This post contains affiliate links. As an Amazon Associate I earn from qualifying purchases, at no extra cost to you.
Winter is the season where most of us grab the same sweater and the same jeans every single day. Warm, yes. Exciting, not really.
These 25 winter outfits are all worn by real women in real homes, mostly in front of the mirror on their way out the door. You will find leather jackets and easy layers, cozy sweaters with jeans, pants that are not jeans, and skirts and sweater dresses with tall boots. Every look comes with one styling tip and a link to the piece on Amazon, so you can recreate your favorite winter outfits in a few clicks.
Jackets and Easy Layers
A good jacket does most of the work in winter. Throw it over a simple top and the right pants, and the outfit is done. These five looks show how a leather jacket, a denim jacket or a shacket can carry a whole outfit.
1. Leather Jacket and Camo Cargo Pants
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A cropped black top, baggy camo cargo pants and an oversized faux leather jacket with white sneakers. Edgy, comfortable and perfect for running errands. The faux leather adds an edge, while the camo print keeps the look relaxed and casual. On really cold days, swap the sneakers for chunky boots and add a scarf in a warm brown or cream.
Tip: Keep the top short and fitted when your pants are baggy. It balances the whole look.
Shop the jacket: AUTOMET Oversized Faux Leather Jacket | And the cargo pants: Eddoyee Wide Leg Cargo Pants
2. Leather Jacket and Olive Cargo Pants
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
Olive green cargo pants, a white high-neck tank and a brown faux leather jacket with chunky sneakers. Earthy colors that are made for cold days. The brown leather and the olive pants pick up the same warm tones, so the outfit looks calm and well planned. It is a great everyday look for school runs, shopping trips or coffee with friends.
Tip: Olive and brown are a winter dream team. Add gold jewelry to make it look polished.
Shop the jacket: KIRUNDO Oversized Faux Leather Jacket | And the tank: ANRABESS High Neck Crop Tank
3. Leather Jacket and Striped Wide-Leg Pants
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
Cream and brown striped wide-leg pants with a simple white top and a brown leather jacket. A relaxed outfit that still looks put together. The stripes make the pants look long and flowy, and the leather jacket gives the soft colors some structure. Add loafers or ankle boots, and the outfit works for a casual workday as well.
Tip: Striped pants are your statement. Keep the top plain and let them stand out.
Shop the jacket: AUTOMET Oversized Faux Leather Jacket | And the shoes: Steve Madden Everlie Loafers
4. Denim Jacket, Leggings and a Beanie
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by ThatGirlTarren
Brown leggings, a cream top, a light denim jacket and a black beanie with cozy boots. The ultimate comfy winter weekend outfit. The leggings and boots keep you warm, the denim jacket adds a casual layer, and the beanie finishes the look. It is perfect for Saturday errands, a walk outside or a cozy coffee date.
Tip: A beanie instantly makes a simple outfit look styled. Pick one in a color that is already in your look.
Shop the denim jacket: Glamaker Zip Up Denim Jacket | And the leggings: CRZ YOGA Butterluxe Leggings
5. The Grey Shacket and Wide Jeans
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
An oversized grey shirt jacket over a simple top with wide dark jeans and an iced coffee. Easy layering for days that start cold and end mild. The shacket is warmer than a shirt and lighter than a coat, which makes it ideal for layering. Wear it open over a tee or a thin sweater, and roll up the sleeves for a relaxed look.
Tip: A shacket works as a shirt indoors and as a light jacket outside. That makes it one of the most useful winter pieces.
Shop the booties: Idyllwind Ankle Booties
Cozy Sweater Winter Outfits
Sweaters are the heart of most winter outfits. The trick is to vary the shape and the neckline: off the shoulder, turtleneck, cropped or oversized. Here are ten easy ways to wear them with jeans.
6. Turtleneck Sweater and Ripped Jeans
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A soft taupe turtleneck sweater with light ripped jeans and brown boots. One of the most classic winter outfits there is. The high neck keeps you warm without a scarf, and the soft taupe color goes with every shade of denim. Brown boots and a matching bag pull the whole outfit together in a simple, elegant way.
Tip: Tuck just the front of an oversized sweater into your jeans to show your waist.
