Winter Looks

STYLE SPOTLIGHT

Women's Denim Bottoms

Women's Sweaters & Cardigans

Women's Jackets

Trendy & New Winter Outfits for Women

Refresh your wardrobe this season with women’s winter outfits and chic styles from Windsor! Embrace the colder months in trendsetting clothes, shoes, and accessories perfect for layering. Winter is all about standout style, so explore winter dresses in mini, midi, and long silhouettes to create stylish holiday outfits. Discover the latest sweater dresses, floral and plaid prints, and classic fabrics like satin, lace, and velvet for holiday parties and winter formals. For an effortlessly cozy vibe, shop trendy sweater dresses, ruched details, and luxe marble and swirl prints.

Find endless winter outfit ideas in Windsor’s collection, featuring this season’s top winter fashion trends. Refresh your look with rich hues like burgundy, plum, hunter green, and oatmeal brown, perfect for any occasion. Style up your casual outfits with soft, cozy sweaters and long-sleeve tops for layering. Keep warm with essential winter layers like plaid shackets, oversized flannels, and sherpa-lined jackets. Complete your everyday winter style with matching sets, long dusters, and statement jackets, like a faux sherpa coat or rhinestone-studded denim jacket, to capture your best winter look.

No winter closet is complete without women’s jeans and chic winter bottoms. Choose dark wash jeans or faux leather leggings to add an edgy twist, or go for paperbag trousers in stylish tie-waist designs. Mix and match plaid mini skirts and faux suede skirts with bodysuits, long-sleeve tops, or cardigans to create versatile looks for family gatherings, work parties, and date nights. Step out in elevated plaid pants, wide-leg jumpsuits, or sleek catsuits to stay on-trend this season.

Complete your winter outfits with must-have accessories. Explore a variety of scarves, berets, and stylish boots, from knee-high boots to heeled booties, perfect for holiday gatherings and outdoor winter activities. Add layered necklaces, bold earrings, and trendy belts to glam up your look. Style up for the season with ankle booties, cowboy boots, and thigh-high boots to make a statement. With quilted crossbody bags and chic clutches, Windsor has everything you need for women’s winter outfits to create looks you’ll love all season long.

How can I layer winter outfits to stay warm without losing style?

Layering is key to winter style, and Windsor’s winter outfits make it easy to stay warm while looking chic. Start with basics like a fitted long-sleeve top or bodysuit, then add a cozy sweater or cardigan. Try layering a plaid shacket or an oversized faux sherpa coat for extra warmth. For dresses, layer a jacket over a sweater dress and finish the look with a scarf and knee-high boots. This approach keeps you comfortable without sacrificing style.

What fabrics are best for stylish winter outfits?

Fabrics like velvet, knit, sherpa, and faux leather are ideal for keeping warm and stylish this winter. Velvet and sherpa are soft and luxurious, perfect for holiday parties and formal events. Knit fabrics, including chunky sweaters and long-sleeve tops, offer warmth and comfort for casual outings. For an edgier look, faux leather pants and skirts add a trendy vibe while keeping you insulated against the cold. Explore Windsor’s range of winter fabrics for outfits that suit every occasion.

What are some winter outfit ideas that can go from day to night?

Transitioning a winter outfit from day to night is all about versatile pieces. Start with a sweater and dark wash jeans for a casual day look, then swap the jeans for a plaid mini skirt and add heeled booties for the evening. Another option is to layer a faux leather jacket over a knit dress for a cozy day look, then add statement jewelry and knee-high boots to elevate it for a night-out look. Windsor’s collection has all the essentials you need to create winter outfits that easily adapt to any time of day.

What accessories should I add to complete my winter outfits?

Winter accessories not only add style but also warmth to any outfit. A plaid scarf, a cozy beret, or a chic knit hat will instantly elevate your winter look. Consider layering with jewelry like chain-link necklaces or hoops for a touch of glam. For footwear, try ankle booties or knee-high boots, which pair well with jeans, skirts, and dresses. And don’t forget a quilted handbag or crossbody purse to hold all your essentials in style!

How do I choose the right winter boots for different outfits?

Choosing the right boots depends on the look you’re going for. Ankle booties are versatile for casual looks and pair well with jeans or leggings. Knee-high and over-the-knee boots offer more coverage and look stunning with dresses, skirts, and holiday outfits. For a bold statement, try heeled booties or even cowboy boots with a plaid dress or faux leather skirt. Windsor’s boot collection has styles for every occasion from everyday wear to festive gatherings, and are designed with comfort in mind.

What are some comfortable yet stylish outfits for winter holidays and gatherings?

