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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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.
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Chic Slay Over-The-Knee Block Heel Boots
Fit & Features
- Block heel
- Faux leather material
- Over-the-knee height
- Pointed toe
- Partial inner zipper closure, back adjustable tie
- Form-hugging design
- Runs true to size
Style Number/Barcode: 07402-1064
Category Name: Dark Cherry Outfits
Price: $44.90
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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Margot One-Shoulder Cowl Neck Mermaid Dress
Special Occasion
Showcase your gorgeous curves in the stunning Margot formal dress designed with a smooth knit fabric with plenty of stretch. It features a one-shoulder neckline with a tank strap and a single spaghetti strap, a sultry sweetheart bust with a draped cowl neck overlay, a ruched bodice, and a floor-length mermaid silhouette to flaunt your figure.
Fit & Features
- Smooth knit fabric with plenty of stretch, stretchy knit lining
- One-shoulder neckline with tank strap, single spaghetti strap
- Sweetheart bust, padded bust, draped cowl neck overlay
- Ruched bodice, high waist seam
- Floor-length mermaid silhouette
- Runs true to size
Style Number/Barcode: 05002-8937
Category Name: Dark Cherry Outfits
Price: $76.90
Availability: In Stock
Available Color: WINE
Available Size: XS, S, M, L, XL
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On the Move Block Heel Ankle Booties
Fit & Features
- 3” stacked block heel, 5” leg opening, 6” shaft height
- Square-shaped toe
- Inner zipper closure
- Black and Brown are faux leather
- Leopard print is faux microsuede
- Runs true to size
Style Number/Barcode: 07403-1842
Category Name: Dark Cherry Outfits
Price: $36.90
Availability: In Stock
Available Color: LEOPARD, BLACK, BROWN
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Trendy Babe Off-The-Shoulder Ruched Lace Top
You'll be a total trendy babe in this airy lace top featuring an off-the-shoulder straight neckline, sheer long fitted sleeves, a ruched side adjustable tie leading to a slit, and an asymmetric mid-length hem. Style with high-rise jeans and mules!
Fit & Features
- Sheer lace fabric with partial knit lining, plenty of stretch
- Off-the-shoulder straight neckline
- Sheer long fitted sleeves
- Ruched side adjustable tie with slit
- Asymmetric mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-5492
Category Name: Dark Cherry Outfits
Price: $29.90
Availability: In Stock
Available Color: BURGUNDY, BLACK
Available Size: XS, S, M, L
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Western Sleek Knee-High Block Heel Boots
Fit & Features
- Stacked block heel
- Distressed faux leather material
- Knee-high
- Pointed toe
- Partial inner zipper closure
- Pull tabs
- Runs true to size
Style Number/Barcode: 07402-1070
Category Name: Dark Cherry Outfits
Price: $42.90
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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Take It Up A Notch Ruched Mini Dress
Take your sultry style up a notch with this ruched mini dress! You'll be sure to turn heads in this little number with its sweetheart neckline, pretty lace detailing, and mini-length, curve-hugging silhouette. Pair with some heels and statement earrings for a gorgeous night-out look.
Fit & Features
- Spaghetti straps with sheer lace detailing
- Sweetheart neckline, built-in padded bust
- Back zipper and hook-eye closure
- Caged seam detailing at the waist
- Ruching, bodycon fit, short-length hem
- Sheer mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4376
Category Name: Dark Cherry Outfits
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flaunt It Satin Strapless Bodycon Mini Dress
Flaunt your gorgeous curves in this iconic satin-knit mini dress featuring a strapless straight neckline, a pleated asymmetric design at the bodice, and a short bodycon silhouette. Style with a rhinestone jewelry set and metallic heels for your next night out.
Fit & Features
- Satin-knit fabric, plenty of stretch
- Strapless straight neckline
- Pleated asymmetric design at bodice
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5889
Category Name: Dark Cherry Outfits
Price: $36.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: S, M, L
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Sleek Look Thigh-High Block Heel Boots
Fit & Features
- Thin block heel
- Faux leather material
- Thigh-high
- Pointed toe
- Partial inner zipper closure
- Back adjustable tie
- Runs true to size
Style Number/Barcode: 07402-1065
Category Name: Dark Cherry Outfits
Price: $44.90
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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Floral Beauty Velvet Flocked Mesh Midi Dress
Showcase your beauty in this lined mesh midi dress designed with a floral velvet flocked pattern for a chic allure. It features a sleeveless sweetheart neckline with a ruched bust, a corset-style bodice with a V-shaped waist seam, a lace-up strappy back for a customized fit, and a midi-length A-line silhouette for that gorgeous flowy vibe.
