Dark Cherry Outfits

Elevate your fall 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.

SHOW FILTER

SORT:

FEATURED
SIZE
COLOR
PRICE
ALL FILTERS
SORT
×
×
×
×



SEE RESULTS
Loading...
×
DARK CHERRY OUTFITS
All Filters
Sort By:
FEATURED
SEE RESULTS

Elevate Your Fall & 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, homecoming, 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 fall outfits at Windsor online or in-store at over 350 retail locations in US and Canada. Whether you're channeling classic glam or adding edge to your look, these outfits are ideal for creating the ultimate 2024 Fall or Winter look.

  • Delightful Impact Corset Slit Chiffon Midi Dress

    A sleeveless chiffon midi dress boasts a sweetheart tie neckline, a corset-inspired bodice with a lace-up back, and a front slit for a stylish flair. Perfect for styling with heels for a dressy occasion.

    Fit & Features

    • Burnout pattern, chiffon fabric lined with stretchy knit
    • Sweetheart tie neckline, shoulder straps
    • Underwire bust, side zipper and hook-eye closure
    • Corset bodice, lace-up back
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3591

    Category Name: Dark Cherry Outfits

    Price: $48.90

    Availability: Out of Stock

    Product Badge:
  • Adorably Sleek Bow Strap Kitten Heel Pumps

    Adorable and chic, these sleek patent faux leather pumps feature a closed pointed toe, a bow accent strap, an adjustable sling-back strap, and a short kitten heel. Style with an oversized blazer.

    Fit & Features

    • Short kitten heel
    • Patent faux leather material
    • Closed pointed toe
    • Bow strap
    • Thin adjustable sling-back strap, buckle detail
    • Runs true to size

    Style Number/Barcode: 07401-5165

    Category Name: Dark Cherry Outfits

    Price: $32.90

    Availability: In Stock

    Available Color: WINE

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

    Product Badge:
  • Sultry Style Lace Trim Sheer Stockings

    Add a sultry style to your party look with these sexy sheer stockings featuring a thigh-high design with a dainty lace trim at the top. Pair with a mini dress and heels!

    Fit & Features

    • Thigh-high sheer design
    • Lace trim

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07306-0368

    Category Name: Dark Cherry Outfits

    Price: $9.90

    Availability: In Stock

    Available Color: BLACK, WHITE

    Available Size: NS

    Product Badge:
    • New Arrival
  • Spooky Babe Spiderweb Sheer Fishnet Tights

    Amp up your Halloween costume with these spooky and sultry sheer fishnet tights featuring a detailed spider and spiderweb design down the front. Perfect for leveling up your witch look, pair with a black mini dress and platform heels!

    Fit & Features

    • Sheer fishnet material
    • High-rise waist
    • Spider and spiderweb design 
    • Form-hugging fit

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07306-0376

    Category Name: Dark Cherry Outfits

    Price: $12.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

    Product Badge:
    • New Arrival
  • Adorable And Chic Pearl Detail Hair Bow Clip

    So adorable, this large bow hair clip is designed with a sheer tulle material embellished with chic faux pearl accents. Includes a secure barrette clip closure.

    Fit & Features

    • Large bow design
    • Sheer tulle material
    • Faux pearl embellishments
    • Barrette clip

    Style Number/Barcode: 07006-0564

    Category Name: Dark Cherry Outfits

    Price: $10.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

    Product Badge:
    • New Arrival
  • Sultry Strapless Floral Jacquard Corset Top

    Strapless and sultry, this floral jacquard corset top is perfect for elevating your date night look! It features front hook-eye closures with flexible boning for structure, a lace-up back for a customized fit, and an angled cropped hem for that snatched silhouette.

    Fit & Features

    • Floral jacquard woven fabric
    • Strapless straight neckline
    • Front hook-eye closures, flexible boning
    • Lace-up back
    • Angled cropped hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-2664

    Category Name: Dark Cherry Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Cute And Cozy Off-Shoulder Knit Sweater

    Keep it cute and cozy in this soft knit sweater featuring an asymmetric off-shoulder neckline with long dolman-style sleeves and a mid-length ribbed hem with a relaxed fit. Complete your fall 'fit with a plaid skirt and ankle booties.