Comfort and style can go hand-in-hand for winter holiday events. A sweater dress with tights and knee-high boots creates a cozy but polished look for family gatherings. If you’re attending a holiday party, try a satin or velvet dress with an oversized blazer and heeled booties. Look for one-shoulder or single-sleeve styles for a modern twist on classic silhouettes. For casual gatherings, a matching plaid set or sherpa-lined jacket paired with dark jeans offers comfort and effortless style. Windsor’s winter collection has options for every event on your calendar this season.

  • Seasonal Chic Plaid Oversized Top

    Embrace a seasonal chic style in this plaid top perfect for coffee runs to casual dates! The top features slouchy long sleeves with button cuffs, a collar V-neckline, and an oversized silhouette on woven fabric with a trendy plaid print. Complete the look in distressed denim.

    Fit & Features

    • Slouchy long sleeves, button cuffs
    • Collar V-neckline
    • Oversized silhouette
    • Plaid print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2272

    Category Name: Winter Looks

    Price: $3.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep Up With Me Puffer Under-The-Knee Boots

    With these puffers under-the-knee boots, they won't be able to keep up with your fashion-forward style! The boots feature a round toe, a sturdy lug sole and heel, an inner zipper closure, a cozy faux fur lining to keep your feet warm, and an adjustable drawstring to customize the style. Complete the look with a cute and cozy jacket for the cold season!

    Fit & Features

    • Round toe
    • Sturdy lug sole and heel
    • Inner zipper closure
    • Under-the-knee shaft 
    • Adjustable drawstring
    • Pufffer material, faux fur lining
    • Runs true to size

    Style Number/Barcode: 07402-0923

    Category Name: Winter Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Endless Possibility Surplice Crop Blouse

    This cropped blouse has endless styling possibilities with your favorite bottoms! It features peasant long sleeves with button cuffs, a lapel collar V-neckline, front flap pockets, a surplice bodice, and an elasticized crop hem on texture lightweight woven fabric. Complete the look in sleek high-rise pants for a casual meeting or dinner party! 

    Fit & Features

    • Peasant long sleeves, button cuffs
    • Lapel collar V-neckline
    • Front flap pockets
    • Surplice bodice
    • Elasticized crop hem
    • Texture lightweight woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2271

    Category Name: Winter Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Not A Drill Denim Foldover Boots

    These trend-forward denim boots are the new style you're looking for! They feature a pointed toe, a thin block heel, a foldover design with frayed trim, and a calf-length shaft. Complete the look with a mini handbag for day or night plans!

    Fit & Features

    • Pointed toe
    • Thin block heel
    • Foldover design, frayed trim
    • Calf-length shaft
    • Denim material
    • Runs true to size

    Style Number/Barcode: 07402-0975

    Category Name: Winter Looks

    Price: $4.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On My Command Faux Leather Knit Combat Booties

    Take on the season in these combat booties with confidence and style! Featuring stylish faux leather details, a front lace-up placket, stretchy knit material, and a sturdy lug rubber sole, these booties combine fashion and function for any adventure. Complete the look in a trendy denim jacket for casual plans!

    Fit & Features

    • Round toe
    • Front lace-up placket
    • Sturdy lug rubber traction sole
    • Faux leather details, stretchy knit material
    • Pull tab for easy on-and-off styling
    • Runs true to size

    Style Number/Barcode: 07403-1708

    Category Name: Winter Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cozy On Down Faux Sherpa Block Heel Booties

    Be bold and cozy in these faux sherpa booties! Crafted from faux suede and sherpa, these comfy yet chic booties feature a pointed toe and block heel for an eye-catching look. Plus, the foldover styling makes it easy to pull on and off! Complete the look in a trendy jacket for a pumpkin patch or coffee with friends!

    Fit & Features

    • Faux suede pointed-toe, block heel
    • Faux sherpa foldover design
    • Pull on-and-off styling
    • Runs true to size

    Style Number/Barcode: 07402-0954

    Category Name: Winter Looks

    Price: $27.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Days In Plaid Button Down Shirt Top

    Get ready for plaid shirt days in this top! It features relaxed long sleeves with buttoned cuffs, a collar neckline, a button-down front, and a plaid print on woven fabric. Style with best-selling bottoms for casual day or evening plans!

    Fit & Features

    • Relaxed long sleeves
    • Collar neckline
    • Button-down front
    • Plaid print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2273

    Category Name: Winter Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Poised in Plaid Belted Shacket

    Keep it poised in a plaid shacket to usher in those winter vibes. The shacket features a collared neckline, a multi-button down front, a belted waist, and a windowpane plaid print on a corduroy fabric. Style this plaid shacket with an adorable top and booties to take you to a coffee date and lunch downtown!

