Dark Cherry Outfits

Elevate your Winter style with dark cherry outfits that are incredibly chic and alluring. From cozy burgundy sweaters to wine-colored layering tops, these luxe fall outfits are all about embracing those deep, rich shades. Opt for a merlot sweater dress with a sleek blazer jacket that transitions effortlessly from day to night. Whether you’re layering up or going for a bold, monochrome look, these outfits will have you stepping out in sophisticated fall fashion that’s as cozy as it is chic.

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DARK CHERRY OUTFITS
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Elevate Your Winter Wardrobe With Dark Red Outfits

Make a bold statement this season with Windsor’s stunning collection of dark cherry outfits showcasing statement-making red apparel. From rich cherry red dresses to dark cherry outfits and deep burgundy shades, this collection offers perfect options for women's workwear, formal events, or Winter Formal. Explore a range of trendy pieces, including dark red skirts, tops, and all-occasion dresses. Complete your look with cropped sweaters, moto jackets, boots, beanies, purses, and more for a cohesive outfit. Capture trendy mob wife outfits for a vibe with an elegant touch.

Shop our updated collection of women's winter outfits at Windsor online, in-app, or in-store at over 350 retail locations in the US and Canada. Whether you're channeling classic glam or adding edge to your look, these outfits are ideal for creating the ultimate 2024-2025 Winter look.

  • Glam Era Rhinestone Bow Spiral Strap Stiletto Heels

    Fit & Features

    • Stiletto heel
    • Open almond toe
    • Dual straps across the foot, spiral strap design up the leg
    • Rhinestone embellishments, bow accents
    • Open back
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-5125

    Category Name: Dark Cherry Outfits

    Price: $40.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Can I Be Mean For A Second Script Baseball Cap

    Fit & Features

    • Cotton material
    • Baseball cap fit
    • Script that reads "Can I Be For A Second"
    • Adjustable back with metal hardware

    Style Number/Barcode: 07302-1745

    Category Name: Dark Cherry Outfits

    Price: $12.90

    Availability: Out of Stock

  • Ribbed Knit Crew Neck Bodycon Mini Dress

    Keep it casually chic in a mini dress that is a total must-have! The short dress features a crew neckline with a racerback design, a mini-length hem, and is composed of a form-hugging ribbed knit fabric. Put your hair in an updo and style with strappy mules for a cute look!

    Fit & Features

    • Crew neckline
    • Sleeveless bodice 
    • Racerback design
    • Mini-length hem
    • Ribbed knit fabric, fully lined 
    • Form-hugging fit, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-0689

    Category Name: Dark Cherry Outfits

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Glam Under-The-Knee Stiletto Boots

    Fit & Features

    • Stiletto heel
    • Faux patent leather material
    • Under-the-knee fit
    • Inner zipper closure
    • Closed pointed toe
    • Runs true to size

    Style Number/Barcode: 07402-1063

    Category Name: Dark Cherry Outfits

    Price: $46.90

    Availability: In Stock

    Available Color: WINE

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9

    Product Badge:
    • Best Seller
  • Adorable Fave Leopard Satin Mini Bubble Skirt

    Fit & Features

    • Satin woven fabric
    • Leopard print
    • High-rise waist
    • Pleating
    • Mini-length bubble hem
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 06401-0723

    Category Name: Dark Cherry Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: XS, S, M, L

  • Sophisticated In Chiffon Strapless Top

    Keep it sophisticated in a chiffon top that is perfect for creating a trendy workwear look or a night out with friends. This long-sleeve crop top features a flattering off-the-shoulder neckline and a wired V-shaped bust with pleated detailing. This elegant going-out top is made of lightweight chiffon fabric and is lined with a stretchy knit fabric that shapes your curves. Style this long sleeve top with high-waist trousers pants with strappy platform heels for an elevated night-out look.

    Fit & Features

    • Off-the-shoulder neckline
    • Wired V notch along the bust
    • Pleated details throughout
    • Long peasant sleeves
    • Crepe/chiffon-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06003-1189

    Category Name: Dark Cherry Outfits

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

  • Lyra Velvet One-Shoulder Rhinestone Cuff Mermaid Dress

    Special Occasion

    Radiate luxe glamour in the Lyra mermaid dress designed with smooth velvet fabric perfect for a formal holiday soiree. It features a one-shoulder neckline, a long fitted sleeve with a glitzy rhinestone-embellished cuff, ruched seams to accentuate your stunning curves, and a floor-length mermaid silhouette accented with a high-cut front slit.

