Winter fashion is all about layering while staying effortlessly chic. From casual to dressy outfits, we’ve got everything covered—think cozy sweaters, long-sleeve tops, and trendy long-sleeve dresses. Pair turtlenecks or bodysuits with midi skirts, pleated skorts, and tights for the perfect winter vibe. Finish the look with on-trend bomber jackets, faux fur coats, or shackets. Whether you're rocking a sweater dress or layering hosiery under skirts, these outfits are absolute must-haves.

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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.

Stylish Moves Criss-Cross Strap Block Heels
Make only stylish moves in these sleek strappy block heels! They feature an open square-shaped toe, thin asymmetric toe straps in a criss-cross design, thin adjustable ankle and heel straps with a buckle, and a thin block heel. Pair with an oversized blazer and a mini handbag to wear from the office to happy hour.

Fit & Features
- Open square toe
- Asymmetric criss-cross toe straps
- Adjustable ankle and heel straps, buckle detail
- Open back
- Thin block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4673

Category Name: Winter Looks

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bundle Up Soft Knit Scarf
Bundle up and feel ultra cozy this season with this adorable soft knit scarf. It features a plush knit material with a stylish shadow-striped design on a long oblong shape. Layer this scarf over a sweater dress paired with ankle booties!

Fit & Features
- Soft knit material
- Shadow striped design
- Long oblong shape
Style Number/Barcode: 07305-0480

Category Name: Winter Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chromatic Babe Cropped Puffer Jacket
Your future is looking chromatic! Create a total babe vibe with this iridescent puffer cropped jacket featuring long sleeves, a standing collar, a front zipper, side pockets, and a back drawcord to customize the fit. The jacket is composed of an iridescent chrome insulated nylon-woven fabric designed to help keep you warm and protected from the elements! Complete the look in sleek booties.

Fit & Features
- Long sleeves, standing collar
- Front zipper, side pockets
- Adjustable back drawcord
- Cropped length
- Iridescent chrome sheen
- Insulated nylon-woven fabric
- Runs true to size
Style Number/Barcode: 06201-0414

Category Name: Winter Looks

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
New Trends Houndstooth Puffer Vest
Layer on this new and trending puffer vest to showcase a fab style this autumn and winter season! The cropped vest features a sleeveless design, a standing collar neckline, front zipper closure, pockets for keeping your hands warm, and a cute houndstooth print. Crafted from an insulated nylon woven fabric, this vest helps keep you warm and protected from the elements. Complete the look in a casual smooth dress for a coffee run and hangouts!

Fit & Features
- Sleeveless design
- Standing collar neckline
- Front zipper closure and pockets
- Cropped hem
- Houndstooth print
- Insulated nylon woven fabric
- Runs true to size
Style Number/Barcode: 06201-0411

Category Name: Winter Looks

Price: $10.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fashion Diva Rhinestone Fold-Over Denim Boots
These fab rhinestone fold-over denim boots were made for a fashion diva like yourself! They feature a mid-calf height, a trendy fold-over design embellished with all-over sparkling rhinestones, a pointed toe, and a comfortable wedge heel. Style with a bodycon dress for a country bar!

Fit & Features
- Mid-calf height
- Fold-over design
- Rhinestone embellishments
- Pointed toe
- Wedge heel
- Denim material
- Runs true to size
Style Number/Barcode: 07402-0989

Category Name: Winter Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Winter Mode Lace-Up Platform Combat Boots
Enter winter mode with these casual and trendy platform combat boots! They feature an above-the-ankle height, a round toe, a front lace-up design, a platform and block heel with a lug sole, and are composed of smooth faux microsuede material. Style with a plaid fringe scarf.

Fit & Features
- Above-the-ankle height, back pull tab
- Round toe
- Front lace-up design, tie closure
- Platform and block heel, lug sole
- Faux microsuede material
- Runs true to size
Style Number/Barcode: 07403-1736

Category Name: Winter Looks

Price: $20.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Layer On The Cozy Vibes Faux Sherpa Denim Jacket
Layer on all the cozy vibes with this adorable faux sherpa denim jacket perf for the season! It features a faux sherpa contrast wide collar, long sleeves with elastic cinched hems, a button-down front, buttoned chest pockets, and a cropped elastic cinched hem. The cotton-blend denim features a cozy faux sherpa lining. Style this trendy jacket over a sweater dress with knee-high boots for a chic 'fit.

Fit & Features
- Faux sherpa contrast wide collar
- Long sleeves, elastic cinched hems
- Button-down front
- Dual buttoned chest pockets
- Cropped elastic cinched hem
- Denim fabric, faux sherpa lining, no stretch
- Runs true to size
Style Number/Barcode: 06203-0516

Category Name: Winter Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Two-Tone Faux Leather Over-The-Knee Boots
These trendy two-tone faux leather boots are a chic staple for the new season. They feature a fitted over-the-knee height with a pointed toe, an inner zipper closure for easy on-and-off styling, a block heel, and a sleek two-tone design with half faux leather and half smooth spandex materials. Pair these boots with a sweater dress for a cool winter vibe.

