dress

    Moody, sculpted, and impossible to ignore. This maxi dress hugs in all the right places with a plunging neckline and statement ring detail that feels made for vacations, sunset dinners, and GNOs!

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Strapless neckline with cutout and hardware inserts
    • Form-hugging silhouette
    • Maxi-length hemline
    • Runs true to size

    Style Number/Barcode: 05102-000348

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Twist of Fate Mini Dress

    Sleek, sculpted, and a little unexpected. This halter mini dress stuns with its high neckline, open back, and drop waist silhouette that flatters every curve while keeping things effortlessly chic from mimosa brunches to date nights.

    Fit & Features

    • Slinky knit fabric, stretchy knit lining
    • High halter neckline with tie closure
    • Open back
    • Drop waist seam
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000577

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: L

  • Wild At Heart Lace Leopard A-Line Mini Dress

    Turn up the heat in this sultry leopard mini dress. The fierce leopard print, lace bust, and flared skirt make it the perfect mix of wild and romantic. Whether it’s a night out or a wine bar evening, this dress brings all the allure.

    Fit & Features

    • Leopard print, mesh fabric, stretchy knit lining
    • Lace bust sweetheart neckline, underwire cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000353

    Category Name: Casual Dresses

    Price: $18.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fall for Knit Long Sleeve Mini Dress

    Cozy, flattering, and totally fall-coded. This ribbed knit mini dress features a sweetheart neckline and subtle ruching that shapes your silhouette while keeping it soft and effortless. Pair it with knee-high boots for a perfect fall day out.

    Fit & Features

    • Hacci rib knit stretch fabric
    • Sweetheart neckline, ruched bust seam
    • Fitted long sleeves
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000354

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Striking Lattice Side Mesh Maxi Dress

    The statement is built into the details. This strapless mesh dress pairs sleek hardware with an elongated fit, making it an easy standout for vacations or night out plans.

    Fit & Features

    • Multi-print, lined mesh fabric with stretch
    • Strapless sweetheart neckline
    • Front keyhole cutout with hardware accent
    • Side lattice tie details
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000356

    Category Name: Casual Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Flirty And Flowy Ribbed Knit Strapless Skater Dress

    Ready before the group chat even replies. This ribbed knit strapless skater dress hugs through the bodice with a flirty drop waist and flowy skirt that moves with you from brunch plans to last-minute invites.

    Fit & Features

    • Ribbed knit fabric, high stretch
      Strapless straight-across neckline
    • Drop waist design
    • Godet detailing
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000008

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutest Plans Floral Eyelet Corset Skater Dress

    Your group chat is already asking where you got it. This floral eyelet corset skater dress cinches you in with a sculpted bodice and flares out into the cutest twirl-ready silhouette for brunch dates, garden parties, and every camera roll moment in between.

    Fit & Features

    • Floral eyelet woven fabric, tulle and knit linings
    • Sleeveless sweetheart neckline, ruched bust, small cutout, tie-front detail
    • Underwire bust support
    • Tie-shoulder straps, side zipper and hook-eye closure
    • Corset bodice with boning, V-shaped waist, ruffled trim
    • Lace-up back design, short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000130

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunkissed Curve Knit Midi Dress

    This striped midi dress was made to highlight every curve with a sculpting rib texture, front cutout detail, and side slit. Dress it up with heels for a night out or keep it elevated with sandals for a chic daytime moment.

    Fit & Features

    • Striped print, rib knit fabric
    • Sweetheart neckline, cutout bust accent
    • Adjustable spaghetti straps
    • Bodycon fit
    • Dual side slits
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000084

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lace-Up Moment Sheer Long Sleeve Mini Dress

    Bring the drama without even trying—this long sleeve mini dress is sheer perfection. With a lace-up front and ruffle trim, it’s the flirty and fab style your night-out look needs.

    Fit & Features

    • Sheer mesh fabric with partial knit lining, high stretch
    • Plunging V-neckline, lace-up front with tie closure, ruffle trim
    • Sheer long fitted sleeves
    • Hidden back zipper with hook-eye closure
    • Drop waist seam
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000401

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Petal Noir Floral Chiffon Maxi Dress

    This halter maxi dress stuns with a draped cowl neckline, bold floral print, and a daring open back that leaves a lasting impression. Flowing and form-flattering, it’s your go-to for romantic date nights and elevated occasions.

