Winter Looks
Cold weather, but make the outfit worth leaving the house for. This on-trend winter edit brings comfy, cozy texture with fold-over sweaters, mock necks, cable knit styles, sweater dresses, and faux fur jackets and coats in ivory, winter white, chocolate brown, and burgundy. Mix in wide-leg or baggy denim, bombers, belted trenches, midi and maxi lengths, hosiery, tights, stirrup leggings, and tall boots. Add faux fur hats, leg warmers, scarves, and gloves for sleek, modern looks ready for photo dumps, tree trimmings, dinner parties, and the gift exchange.
Now Trending
STYLE SPOTLIGHT
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.
-
Chic Mood Removable Faux Fur Lace Tie-Front Top
Soft drama, no hesitation. This lace tie-front top brings sheer texture and plush faux fur trim together for plans that call for chic confidence.
Fit & Features
- Sheer lace fabric, moderate stretch
- Long sleeves
- Tie-front closure
- Removable faux fur trims at the collar and cuffs
- Faux fur trims attach with loop and button closures
- Cropped length
- Runs true to size
Style Number/Barcode: 06202-000077
Category Name: Winter Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Kangol Tropic™ 504 Black 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: 07302-000229
Category Name: Winter Looks
Price: $23.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- "Kangol" embroidery and logo
-
Sweet Drama Removable Faux Fur Lace Cardigan
Soft, sweet, and a little extra—in the best way. This sheer lace cardigan layers on romance with faux fur trim for the perfect amount of drama.
Fit & Features
- Sheer lace fabric
- Faux fur trim at collar and cuffs, loop and button attachments
- Hook-eye front closures
- Long sleeves
- Cropped length
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06202-000078
Category Name: Winter Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Cold Girl Couture Faux Fur Mini Dress
Cool-girl glam, but make it cozy. This faux fur tube mini dress blends sleek confidence with a soft touch—perfect for nights when the vibe is effortless luxury.
Fit & Features
- Crepe fabric
- Faux fur strapless neckline trim
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000897
Category Name: Winter Looks
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sweep Me Away Ribbed Off Shoulder Midi Dress
This is that “effortless but still unbelievably chic” dress you reach for when you want comfort without sacrificing the vibe. The ribbed knit hugs smoothly, the foldover neckline drapes just right, and the side slit keeps things subtly daring.
Fit & Features
- Soft ribbed knit fabrication, smooth lining
- Foldover off shoulder neckline
- Long fitted sleeves
- Side slit design
- Midi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000452
Category Name: Winter Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Effortlessly Polished Mock Neck Mini Dress
This is the kind of dress you reach for when you want to look pulled together without overthinking it. Clean lines, a smooth ribbed fit, and a mock neck give it that quiet confidence that works day to night with a quick switch of shoes.
Fit & Features
- Soft ribbed knit fabric with comfortable stretch
- Mock neckline
- Long fitted sleeves
- Bodycon silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000460
Category Name: Winter Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Lowkey Allure Knit Off-The-Shoulder Top
Soft, curve-loving, and doing the most without trying. This off-the-shoulder knit top hugs in all the right places and goes from casual plans to dressed-up nights without a second thought.
Fit & Features
- Off-the-shoulder sweetheart neckline
- Long fitted sleeves
- Twist-front bust detail
- Mid-length hem, form-hugging fit
- Ribbed knit fabric with high stretch
- Runs true to size
Style Number/Barcode: 06002-000473
Category Name: Winter Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Second Look Obsession Long Sleeve Crop Top
This is the top you keep coming back to. A rib knit long sleeve V-neck crop top with hidden front hook and eye closures that layers clean or stands strong on its own for nights out, coffee runs, and everything in between.
Fit & Features
- Stretch rib knit fabric
- Fitted long sleeves
- V-neckline
- Hidden front hook and eye closures
- Fitted crop-length silhouette
- Runs true to size
Style Number/Barcode: 06002-000474
Category Name: Winter Looks
Price: $32.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Icon Status Platform Knee Boots
Step into your spotlight moment. These faux leather platform boots bring major retro energy with a sleek knee-high silhouette and bold block heel. Equal parts statement and staple—perfect for everyday wear.