Fit & Features
- Over-the-knee height
- Pointed toe
- Inner zipper closure
- Block heel
- Two-tone design
- Half faux leather material, half smooth spandex material
- Runs true to size
Style Number/Barcode: 07402-0920

Category Name: Winter Looks

Price: $12.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Model Strut Rhinestone Fishnet Stiletto Booties
These fishnet stiletto booties will inspire you to strut like a model! They feature a closed pointed toe, a stiletto heel, and closed ankle on faux leather material, and a sheer fishnet rhinestone-embellished overlay with an adorable bow on an elastic band. Complete the look with a chic mini purse for an evening in the city!

Fit & Features
- Faux leather closed pointed-toe
- Faux leather stiletto heel, closed ankle
- Sheer fishnet rhinestone-embellished overlay
- Elastic band with bow
- Above-the-ankle shaft
- Runs true to size
Style Number/Barcode: 07403-1714

Category Name: Winter Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Hello Fabulous Fuzzy Platform Slippers
Say hello to fabulous! These cartwheel-worthy fuzzy platform slippers are sure to give you that Y2K feel. They feature a square toe, a wide foot strap, and a chunky platform sole and heel on soft fuzzy material. Complete the look in a cute smooth dress for a casual hang!

Fit & Features
- Square toe
- Wide foot strap
- Chunky platform sole and heel
- Soft fuzzy material
- Runs true to size
Style Number/Barcode: 07408-0111

Category Name: Winter Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Places To Be Seen Faux Leather Thigh-High Boots
You've got places to be seen in these faux leather thigh-high boots! They feature a square toe, a chunky sole and short block heel, a hoop metal strap accent, and an over-the-knee shaft height with pull tabs for easy on-and-off styling. Complete the look in a sleek crop jacket for a dinner and movie downtown!

Fit & Features
- Square toe
- Chunky sole, short block heel
- Hoop metal strap accent
- Thigh-high, over-the-knee shaft height
- Pull tabs, easy-on-and-off styling
- Faux leather material
- Runs true to size
Style Number/Barcode: 07402-0961

Category Name: Winter Looks

Price: $9.97 $66.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All About The Drama Extra-Large Hoop Earrings
With these sleek extra-large hoop earrings, it's all about the drama! They feature an extra-large hoop design and include an omega closure. Style these statement hoops with a simple snake chain necklace to let the focus be on your trendy earrings!

Fit & Features
- Extra-large hoop design
- Omega closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1769

Category Name: Winter Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Point Me To Chic Rhinestone Stiletto Booties
These faux leather booties will point you to chic! They feature a pointed toe with a rhinestone-embellished oval charm, an inner zipper closure, and a stiletto heel. Complete the look in a sweater midi dress for date night!

Fit & Features
- Pointed-toe
- Oval rhinestone-embellished charm
- Inner zipper closure
- Stiletto heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1713

Category Name: Winter Looks

Price: $4.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
In Love Lace-Up Knee High Boots
Fall in love with these faux suede boots with endless styling possibilities! They feature an almond toe, inner zipper closure, a short block heel, and a knee-high shaft with a trendy lace-up back. Complete the look in a chic trench coat for a dinner and show downtown!

Fit & Features
- Almond toe
- Inner zipper closure
- Short block heel
- Knee-high shaft, lace-up back, tie closure
- Faux suede material
- Runs true to size
Style Number/Barcode: 07402-0964

Category Name: Winter Looks

Price: $12.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Layer Up Sleeveless Puffer Vest With Pockets
Style up your look in this puffer vest for the chilly season ahead! Featuring a sleeveless design with a standing collar neckline, front zipper closure, and an elasticized cropped hem. Crafted with an insulated nylon woven fabric and hidden side pockets with snap-button closures for extra comfort and warmth. Complete the look in a basic long sleeve top and jeans for a coffee run and errands!

Fit & Features
- Sleeveless standing collar neckline
- Front zipper closure
- Hidden side pockets with snap-button closures
- Elasticized cropped hem
- Insulated nylon woven fabric for warmth
- Puffer design
- Runs true to size
Style Number/Barcode: 06201-0428

Category Name: Winter Looks

Price: $18.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Keep It Cozy Faux Fur-Lined Denim Jacket
This trendy faux fur-lined denim jacket will keep your winter look cozy and cute! It features a collared neckline with a faux fur trim, long sleeves with faux fur cuffs, a zip-front design, side pockets, and a cropped hem. The denim fabric includes an ultra-plush faux fur lining. Layer this jacket over a fitted bodysuit with cargo pants and mules.

