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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Blooming Bouquet Sleeveless Floral Mesh Mini Dress
Get ready to bloom in this floral mesh mini dress at a girl's brunch or evening soiree! The sleeveless crew neckline and bodycon silhouette highlight your curves, while the bold floral print and mesh fabric add a touch of feminine charm. Complete the look in simple stiletto heels.
Fit & Features
- Blooming floral print
- Sheer mesh fabric with knit lining, plenty of stretch
- Crew neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5612
Category Name: Dark Cherry Outfits
Price: $36.90
Availability: In Stock
Available Color: PLUM
Available Size: L
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Edgy Stride Buckle Strap Ankle Booties
Fit & Features
- 3” block heel, 5" leg opening, 4.5" shaft height
- Faux leather material
- Ankle-high
- Pointed toe
- Dual strap design with buckle detailing, cutout accents
- Back zipper closure
- Comes in Black and Leopard print
- Runs true to size
Style Number/Barcode: 07403-1838
Category Name: Dark Cherry Outfits
Price: $16.97 $45.90
On Sale: Yes
Availability: In Stock
Available Color: LEOPARD, BLACK
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- Sale
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The One You Need Mini Dress
Step out in style with this sexy ribbed knit mini dress, perfect for brunch with your besties or a relaxed weekend outing. Its minimalist bodycon silhouette pairs effortlessly with an oversized denim jacket or a fitted blazer for a look that's polished yet effortlessly chic. The dress's flattering V-neckline is ideal for showcasing delicately layered necklaces, adding a sweet and enchanting touch to your ensemble.
Fit & Features
- Sleeveless V-neckline
- Thin bungee straps
- Strapless bra recommended
- Mini-length bodycon silhouette
- Ribbed knit fabric
- Figure-hugging fit, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-0500
Category Name: Dark Cherry Outfits
Price: $10.97 $24.90
On Sale: Yes
Availability: In Stock
Available Color: TAN, BLACK
Available Size: L, S, M, XL
Product Badge:- Sale
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Wendy Sleeveless Mermaid Glitter Formal Dress
Special Occasion
Dazzle all day and night in the Wendy sleeveless glitter formal dress at weddings or parties! Crafted from glitter fabric, this dress will make you shine like a star at any event. The square neckline and adjustable spaghetti straps flatter and support, while the mermaid silhouette and floor-length hem add an ethereal touch making you feel so stunning! Complete the look with a dainty necklace.
Fit & Features
- Glitter fabric, additional fabric layer at the bust, moderate stretch
- Adjustable spaghetti straps
- Mermaid silhouette
- Runs true to size
Style Number/Barcode: 05002-8488
Category Name: Dark Cherry Outfits
Price: $69.90
Availability: In Stock
Available Color: WINE, HUNTER, MAUVE
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Adele Sleeveless Lace Mermaid Dress With Bolero
Special Occasion
Create an elegantly chic look in the Adele mermaid dress designed with sheer lace fabric with a full-length knit lining. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a floor-sweeping mermaid silhouette to showcase your gorgeous curves, and a sheer lace long sleeve bolero for added coverage that can be removed.
Fit & Features
- Sheer lace fabric with knit lining, moderate stretch
- Square neckline
- Adjustable spaghetti straps
- Underbust and high waist seams
- Floor-length mermaid silhouette
- Removable sheer lace long sleeve bolero
- Runs true to size
Style Number/Barcode: 05002-8783
Category Name: Dark Cherry Outfits
Price: $79.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M
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Fleece Shaper Leggings
Comfy and flattering, these fleece leggings are perfect for lounging, traveling, and the office! They feature a high-waist fit with tummy control to smooth and shape your figure. These fleece-lined leggings will keep you cozy while appearing incredibly chic paired with an elevated crop top and tailored blazer or moto jacket for a fierce #OOTD look.
Fit & Features
- Tummy control waistband
- Skinny leg fit
- Cozy fleece-lined knit fabric
- Moderate stretch
- Sizes run small
Style Number/Barcode: 06502-1228
Category Name: Dark Cherry Outfits
Price: $6.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Alisa Lace Sequin Back Mermaid Formal Dress
Special Occasion
Find yourself captivating in the Alisa long formal dress at your next black-tie affair! The sleek stretchy knit fabric reveals a gorgeous sheer floral lace back design embroidered with shimmering sequins for a luxe shine. Her sleeveless bodice is shaped with a draped cowl neckline with a padded bust and adjustable spaghetti straps for a customized fit. She features ruching at the waist and back to accentuate your stunning curves on the floor-sweeping mermaid silhouette accented with a cascading train. Complete your look with a rhinestone jewelry set and stiletto heels.
