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.

  • Ella Cowl Neck Satin Dress
    Special Occasion

    Enchant the room instantly in this gorgeous floor-length gown! Ella features a stunning sleeveless cowl neck, flattering high slit, and sleek spaghetti straps. She is composed of a lined satin stretch fabric that offers a form-hugging fit with a moderate stretch. Wear with sparkling earrings and metallic heels for a truly glam look. 

    Fit & Features
    • Cowl neck, sleek spaghetti straps
    • Form-fitting silhouette, high-side slit
    • Floor-length hem
    • Subtle shine satin fabric, moderate stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05002-1352

    Category Name: Dark Cherry Outfits

    Price: $19.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

  • True Perfection Pleated Satin Skater Dress

    A sleeveless satin mini dress features a flattering pleated square neckline and skater silhouette perfect for all-night dancing. Style with jewelry and heels for the school dance.

    Fit & Features

    • Satin fabric, bust lining, minimal stretch
    • Pleated square neckline
    • Spaghetti straps
    • Skater mini-length fit
    • Runs true to size

    Style Number/Barcode: 05101-3602

    Category Name: Dark Cherry Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: M, L

  • Shimmering Rhinestone Heart Bag Charm

    Fit & Features

    • Rhinestone embellished heart charm
    • Rhinestone embellished fabric strap
    • Keyring
    • Lobster clasp

    Style Number/Barcode: 07308-0666

    Category Name: Dark Cherry Outfits

    Price: $10.90

    Availability: In Stock

    Available Color: SILVER

    Available Size: NS

  • Lila Formal Open-Back Sequin Mermaid Dress

    Special Occasion 

    Bring dazzle and shine to your evening with a prom dress that radiates elegance. The dress features a sleeveless V-neckline, sleek spaghetti straps, a multi-cross-strap design, sparkling sequins set in an intricate damask pattern, and a mermaid silhouette. The dress is composed of a lined mesh-knit fabric that offers a form-hugging fit with slight stretch. Complete your prom look with rhinestone heels and a clutch.

    This dress is the perfect pick for Prom 2023! Not exactly your style? You’ll love other prom dresses.

    Fit & Features

    • Sleeveless V-neckline, padded cups
    • Spaghetti straps
    • Multi-cross-strap back design 
    • Sequins, damask print
    • Mermaid silhouette
    • Lined mesh-knit fabric, form-hugging fit, minimal stretch
    • Sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05002-1746

    Category Name: Dark Cherry Outfits

    Price: $14.97 $109.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glamorous Nights Mesh And Crepe Ruched Mini Dress

    Fit & Features

    • Sheer mesh fabric with crepe knit lining, moderate stretch
    • Sleeveless square neckline, pleated surplice design
    • Spaghetti tie-up straps
    • Hidden back zipper with hook-eye closure
    • Ruching
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5715

    Category Name: Dark Cherry Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: WINE

    Available Size: S, M, L

  • Floral Charm Three-Pack Sock Set

    Fit & Features

    • Pack includes three pairs of socks
    • Knit fabrication
    • Above-ankle length
    • Variety of floral prints

     

    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: 07306-0388

    Category Name: Dark Cherry Outfits

    Price: $9.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: NS

  • Doll It Up Open Back Ribbed Sweater

    Embrace a modern twist on knitwear with this double V-neck sweater. The deep V-neckline at the front and back offers a hint of allure, while the soft ribbed texture provides both warmth and a flattering fit that accentuates the waist. This long-sleeve sweater is a stylish choice for both casual and sophisticated looks. It's a versatile piece that pairs seamlessly with anything from denim to high-waist trousers, making it a must-have for your seasonal wardrobe.

    Fit & Features

    • Surplice neckline
    • Long dolman sleeves
    • Partially open back with bar strap accent
    • Banded crop hemline
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1761

    Category Name: Dark Cherry Outfits

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Vibe Halter Drop Waist Skater Dress

    Bring a cute vibe to brunch or a party in this halter skater dress showcasing a deep V-neckline and a pleated silhouette for flirty flare. Pair with earrings.

    Fit & Features

    • Poplin woven fabric with knit lining, minimal stretch
    • Deep V-neckline, dart seams at bust
    • Tie-back halter straps, partially open back, lower back zipper with hook-eye closure
    • V-shaped drop waist
    • Pleated short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3516

    Category Name: Dark Cherry Outfits

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Whimsical Rhinestone Butterfly Bag Charm

    Fit & Features

    • Butterfly charm, fabric puff design
    • Iridescent rhinestone embellishments
    • Chain-link connector
    • Keyring
    • Lobster clasp

    Style Number/Barcode: 07308-0661

    Category Name: Dark Cherry Outfits

    Price: $2.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winslow Formal Satin Lace-Up Dress

    Special Occasion

    The Winslow is absolute perfection! Gracefully glide into prom in this satin formal dress featuring a sleek, sleeveless, cowl neck and adjustable spaghetti straps atop a form-fitting bodice that leads to her open back with a lace-up closure. Plus, she has convenient hidden side pockets to keep your hands warm. Feel effortless in her floor-length hem with a front slit perfect for flaunting a glam pair of heels. The formal dress is composed of smooth satin with lining and no stretch.