    Fit & Features

    • Velvet fabric with knit lining, moderate stretch
    • One-shoulder neckline
    • Long fitted sleeve with rhinestone embellished cuff, slit with dual rhinestone buttons
    • Back zipper with hook-eye closure
    • Ruched seams
    • High front slit, floor-length mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05002-8665

    Category Name: Dark Cherry Outfits

    Price: $79.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

  • Clarice Sequin Beaded Lace A-Line Mini Dress

    Special Occasion

    Show off your beauty in the adorable Clarice formal mini dress designed with lined lace fabric and clear sequin and beaded embroidery for a soft glam look. It features a sleeveless square neckline with an underbust seam, adjustable tank straps for a customized fit, and a short A-line silhouette.

    Fit & Features

    • Lined lace fabric
    • Clear sequin and beaded embroidery
    • Square neckline, underbust seam
    • Adjustable tank shoulder straps
    • Back zipper closure
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05001-2518

    Category Name: Dark Cherry Outfits

    Price: $79.90

    Availability: In Stock

    Available Color: WHITE, PINK

    Available Size: XS, S, M, L, XL

  • Trendy Textures Long Sleeve Mini Dress

    Keep it trendy chic in a mini dress that features a fab textured design, an off-the-shoulder neckline with a foldover accent, and fitted long sleeves. Complete outfit with heels for the perfect date night look!

    Fit & Features

    • Textured mesh fabrication, stretchy knit lining
    • Off-the-shoulder neckline
    • Foldover accent at the bust
    • Fitted long sleeves
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05101-3722

    Category Name: Dark Cherry Outfits

    Price: $38.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • Freida Velvet Ruffled One-Shoulder Mermaid Dress

    Special Occasion

    Exude bold elegance in the Freida mermaid dress designed with luxe smooth velvet fabric for your next black-tie affair. It features a one-shoulder neckline with a dramatic ruffled design, chic pleating at the bodice and waist, a faux wrap-front creating a high slit, and a floor-length mermaid silhouette to hug your curves.

    Fit & Features

    • Velvet fabric with top knit lining, moderate stretch
    • One-shoulder neckline with ruffled design, no-slip strip, padded bust
    • Pleating at the bodice and waist
    • Back zipper with hook-eye closure
    • Faux wrap-front design, high slit
    • Floor-length mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05002-8709

    Category Name: Dark Cherry Outfits

    Price: $89.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L, XL

  • Sultry Chic Flocked Floral Sheer Mesh Top

    Fit & Features

    • Sheer mesh fabric with velvet flocked floral pattern, moderate stretch
    • Cowl neckline
    • Hidden sheer mesh bralette with underwire, eyelash lace trim, back hook-eye closures
    • Adjustable spaghetti straps
    • Ruched side seams
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-5522

    Category Name: Dark Cherry Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Myra Formal High Slit Dress

    Special Occasion 

    The Myra formal dress brings all the luxe, elevating your evening with timeless elegance! The long formal dress features a sweetheart neck with a built-in padded bust that offers support to her flattering, off-the-shoulder neckline with short-sleeve cuffs.  The flattering, relaxed fit bodice leads to a curve-hugging floor-length mermaid silhouette that is accented with a sexy high side slit. Complete your captivating formal outfit with dazzling duster earrings and open-toe heels.

    Fit & Features 

    • Off-shoulder neckline, short-sleeve cuffs
    • Sweetheart neck, built-in padded bust
    • Back zipper, hook-eye closure
    • Floor-length A-line silhouette
    • High side slit
    • Lined crepe fabric
    • Curve-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05002-2403

    Category Name: Dark Cherry Outfits

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Energy Glitter Mesh Cutout Mini Dress

    Fit & Features

    • Sheer glitter mesh fabric with partial knit lining, plenty of stretch
    • Deep V-neckline with twist-front design, waist cutout
    • Sheer long balloon sleeves with elastic cinched hems
    • High waist, ruched side seams
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5808

    Category Name: Dark Cherry Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S, M, L

  • Flawless Allure Crepe Tube Mini Dress

    Keep it flawless in a mini dress that features a sleeveless square neckline and faux front pockets with trendy flap closure. Complete look with a blazer for the perfect workwear outfit. 