Fit & Features
- Stretchy knit fabric, sheer floral lace back with sequins, short knit lining
- Sleeveless cowl neckline, padded bust
- Adjustable spaghetti straps
- Back zipper closure with hook and eye closure
- Ruched seams
- Mermaid fit with train
- Runs true to size
Style Number/Barcode: 05002-8063
Category Name: Dark Cherry Outfits
Price: $99.90
Availability: In Stock
Available Color: WINE, NAVY, GOLD
Available Size: S, XS
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Elevated Basic Ruched Mesh Bodysuit
Step up your everyday look with this elevated basic bodysuit. The one-piece top features long sheer bishop sleeves, a square neckline, front and back ruched detailing, and a thong bottom. The sheer mesh fabric has a lightweight knit lining. Style this bodysuit with your fave pair of denim and chic mules.
Fit & Features
- Long sheer bishop sleeves, elastic cinched hems
- Square neckline
- Front and back ruched detailing
- Thong bottom, dual snap button closure
- Sheer mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4236
Category Name: Dark Cherry Outfits
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sangria Sunset Strapless Paisley Satin Crop Top
The perfect paisley satin crop top to wear during sunset cocktail hour! Crafted from a silky satin fabric with a summery paisley print, this crop top elevates every outfit. It features a strapless neckline and stretchy smocked back, a flirty tie design, and a pointed cropped hem that flaunts your figure. Complete the look in denim jeans and strappy sandals.
Fit & Features
- Paisley print, satin fabric, no stretch
- Strapless neckline
- Tie back design, smocked back
- Pointed cropped length
- Runs true to size
Style Number/Barcode: 06003-2614
Category Name: Dark Cherry Outfits
Price: $26.90
Availability: In Stock
Available Color: BURGUNDY, BROWN
Available Size: XS, S, M, L
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Renaissance Spell Lace-Up Satin Corset
Transform into a captivating beauty in this satin corset top perfect for dressing up for parties or dates! The sleeveless square neckline and wide shoulder straps accentuate your figure, while the flexible boning provides support. The cropped hem and lace-up back add a touch of allure, all crafted from luxurious satin fabric. Complete the look in a sultry mini skirt.
Fit & Features
- Satin fabric, sewn-in knit lining, minimal stretch
- Wide shoulder straps
- Side zipper and hook-eye closure
- Lace-up
- Flexible boning
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-2680
Category Name: Dark Cherry Outfits
Price: $36.90
Availability: In Stock
Available Color: RED, GREEN, MAUVE, LEOPARD, RAISIN, BLUSH
Available Size: XS, S, M, L
Product Badge:- Sale
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Kindra High-Slit Mermaid Halter Dress
Special Occasion
Go bold in a long mermaid dress that features a plunging halter neckline with a U-shaped bust, adjustable neck ties, ruching, a high side slit, and a captivating mermaid silhouette. Complete your formal outfit with a sleek rhinestone clutch.
Fit & Features
- Lined mesh fabrication, moderate stretch
- Plunging halter neckline, U-shaped bust
- Halter neck ties
- High side slit
- Ruching
- Mermaid silhouette
- Long length hem
- Runs true to size
Style Number/Barcode: 05002-8924
Category Name: Dark Cherry Outfits
Price: $74.90
Availability: In Stock
Available Color: RED, NAVY
Available Size: XS, S, M, L, XL
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Marie Cowl Neck Sequin Mini Dress
Special Occasion
Oh-so-alluring, create a bold formal look in the Marie sleeveless sequin mini dress. She features a draped cowl neckline, adjustable spaghetti straps, an open back with a lace-up strappy design for a customized fit, and a short, curve-hugging, bodycon silhouette. The lined mesh fabric features all-over sequin embroidery in a chic scroll pattern. Complete the outfit with classic stiletto heels.
Fit & Features
- Sleeveless cowl neckline
- Adhesive bra recommended
- Adjustable spaghetti straps
- Open back, lace-up strappy design, tie closure
- Lower back zipper, hook and eye closure
- Mini-length hem, fitted bodycon silhouette
- Sheer mesh fabric, full knit lining, moderate stretch
- Sequin embroidery, scroll pattern
- Runs true to size
Style Number/Barcode: 05001-1119
Category Name: Dark Cherry Outfits
Price: $29.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sariah Lace-Up Glitter Knit Mermaid Dress
Special Occasion
Show up and shine at your black-tie affair in the Sariah lace-up glitter knit mermaid dress! The gorgeous glitter knit fabric is lined with a smooth knit and offers plenty of stretch. The dress is shaped with a V-neckline with a built-in padded bust, and spaghetti straps that lead to her sultry open back with a lace-up strappy design. Her bodice has alluring corset-style seams for a stylishly snatched look. The floor-length hem is accented with a high-cut front slit along the curve-hugging mermaid silhouette. Complete your look with rhinestone chandelier earrings.
