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.

SHOW FILTER

SORT:

MOST POPULAR
SIZE
COLOR
PRICE
ALL FILTERS
SORT
×
×
×
×



SEE RESULTS
Loading...
×
DARK CHERRY OUTFITS
All Filters
Sort By:
MOST POPULAR
SEE RESULTS

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.

  • It-Girl Style One-Shoulder Neck Tie Knit Top

    Chic and so on-trend, this stretchy knit top features an asymmetric one-shoulder neckline with an attached neck tie for that it-girl vibe. The front ruching will accentuate your curves on the fitted midi-length silhouette.

    Fit & Features

    • Stretchy smooth knit fabric
    • One-shoulder neckline with tank strap
    • Attached neck tie
    • Front ruching
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-5437

    Category Name: Dark Cherry Outfits

    Price: $21.90

    Availability: In Stock

    Available Color: BURGUNDY, BLACK

    Available Size: L

  • Cozy Glam Cable Knit Long Sleeve Bolero

    Shop Matching Top: Cozy Glam Cable Knit Tube Top

    Fit & Features

    • Cable knit fabric with plenty of stretch
    • Open front
    • Long sleeves
    • Cropped hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06005-2117

    Category Name: Dark Cherry Outfits

    Price: $32.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • Sparkle Step Glitter Lurex Block Heels

    Bring the shimmer and shine when you step out in these eye-catching glitter lurex heels! They feature a slim ankle strap, an open almond toe with a toe strap, a stabilizing block heel, and a back zipper. Shoes are constructed with a metallic glitter material and have a faux leather footbed. Complete the look with a skater dress and rhinestone anklet.

    Fit & Features

    • Closed-back 
    • Adjustable ankle strap
    • Open almond toe, strap
    • Block heel
    • Back zipper closure
    • Glitter lurex material
    • Runs true to size

    Style Number/Barcode: 07401-0203

    Category Name: Dark Cherry Outfits

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

  • Simply A Stunner Lace-Up Bodycon Satin Mini Dress

    Bring all the iconic vibes in this satin mini dress to school dances or dressy birthdays! The spaghetti straps, and V-neckline with padded bra cups flatter while the bodycon silhouette accentuates your figure. With a sexy lace-up back and a mini-length hem, this dress is perfect for a night out. Complete the look in block heels and earrings!

    Fit & Features

    • Satin fabric, bust knit lining, minimal stretch
    • Spaghetti straps
    • V-neckline
    • Padded bra cups
    • Lace-up back
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5624

    Category Name: Dark Cherry Outfits

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RAISIN

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Nadia Rhinestone Sheer Mesh Formal Dress

    Special Occasion

    Bring the glitzy allure in the iconic Nadia formal dress designed with sheer mesh fabric, a knit bodysuit lining, and all-over tonal rhinestone embellishments in a gorgeous starburst center design. It features a sleeveless V-neckline, adjustable spaghetti straps for a customized fit, a cheeky bodysuit bottom, and a floor-length sheer mesh A-line silhouette accented with dual side slits for added drama.

    Fit & Features

    • Sheer mesh fabric with knit bodysuit lining
    • Tonal rhinestone starburst center embellished design
    • V-neckline
    • Adjustable spaghetti straps
    • Back zipper closure
    • Floor-length sheer mesh A-line silhouette, dual side slits
    • Runs true to size

    Style Number/Barcode: 05002-8776

    Category Name: Dark Cherry Outfits

    Price: $169.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Loaded With Glam Halter Rhinestone Mesh Mini Dress

    This rhinestone mesh mini dress is a glam style perfect for the school dance or party. The mini-length dress features a halter neckline, a tie-back design, and side ruched seams that effortlessly hug your curves along the bodycon silhouette. The mesh-lined fabric is adorned with countless rhinestones for a glam look. 

    Fit & Features

    • Mesh-lined fabric, moderate stretch
    • Halter neckline with spaghetti strap tie
    • Tie-back design
    • Rhinestone embellishments
    • Ruched side seams
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-5704

    Category Name: Dark Cherry Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

  • Pippa High-Slit Open Back Lace Dress

    Special Occasion

    Grace the room with a long lace dress that features a sleeveless square neckline, adjustable spaghetti straps, a bold open back design, and a long-length hem accented with a high side slit. Complete formal outfit with glitter mesh heels.

    Fit & Features

    • Lined floral lace fabrication
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Open-back design
    • High side slit
    • Long length hem
    • Runs true to size

    Style Number/Barcode: 05002-8777

    Category Name: Dark Cherry Outfits

    Price: $59.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L, XL

  • Show Up Satin One-Shoulder Midi Dress

    Show them up, girl! Look elegantly sleek in this one-shoulder midi and walk right in looking like a million bucks! It features a curve-hugging silhouette with a thigh-high front slit. Complete the look with chrome heels.

    Fit & Features

    • One-shoulder neckline, single spaghetti strap
    • Asymmetric neckline
    • Ruching at the side slit
    • Midi-length silhouette
    • Satin-like fabric, pretty sheen finish 
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-0894

    Category Name: Dark Cherry Outfits

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Something About Her Strappy Back Bodycon Midi Dress

    Eyes will linger as you stroll away in this sleeveless midi dress at cocktail parties!  Featuring a square neckline and spaghetti strap ties for a chic look. The strappy open back and lower ruched seam add alluring details to the bodycon fit. Complete the look with a clutch and heels.

    Fit & Features

    • Smooth knit stretchy fabric
    • Square neckline
    • Spaghetti strap ties
    • Strappy open back, lower ruched seam
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3298

    Category Name: Dark Cherry Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: RAISIN

    Available Size: L

  • Vintage Glam Platform Mary Jane Heels

    Fit & Features

    • Block heel
    • Faux nubuck material
    • Closed pointed-toe
    • Adjustable ankle strap with rhinestone buckle
    • Platform sole
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-5070

    Category Name: Dark Cherry Outfits

    Price: $32.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 6, 6.5, 7, 7.5, 8, 8.5, 9

    Product Badge:
    • Best Seller
  • Millie Lace-Up Slim Long Formal Dress

    Special Occasion

    Bring glamorous vibes in the Millie formal dress as a stunning bridesmaid, wedding guest, or attending a banquet! The square neckline and spaghetti straps accentuate your figure, while the lace-up back adds a touch of elegance. With a side slit and slim silhouette, this long dress exudes sophistication and style. Complete the look with earrings and sleek stiletto heels.

    Fit & Features

    • Smooth knit fabric, moderate stretch
    • Square neckline
    • Spaghetti straps
    • Lace-up back, side slit
    • Slim silhouette
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05002-9011

    Category Name: Dark Cherry Outfits

    Price: $59.90

    Availability: In Stock

    Available Color: EGGPLANT

    Available Size: XS, S, M, L, XL

  • Kaleen Sleeveless Satin Wrap Midi Dress

    Special Occasion

    Bring elegance in a midi dress that features a sleeveless cowl neckline, ruching to enhance curves, and a wrap silhouette accented with a high-side slit. Complete the formal outfit with silver heels.

    Fit & Features

    • Satin fabrication
    • Sleeveless cowl neckline, padded bust
    • Ruching, back zipper and hook-eye closure
    • High side slit
    • Wrap silhouette
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05001-2523

    Category Name: Dark Cherry Outfits

    Price: $59.90

    Availability: In Stock

    Available Color: HUNTER, WHITE

    Available Size: XS, S, M, L, XL

  • Celina Glitter Knit Mermaid Dress

    Special Occasion

    Turn heads and make a sparkly statement in the stunning Celina dress! She features a sleeveless cowl neckline, spaghetti straps that lead to a cross-back design, front ruched detailing, and a floor-length mermaid silhouette with a thigh-high slit. Complete the look with rhinestone statement earrings and chic heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps, cross-back design
    • Front ruching
    • Floor-length mermaid silhouette, high front slit
    • Curve-hugging fit
    • Glitter knit fabric, short knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05002-1718

    Category Name: Dark Cherry Outfits

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spotlight Moment V-Neck Surplice Midi Dress

    You'll love every moment in the spotlight wearing this sleeveless midi dress at parties and date nights! Boasting a surplice V-neckline and spaghetti straps, this bodycon dress accentuates your curves for a flattering look. The asymmetrical midi hem adds a touch of elegance, making it a must-have for dressy occasions. Complete the look with a clutch, heels, and earrings for a flawless finish!

    Fit & Features

    • Smooth knit fabric with stretch
    • Spaghetti straps
    • Surplice
    • Bodycon silhouette, midi-length
    • Runs true to size

    Style Number/Barcode: 05101-3028

    Category Name: Dark Cherry Outfits

    Price: $36.90

    Availability: In Stock

    Available Color: WINE, HUNTER, SLATE

    Available Size: XS, S, M, L, XL

  • Anisley Strapless High Slit Slim Formal Dress

    Special Occasion

    Sweeping everyone off their feet is easy in the Ainsley formal dress as a striking bridesmaid, wedding, or banquet guest! Made of luxurious slinky knit fabric, this dress attracts attention. The strapless neckline and slim silhouette create a sophisticated look, while the pleated side seams add a touch of texture. The high side slit and floor-length hem provide an alluring twist, perfect for any formal occasion. Complete the look with earrings and heels.