Fit & Features
- 4” Block heel, 7.5" leg opening, 15.5" shaft height
- Square toe
- Inner side zipper closure
- Knee-high shaft silhouette
- Sleek faux leather material
- Runs true to size
Style Number/Barcode: 07402-000125
Category Name: Winter Looks
Price: $48.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Easy Does It Ribbed Zip Up Romper
One zip and you’re fully styled—no second-guessing required. This ribbed romper hugs just right with a sleek, streamlined fit that works for coffee runs, casual plans, and last-minute hangs.
Fit & Features
- Soft ribbed knit fabric with comfortable stretch
- Long sleeves with a fitted silhouette
- Split neckline with front zipper detail
- Short romper length with clean finished hems
- Pull on style with a body hugging fit
- Runs true to size
Style Number/Barcode: 06503-000222
Category Name: Winter Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Wrapped In Charm Off-Shoulder Mini Dress
This mini dress is that perfect mix of soft and sculpted—the one you reach for when you want to look undone in a chic way. The foldover off-shoulder neckline adds a flirty twist, while the rib knit hugs you with just the right amount of confidence.
Fit & Features
- Soft rib knit fabric with stretch
- Foldover off-shoulder neckline with subtle twist detail
- Fitted long sleeves
- Bodycon silhouette
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000469
Category Name: Winter Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Check Please Plaid Mini Skort
Prep but make it playful. This plaid mini skort gives you that flirty skirt look with the hidden comfort of shorts—aka your new go-to for coffee runs, brunch plans, or anything that needs a little “effortless but put-together” look. Shop the matching trench coat.
Shop The Matching Trench Coat: Check Please Plaid Trench Coat
Fit & Features
- Plaid pattern, wool-blend fabric, stretchy knit shorts lining
- Mid-rise waist
- Back zipper and hook-eye closure
- Front faux wrap skirt overlay
- Shorts bottom
- Runs true to size
Style Number/Barcode: 06403-000071
Category Name: Winter Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Statement Season Faux Leather Trench Coat
Statement season starts here. This sleek faux leather trench coat brings a chic attitude with a perfectly structured fit—made for nights out, city strolls, and every unapologetically confident moment in between. Style with the matching mini skort.
Shop Matching Bottoms: Statement Season Faux Leather Mini Skort
Fit & Features
- Patent faux leather fabric, crinkle texture
- Lapel collar, back flap accent
- Long sleeves, strap details
- Open front, tie-front belt
- Long-length hem
- Structured fit
- Runs true to size
Style Number/Barcode: 06204-000073
Category Name: Winter Looks
Price: $9.97 $79.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Patent faux leather fabric, crinkle texture
-
Flirt in Motion Plaid Pleated Mini Skort
This mini skort blends preppy and playful with pleated plaid, lace trim, and built-in shorts that keep every move stress-free. Equal parts cute and cheeky—it’s the piece you reach for weekly.
Fit & Features
- Plaid printed knit fabric
- Wide mid-rise waistband
- Pleated overlay skirt with built-in shorts for coverage
- Scalloped lace trim
- Mini-length skort silhouette
- Runs true to size
Style Number/Barcode: 06503-000228
Category Name: Winter Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Low-Key Chic Sheer Mesh Long Sleeve Top
Minimal, but never boring. This sheer mesh long sleeve top slips on effortlessly and adds that quiet confidence factor your closet loves.
Fit & Features
- Sheer mesh fabric with high stretch
- Long sleeves
- Crew neckline
- Fitted silhouette
- Cropped length
- Runs true to size
- Bralette pictured not included
Style Number/Barcode: 06001-000428
Category Name: Winter Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Confident Energy Faux Fur Bra Top
Confident energy only. This faux fur bra top serves bold texture with a barely-there fit that’s made for night-out plans, festival 'fits, or layered under a leather jacket when you’re feeling fearless.