    Fit & Features

    • Soft knit fabric with plenty of stretch
    • Asymmetric off-shoulder neckline
    • Long dolman sleeves
    • Mid-length ribbed hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06005-2068

    Category Name: Dark Cherry Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: BURGUNDY, OATMEAL

    Available Size: XS, S, M, L

    Product Badge:
  • Classic And Cozy Striped Knit Oversized Cardigan

    Elevate your cozy looks with this classic striped ribbed knit cardigan designed with a chic oversized silhouette. It features a V-neckline with a button-down front, long sleeves with tapered hems, and a mid-length relaxed fit to pair with pleated mini skirts and knee-high boots.

    Fit & Features

    • Ribbed knit fabric
    • Striped pattern
    • V-neckline
    • Button-down front
    • Long sleeves with tapered hems
    • Mid-length hem
    • Oversized fit

    Style Number/Barcode: 06005-2211

    Category Name: Dark Cherry Outfits

    Price: $52.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S/M, M/L

    Product Badge:
    • New Arrival
  • Perfectly Cozy Chunky Knit Cardigan

    This perfectly cozy cardigan is designed with a chunky ribbed knit fabric for that comfy and chic vibe. It features a V-neckline, a complete button-down front, long dolman-style sleeves, and a mid-length hem with a relaxed fit.

    Fit & Features

    • Chunky ribbed knit fabric
    • V-neckline
    • Complete button-down front
    • Long dolman sleeves
    • Mid-length hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06005-2209

    Category Name: Dark Cherry Outfits

    Price: $54.90

    Availability: In Stock

    Available Color: GRAY

    Available Size: S/M, M/L

    Product Badge:
    • New Arrival
  • Kaleigh Off Shoulder Dress

    Special Occasion

    Turn heads in this sexy, off-the-shoulder formal dress. Draped to perfection, the silky-smooth knit fabric elegantly wraps around your shoulders and hugs your body's curves, accentuating an hourglass figure. This stunning, floor-length gown strikes the perfect balance between sophistication and allure, with its sculptural ruched detailing and bold, thigh-high slit. Style this captivating dress with strappy heels and a sleek satin clutch for an unforgettable evening look.

    Fit & Features

    • Asymmetrical off-the-shoulder neckline
    • Ruched side detailing
    • High side slit
    • Form-hugging fit
    • Smooth knit fabric, plenty of stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05002-6571

    Category Name: Dark Cherry Outfits

    Price: $9.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On-Trend Distressed Knit Mock Neck Sweater

    This cute and trendy ribbed knit sweater features a mock neckline, long dolman-style sleeves, and a distressed cropped hem with a relaxed fit. Perf for everyday, pair with high-rise jeans and sneakers.

    Fit & Features

    • Knit fabric with ribbed hems
    • Mock neckline
    • Long dolman sleeves
    • Distressed cropped hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06005-2207

    Category Name: Dark Cherry Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • New Arrival
  • Wrapped In Stylish Crepe Mini Dress

    Get all wrapped up in this stylish sleek crepe dress. Dance the night away at that upcoming wedding or ring in the festivities in this statement wrap mini dress. The dress features a sleeveless square neckline, spaghetti straps, and a ruched wrap silhouette that hugs curves in all the right places. The dress is composed of a crepe fabric that offers a moderate stretch. Complete your look with rhinestone earrings and trendy mules.

    Fit & Features

    • Sleeveless square neckline, square back design
    • Spaghetti straps
    • Strapless bra recommended
    • Ruched wrap-front detail 
    • Mini-length bodycon silhouette 
    • Crepe knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-3794

    Category Name: Dark Cherry Outfits

    Price: $5.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Snatched Strapless Lace Trim Corset Top

    Chic and snatched will be your vibe in this woven corset designed with a dainty lace trim at the strapless neckline. It features front hook-eye closures and flexible boning for structure, a lace-up back for a customized fit, and an angled cropped hem perfect for pairing with high-rise bottoms.