Fit & Features
- Collared neckline, faux fur trim
- Long sleeves, faux fur cuffs
- Complete zip-front
- Dual side pockets
- Cropped hem
- Denim fabric, soft faux fur lining, no stretch
- Runs true to size
Style Number/Barcode: 06203-0512

Category Name: Winter Looks

Price: $9.97 $56.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always Slick Faux Leather Puffer Jacket
Elevate your cold weather look with this faux leather puffer jacket! Its comfy long sleeves with elasticized cuffs, crop hem, and standing collar neckline help keep you extra warm while the front zipper closure and pockets create functionality. The puffer jacket is designed with a sleek faux leather fabric with an insulated nylon-woven lining that helps keep you warm and protected from the elements. Complete the look in trendy denim jeans.

Fit & Features
- Long sleeves, elasticized cuffs
- Standing collar neckline
- Front zipper closure
- Lined pockets
- Elasticized crop hem
- Faux leather fabric, insulated nylon-woven lining
- Runs true to size
Style Number/Barcode: 06201-0442

Category Name: Winter Looks

Price: $10.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Coolness In Check Faux Sherpa Bomber Jacket
Keep your coolness in check with this faux sherpa bomber jacket perf for casual styling! It features a collared neckline, long sleeves with tapered hems, a zip-front design, lined side pockets, and a relaxed fit. The lined cozy faux sherpa fabric features a trendy checkered print pattern. Layer this bomber jacket over a crop top with faux leather pants and combat boots!

Fit & Features
- Collared neckline
- Long sleeves, tapered hems
- Complete zip-front design
- Dual lined side pockets
- Relaxed fit
- Checkered print, faux sherpa fabric, smooth woven lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0409

Category Name: Winter Looks

Price: $12.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Second Look Turtleneck Open Back Sweater
This cozy crop sweater will make everyone do a double-take! Featuring slouchy long sleeves with ribbed cuffs, a turtle neckline, and a cute surplice open back design on a relaxed silhouette on ultra-soft knit fabric. Complete the look in a mini skirt and your favorite boots for a coffee date or pumpkin patch.

Fit & Features
- Long sleeves, ribbed cuffs
- Turtle neckline
- Surplice open back
- Relaxed silhouette, cropped hem
- Ultra-soft rib knit sweater fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1744

Category Name: Winter Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Cuddles Tie-Back Sweater
It's not a casual fling, this tie-back cable knit sweater is in for the long haul. It features a crew neck, cuffed long sleeves, and a keyhole back with tie detail. Perfect for styling with best-selling bottoms and your favorite boots!

Fit & Features
- Crew neck
- Cuffed long sleeves
- Keyhole back, tie detail
- Cropped hem
- Cable knit design
- Runs true to size
Style Number/Barcode: 06005-1743

Category Name: Winter Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Check Ya Later Plaid Flannel Shacket
This plaid flannel shacket will make you look effortlessly stylish! With long sleeves, button cuffs, and a classic collar neckline, you'll be the talk of the town. Featuring a button-down front, front pocket, and oversized silhouette, and is crafted on soft flannel woven fabric with a classic plaid print you'll adore this season. Style with sleek leggings and boots for the perf cold-weather fit'!

Fit & Features
- Long sleeves with button cuffs
- Collar neckline
- Button-down front, pocket
- Oversized silhouette
- Soft flannel woven fabric
- Plaid print
- Runs true to size
Style Number/Barcode: 06204-1609

Category Name: Winter Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
What A Cutie Knit Pom Beanie
You'll look like a total cutie in this knit beanie! Featuring a furry pom top, and a fair isle pattern, and is composed of cozy knit material. Complete the look in a puffer vest for cold days!

Fit & Features
- Furry pom top
- Fair isle pattern
- Knit material
- Warm and soft design
Style Number/Barcode: 07302-1515

Category Name: Winter Looks

Price: $3.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Touch Faux Wool Beret
This beret will add a chic touch to all of your 'fits this season! It features a classic beret design and is composed of a faux wool material. Style with an oversized blazer and ankle booties for a city trip!

Fit & Features
- Classic beret design
- Faux wool material
- Moderate stretch
Style Number/Barcode: 07302-1486

Category Name: Winter Looks

Price: $6.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fall Favorite Turtleneck Braided Sleeve Sweater
Look no further for your new favorite turtleneck sweater this season! It features long sleeves with an eye-catching braided design, a cropped hem, and is crafted from a soft rib knit fabric perfect for keeping cozy and cute. Complete the look in a trendy pleated mini skirt for a coffee date and movie!

Fit & Features
- Long sleeves, braided design
- Turtleneck
- Cropped hem
- Soft rib knit fabric
- Runs true to size
Style Number/Barcode: 06005-1751

Category Name: Winter Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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