Fit & Features
- Stretchy glitter knit fabric with knit lining
- Sleeveless V-neckline with padded bust
- Spaghetti straps
- Open back with lace-up straps, tie closure
- Corset seams, high waist seam
- Mermaid silhouette with high front slit
- Runs true to size
Style Number/Barcode: 05002-7804
Category Name: Dark Cherry Outfits
Price: $69.90
Availability: In Stock
Available Color: WINE, PINK
Available Size: XS, S, M, L
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Astrid High-Slit Glitter Mermaid Dress
Special Occasion
Radiate glamour in a long glitter dress that features a sleeveless sweetheart neckline with a draped cowl neck overlay, spaghetti straps, and a captivating mermaid silhouette that is accented with a high side slit. Complete your formal outfit with a rhinestone clutch.
Fit & Features
- Glitter knit fabric with knit lining at the bust, plenty of stretch
- Sweetheart neckline with padded bust, draped cowl neck overlay
- Spaghetti straps
- Long length hem
- High side slit
- Mermaid silhouette
- Runs true to size
Style Number/Barcode: 05002-8872
Category Name: Dark Cherry Outfits
Price: $59.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Janie Formal One Shoulder Dress
Special Occasion
Bring the elegance in our Janie dress that reflects glamour for your next special evening. She features a sleek one-shoulder neckline, a ruched bodice, a high waist seam, and a floor-length skirt with a sexy high side slit and ruched detailing. The dress is composed of a comfortable knit fabric with a moderate stretch. Complete your stunning evening outfit with rhinestone earrings and strappy stiletto heels.
Fit & Features
- One-shoulder neckline | Tank strap
- Adhesive bra recommended
- High side slit with ruched seam
- Floor-length silhouette
- Sleek knit lined fabric
- Fits true to size | Moderate stretch
Style Number/Barcode: 05002-1020
Category Name: Dark Cherry Outfits
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Moves Ruffled Tie-Front Knit Crop Top
Make major flirty moves and create an enticing aura in this ruffled tie-front crop top! Designed with a stretchy smooth knit fabric, it features a sultry V-neckline with a tie-front design, ruffled hems for that girly flair, spaghetti straps, and an asymmetric cropped hem. Style with the matching midi skirt for a girl's night out!
Shop Matching Bottoms: Flirty Moves Ruffled Slit Knit Midi Skirt
Fit & Features
- Double-lined stretchy smooth knit fabric
- V-neckline, tie-front design
- Ruffled hems
- Spaghetti straps
- Asymmetric cropped hem
- Runs true to size
Style Number/Barcode: 06001-5451
Category Name: Dark Cherry Outfits
Price: $16.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: S, M, L
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Chic Choice Knit Off-The-Shoulder Maxi Dress
This trendy ribbed knit maxi dress is a chic choice for the season offering plenty of stretch for comfortable wear. It features an off-the-shoulder fold-over neckline, long fitted sleeves, and a maxi-length bodycon silhouette accented with a back slit.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Off-the-shoulder neckline, fold-over design
- Long fitted sleeves
- Back slit
- Maxi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-2104
Category Name: Dark Cherry Outfits
Price: $42.90
Availability: In Stock
Available Color: BLUE
Available Size: S, M, L
Product Badge:- Best Seller
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Rashida Lattice Back Glitter Dress
Special Occasion
Catch the light when you take our dazzling Rashida mini for a twirl! She features a sleeveless V-neckline, lightly padded cups, a double-row of spaghetti straps, a lace-up back design, and a skater silhouette. The short dress is composed of a lined glitter woven fabric that offers a form-hugging fit with a moderate stretch. Style the mini dress with rhinestone heels.
Fits & Features
- Sleeveless V-neckline, lightly padded cups
- Lattice-tie back
- Lower back hook and eye closure with zipper
- Swingy, A-line skater skirt
- Glitter knit material, fully lined
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05001-0083
Category Name: Dark Cherry Outfits
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Kairi Off-The-Shoulder Glitter Mesh Formal Dress
Special Occasion
The gorgeous Kairi glitter mesh formal dress will make any occasion a glitzy and glamorous affair! Crafted with a sheer glitter mesh fabric with a knit lining, this long dress offers plenty of stretch so you can feel comfortable and confident. Her bodice is shaped with an off-the-shoulder cowl neckline with chic draped short sleeves for a soft feminine look. Her all-over ruching brings sultry vibes and will accentuate your stunning curves on her slim-fit silhouette. Her asymmetric hem creates a thigh-high side slit to reveal some leg and your fabulous heels. Complete your look with rhinestone hoops.