    Fit & Features

    • Woven crepe fabrication, moderate stretch, stretchy knit lining
    • Sleeveless square neckline
    • Faux front pockets with flap closure
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05101-3811

    Category Name: Dark Cherry Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: GRAY

    Available Size: XS, S, M, L

  • Classic Charm Plaid Wrap Skort

    Shop Matching Jacket: Classic Charm Plaid Trench Coat

    Fit & Features

    • Faux wool fabrication
    • Mid-rise waist, back zipper and hook-eye closure
    • Mini skirt wrap overlay
    • Hidden stretchy knit shorts
    • Plaid pattern
    • Runs true to size

    Style Number/Barcode: 06403-1065

    Category Name: Dark Cherry Outfits

    Price: $32.90

    Availability: In Stock

    Available Color: GRAY

    Available Size: XS, S, M, L, XL

    Product Badge:
    • Best Seller
  • Petal Perfection Floral Ruched Midi Dress

    Make a charming impression in a midi dress that features a sleeveless cowl neckline with a bralette-like lace trim, adjustable spaghetti straps, a floral print, and ruching throughout. Complete the date night outfit with stiletto heels. 

    Fit & Features

    • Lined mesh fabrication
    • Sleeveless cowl neckline, lace trim
    • Adjustable spaghetti straps
    • Floral print
    • Ruching
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3794

    Category Name: Dark Cherry Outfits

    Price: $44.90

    Availability: In Stock

    Available Color: PLUM

    Available Size: XS, S, M, L

  • Fierce Aura Wide-Leg Leopard Print Denim Jeans

    Fit & Features

    • Denim fabrication
    • High-rise waist
    • Single-button and hidden zipper closure
    • Traditional five-pocket with belt loop design
    • Leopard print
    • Wide-leg hem
    • Runs true to size

    Style Number/Barcode: 06602-0540

    Category Name: Dark Cherry Outfits

    Price: $49.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: XS, S, M, L

  • Chic Status Brocade Satin Strapless Corset Top

    Fit & Features

    • Satin woven fabric with tonal brocade pattern
    • Strapless sweetheart neckline
    • Flexible boning
    • Front hook-eye closures
    • Lace-up back
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2670

    Category Name: Dark Cherry Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: BURGUNDY, BEIGE

    Available Size: XS, S, M, L

  • Sculpted Chic Ruched Midi Skirt

    Shop Matching Top: Sculpted Chic Ruched Halter Top

    Fit & Features

    • Smooth knit fabric with mini-length knit lining, plenty of stretch
    • High-rise waist
    • Ruching 
    • High side-slit with drawstring
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-1083

    Category Name: Dark Cherry Outfits

    Price: $29.90

    Availability: In Stock

    Available Color: PLUM

    Available Size: XS, S, M, L

  • Level Up Sleek Faux Leather Strapless Corset Top

    Fit & Features

    • Faux leather lined fabric
    • Strapless sweetheart neckline
    • Flexible boning, front hook-eye closures
    • Lace-up back with satin ribbon
    • Mid-length angled hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-2668

    Category Name: Dark Cherry Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Sultry Era Satin Strapless Corset Top

    Fit & Features

    • Satin woven fabric
    • Strapless sweetheart neckline
    • Flexible boning, front hook-eye closures
    • Lace-up back with satin ribbon
    • Mid-length angled hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-2665

    Category Name: Dark Cherry Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: TEAL

    Available Size: XS, S, M, L

  • Sculpted Chic Ruched Halter Top

    Shop Matching Bottoms: Sculpted Chic Ruched Midi Skirt

    Fit & Features

    • Smooth knit fabric with plenty of stretch
    • Cowl neckline with halter tie-back spaghetti straps, beaded detailing
    • Ruching
    • Open back with lower tie-back spaghetti straps, beaded detailing
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5554

    Category Name: Dark Cherry Outfits

    Price: $26.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S, M, L

  • Sultry And Luxe Glitter Velvet Bodycon Mini Dress

    Show up looking sultry and luxe in this glitter velvet mini dress featuring a sleeveless sweetheart neckline with a wrap-front design and front pleated detailing to accentuate your stunning curves. The short bodycon silhouette makes it perfect for a night out paired with stiletto heels.

    Fit & Features

    • Glitter velvet fabric, moderate stretch
    • Sweetheart neckline, wrap-front design
    • Spaghetti straps
    • Pleating
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5861

    Category Name: Dark Cherry Outfits

    Price: $36.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

  • Luxe Impression Velvet Bubble Skort

    Fit & Features

    • Velvet fabrication
    • Drop-waist design
    • Pleats
    • Bubble skirt overlay 
    • Hidden shorts
    • Runs true to size

    Style Number/Barcode: 06403-1078

    Category Name: Dark Cherry Outfits

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L