     Fit & Features

    • Collared neckline
    • Long sleeves, single button detail
    • Complete button-down front
    • Dual buttoned chest pockets
    • Tie-waist belt
    • Windowpane striped pattern, corduroy fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1637

    Category Name: Winter Looks

    Price: $18.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Looking Sweet Corset Crop Hoodie

    Look and feel sweet in this crop hoodie perfect for layering over your casual outfits! The hoodie features slouchy long sleeves, a hoodie neckline, a front zipper closure, a corset-seam bodice for a snatched appearance, and a fitted crop hem on smooth scuba knit fabric. Complete the look with the matching sweatpants for coffee runs or errands!

    Shop Matching Bottoms: Operation Cute Wide-Leg Cargo Sweatpants

    Fit & Features

    • Slouchy long sleeves
    • Hoodie neckline
    • Front zipper closure
    • Corset-seam bodice
    • Fitted crop hem
    • Smooth scuba knit fabric
    • Runs true to size

    Style Number/Barcode: 06202-0424

    Category Name: Winter Looks

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Kick Up A Storm Faux Leather Western Boots

    Kick up a stylish storm in these faux leather western boots! They feature a sleek pointed-toe, inner zipper closure, a block heel, trendy western-inspired stitching, and the perfect under-the-knee length with side pull tabs for easy on-and-off styling. Complete the look with a cowboy hat for a bachelorette or country concert!

    Fit & Features

    • Pointed-toe, block heel
    • Inner zipper closure
    • Western-inspired stitching
    • Under-the-knee shaft length
    • Side pull tabs, easy-on-and-off styling
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0973

    Category Name: Winter Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Ombre Stripe Tie Back Crop Sweater

    You'll be a gorgeous sunset view in this ombre striped sweater! The top features fitted long sleeves, a crew neckline, a form-hugging fit, a cropped hem, and a sassy tie-back design on fuzzy and soft rib knit wool-blend sweater fabric. Complete the look in sleek faux leather pants for a dinner and movie!

    Fit & Features

    • Fitted long sleeves
    • Crew neckline
    • Form-hugging fit
    • Crop hem, tie-back design
    • Ombre striped pattern
    • Fuzzy sweater knit wool-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1745

    Category Name: Winter Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Coolest Vibes Zip-Front Bomber Jacket

    This sleek zip-front bomber jacket will give off the coolest vibes for perfect fall and winter 'fits. It features a ribbed knit collar, long sleeves with cinched hems, a complete zip-front design, buttoned pockets, a mid-length cinched hem, and a trendy oversized silhouette for that relaxed look. The sleek woven fabric includes a filling and a lining. Channel that trendy girl energy by styling with layered chain necklaces and ankle booties!

    Fit & Features

    • Ribbed knit collar
    • Long sleeves, elastic cinched hems
    • Complete zip-front
    • Dual buttoned pockets
    • Mid-length elastic cinched hem
    • Sleek woven fabric, filling, lining
    • Oversized silhouette

    Style Number/Barcode: 06204-1669

    Category Name: Winter Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Girl Energy Houndstooth Knit Mini Dress

    Bring the chic girl energy to your fall wardrobe with this trendy mini dress! It features a sleeveless square neckline, spaghetti straps, a mini-length hem, and a bodycon silhouette to showcase your curves. The knit fabric features an all-over houndstooth pattern for an elevated vibe. Style this mini dress with a faux leather moto jacket and combat boots!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length hem
    • Bodycon silhouette
    • Houndstooth pattern
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5410

    Category Name: Winter Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Another Day Long Sleeve Sweater Midi Dress

    Another day, another slay in this sweater midi dress - perfect for pumpkin patches, grabbing a PSL, or meeting up with friends! The knee-length dress features fitted long sleeves, a crew neckline, a bodycon silhouette, and a flirty front slit on soft and stretchy rib knit fabric. Complete the look in booties and a chic crossbody bag.

    Fit & Features

    • Fitted long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Front slit accent
    • Midi-length hem
    • Soft, stretchy sweater rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5305

    Category Name: Winter Looks

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get My Attention Fitted Ankle Combat Boots

    Call for all the attention in these trendy fitted ankle combat boots this fall and winter season! They feature a fitted ankle design, a round toe, a bold platform lug sole, and are composed of a sleek faux leather material. Style these ankle boots with a bomber jacket. 

    Fit & Features

    • Fitted ankle design
    • Round toe
    • Platform lug sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1709

    Category Name: Winter Looks

    Price: $8.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cute March Faux Leather Lug Combat Booties

    Take a cute march around in these combat booties! The faux leather boots feature a round toe, a sturdy traction lug sole and short heel, a front lace-up placket, and a back pull tab for easy on-and-off styling. Complete the look in a plaid shacket for casual plans!