    Fit & Features

    • Smooth woven fabric with lace trim and knit lining, minimal stretch
    • Strapless straight neckline
    • Front hook-eye closures, flexible boning
    • Lace-up back
    • Angled cropped hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-2654

    Category Name: Dark Cherry Outfits

    Price: $36.90

    Availability: In Stock

    Available Color: PLUM

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Edgy Mood High Rise Skinny Jeans

    Fit & Features

    • Denim knit fabrication
    • High-rise waist
    • Single button with hidden zipper closure
    • Traditional five-pocket with belt loop design
    • Slit accents at knees
    • Skinny leg fit 
    • Runs true to size

    Style Number/Barcode: 06602-0530

    Category Name: Dark Cherry Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 1, 3, 5, 7, 9, 11, 13

    Product Badge:
    • New Arrival
  • Sorry I'm Late, I Stopped For Coffee Baseball Cap

    The perfect baseball cap for all coffee lovers! This adorable hat features an embroidered script reading, "sorry I'm late, I stopped for coffee," and includes a back adjustable strap with a metal buckle.

    Fit & Features

    • Classic baseball cap design
    • Round top
    • Curved brim
    • Embroidered script reading, "sorry I'm late, I stopped for coffee"
    • Back adjustable strap with metal buckle

    Style Number/Barcode: 07302-1729

    Category Name: Dark Cherry Outfits

    Price: $12.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: NS

    Product Badge:
    • New Arrival
  • Reina Glitter Velvet High Slit Formal Dress

    Special Occasion

    Radiate a gorgeous shine in the Reina formal dress crafted with glitter velvet fabric for a stunning shimmer. A glamorous choice for your next dressy affair, it features a sleeveless sweetheart neckline with asymmetric pleating at the bodice, a pleated faux wrap-front design creating a high-cut front slit, and a slim-fit silhouette to showcase your curves.

    Fit & Features

    • Glitter velvet fabric
    • Sweetheart neckline, asymmetric pleated bodice
    • Spaghetti straps
    • Pleated faux wrap-front design
    • Thigh-high front slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05002-8690

    Category Name: Dark Cherry Outfits

    Price: $69.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Pickleball Social Club Baseball Cap

    Fit & Features

    • Two-tone design
    • Round top
    • Curved brim
    • Vintage-like wash
    • Embroidered script reading "Pickleball Social Club" 
    • Two pickleball paddles graphic
    • Adjustable back strap with metal buckle

    Style Number/Barcode: 07302-1722

    Category Name: Dark Cherry Outfits

    Price: $14.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: NS

    Product Badge:
    • New Arrival
  • 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: $6.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Style Ribbed Knit Oversized Sweater

    Comfy and cozy, this ribbed knit sweater features a mock neckline, long dolman-style sleeves, short side slit accents, and the perfect oversized fit. Pair with biker shorts for a casual look, or a faux leather mini skirt for a dressier vibe.

    Fit & Features

    • Ribbed knit fabric
    • Mock neckline
    • Long dolman sleeves
    • Short side slits
    • Oversized fit

    Style Number/Barcode: 06005-2206

    Category Name: Dark Cherry Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: OFF, WHITE, GREEN

    Available Size: S/M, M/L

    Product Badge:
    • New Arrival
  • 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: $6.97

    Availability: Out of Stock

    Product Badge:
  • Sleek Flair Buckle Front Shoulder Bag

    This trendy shoulder bag features a small rectangular-shaped design with a sleek buckle front accent and a short shoulder strap. Style with hoop earrings.

    Fit & Features

    • Faux leather material
    • Rectangular-shaped design
    • Buckle front accent
    • Short shoulder strap

    Style Number/Barcode: 07203-2045

    Category Name: Dark Cherry Outfits

    Price: $24.90

    Availability: In Stock

    Available Color: IVORY-2

    Available Size: NS

    Product Badge:
    • New Arrival
  • Wild Sparkle Leopard Print Sequin Crop Top

    The sleeveless top features a cowl neckline, criss-cross straps that lead to a lace-up back, clear sequins, a trendy leopard print, and an asymmetrical cropped hem. Complete the look with the matching mini skirt for the ultimate GNO outfit!

    Shop Matching Mini Skirt: Wild Sparkle Leopard Print Sequin Mini Skirt

    Fit & Features

    • Woven-knit fabrication
    • Sleeveless cowl neckline
    • Criss-cross lace-up straps
    • Leopard print
    • Clear sequins
    • Asymmetrical cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2647

    Category Name: Dark Cherry Outfits

    Price: $22.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • 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

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Vibes Sheer Lace Bow Stockings

    Fit & Features

    • Sheer nylon fabrication
    • Lace and mini bow trim

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07306-0372

    Category Name: Dark Cherry Outfits

    Price: $10.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: NS

    Product Badge:
    • New Arrival