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.
-
Peek the Drama Long Sleeve Crop Top
A little tease, a lot of style—this crop top serves up major attitude with flirty keyhole cutouts and a sleek fit. Perfect for pairing with cargos, minis, or anything that lets the top do the talking.
Fit & Features
- Knit stretchy fabric
- Fitted long sleeves
- Crew neck
- Front keyhole cutouts
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06005-000136
Category Name: Winter Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Laidback Cutie Striped Knit Sweater
Laidback but cute with your fave denim—this striped crew neck crop sweater is made for coffee dates, study sessions, and chill weekends.
Fit & Features
- Striped pattern, stretchy knit fabric
- Crew neck
- Relaxed long sleeves
- Cropped-length hem
- Runs true to size
Style Number/Barcode: 06005-000135
Category Name: Winter Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Coffee Run Striped Sweater Topper
Easy, cozy, and effortlessly cute—this striped knit sweater topper is your new go-to for errands, study sessions, or hangouts.
Fit & Features
- Striped pattern, knit fabric
- Crew neckline
- Long sleeves
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06005-000145
Category Name: Winter Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sunday Edit Off-The-Shoulder Sweater
The sweater that says “effortless but cute” every time. With a slouchy off-the-shoulder neckline and relaxed fit, it’s perfect for a cozy-meets-chic vibe.
Fit & Features
- Soft knit stretchy fabric
- Off-the-shoulder neckline
- Long sleeves
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06005-000139
Category Name: Winter Looks
Price: $32.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
-
Falling for Knits Crop Sweater
Cozy with a little edge. This cable knit crop sweater levels up your casual days with subtle distressed accents and a cute vibe—perfect for coffee runs, study dates, or layering over slip dresses.
Fit & Features
- Cable knit soft fabric
- Crew neck
- Long sleeves
- Cropped-length hem with distressed accents
- Runs true to size
Style Number/Barcode: 06005-000138
Category Name: Winter Looks
Price: $7.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Season Chill Cable Knit Crop Sweater
A cozy classic, reimagined for fall. This cropped cable knit sweater features a soft ribbed texture and Henley-style buttons for a laid-back yet polished feel. Pair it with high-rise denim or a mini skirt for your ultimate fall uniform.
Fit & Features
- Soft cable knit fabric
- Crew neckline with henley-style buttons
- Long sleeves
- Cropped-length hem
- Runs true to size
Style Number/Barcode: 06005-000137
Category Name: Winter Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Soft Statement Knit Mock Neck Bodysuit
For when you want that clean, put-together vibe with zero effort. This knit mock neck bodysuit hugs in all the right places and layers like a dream—your go-to for jeans, minis, and everything in between.
Fit & Features
- Textured knit fabric, moderate stretch
- Mock neckline
- Long fitted sleeves
- Thong-cut bottom
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-000146
Category Name: Winter Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cool Season Varsity 24 Sweater
Sporty meets street. This varsity-inspired cropped sweater keeps it casual with a bold number graphic and cozy knit feel—made for styling with your favorite bottoms and boots!
Fit & Features
- Soft knit fabric
- Crew neck
- Long sleeves
- Front '24'
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06005-000144
Category Name: Winter Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Effortless Chic Knit Off-The-Shoulder Long Sleeve Bodysuit
When your outfit needs a little “I didn’t try, but I did.” This off-the-shoulder knit bodysuit brings a soft, form-hugging fit with just the right touch of allure. Pair it with denim for the day or dress it up for the night—either way, it’s your go-to for instant polish.
Fit & Features
- Textured knit fabric, moderate stretch
- Off-the-shoulder scoop neckline
- Long fitted sleeves
- Thong-cut bottom
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-000539
Category Name: Winter Looks
Price: $34.90
Availability: In Stock
Available Color: RAISIN
Available Size: XS, S, M, L
- Textured knit fabric, moderate stretch
-
Level Up Ribbed Knit Long Sleeve Topper
Layered looks just got interesting. This ribbed knit long sleeve topper frames your outfit with an ultra-cropped cut that feels styled without trying too hard—perfect for nights out, casual plans, or that last-minute outfit switch.
Fit & Features
- Ultra-cropped topper silhouette
- Ribbed knit fabric with high stretch
- Long fitted sleeves
- Crew neckline
- Front button details
- Runs true to size
- Bandeau pictured not included
Style Number/Barcode: 06005-000148
Category Name: Winter Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
-
Not Your Basic Grommet Sweater
Prep meets punk in the best way possible. This grommet sweater gives classic knit energy with a rebellious twist—distressed edges, metal details, and all the attitude you need to stand out.
Fit & Features
- Soft knit fabric
- Crew neckline
- Long sleeves
- Allover grommet accents
- Distressed hem and cuffs
- Runs true to size
Style Number/Barcode: 06005-000141
Category Name: Winter Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Wrapped In Cozy Cable Knit Bolero
Layer it, love it, live in it—this oversized cable knit bolero has endless styling possibilities! From layering over your casual fit to keeping warm over a formal dress.