    Fit & Features

    • Sleeveless, cowl neck, adjustable spaghetti straps
    • Form-fitting bodice, open-back, lace-up closure
    • Back zipper closure, hidden side pockets
    • A-line silhouette, floor-length hem
    • Smooth satin, lined, no stretch
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05002-7869

    Category Name: Dark Cherry Outfits

    Price: $49.97 $109.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Glitz Glitter Cold-Shoulder Mini Dress

    Bring the sultry glitz in this glitter mesh mini dress featuring a sweetheart cross-front neckline, a cold-shoulder design with spaghetti straps and short-sleeve cuffs, and an alluring corset bodice with sheer inserts and flexible boning for structure. The ruched side and back seams will accentuate your gorgeous curves along the bodycon silhouette.

    Fit & Features

    • Sheer glitter mesh fabric with partial knit lining, plenty of stretch
    • Sweetheart cross-front neckline
    • Cold-shoulder design, spaghetti straps, short-sleeve cuffs
    • Corset bodice with sheer inserts, flexible boning
    • Ruching down the side and back seams
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5758

    Category Name: Dark Cherry Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

  • Glitzy Rhinestone Tequila Bottle Bag Charm

    Fit & Features

    • Tequila bottle charm, fabric puff design
    • Rhinestone embellishments
    • Script reading, "Tequila, XXX, -1869-"
    • Chain-link connector
    • Beaded accent, tassel detail
    • Keyring
    • Lobster clasp

    Style Number/Barcode: 07308-0665

    Category Name: Dark Cherry Outfits

    Price: $2.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Layci Formal High Slit Dress

    Special Occasion

    Create a memorable impression in our breathtaking Layci dress! She features a straight off-the-shoulder neckline with a fold-over accent and princess seams. Her slim-fit bodice leads to an elongating floor-length silhouette that is accented with a high side slit to showcase your glam heels! The dress is composed of a crepe fabric that offers a form-hugging fit with a moderate stretch. Complete the look with a sleek clutch.

    Fit & Features

    • Off-the-shoulder neckline, fold-over design
    • Slim-fit bodice, princess seams 
    • Form-hugging silhouette
    • Floor-length hem, high-cut slit
    • Crepe fabric, sewn-in lining, moderate stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05002-6795

    Category Name: Dark Cherry Outfits

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Liza Ruched Velvet Bodycon Mini Dress

    Special Occasion

    Fall head over heels for the Liza velvet mini dress to make your showstopping entrance and exit! The luxe dress captivates in a ruched bodycon silhouette that flaunts your curves while the wrapped design gives the illusion of an hourglass figure. Pair with heels.

    Fit & Features

    • Velvet fabric with knit lining, moderate stretch
    • Wired V-neckline, adjustable spaghetti straps
    • Hidden back zipper with hook-eye closure
    • All-over ruching
    • Faux wrap-front design
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05001-2319

    Category Name: Dark Cherry Outfits

    Price: $54.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M

  • Stop And Stare Backless Long Sleeve Top

    Everyone will stop and stare at you in this crop top featuring a flirtatious open back and a cropped hem on buttery smooth fabric. Complete the look in high-waisted jeans.

    Fit & Features

    • Buttery smooth knit fabric, plenty of stretch
    • High crew neckline
    • Long fitted sleeves
    • Open back, top spaghetti strap, lower back twisted strap
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-5455

    Category Name: Dark Cherry Outfits

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: In Stock

    Available Color: MAUVE

    Available Size: M

    Product Badge:
    • Sale
  • Leanna Ruffle Glitter Mesh Skater Dress

    Special Occasion

    The Leanna glitter mesh skater dress features a fitted ruched bodice with a sheer waist insert and a cascading ruffled skater skirt creating an iconic fit-and-flare silhouette for a voluminous effect. Style with metallic heels for homecoming or a formal party!

    Fit & Features

    • Sheer glitter mesh fabric with partial knit lining, minimal stretch
    • V-neckline with padded bust, ruching
    • Adjustable spaghetti straps, hidden back zipper with hook-eye closure
    • Sheer waist insert, ruching, flexible boning, sheer back
    • Ruffled tiered skater skirt
    • Fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05001-2434

    Category Name: Dark Cherry Outfits

    Price: $79.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: 9

  • Milana Velvet Corset A-Line Formal Dress

    Special Occasion

    Enter your sultry chic era in the Milana velvet formal dress featuring a sleeveless pleated square neckline, a snatching corset bodice with contrast piping, and adjustable spaghetti straps for a customized fit. The ruched detailing at the waist will accentuate your curves, leading to a high-cut front slit on the floor-sweeping A-line silhouette. Complete your look with a gemstone necklace and stiletto heels.