Shop the boots: DREAM PAIRS Chelsea Boots
7. Pink Striped Turtleneck and Black Pants
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A bold pink and burgundy striped turtleneck with black wide-leg pants and white sneakers. A happy color for grey winter days. The black pants keep the bright stripes grounded, so the look feels fun but never too loud. White sneakers make it casual, while black boots turn it into an outfit for the office.
Tip: Bright stripes look best with black. It keeps the outfit calm and lets the color shine.
Shop the striped top: Trendy Queen Striped Long Sleeve Top | And the sneakers: New Balance 515 Sneakers
8. Checkered Sweater and Leggings
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Meghan Sisco
A brown and white checkered sweater with brown leggings and cozy boots. Comfortable, warm and very cute for a day at home. The bold checkered pattern brings personality, and the leggings keep everything comfortable and warm. It is the perfect outfit for a lazy Sunday, a movie night or working from home in winter.
Tip: A patterned sweater is a whole outfit on its own. Keep the rest in one matching color.
Shop the boots: DREAM PAIRS Platform Boots
9. Flower Sweater and Light Jeans
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A cream sweater with a big brown flower pattern, light wash jeans and a brown bag. Playful and cozy at the same time. The flower pattern feels happy and playful, and it brightens up even the greyest winter day. Keep the rest of the look simple with light jeans, so the sweater stays the star of the outfit.
Tip: Fun prints look most modern with simple, light denim.
Shop the sweater: CIDER Flower Pattern Sweater | And the jeans: Levi’s 501 90s Jeans
10. Cream Sweater and Ripped Wide Jeans
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A chunky cream knit sweater with ripped wide-leg jeans and sneakers. A soft neutral look you can wear all season. The cream color looks clean and expensive, and the chunky knit feels wonderfully cozy. The ripped jeans add a casual touch, so the outfit works for shopping, brunch or a relaxed day out.
Tip: Cream knits look expensive. Look for chunky textures and a slightly cropped fit.
Shop the sweater: LILLUSORY Oversized Knit Sweater | And the sneakers: LUCKY STEP Classic Sneakers
11. Off-Shoulder Sweater and Light Jeans
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Meghan Sisco
A dusty rose off-the-shoulder sweater with light skinny jeans and brown booties. Soft, feminine and still very easy. The soft rose color is very flattering, and the open shoulders make the sweater feel a little special. Light jeans keep the outfit casual enough for daytime, while booties make it look polished.
Tip: Off-shoulder sweaters need a strapless bra. It keeps the look clean.
Shop the sweater: Zenlonr Off Shoulder Sweater | And the bra: Lusait Strapless Bra
12. Chocolate Off-Shoulder Sweater and Dark Jeans
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A chocolate brown off-the-shoulder sweater with dark wide-leg jeans and a brown shoulder bag. Warm tones that feel just right for winter. The rich brown color feels warm and cozy, and the off-shoulder neckline adds an elegant touch. Dark jeans and a matching bag make the look easy, but still put together for a dinner out.
Tip: Chocolate brown is a softer alternative to black. It goes with every shade of denim.
Shop the sweater: LILLUSORY Off Shoulder Sweater
13. White Off-Shoulder Top and Ripped Jeans
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A fitted white off-shoulder long-sleeve top with light ripped jeans and white sneakers. Clean, bright and great for a winter brunch. The white top and light denim make the outfit feel fresh and bright, even on a cold day. Throw on a camel coat and a scarf when you step outside, and the look stays clean and elegant.
Tip: An all-light outfit looks fresh in winter. Add a camel coat when you head out.
Shop the top: Trendy Queen Off Shoulder Top | And the sneakers: adidas Breaknet Sleek Sneakers
14. Black Off-Shoulder Top and Loose Jeans
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A black off-the-shoulder top with loose light jeans and pointed heels. A simple date night outfit for cold evenings. The black top looks chic and a little sexy, while the loose jeans keep the outfit relaxed. Swap the heels for boots on a cold evening, and add a long coat for a perfect date night look.
Tip: Swap sneakers for pointed heels and the same jeans go from day to night.
Shop the jeans: Levi’s Superlow Loose Jeans | And the heels: Elisabet Tang Pointed Heels
15. Green Sweater Vest and Wide Jeans
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
An olive green sweater vest over a white top with wide-leg jeans. A smart, slightly preppy look for work or school. The vest gives a simple white top and jeans a smart, slightly preppy twist. It is warm enough for chilly offices and classrooms, and the olive green adds a fresh color to your winter wardrobe.