Fit & Features
- Cable knit soft fabric
- Oversized long sleeves
- Open front design
- Cropped-length hem
- Runs true to size
Style Number/Barcode: 06005-000160
Category Name: Winter Looks
Price: $29.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
-
Wrapped Up Cute Off-The-Shoulder Dress
Serving soft girl vibes with a flirty edge, this off-the-shoulder sweater dress hugs just right. Perfect for latte runs, weekend plans, or anytime you want cozy and cute in one move.
Fit & Features
- Soft cable knit fabric with stretch
- Off-the-shoulder folded neckline
- Fitted long sleeves
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 06005-000153
Category Name: Winter Looks
Price: $42.90
Availability: In Stock
Available Color: TAUPE, BROWN, BURGUNDY
Available Size: S, M, L
Product Badge:- Best Seller
-
Seasons Favorite Off-The-Shoulder Midi Dress
A sweater dress, but elevated. With its foldover neckline and bodycon silhouette, this midi dress is a go-to for chic fall days or nights.
Fit & Features
- Rib knit fabric, moderate stretch
- Off-the-shoulder folded neckline, cinched seam
- Fitted long sleeves
- Bodycon fit, midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000162
Category Name: Winter Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Giddy Up Knit Horse Cardigan
A little western, a lot of cozy—this button-down cardigan features a playful horse knit pattern and collar detail that make it anything but basic.
Fit & Features
- Horse pattern, soft knit fabric
- Oversized long sleeves with striped cuffs
- Collared neckline
- Button-down front closures
- Relaxed fit hem
- Runs true to size
Style Number/Barcode: 06005-000167
Category Name: Winter Looks
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Everyday Chic Boat Neck Crop Sweater
The definition of throw-on-and-go. This soft knit sweater keeps it classic with a boat neckline and cropped silhouette that flatters every outfit this fall and winter!
Fit & Features
- Soft fuzzy knit fabric
- Long sleeves
- Boat neckline
- Cropped-length hem
- Runs true to size
Style Number/Barcode: 06005-000166
Category Name: Winter Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cuddle Season Crop Sweater
A cozy essential with a cool-girl twist. This fuzzy rib knit quarter zip sweater brings the perfect mix of soft and slouchy for those “cute but comfy” days with a coffee in hand!
Fit & Features
- Fuzzy rib knit fabric
- Quarter zip-up front closure collar neckline
- Slouchy long sleeves
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06005-000164
Category Name: Winter Looks
Price: $36.90
Availability: In Stock
Available Color: BROWN, TAUPE
Available Size: XS, S, M, L
-
Wrap Me Up Cable Knit Cardigan
For when “just one more layer” becomes the whole look. This cable knit cardigan brings plush texture and balloon sleeves that add instant cozy-chic energy—perfect for layering over any outfit.
Fit & Features
- Soft cable knit fabric
- Balloon long sleeves
- Open front design
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06005-000168
Category Name: Winter Looks
Price: $12.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cozy Twist Cable Knit Tie Back Sweater
A little preppy, a little playful—the cable knit sweater to add a cute flair to your everyday rotation, with a crop hem and tie-back detail that elevates every high-rise bottom.
Fit & Features
- Cable knit fabric
- Long sleeves
- Crew neck
- Tie-back detail
- Crop hem
- Runs true to size
Style Number/Barcode: 06005-000169
Category Name: Winter Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Effortless Edit Collar Knit Sweater
Classic, cozy, and a little bit polished. This collared crop sweater gives laid-back luxe with its soft textured knit and relaxed silhouette—your go-to for everything from latte runs to weekend plans.
Fit & Features
- Soft texture knit fabric
- Collared neckline
- Long sleeves
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06005-000171
Category Name: Winter Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Season Shift Mock Neck Crop Sweater
Soft knit, sporty stripes, and a cropped hem—this zip-up sweater makes autumn layering a breeze. Pair with denim and booties for crisp strolls, latte runs, or any fall plans.
Fit & Features
- Soft knit fabric
- Long sleeves with striped cuffs
- Zip-up mock neckline
- Cropped-length hem
- Runs true to size
Style Number/Barcode: 06005-000170
Category Name: Winter Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cozy Intentions Knit Duster Cardigan
Wrapped in ease, this knit duster cardigan is your new everything layer. With its tie waist, convenient pockets, and relaxed silhouette, it brings that perfect mix of cozy and cool—made for coffee runs, casual plans, and soft girl strolls.
Fit & Features
- Soft knit fabric
- Collar neckline
- Long sleeves
- Tie-front waist belt
- Front pockets
- Longline hem
- Runs true to size
Style Number/Barcode: 06005-000165
Category Name: Winter Looks
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Snug Luxe Off-The-Shoulder Crop Top
Cozy meets flirty—this rib knit crop sweater top brings soft texture and an off-the-shoulder foldover neckline that feels made for fall nights.
Fit & Features
- Rib knit stretch fabric
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Crop fitted hem
- Runs true to size
Style Number/Barcode: 06005-000172
Category Name: Winter Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Weekend Mood Oversized Sweater
This oversized sweater keeps it effortlessly chic with a slouchy fit and soft knit texture that feels like your coziest day ever—just styled better. Pair it with mini skirts, tall boots, or your favorite denim for all-season cuteness.
Fit & Features
- Soft rib knit fabric
- Crew neckline
- Relaxed long sleeves
- Oversized fit
- Pullover styling
Style Number/Barcode: 06005-000182
Category Name: Winter Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free