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.

  • Rich Mood Solid Beret

    The kind of accessory that instantly changes the energy of the outfit. Clean lines and a classic shape make this beret feel confident, elevated, and styled on purpose.

    Fit & Features

    • Woven felt fabric
    • Classic beret silhouette
    • Soft structured crown

    Style Number/Barcode: 07302-000221

    Category Name: Winter Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always Polished Classic Beret

    That instant polish piece you reach for when the outfit needs a little more thoughtfulness. Clean, classic, and endlessly wearable, this beret brings an elevated finish without feeling try-hard.

    Fit & Features

    • Woven felt fabric
    • Classic beret silhouette
    • Soft structured crown

    Style Number/Barcode: 07302-000219

    Category Name: Winter Looks

    Price: $4.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cuddle Club Teddy Bear Slipper And Socks Set

    Cozy just got cuter. This teddy bear slipper and sock set is basically a hug for your feet—soft, fuzzy, and perfect for lazy mornings or all-day lounging.

    Fit & Features

    • Slippers and socks set
    • Plush faux sherpa teddy bear embroidered slippers
    • Hard sole bottom
    • Matching teddy bear fuzzy socks included

    Style Number/Barcode: 07308-000083

    Category Name: Winter Looks

    Price: $4.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paris Plans Faux Suede Beret

    The finishing touch that makes the whole look feel intentional. Soft faux suede gives this beret an elevated feel that works just as well with casual layers as it does with dressed-up moments.

    Fit & Features

    • Faux suede fabric
    • Classic beret silhouette
    • Soft structured crown
    • Lightweight comfortable fit
    • Adjustable inner strings for a snug fit

    Style Number/Barcode: 07302-000225

    Category Name: Winter Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sculpted Step Wide Fit Boots

    Sleek, comfy, and quietly bold—these under-the-knee boots give you that polished silhouette with a soft kitten heel you can wear all day. The pointed toe sharpens the vibe, while the wide-fit design keeps everything easy, confident, and effortlessly cool.

    Fit & Features

    • 3” kitten heel, 8” leg opening, 15” shaft
    • Pointed-toe
    • Inner zipper closure
    • Under-the-knee length
    • Wide fit silhouette
    • Luxe fit cushioned insole
    • Glossy faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000109

    Category Name: Winter Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 6.5, 7.5

  • Polished Prep Patent Loafers

    These patent loafers bring a sleek, polished vibe to your everyday rotation. Glossy and structured with that classic preppy shape, they turn even a jeans-and-sweater day into something effortlessly put-together.

    Fit & Features

    • Square toe design
    • Classic penny strap detail
    • Cushioned footbed for all-day wear
    • Low-profile sole with sturdy traction
    • Glossy patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07405-000024

    Category Name: Winter Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Late Night Layers Open Back Crop Top

    Serving sleek, after-dark vibes, this fitted mock-neck crop top brings instant cool-girl confidence. The open-back cutout and adjustable tie give it that bold, photo-ready edge you’ll want for every night out.

    Fit & Features

    • Stretch knit fabric
    • Mock neckline with fitted long sleeves
    • Dramatic open back with center O-ring detail
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000368

    Category Name: Winter Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Icon Faux Leather Capri Pants

    Take charge in these high-rise faux leather capri pants designed with sleek pintuck seams and a wide-leg silhouette that means business (and a little bit of drama).

    Fit & Features

    • Faux leather fabric, slight stretch
    • High-rise waist
    • Back zipper closure
    • Pintuck seam detailing
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-000020

    Category Name: Winter Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Play It Cool Varsity Bomber Jacket

    Retro edge meets city cool. This varsity-inspired faux leather bomber brings all the vintage vibes with bold color blocking, striped rib knit trim, and embroidered “NEW YORK BROOKLYN” detailing that keeps it effortlessly street.

    Fit & Features

    • Varsity-inspired color block design
    • Faux leather fabric, sewn-in quilted woven lining
    • Collar neckline, long sleeves with striped rib knit cuffs
    • Snap-button down closures
    • Embroidered "NEW YORK BROOKLYN" script
    • Front pockets, relaxed fit, striped rib knit hem
    • Runs true to size

    Style Number/Barcode: 06204-000104

    Category Name: Winter Looks

    Price: $29.97 $69.90

    On Sale: Yes

    Availability: In Stock

    Available Color: GREEN

    Available Size: S/M, M/L

    Product Badge:
    • Sale
  • Cool Girl Sleek Faux Leather Cropped Pants

    Meet the pants that instantly turn every sidewalk into a runway. These faux leather wide-legs serve major cool-girl energy with their sleek sheen and relaxed, cropped silhouette. Dress them up with heels or down with sneakers—either way, they’re giving confidence, attitude, and effortless style.

    Fit & Features

    • Faux leather fabrication with a smooth, coated finish
    • Mid-rise waist, belt loops, front button closure
    • Straight-leg silhouette with a relaxed, cropped length
    • Functional side pockets and back faux welt pockets
    • Runs true to size

    Style Number/Barcode: 06402-000021

    Category Name: Winter Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Latte Love Plush Keychain

    Your daily dose of cute. This plush latte keychain brings cozy coffee vibes everywhere you go, complete with fuzzy details, a smiley face, and a gold-tone clip. Perfect for your keys, tote, or backpack—it’s basically happiness to-go.

    Fit & Features

    • Soft plush latte cup design with embroidered face, and arms
    • Ribbed “sleeve” detail for cozy texture
    • Attached keyring and lobster clasp

    Style Number/Barcode: 07308-000087

    Category Name: Winter Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Latte Love Plush Keychain

    Take your love for coffee everywhere with this adorable plush mug keychain. Soft, fuzzy, and irresistibly cute, it’s the perfect little pick-me-up for your keys, tote, or backpack.

    Fit & Features

    • Mini plush mug with embroidered smile detail
    • Soft faux fur fabric
    • Attached keyring and clasp

    Style Number/Barcode: 07308-000085

    Category Name: Winter Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet And Snug Cable Knit Mini Dress

    Cozy meets curve-hugging. This cable knit mini brings that soft, flirty energy with a foldover off-the-shoulder neckline and bell sleeves for extra charm. Perfect for date nights in or dressing up your coffee run fit.

    Fit & Features

    • Soft cable knit fabric, stretch knit lining
    • Foldover off-the-shoulder neckline
    • Long bell sleeves
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000395

    Category Name: Winter Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • After Hours Attitude Cutout Off-The-Shoulder Top

    Low effort, high impact—this top does the flirting for you. The off-the-shoulder neckline and sleek cutout bring just enough drama for nights out, styled your way.

    Fit & Features

    • Ribbed sweater knit fabric with high stretch
    • Off-the-shoulder neckline
    • Front bust cutout detail
    • Long fitted sleeves
    • Cropped hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-000271

    Category Name: Winter Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Urban Edge Camouflage Puffer Jacket

    Your cold-weather edge, unlocked. This camo puffer jacket brings structured warmth with a soft quilted feel and a button-up front—made for styling with denim or leggings for a streetwear vibe.

    Fit & Features

    • Camouflage print, woven lined fabric
    • Collar neckline
    • Long sleeves
    • Button-down front closure
    • Puffer insulated design
    • Runs true to size

    Style Number/Barcode: 06201-000080

    Category Name: Winter Looks

    Price: $9.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep Them Curious Tie Back Mini Dress

    This dress keeps it minimal from the front and magnetic from the back—the open cut and tie detail gives just enough drama while the rib knit smooths everything into place. It’s an easy yes for plans when simple feels the sexiest.

    Fit & Features

    • Rib knit fabric with subtle texture
    • Boat neckline with long fitted sleeves and flared cuffs
    • Bodycon silhouette through the bodice and skirt
    • Open back design with wide band and tie-back closure
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000402

    Category Name: Winter Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Esmerelda Denim Rhinestone Bodycon Mini Dress

    Special Occasion

    Built for that slow-motion entrance, this denim bodycon mini dress catches the light with every step thanks to its rhinestone-studded corset design. Luxe structure meets after-dark sparkle, giving you a look that feels polished, powerful, and impossible to forget.

    Fit & Features

    • Denim fabric with allover rhinestone embellishment
    • Strapless neckline with structured corset bodice, flexible boning
    • Back zipper and hook-eye closure
    • Front pockets for convenience
    • Bodycon mini silhouette
    • Runs true to size

     

    Where to Wear:

    GNO, bachelorettes, date nights, birthdays, holiday parties

    Style Number/Barcode: 05001-000634

    Category Name: Winter Looks

    Price: $19.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Yours Off-Shoulder Mini Dress

    A little flirty, a little free—this off-shoulder mini dress brings effortless charm with every move. The flowy sleeves and fitted hem keep it soft, flattering, and ready for any occasion.

    Fit & Features

    • Soft knit stretchy fabric
    • Off-shoulder neckline 
    • Long sleeves
    • Fitted mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000618

    Category Name: Winter Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City Drift Oversized Jacket

    Cool-girl comfort meets vintage soul. This oversized jacket gives that perfectly worn-in feel with coated fabric, quilted lining, and a cozy corduroy collar. Toss it over flowy dresses or denim jeans for an effortless vibe this season.

    Fit & Features

    • Coated, vintage-inspired, cotton-blend woven fabric
    • Quilted woven lining
    • Long sleeves, snap-button straps
    • Corduroy collar neckline
    • Front zipper and snap-button closures, front flap pockets
    • Oversized fit

    Style Number/Barcode: 06201-000083

    Category Name: Winter Looks

    Price: $9.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Street Queen Faux Leopard Fur Moto Jacket

    Born to stand out. This cropped faux leather moto jacket brings major attitude with its plush leopard faux fur lining and trim. Equal parts edgy and luxe—it’s the perfect layer for nights out or cold-weather fierceness.

    Fit & Features

    • Faux leather fabric, faux leopard fur lining
    • Faux leopard collar neckline with buckle strap accent
    • Front zip-up closure
    • Long sleeves with faux leopard fur cuffs
    • Front pockets
    • Faux leopard fur crop hem
    • Runs true to size

    Style Number/Barcode: 06201-000082

    Category Name: Winter Looks

    Price: $19.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Frosted Charm Faux Fur Hem Mini Dress

    This mini dress is the definition of winter glam—sleek brushed knit meets a plush faux fur hem that adds instant drama. It’s soft, stretchy, and serves that effortless luxe vibe from brunch to chic winter nights.

    Fit & Features

    • Brushed knit fabric with stretch
    • Crew neckline
    • Fitted long sleeves
    • Bodycon silhouette
    • Plush faux fur mini hem for a statement finish
    • Runs true to size

    Style Number/Barcode: 05102-000888

    Category Name: Winter Looks

    Price: $44.90

    Availability: In Stock

    Available Color: IVORY-2

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Kangol Tropic™ 504 Beige Beret

    Instantly raises your outfit IQ. This iconic Kangol beret adds that effortless, editorial touch. Whether you’re pairing it with a moto jacket or oversized blazer, it’s your go-to for any look this season.

    Fit & Features

    • "Kangol" embroidery and logo
    • Tropic™ yarn for a lightweight and comfortable fit
    • Classic beret silhouette

    Style Number/Barcode: 07302-000230

    Category Name: Winter Looks

    Price: $4.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Majorly Chic Ribbed Knit Mock Neck Midi Dress

    Meet the midi dress that makes minimal feel major. The mock neck and keyhole detail bring a chic vibe, while the ribbed knit stretch keeps it comfy enough from brunch meet-ups to dinner dates.

    Fit & Features

    • Ribbed hacci knit fabric with knit lining, high stretch
    • Sleeveless mock neckline
    • Keyhole cutout at the bust
    • Angled seams under the bust
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000422

    Category Name: Winter Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cold Front Confidence Faux Fur Denim Trench Coat

    Layered up, but make it fashion. This tinted denim long trench coat with faux shag fur trim brings instant attitude to any outfit, perfect for stepping out when the look needs to do the talking.

    Fit & Features

    • Structured tinted denim fabrication, sewn-in knit lining
    • Long sleeves with faux shag fur cuffs
    • Long trench coat silhouette with a tie waist belt
    • Faux shag fur trim detailing along the collar and edges
    • Open front design
    • Runs true to size

    Style Number/Barcode: 06203-000026

    Category Name: Winter Looks

    Price: $69.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: S, M, L, XL

    Product Badge:
    • Best Seller