Tip: A sweater vest adds warmth without bulk. Layer it over a tee or a long-sleeve top.
Shop the vest: CIDER Cropped Sweater Vest | And the jeans: Flvsun High Waisted Wide Leg Jeans
Pants That Are Not Jeans
Need a break from denim? Corduroy, cargo, leopard and polka dot pants make simple winter outfits look fresh, and they pair with the sweaters you already own.
16. Brown Corduroy Pants and a Square-Neck Top
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
Wide brown corduroy pants with a fitted brown square-neck top and white sneakers. Tonal, cozy and very winter. The matching brown tones make the look feel calm, cozy and very put together. Corduroy is warmer than denim, so it is a great alternative for cold days when you still want to look stylish.
Tip: Corduroy is warmer than denim. Wear it head to toe in one color for an easy, elevated look.
Shop the pants: Acelitt Wide Leg Corduroy Pants | And the top: AUTOMET Square Neck Ribbed Top
17. Leopard Pants and a White Top
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
Leopard print wide-leg pants with a fitted white long-sleeve top and a brown bag. A bold but easy look. The leopard print adds a bold touch, but because it is a neutral print, it is still easy to wear. A simple white top keeps the focus on the pants, and a brown bag ties the colors together.
Tip: Leopard acts like a neutral. Pair it with white, black or brown and it always works.
Shop the top: AUTOMET Boat Neck Long Sleeve Top
18. Grey Henley and Wide-Leg Jeans
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A grey henley top with light wide-leg jeans and New Balance sneakers. The everyday winter uniform that never fails. The grey henley and light jeans are a simple pair you can wear almost every day. New Balance sneakers keep it sporty, and a long coat or puffer jacket turns it into a real winter outfit.
Tip: A henley looks a little more styled than a plain tee. Leave the top buttons open.
Shop the jeans: Levi’s Ribcage Wide Leg Jeans | And the top: ANRABESS Henley Long Sleeve Top
19. Polka Dot Pants and a Long-Sleeve Top
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
Brown wide-leg pants with little dots, a white square-neck long-sleeve top and a brown bag. Playful and still very wearable. The tiny dots add a playful detail without feeling too busy, and the white top keeps everything clean. It is a fun alternative to plain jeans and looks great with sneakers or ankle boots.
Tip: Small patterns in brown or cream are easier to style than bright ones.
Shop the pants: LAMIEN High Waisted Polka Dot Jeans | And the top: ANRABESS Long Sleeve Top
20. The Taupe Sweatsuit
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A taupe hoodie and matching wide sweatpants with a cap and a coffee. The comfiest winter outfit for travel days and lazy weekends. The soft taupe color looks calm and elegant, even though the outfit is basically loungewear. A cap, a coffee and a nice bag make it feel styled, perfect for travel days or slow weekends.
Tip: A matching set looks intentional. Add a nice bag and sunglasses and it is ready for the outside world.
Shop the set: Trendy Queen 2 Piece Lounge Set
Skirts, Sweater Dresses and Tall Boots
Yes, you can wear skirts and dresses in winter. Add tall boots, tights or a cozy knit on top, and you stay warm while looking a little more dressed up.
21. Brown Sweater and a Plaid Midi Skirt
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A brown sweater with a brown plaid midi skirt and dark boots. Cozy, a little vintage and perfect for the holidays. The plaid skirt brings a cozy, vintage feel, and the brown sweater matches its warm colors. Add tights and boots, and you have a lovely outfit for Christmas markets, family dinners or the office.
Tip: Match your sweater to one color in the plaid. It ties the whole look together.
Shop the sweater: NIeyook Oversized Pullover Sweater
22. Brown Sweater Dress and Knee-High Boots
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A brown knit sweater dress with a lace hem and tall tan boots. A dress outfit that keeps you warm all day. The lace hem adds a soft, feminine detail, and the tall boots keep your legs warm. A sweater dress is a complete outfit in one piece, so it is the easiest way to look dressed up in winter.
Tip: Tall boots close the gap between dress and knees, so you stay warm without tights.