    Fit & Features

    • Round toe
    • Sturdy traction lug sole and heel
    • Front lace-up placket
    • Back pull tab
    • Easy-on-and-off styling
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1710

    Category Name: Winter Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Let Your Sparkle Shine Under-The-Knee Boots

    Let your sparkle shine in these under-the-knee boots with each strut you take! They feature a pointed toe, an inner zipper closure, a stiletto heel, and all-over mini rhinestone embellishments that glitter under the lights. Complete the look in a sleek blazer for a girl power moment!

    Fit & Features

    • Pointed toe
    • Inner zipper closure
    • Stiletto heel
    • All-over mini rhinestone embellishments
    • Under-the-knee shaft height
    • Runs true to size

    Style Number/Barcode: 07402-0948

    Category Name: Winter Looks

    Price: $9.97 $65.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Glitzy Small Rhinestone Hoop Earrings

    So glitzy, these small rhinestone hoop earrings will create that gorgeous shine. The chunky hoops feature an open-ended design with all-over sparkling rhinestone embellishments. Include a post-back closure. Take your glamour to the next level by styling these rhinestone hoops with metallic heels!

    Fit & Features

    • Small chunky hoops
    • Open-ended design
    • Round rhinestone embellishments
    • Post-back closure, rubber stopper


    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-1714

    Category Name: Winter Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Deets Three-Pack Hoop Earring Set

    You'll love styling your casual 'fits with the trendy deets of this hoop earring set! The multi-pack features three pairs of hoop earrings including flat chunky hoops, thin textured hoops, and chain-link hoops. All include post-back closures. Add this set to your everyday jewelry lineup with a layered charm necklace and a dainty rhinestone ring!

    Fit & Features

    • Three pairs of hoop earrings
    • Open-ended designs
    • Flat chunky hoops
    • Thin textured hoops
    • Chain-link hoops
    • Post-back closures


    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-1694

    Category Name: Winter Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Elevated Everyday Glam Five-Pack Ring Set

    Create an elevated everyday glam style with this ring set. The multi-pack features five rings, including a thin ring with a chain-link design and a center gemstone accent, a thin ring with an oval-shaped pattern, a thin ring with mini rhinestones, and two chunky dome rings. Pair this set with a dainty charm necklace.

    Fit & Features

    • Five-pack ring set
    • Thin ring, chain-link design, gemstone accent
    • Thin ring, oval-shaped pattern
    • Thin ring, rhinestones
    • Two chunky dome rings

    Style Number/Barcode: 07004-0358

    Category Name: Winter Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Style Staple Canvas Woven Belt

    This canvas woven belt is one of those trendy style staples that need to be in your closet. It features a double D-ring buckle on a canvas woven material with faux leather strap accents. Pair this casual belt with a crop top and cargo pants!

    Fit & Features

    • Double D-ring buckle
    • Canvas woven material
    • Faux leather straps
    • Adjustable fit

    Style Number/Barcode: 07301-0678

    Category Name: Winter Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fuzzy Feels Chenille High-Rise Jogger Pajamas

    Get cozy lounging in these chenille jogger pajamas! They feature a high-rise elasticized waistband, a skinny jogger-leg silhouette, and ribbed cuffs on ultra-soft and cozy chenille knit fabric. Complete the look in the matching pajama top and robe for a chill night in!

    Shop Matching Pajama Top: Hello Cutie Chenille Crop Pajama Top

    Shop Matching Robe: Tied In Cozy Chenille Tie-Waist Robe

    Fit & Features

    • High-rise elasticized waistband
    • Skinny jogger-leg silhouette
    • Ribbed cuffs
    • Ultra-soft chenille knit fabric
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 07103-0940

    Category Name: Winter Looks

    Price: $13.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Days Quilted Nylon Shoulder Bag

    This trendy quilted nylon shoulder bag was made for those lowkey casual days. It features a medium size with a top shoulder strap, a slouchy silhouette, and a quilted design on the nylon fabric. The top zipper closure leads to a spacious woven interior with a single zippered pocket. Style with sleek hoops and ankle booties for a cute on-the-go look.

    Fit & Features

    • Medium size
    • Top shoulder strap
    • Slouchy silhouette
    • Fully quilted design
    • Nylon fabric
    • Top zipper closure
    • Spacious woven interior, zippered pocket

    Style Number/Barcode: 07203-1420

    Category Name: Winter Looks

    Price: $3.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bling Babe Rhinestone Foldover Stiletto Boots

    Flaunt these blinged out stiletto boots like the babe you are! They feature a sleek pointed-toe, an inner zipper closure, a foldover design with glitzy rhinestone embellishments, and have an under-the-knee shaft height. Complete the look with a glam handbag for dinner and drinks!

    Fit & Features

    • Pointed-toe
    • Stiletto heel
    • Inner zipper closure
    • Foldover rhinestone embellishments
    • Under-the-knee shaft height
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0950

    Category Name: Winter Looks

    Price: $9.97 $58.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale