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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MOST POPULARElevate 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.
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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