Shop the boots: DREAM PAIRS Knee High Boots
23. Black Sweater Dress and Suede Boots
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A short black sweater dress with brown suede knee-high boots and a brown bag. Simple, chic and perfect for dinner. The black dress looks chic and simple, and the brown suede boots make it feel warmer and more relaxed. Add a long coat and gold jewelry, and the outfit is ready for dinner or a holiday party.
Tip: Brown boots soften an all-black dress and look more relaxed than black ones.
Shop the dress: Trendy Queen Sweater Dress | And the boots: Pasuot Suede Knee High Boots
24. Black Cardigan, Ruffle Skirt and Cowboy Boots
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A fitted black cardigan with a cream ruffle mini and tan cowboy boots. A fun, flirty look for a holiday party. The ruffle skirt feels sweet and festive, and the cowboy boots give it a cool, modern edge. A fitted black cardigan keeps the top neat, so the outfit looks fun without being too much.
Tip: Cowboy boots make a sweet skirt look cooler. Keep the top fitted and dark.
Shop the boots: Pasuot Western Cowboy Boots | And the cardigan: PRETTYGARDEN Knit Cardigan
25. Cream Sweater, Mini Skirt and Tall Boots
By loading the tweet, you agree to Twitter's privacy policy.
Learn more
Outfit by Samantha Erickson
A cream oversized sweater with a brown corduroy mini skirt and brown knee-high boots. Cozy on top, leggy on the bottom. The oversized sweater keeps you warm, and the short corduroy skirt shows off the tall boots. It is a flattering winter formula that looks cute for brunch, shopping or a casual night out.
Tip: Oversized on top and short on the bottom is a winter formula that flatters almost everyone.
Shop the skirt: CIDER Corduroy Mini Skirt | And the sweater: PRETTYGARDEN Oversized Sweater | And the boots: Dolls Kill Knee High Boots
How to Build Your Own Winter Outfits
You do not need a huge closet. A few warm basics that go together give you dozens of winter outfits.
| Piece | Why you need it | Wear it with |
|---|---|---|
| Oversized sweater | Warm and cozy, and it looks styled with little effort | Jeans, skirts, leggings |
| Faux leather jacket | Adds an edge to simple tops and pants | Cargo pants, jeans, wide pants |
| Wide-leg jeans | Go with every sweater and every shoe | Sweaters, henleys, off-shoulder tops |
| Knee-high boots | Make skirts and dresses winter-proof | Sweater dresses, mini and midi skirts |
| Matching lounge set | The comfiest outfit that still looks put together | Sneakers, a cap, a nice bag |
Five rules for easy winter style
- Stick to warm neutrals: brown, cream, camel and grey all mix and match.
- Play with texture: knit, corduroy, leather and suede make simple colors look rich.
- Balance the shapes: fitted on top with wide pants, or oversized on top with a short skirt.
- Add one pop of color: a pink stripe or a green vest wakes up a winter wardrobe.
- Invest in boots: one pair of tall boots and one pair of ankle boots cover almost every look.
FAQ
What should I wear in winter to look stylish but stay warm?
Start with a cozy sweater or a long-sleeve top, add jeans or corduroy pants, and finish with a jacket and warm boots. Layering lets you look styled indoors and stay warm outside.
Can I wear a skirt in winter?
Yes. Pair a midi or mini skirt with knee-high boots or tights and a chunky sweater. A sweater dress with tall boots works the same way.
What colors are best for winter outfits?
Warm neutrals like chocolate brown, camel, cream and grey are winter classics. Burgundy, olive and a bright pink stripe add color.
What shoes go with winter outfits?
Ankle boots, knee-high boots and cowboy boots are the most useful. Clean white sneakers also work on dry days.
How do I make my winter outfits look less boring?
Change one piece: try a pattern like leopard or plaid, a new neckline like off-the-shoulder, or a different pant like cargo or corduroy.
Save These Winter Outfits for Later
Winter style does not have to mean the same sweater every day. Pick a few of these looks, shop the pieces you are missing, and mix them with what you already own.
Save this post to your Pinterest board so you have all 25 winter outfits ready on the next cold morning.
More outfit ideas on Awakina: 25 Black Skirt Outfit Ideas You’ll Absolutely Adore and 20 Casual Spring Outfits You’ll Want to Wear Every Day