    Fit & Features

    • Floral print, chiffon-lined fabric
    • Halter cowl neckline
    • Open back design, zipper and hook-eye closure
    • Curve-hugging silhouette
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000577

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    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
  • 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
  • Weekend Plans Ruffle A-Line Romper

    Your plans just found their outfit—this romper is all about fun with a flirty edge. The tie-back halter straps, ruffle overlay, and A-line fit make it a go-to for nights out or weekend parties.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Sleeveless V-neckline
    • Tie-back halter straps, partially open back
    • Ruching, drop waist
    • Mini-length tiered ruffle overlay, hidden fitted shorts
    • Romper in size small is 29" shoulder to hem with a 9" front rise and a 1" inseam
    • Runs true to size

    Style Number/Barcode: 06503-000155

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Plans Plaid Romper

    Sweet, flirty, and made for your next “what should I wear?” moment. This strapless plaid romper brings easy charm with its ruched bodice, ruffle skirt detail, and bow accent that seals the deal.

    Fit & Features

    • Plaid print, stretchy knit fabric
    • Strapless neckline with front bow detail
    • Ruched, fitted bodice
    • Tiered ruffle mini-length hem, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000164

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling Off-Shoulder Skater Dress

    This chiffon mini dress features an off-the-shoulder ruffle neckline with delicate lace trim and a flirty skater skirt, creating a dreamy silhouette perfect for family brunches, bridal events, and dressy occasions.

    Fit & Features

    • Chiffon-lined fabric
    • Ruffle trim off-the-shoulder neckline, tie-front
    • Corset-seamed bodice
    • Skater silhouette, drop waist seam
    • Lace trim mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000684

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soft Stunner Off-The-Shoulder Mini Dress

    A little cozy, a little glam—this off-the-shoulder knit mini brings that effortless “I just threw this on” sparkle. The foldover neckline and body-hugging fit keep things soft, sleek, and low-key irresistible.

    Fit & Features

    • Rib knit stretchy fabric with shimmer
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000197

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Attitude Ribbed Knit Off-The-Shoulder Midi Dress

    A sleek off-the-shoulder midi dress with just the right dose of attitude. The ribbed knit snatches softly, the cutout adds that chic twist, and the midi length keeps the whole look effortlessly elevated.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Off-the-shoulder sweetheart neckline, no-slip strip, center hardware accent
    • Keyhole cutout below the bust
    • Long fitted sleeves
    • High-cut front slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000222

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Twist Bodycon Mini Dress

    Meet the mini that serves soft vibes in the front and a major moment in the back. This long sleeve dress hugs your shape with a sleek, stretchy feel while the scoop neckline keeps things subtly flirty. But the real plot twist? A double-twist open-back design that turns every exit into an entrance.

    Fit & Features

    • Textured knit stretch fabric
    • Scoop neckline
    • Fitted long sleeves
    • Statement cutout back, double-twist design
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000220

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Unforgettable Entrance Plunge Neck Maxi Dress

    This maxi dress doesn’t blend in—it arrives. This plunging cowl neck maxi dress drapes smoothly through the body with a halter neckline that feels bold, polished, and intentionally striking. Pair with heels for date night, dressy celebrations, or a sultry vacation look.

    Fit & Features

    • Smooth knit-lined fabric with high stretch
    • Halter neckline with plunging cowl front
    • Open back with adjustable tie closure
    • Fitted bodice that skims the waist and hips
    • High side slit for movement
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000736

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty In Motion Halter Mini Dress

    Caught a vibe and dressed for it. This halter mini dress cinches at the waist with a flowy A-line skirt that moves with you—perfect for weekends that start with plans and end wherever.

    Fit & Features

    • Smooth stretch material
    • Halter neckline with open back, tie straps
    • Ruched waist detail
    • A-line mini silhouette with pleated skirt
    • Runs true to size

    Style Number/Barcode: 05102-000358

    Category Name: Casual Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: ROYAL

    Available Size: XS, S, M, L