Fit & Features
- Sheer mesh fabric with floral velvet flocked pattern, knit lining, moderate stretch
- Sweetheart neckline, ruched bust with adjustable drawstring, keyhole cutout
- Adjustable spaghetti straps, side zipper with hook-eye closure
- Corset-style bodice, V-shaped high waist seam, lace-up strappy back
- Dual side pockets, front slit
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3760
Category Name: Dark Cherry Outfits
Price: $49.90
Availability: In Stock
Available Color: WINE
Available Size: XS, S, M, L
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Sleek Western Under-The-Knee Stiletto Boots
Fit & Features
- Thin stiletto heel
- Faux leather material
- Under-the-knee height
- Pointed toe
- Partial inner zipper closure
- Pull tabs
- Runs true to size
Style Number/Barcode: 07402-1111
Category Name: Dark Cherry Outfits
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: 5.5, 6, 7, 7.5, 8, 8.5, 9, 10
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High Waist Paperbag Skinny Dress Pants
Keep it chic with paper bag waist pants to dress up your outfit. The pants feature a tie-front belt to cinch the waist, slanted front pockets, a skinny leg fit, and a tapered hem. For a look that's ready to make an impression in office attire or date night outfits, pair these pants with a fab blouse and open-toe heels.
Fit & Features
- High-rise paper bag waist
- Hidden front zipper closure
- Tie-front belt
- Slanted front pockets
- Pleated detailing
- Woven fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06402-1167
Category Name: Dark Cherry Outfits
Price: $31.87 $39.90
On Sale: Yes
Availability: Out of Stock
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Captivating Charm Sleeveless Tie Back Satin Skater Dress
Your charm and this satin skater dress will make you the most captivating one at the school dance or banquet! Featuring a square neckline and delicate shoulder straps, this dress is designed to flatter your figure. The low back with a tie adds a touch of playfulness, while the drop waist seam and skater silhouette create a stunning shape. Complete the look in high heels and jewelry!
Fit & Features
- Satin fabric lined with stretchy knit
- Square neckline
- Shoulder straps
- Low back with tie, zipper and hook-eye closure
- Skater silhouette
- Sticky bra or pasties recommended
- Runs true to size
Style Number/Barcode: 05101-3509
Category Name: Dark Cherry Outfits
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: RAISIN
Available Size: S, M, L
Product Badge:- Sale
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Adorable Glam Rhinestone Bow Cutout Corset Top
Fit & Features
- Ponte knit fabric, moderate stretch
- Strapless straight neckline
- Three bust cutouts, rhinestone bow accents
- Fitted mid-length hem
- Runs true to size
Style Number/Barcode: 06001-5534
Category Name: Dark Cherry Outfits
Price: $29.90
Availability: In Stock
Available Color: BLACK, WHITE
Available Size: XS, S, M, L
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Polished Glam Belted Wide Leg Pants
Fit & Features
- Knit fabrication
- High-rise waist, back zipper and hook-eye closure
- Belted waist with metal grommets
- Front vertical seams
- Straight-leg
- Flared wide-leg hem
- Runs true to size
Style Number/Barcode: 06502-2546
Category Name: Dark Cherry Outfits
Price: $42.90
Availability: In Stock
Available Color: BURGUNDY, BLACK
Available Size: XS, S, M, L
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Fierce Look Animal Print Mesh Halter Mini Dress
Show off a fierce allure in this airy mesh mini dress designed with an abstract animal print that will turn heads. It features a sleeveless draped cowl neckline, a halter strap design with sleek O-ring accents, and a short bodycon silhouette to highlight your gorgeous curves.
Fit & Features
- Sheer mesh fabric with knit lining, plenty of stretch
- Abstract animal print
- Asymmetric cowl neckline
- Halter strap design, metal O-ring accents
- Partially open back
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5964
Category Name: Dark Cherry Outfits
Price: $36.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
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Get With It Faux Leather Skirt
Get your look on point in a skirt that slays! The stylish versatile skirt is the one staple piece you need to create a head-turning night-out outfit with the squad. The skirt features a high-rise waist, a short-fitted design, and is composed of faux leather fabric. Complete your chic outfit with a bodysuit and a blazer.