Fit & Features
- Stretchy sheer glitter mesh fabric with knit lining
- Off-the-shoulder cowl neckline
- Draped short sleeves
- All-over ruching
- Asymmetric hem, high side slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05002-8453
Category Name: Dark Cherry Outfits
Price: $59.90
Availability: In Stock
Available Color: WINE
Available Size: XS, S, M
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Marisol Lace-Up Column Sequin Satin Formal Dress
Special Occasion
Make a jaw-dropping entrance in the Marisol sequin satin formal dress at black-tie banquets, weddings, or school dances! A square neckline and spaghetti straps accentuate the figure while the lace-up open back adds a touch of drama. The floor-length column silhouette flows into the front slit for movement, showcasing a mesmerizing sequin scroll pattern on luxurious satin fabric. Complete the look with a glam hair accessory, heels, and necklace for a flawless evening!
Fit & Features
- Sequin scroll pattern, satin fabric lined with stretchy knit
- Lace-up
- Back zipper and hook-eye closure
- Padded bra cups
- Front slit
- Column silhouette
- Runs true to size
Style Number/Barcode: 05002-8284
Category Name: Dark Cherry Outfits
Price: $119.90
Availability: In Stock
Available Color: WINE, BROWN, HUNTER
Available Size: XS, S, M, L
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Miriam Pearl Beaded Formal Mini Dress
Special Occasion
Turn heads with your glitzy aura in the Miriam formal mini dress crafted with lined mesh fabric and all-over faux pearl and beaded embroidery for a gorgeous look. It features a sleeveless sweetheart neckline, tank shoulder straps, an open back with a lace-up strappy design for a customized fit, and a short flowy A-line silhouette.
Fit & Features
- Sheer mesh fabric with knit lining, moderate stretch
- All-over faux pearl and beaded embroidery
- Sweetheart neckline, underbust seam
- Tank shoulder straps
- Open lace-up back
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05001-2520
Category Name: Dark Cherry Outfits
Price: $79.90
Availability: In Stock
Available Color: WHITE, WINE
Available Size: XS, S, M, L, XL
Product Badge:- Best Seller
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Perfectly Poised Plunging Chiffon Romper
Make it poised and chic in this dressy romper for the perfect going-out look for all of your special occasions. This sheer long-sleeve romper features a plunging surplice V-neckline and a high-rise silhouette with a matching tie belt that cinches at the waist. Complete your dressy romper look with sparkling rhinestone chandelier earrings and matching spiral heels.
Fit & Features
- Plunging surplice V neckline
- Sheer chiffon long sleeves with elastic banded hems
- Tie-waist belt with belt loops
- Wide-leg shorts
- Crepe fabric with moderate stretch
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06503-0230
Category Name: Dark Cherry Outfits
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bloom With A View Floral Ruffle Midi Dress
Turn heads in this floral mesh midi dress at parties and on dates! Featuring a flirty v-neckline and bungee spaghetti straps, and a bodycon silhouette that accentuates your curves. The asymmetrical-cut ruffled midi-length hem adds a touch of playfulness to the elegant watercolor floral print in airy mesh-lined fabric. Complete the look in a cute open-front cardigan and heels!
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Bodycon silhouette
- Asymmetrical-cut ruffled midi-length hem
- Watercolor floral print
- Airy mesh fabric, short stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2987
Category Name: Dark Cherry Outfits
Price: $42.90
Availability: In Stock
Available Color: WINE, BROWN
Available Size: XS, S, M, L, XL
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Karen Formal Sweetheart Halter Corset Satin Dress
Special Occasion
Radiate sexy elegance in the Karen formal satin long dress as a stunning bridesmaid or wedding guest! Boasting a luxe satin fabric that feels silky on your skin, she features a sweetheart halter strap neckline atop a built-in padded underwire bust eliminating a need for a bra and a figure-enhancing corset bodice with flexible boning for the perfect hourglass look. The side pleated seam effortlessly hugs your waistline leading to the slim fit silhouette showcasing an asymmetrical high front slit that flaunts your legs! Finish the look with grand rhinestone earrings and a bracelet for a glamorous effect.
Fit & Features
- Silky satin stretch fabric, bust knit lining
- Built-in padded underwire bust
- Sweetheart halter strap neckline with button closures
- Built-in padded underwire bust, corset bodice
- Back zipper and hook-eye closure
- Slim fit silhouette
- Runs true to size
Style Number/Barcode: 05002-8244
Category Name: Dark Cherry Outfits
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale