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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Casual Admiration Long Sleeve Rib Knit Crop Top
This rib knit crop top features fitted long sleeves, a classic crew neckline, and a fitted U-cut hem that flaunts your figure. Style with a mini skirt and boots for any occasion.
Fit & Features
- Stretchy rib knit fabric
- Fitted long sleeves
- Crew neckline
- U-cut cropped hem
- Runs true to size
Style Number/Barcode: 06005-2059
Category Name: Dark Cherry Outfits
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adorably Chic Polka Dot Slingback Stiletto Heels
Fit & Features
- Stiletto heel
- Adjustable slingback strap
- Closed pointed-toe
- Sheer mesh polka dot pattern
- Small bow accent
- Faux leather insole
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-5077
Category Name: Dark Cherry Outfits
Price: $30.90
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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Sultry Vibe Plunge Halter Faux Leather Crop Top
Take on a sultry vibe in this faux leather crop top featuring a plunge halter V-neckline and an adjustable belted crop hem for an edgy flair. Style with a mini skirt for a night out.
Fit & Features
- Faux leather fabric, sewn-in lining, minimal stretch
- Plunge halter V-neckline with hook closure
- Adjustable belted crop hem
- Runs true to size
Style Number/Barcode: 06001-5445
Category Name: Dark Cherry Outfits
Price: $13.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: BURGUNDY
Available Size: L
Product Badge:- Sale
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Chic Unleashed Under-The-Knee Scrunch Boots
Fit & Features
- Block heel
- Under-the-knee fit
- Closed pointed-toe
- Scrunch detailing
- Faux microsuede material
- Runs true to size
Style Number/Barcode: 07402-1042
Category Name: Dark Cherry Outfits
Price: $46.90
Availability: In Stock
Available Color: TAUPE
Available Size: 6, 7, 7.5, 8, 8.5, 9
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Wild Side Chic Leopard Print Handbag
Fit & Features
- Faux leather material
- Top-handle with dual O-rings
- Top zipper closure
- Half-moon shaped body
- Leopard print
Style Number/Barcode: 07203-2066
Category Name: Dark Cherry Outfits
Price: $24.90
Availability: Out of Stock
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Something More High Waist Ponte Pencil Skirt
Create the perfect polished look in a high-waist pencil skirt. From the office to happy hour this bodycon midi skirt is the fashion essential for every wardrobe. This high-waist silhouette is made of double-lined Ponte knit fabric with minimal stretch for a sleek and structured look. Pair this pencil skirt with a bodysuit blouse and blazer for an office-ready ensemble or style it with a corset top for a flirty date night look.
Fit & Features
- High-rise waist
- Form-hugging fit
- Knee-length hem
- Pull-on/off styling
- Double ponte-lined fabric
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06501-2105
Category Name: Dark Cherry Outfits
Price: $9.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All The Elegance Satin Slip Midi Dress
Captivate in this elegant satin slip midi dress perfect for rehearsal dinners or cocktail parties! The midi-length dress features a sleek cowl neckline, adjustable spaghetti straps, a flattering curve-hugging silhouette, and a flirty side slit along the hem. Complete the look in stiletto heels and a clutch!
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Curve-hugging silhouette
- Side slit, midi-length hem
- Silky woven satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-3074
Category Name: Dark Cherry Outfits
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: WINE
Available Size: S, M
Product Badge:- Sale
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Runway Ready Under-The-Knee Scrunch Boots
Fit & Features
- Block heel
- Under-the-knee fit
- Closed pointed-toe
- Scrunch detailing
- Faux microsuede material
- Runs true to size
Style Number/Barcode: 07402-1043
Category Name: Dark Cherry Outfits
Price: $46.90
Availability: In Stock
Available Color: BROWN
Available Size: 6, 6.5, 7, 7.5, 8, 8.5, 9
Product Badge:- Best Seller
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Shine Bright Skater Dress
Shine bright in this glitter skater dress! Bring the glow to your next date-night out on the town in a glitter dress that features a plunging V-neckline that flatters, spaghetti straps that lead to a trendy sheer floral lace back detail, and a twirl-worthy skater silhouette. Complete your glowing outfit with chandelier earrings and strappy heels.
Fit & Features
- Deep V-neckline, spaghetti straps
- Adhesive bra recommended
- Sheer lace back, exposed zipper
- Lower back cutout
- High waistband, skater silhouette skirt
- Glitter knit fabric, moderate stretch
- Runs true to size
The saturation of glitter varies. Glitter may transfer.
Style Number/Barcode: 05101-1707
Category Name: Dark Cherry Outfits
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
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Modern Chic One-Shoulder Crop Top
A modern and chic crop top features an asymmetrical one-shoulder neckline with ruched seams. Perfect for styling with high-rise jeans and mules.
Fit & Features
- Double-lined modal blend knit fabric, moderate stretch
- One-shoulder asymmetrical neckline
- Ruched seams
- Cropped length hem
- Runs true to size
Style Number/Barcode: 06001-5457
Category Name: Dark Cherry Outfits
Price: $24.90
Availability: In Stock
Available Color: WINE, BLACK
Available Size: XS, S, M, L
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Chic Icon Sling-Back Kitten Heel Pumps
Fit & Features
- Stiletto kitten heel
- Patent faux leather closed pointed-toe
- Adjustable sling-back strap, buckle detail
- Faux leather padded insole
- Runs true to size
Style Number/Barcode: 07401-5213
Category Name: Dark Cherry Outfits
Price: $28.90
Availability: In Stock
Available Color: BLACK/WHITE-2, BLACK
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 10
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Preppy Chicness Lace Trim Plaid Bodycon Dress
This plaid mini dress features a lace rose trim square neckline, spaghetti strap ties, and a flattering bodycon silhouette perfect for casual plans.
Fit & Features
- Plaid print, knit fabric with minimal stretch
- Lace rose trim square neckline
- Spaghetti strap ties
- Back zipper closure
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5836
Category Name: Dark Cherry Outfits
Price: $19.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: BURGUNDY
Available Size: M, L
Product Badge:- Sale
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Sleek Allure Faux Leather Wrap-Front Mini Skirt
Fit & Features
- Faux leather fabric with moderate stretch
- High-rise waist
- Hidden back zipper with hook-eye closure
- Faux wrap-front design, rectangular metal buckle
- Ruching
- Mini-length form-hugging fit
- Runs true to size
Style Number/Barcode: 06401-0713
Category Name: Dark Cherry Outfits
Price: $13.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
Product Badge:- Sale
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Fran Formal Crepe Sweetheart Long Dress
Special Occasion
Easy to impress and so chic, the Fran formal crepe long dress exudes sophistication on bridesmaids, wedding guests, and banquets! She features a classy sweetheart neckline with a pleated bust, spaghetti straps, and a flattering slim-fit silhouette with a high front slit and long-length hem. The formal dress is crafted from sleek crepe knit fabric offering plenty of stretch. Complete the look with a necklace and earring set!
Fit & Features
- Sleeveless sweetheart neckline
- Pleated bust, spaghetti straps
- Slim fit silhouette
- High front slit, long-length hem
- Crepe knit fabric, moderate stretch
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05002-7925
Category Name: Dark Cherry Outfits
Price: $49.90
Availability: In Stock
Available Color: BURGUNDY, BLACK
Available Size: XS, S, M, L, XL
Product Badge:- Best Seller
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Flutter Away Layered Skater Dress
Flutter away in a twirl-worthy skater dress! The dress features a sleeveless wrap V-neckline, adjustable spaghetti straps, and a tiered skater silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with a minimal stretch. Complete look with mules and dainty rings.
Fit & Features
- Sleeveless V-neckline, wrap-front design
- Adjustable spaghetti straps
- Back zipper, hook and eye closure
- Tiered skater skirt
- Chiffon fabric, knit lining, minimal stretch
- Fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05101-1458
Category Name: Dark Cherry Outfits
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Artsy Essence Sleeveless Floral Abstract Mesh Midi Dress
This sleeveless midi dress features a cowl neckline, spaghetti straps that crisscross along the back, side ruched seams that hug your curves along the bodycon silhouette, and a flirty side slit. The floral abstract print adds an artsy element to the mesh-lined fabric.
Fit & Features
- Floral abstract print, mesh-lined fabric, moderate stretch
- Cowl neckline
- Spaghetti straps, crisscross back
- Side ruched seams
- Side slit
- Bodycon midi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-3394
Category Name: Dark Cherry Outfits
Price: $19.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: PLUM
Available Size: XS, S, M, L
Product Badge:- Sale
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Sparkle And Glow Glitter Mesh Platform Heels
Fit & Features
- Block heel
- Glitter mesh material
- Open almond toe
- Single strap-over-toe design
- Adjustable ankle strap with small buckle
- Platform sole
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-5043
Category Name: Dark Cherry Outfits
Price: $30.90
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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Enticing Sass Halter Cutout Wide-Leg Jumpsuit
Unlock the sass in this sleeveless knit jumpsuit featuring a sultry halter neckline, a cutout front, and a flattering wide-leg silhouette perfect for styling with sandals. The smooth knit fabric offers a comfortable stretch.