Fit & Features
- Wide high-rise waistband
- Bodycon fit
- Mini-length hem
- Faux leather fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0347
Category Name: Dark Cherry Outfits
Price: $16.90
Availability: Out of Stock
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Stylish Embrace Cable Knit Midi Dress
Embrace a cozy vibe in a cable knit dress that features a trendy v-neckline, fitted long sleeves, and a midi-length hem. Complete look with ankle booties!
Fit & Features
- Unlined cable knit fabrication
- V-neckline
- Fitted long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 06005-2097
Category Name: Dark Cherry Outfits
Price: $42.90
Availability: In Stock
Available Color: MOCHA
Available Size: XS, S, M, L
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Adorably Flirty Lace Trim Drop Waist Skater Dress
Adorably flirty, this woven skater dress is designed with a strapless straight neckline accented with a satin ribbon detail, a chic corset-style bodice with a dainty lace trim, and a lace-up back for a customized fit. The on-trend drop waist seam leads to a short pleated skater silhouette with the cutest sheer lace hem.
Fit & Features
- Lined poplin woven fabric, minimal stretch
- Strapless straight neckline, satin ribbon detail, no-slip strip
- Corset-style bodice, flexible boning, lace trim design
- Lace-up back, side zipper with hook-eye closure
- Drop waist seam
- Short pleated skater silhouette, sheer lace hem
- Runs true to size
Style Number/Barcode: 05101-3707
Category Name: Dark Cherry Outfits
Price: $52.90
Availability: In Stock
Available Color: WINE
Available Size: XS, S, M, L, XL
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Amp It Up Faux Leather Platform Boots
Amp up your cold-weather 'fits with these sleek faux leather platform boots with an above-the-ankle height. They feature a trendy square-shaped toe, an inner zipper closure for effortless styling, and a tall block heel.
Fit & Features
- Tall block heel
- Faux leather material
- Above-the-ankle height
- Square toe
- Inner zipper closure
- Platform sole
- Runs true to size
Style Number/Barcode: 07403-1803
Category Name: Dark Cherry Outfits
Price: $39.90
Availability: In Stock
Available Color: WINE, BLACK
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Chic Strides Faux Leather Under-The-Knee Boots
Fit & Features
- Block heel
- Faux leather material
- Under-the-knee fit
- Inner zipper closure
- Crinkle detailing
- Closed almond toe
- Runs true to size
Style Number/Barcode: 07402-1115
Category Name: Dark Cherry Outfits
Price: $48.90
Availability: In Stock
Available Color: BROWN
Available Size: 5.5
Product Badge:- Best Seller
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Adorable Aura Drop Waist Bubble Hem Skater Dress
Show off an adorable aura in this flirty short skater dress featuring a sleeveless square neckline with a ruched bust, ruched tank-like shoulder straps, a trendy drop waist seam, and a ruched bubble hem. Style with platform heels for a party!
Fit & Features
- Woven fabric with knit lining, moderate stretch
- Square neckline, ruched bust
- Ruched tank-like shoulder straps
- Dual front vertical seams, back zipper with hook-eye closure
- Drop waist seam
- Skater silhouette, ruched bubble hem
- Runs true to size
Style Number/Barcode: 05101-3711
Category Name: Dark Cherry Outfits
Price: $46.90
Availability: In Stock
Available Color: WINE
Available Size: S, M, L
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Iconic Moment Faux Leather Slouchy Shoulder Bag
Fit & Features
- Faux leather material
- Top handle
- Slouchy tote body
- Crinkle detailing
Style Number/Barcode: 07203-2095
Category Name: Dark Cherry Outfits
Price: $29.90
Availability: Out of Stock
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Slay It With Style Faux Leather Mini Skirt
Slay your day in style with this faux leather mini skirt! It features a high-rise waist and a front seam detail with a sultry side slit. This skirt is composed of faux leather fabric with a subtle sheen finish and moderate stretch. Complete your fashionista-approved look with strappy heels and an edgy chain belt.
Fit & Features
- High-rise waist
- Back zipper closure
- Front seam, sexy high slit
- Unlined, faux leather fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06401-0043
Category Name: Dark Cherry Outfits
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
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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