    Fit & Features

    • Velvet lined fabric, moderate stretch
    • Pleated square neckline
    • Corset bodice with contrast piping
    • Adjustable spaghetti straps, back zipper closure
    • Ruching at the waist, high front slit
    • Floor-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05002-7550

    Category Name: Dark Cherry Outfits

    Price: $69.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Forever Sweet Long Sleeve Drop Waist Skater Dress

    Stay forever sweet in this skater dress featuring a sleek square neckline and ruching that flatters your figure. Pair with heels.

    Fit & Features

    • Stretchy smooth knit fabric
    • Square neckline
    • Long fitted sleeves
    • Ruching
    • Drop waist
    • Mini-length tiered skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3745

    Category Name: Dark Cherry Outfits

    Price: $32.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S, M, L

  • Upgrade Ya Liquid Leggings

    Elevate your faux leather leggings for a high-shine finish for a sleek and fierce look. Create a captivating going-out look with these high-waist leggings with a flattering wide waistband and skinny-leg silhouette. Style your faux leather leggings outfit with a lace bustier and sparkly statement earrings.

    Fit & Features

    • Wide high-rise waistband
    • Skinny leg design 
    • Pull-on/off styling
    • Stretchy faux leather fabric
    • Runs true to size

    Style Number/Barcode: 06502-2110

    Category Name: Dark Cherry Outfits

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lainey Ruffled High Slit Long Formal Dress

    Special Occasion

    Bring the flirtatious flair to your fancy affair with the alluring details of the Lainey ruffled high slit long formal dress! Crafted from a sleek and stretchy knit fabric, she features a sleeveless V-neckline, bungee spaghetti straps that lead to a bold open back with a cross-back strappy design, a fitted bodice, a floor-length hem with a thigh-high front slit accented with a ruffled trim, and a slim-fit silhouette. Style this long dress with rhinestone statement earrings and metallic heels!

    Fit & Features

    • Sleeveless V-neckline, bungee spaghetti straps
    • Open back, cross-back strappy design
    • Fitted bodice, high waist seam
    • Floor-length hem, thigh-high front slit, ruffled trim, slim-fit silhouette
    • Sleek knit fabric, knit lining at the bust, plenty of stretch
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05002-7821

    Category Name: Dark Cherry Outfits

    Price: $49.90

    Availability: In Stock

    Available Color: BURGUNDY, HUNTER

    Available Size: XS, S, M, L

  • Floral Fantasy Long Sleeve Mesh Bustier

    Unlock a floral fantasy to your vibe with this long sleeve mesh bustier showcasing a sultry off-the-shoulder neckline adorned with long fitted sleeves and a cropped hem that flaunts your figure. Pair with jeans.

    Fit & Features

    • Floral printed-sheer mesh fabric with partial knit lining, plenty of stretch
    • Off-the-shoulder neckline
    • Long fitted sleeves
    • Front flexible boning, back zipper with hook-eye closure
    • All-over ruching
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5483

    Category Name: Dark Cherry Outfits

    Price: $26.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

  • Sleek Stunner Long Sleeve Backless Mini Dress

    Showcase a stunning sleek vibe in this curve-hugging mini dress designed with smooth knit fabric offering plenty of stretch. It features a boat neckline, a deep V-shaped open back that will turn heads, long fitted sleeves, and a ruched short bodycon silhouette.

    Fit & Features

    • Double-lined smooth knit fabric, plenty of stretch
    • Boat neckline
    • V-shaped open back
    • Long fitted sleeves
    • Front asymmetric seam, ruching
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5984

    Category Name: Dark Cherry Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Be With You Off-The-Shoulder Skater Dress

    An off-the-shoulder dress features side ruched seams that accentuate your curves along a skater mini-length silhouette with an uneven hem. Perfect for the school dance or a party.

    Fit & Features

    • Smooth knit fabric, stretchy knit lining
    • Off-the-shoulder folded neckline
    • Side ruched seams
    • Skater mini-length fit, uneven hem
    • Runs true to size

    Style Number/Barcode: 05101-3627

    Category Name: Dark Cherry Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

  • A Little Bit Chic Floral Velvet Burnout Mini Dress

    Create a chic night-out look with this bodycon mini dress designed with a stretchy knit fabric with a floral velvet burnout pattern. It features a sleeveless crew neckline, tank shoulder straps, and a short curve-hugging silhouette to flaunt your stunning figure.

    Fit & Features

    • Sheer mesh fabric with knit lining, plenty of stretch
    • Floral velvet burnout pattern
    • Crew neckline
    • Tank straps
    • Ruched side seams
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3676

    Category Name: Dark Cherry Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S