Fit & Features
- Faux fur fabric
- Sleeveless triangle design
- Halter tie-back spaghetti straps
- Open back, lower tie-back spaghetti straps
- Ultra-cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06003-000272
Category Name: Winter Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Soft Focus Confidence Bodycon Mini Dress
Clean lines, smooth moves. This brushed knit mini dress hugs just right with a sleek high neckline and long sleeves, making it an easy yes for brunch, coffee dates, and everything that turns into plans.
Fit & Features
- Brushed knit fabric with a smooth, stretchy feel
- Sleek high neckline
- Long fitted sleeves
- Bodycon mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000528
Category Name: Winter Looks
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Game Day Muse Varsity Knit Tunic Top
Sporty, but make it stylish. This varsity knit tunic top brings that borrowed from the boys vibe with an oversized fit, breathable open knit, and bold number graphic that pairs perfectly with your favorite bottoms.
Fit & Features
- Knit fabric
- Striped crew neckline
- Short sleeves with star graphic design
- Front "24" graphic
- Relaxed silhouette
- Runs true to size
Style Number/Barcode: 06005-000292
Category Name: Winter Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Layered Up Energy Knit Long Sleeve Bolero
Proof that the little layer makes the whole outfit. This knit long sleeve bolero adds just enough texture and shape to elevate your basics, from bandeaus and tanks to sleek dresses.
Fit & Features
- Textured knit fabric, moderate stretch
- Long loose sleeves, tapered ribbed hems
- Open front
- Ultra-cropped hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06005-000408
Category Name: Winter Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Back In Stock
-
Low Key Cool Long Sleeve Top
Easy, flattering, and quietly bold. This asymmetrical long sleeve top drapes just right with a body-hugging fit that works for casual plans, denim moments, or dressing up without overthinking it.
Fit & Features
- Soft hacci knit fabric with stretch
- Asymmetrical off-the-shoulder neckline. long fitted sleeves
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000480
Category Name: Winter Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Lowkey Polished Long Sleeve Crop Top
Clean, confident, and a little unexpected—this top gets it. The fitted long sleeve boatneck crop top hugs just right and layers like a dream, whether you’re heading out or keeping it casual but intentional.
Fit & Features
- Soft stretch knit fabric with a smooth feel
- Fitted long sleeves
- Boatneck neckline
- Cropped length hem
- Runs true to size
Style Number/Barcode: 06001-000479
Category Name: Winter Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Wrapped Up Off-The-Shoulder Top
Soft, sleek, and subtly flirty. This off-shoulder top features a twisted neckline and a smooth, body-hugging fit that instantly elevates denim, casual or going-out bottoms.
Fit & Features
- Smooth knit fabric, high stretch
- Folded off-the-shoulder neckline, knotted accent
- Fitted long sleeves
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000476
Category Name: Winter Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Casually Chic Knit Off-The-Shoulder Top
A chic neckline moment with just enough attitude. This off-the-shoulder knit top hugs in all the right places and turns everyday denim into a full look.
Fit & Features
- Off-the-shoulder neckline with ruched fold-over design
- Long sleeves
- Mid-length hem
- Form-hugging fit
- Smooth knit fabric with high stretch
- Runs true to size
Style Number/Barcode: 06001-000477
Category Name: Winter Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bold Mode Shield Sunglasses
Meet the shades that do all the talking before you even walk in. These shield sunglasses bring a high-impact, bold vibe that makes every outfit feel instantly elevated.
Fit & Features
- Oversized shield silhouette with a bold, modern profile
- Wrap-style single lens for wide, sleek coverage
- Lightweight plastic frame for comfortable wear
- Mirrored lens finish
- Built-in nose pads
Style Number/Barcode: 07008-000123
Category Name: Winter Looks
Price: $10.90
Availability: In Stock
Available Color: BLACK
Available Size: NS