Fit & Features
- Smooth knit fabric, moderate stretch
- Halter neckline, spaghetti strap tie
- Cutout front
- Wide-leg silhouette
- Jumpsuit has a 12.5” front rise with a 33” inseam
- Runs true to size
Style Number/Barcode: 06502-2535
Category Name: Dark Cherry Outfits
Price: $34.90
Availability: In Stock
Available Color: PLUM, TAUPE
Available Size: XS, S, M, L
Product Badge:- Sale
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Cute And Comfy Zip-Front Cropped Knit Hoodie
Fit & Features
- Sweater knit fabric with plenty of stretch
- Drawstring hooded neckline
- Zip-front
- Long sleeves with ribbed hems
- Fitted cropped ribbed hem
- Runs true to size
Style Number/Barcode: 06005-2126
Category Name: Dark Cherry Outfits
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Abigail Ruched Satin Mermaid Dress
Special Occasion
Get a stunning look in the gorgeous and chic Abigail mermaid dress! She features a sleeveless bodice, adjustable spaghetti straps that lead to a cross-back design, a V-neckline, and a sheer lace back panel with zipper closure. Her high waist leads to a curve-hugging mermaid silhouette with a floor-length skirt, front ruched detailing, and a thigh-high front slit. Pair the sleek satin dress with a rhinestone collar necklace and strappy heels.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Back zipper and hook and eye closure, sheer lace panel, cross straps
- Ruched detailing on bodice and waist, thigh-high slit
- Form-fitting long hem, mermaid silhouette
- Luxe satin knit fabrication
- Form-hugging fit, moderate stretch
- Sticky bra recommended
- Runs true to size
Style Number/Barcode: 05002-1198
Category Name: Dark Cherry Outfits
Price: $29.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Monica V-Neck Lace-Up Ruffle Slim Formal Dress
Special Occasion
Looking impressive is effortless in the Monica slim formal dress perfect for wedding guests, bridesmaids, or banquets! She features a flattering V-neckline and adjustable spaghetti straps that highlight your feminine features, while the lace-up back adds a touch of chic. With a high front slit and ruffled slim silhouette, this floor-length dress will make you feel like a modern-day goddess. Complete the look in high heels.
Fit & Features
- Mesh fabric with lining, moderate stretch
- V-neckline
- Adjustable spaghetti straps
- Lace-up back, lower zipper and hook-eye closure
- Front slit
- Ruffled slim silhouette
- Runs true to size
Style Number/Barcode: 05002-8666
Category Name: Dark Cherry Outfits
Price: $79.90
Availability: In Stock
Available Color: WINE
Available Size: XS, S, M, L
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Pattern Play Houndstooth Sling-Back Kitten Heel Pumps
Fit & Features
- Stiletto kitten heel
- Woven material exterior, closed pointed-toe
- Houndstooth pattern
- Adjustable sling-back strap, buckle detail
- Faux leather padded insole
- Runs true to size
Style Number/Barcode: 07401-5214
Category Name: Dark Cherry Outfits
Price: $12.97 $28.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK/WHITE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- Sale
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Sleek Vibes Satin Mini Dress
Bring sleek and chic vibes to your night-out look with this stunning satin mini dress. It features a sleeveless cowl neckline, spaghetti straps, a high waist seam, and a short, curve-hugging silhouette. Complete the outfit with hoop earrings and new heels.
Shop Long Version: Windsor's Lola Dress Collection
Fit & Features
- Cowl neckline
- Spaghetti straps
- High waist seam
- Mini-length, form-hugging fit
- Stretch satin fabric, knit lining at the bust
- Runs true to size
Style Number/Barcode: 05103-3815
Category Name: Dark Cherry Outfits
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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My Sparkle Glitter Lace-Up Mini Dress
Own your sparkle in this glitter mini dress for a dazzling club entrance! Featuring a sleeveless V-neck, spaghetti straps, strappy lace-up open back, side ruched seams, and a bodycon silhouette that flatters without compromising on style. Showcase your sparkling personality and complete the look in strappy block heels!
Fit & Features
- Sleeveless V-neckline, spaghetti straps
- Strappy lace-up open back
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Glitter knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-5419
Category Name: Dark Cherry Outfits
Price: $36.90
Availability: In Stock
Available Color: BLUE
Available Size: L