    Fit & Features

    • Slinky knit fabric, short stretchy knit lining
    • Strapless neckline
    • Side pleated seams
    • High side slit
    • Slim silhouette
    • Runs true to size

    Style Number/Barcode: 05002-9132

    Category Name: Dark Cherry Outfits

    Price: $59.90

    Availability: In Stock

    Available Color: PEACH, WINE, BROWN

    Available Size: XS, S, M, L, XL

  • Cozy Glam Cable Knit Tube Top

    Shop Matching Bolero: Cozy Glam Cable Knit Long Sleeve Bolero

    Fit & Features

    • Cable knit fabric with plenty of stretch
    • Strapless elasticized straight neckline
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-2118

    Category Name: Dark Cherry Outfits

    Price: $26.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Total Allure Mock Neck Side Slit Midi Dress

    A sleeveless mesh midi dress featuring a mock neckline with a chic scarf accent, a bodycon fit, and a flirty side slit. Perfect for styling with stiletto heels and a clutch.

    Fit & Features

    • Mesh fabric, sewn-in knit lining, moderate stretch
    • Mock neckline with a scarf accent
    • Back zipper and hook-eye closure
    • Side ruched seams
    • Side slit
    • Bodycon midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3737

    Category Name: Dark Cherry Outfits

    Price: $49.90

    Availability: In Stock

    Available Color: WINE, BLACK

    Available Size: M, S, L

  • Chic Structure Long Sleeve Cropped Corset Top

    Fit & Features

    • Woven fabric with minimal stretch
    • Collared V-neckline
    • Button-down front closure
    • Long sleeves with dual button details
    • Corset-like bodice with flexible boning, side smocked accents
    • Angled cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2660

    Category Name: Dark Cherry Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

  • Live It Up Sequin Mini Dress

    Hey babe, live it up and light up the dance floor in this stunning sequin mini dress! It features a sleeveless square neckline, bungee spaghetti straps, and a short, form-hugging silhouette. The sheer mesh fabric includes a full knit lining and has a chic all-over sequin scroll embroidered design. Complete the look with platform heels.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Mini-length, form-fitting silhouette
    • Sheer mesh fabric, knit lining, moderate stretch
    • Sequin scroll embroidered design
    • Runs true to size

    Style Number/Barcode: 05101-1191

    Category Name: Dark Cherry Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Style Satin Cropped Tube Top

    This silky sleek satin top is designed with a strapless straight-across neckline, a smocked back for added stretch with an adorable tie-back design, and a chic cropped hanky hem. Perfect for styling with jeans and mules.

    Fit & Features

    • Satin woven fabric
    • Strapless straight neckline
    • Smocked back
    • Tie-back design
    • Cropped hanky hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-2617

    Category Name: Dark Cherry Outfits

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BURGUNDY, COGNAC

    Available Size: M, L, XS, S

    Product Badge:
    • Sale
  • Joyful Glam Layered Cross Charm Necklace

    Fit & Features

    • Layered double-row design
    • Mini cross charms
    • Lobster clasp closure

    Style Number/Barcode: 07002-1967

    Category Name: Dark Cherry Outfits

    Price: $10.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Roaring Glam Sleeveless Leopard Print Cropped Corset

    Fit & Features

    • Sheer mesh fabric with knit lining, moderate stretch
    • Leopard print
    • Strapless straight neckline
    • Flexible boning, back zipper with hook-eye closure
    • Front and back ruching
    • Fitted angled cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5567

    Category Name: Dark Cherry Outfits

    Price: $24.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: XS, S, M, L

  • Sheerly Sultry V-Neck Lace Crop Top

    Everyone will notice how sultry you look in this lace crop top perfect for adding romance into your style! Adorned with delicate spaghetti straps, a playful V-neckline with a ribbon tie, and a sheer fitted crop hem. Complete the look in high-rise jeans for a casual date night.

    Fit & Features

    • Sheer lace fabric, lined bust
    • Spaghetti straps
    • V-neckline with ribbon tie
    • Fitted crop silhouette
    • Runs true to size

    Style Number/Barcode: 06001-5393

    Category Name: Dark Cherry Outfits

    Price: $19.90

    Availability: In Stock

    Available Color: BURGUNDY, BLACK

    Available Size: XS, S, M, L

  • Cool Girl Energy Camo Cargo Pants

    Fit & Features

    • Camouflage twill woven fabric, no stretch
    • Mid-rise waist, belt loops, back buckle strap accents
    • Hidden front zipper with button closure
    • Dual front pockets, dual faux back pockets, large side flap pockets
    • Straight-leg fit, drawstring ankle
    • Pants in size small have a 10" front rise with a 31" inseam
    • Runs true to size

    Style Number/Barcode: 06302-0845

    Category Name: Dark Cherry Outfits

    Price: $49.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: S, M, L