Streetwear makes a statement with layers, textures, and striking designs that keep you warm and fashionable when winter arrives. Winter streetwear combines style and utility, from comfortable hoodies layered under chic overcoats to giant puffer jackets. The winter months have countless opportunity to play around with your appearance, thanks to choices like combat boots, military vests, and clunky sneakers. To help you plan your wardrobe, here are 38 of the greatest streetwear looks for men this winter.
1. Oversized Puffer Jacket + Tapered Joggers
The puffer jacket is a winter streetwear staple. Opt for an oversized, voluminous style to stay warm while making a statement. Pair it with tapered joggers for a sleek contrast that balances the bulk of the jacket. Complete the look with chunky sneakers for a modern, sporty vibe.
Top: An oversized puffer jacket is both practical and stylish, offering warmth and a voluminous silhouette that stands out.
Bottom: Tapered joggers streamline the look, balancing the bulkiness of the puffer jacket, making it both sleek and comfortable.
2. Layered Hoodie + Longline Coat
A hoodie layered under a longline coat offers a blend of streetwear and sophistication. The hoodie brings a laid-back, casual feel, while the longline coat adds structure and class. Pair with slim-fit jeans and high-top sneakers for a street-meets-refined winter look.
Top: A hoodie offers casual comfort, while the longline coat adds structure and an elegant edge to the outfit.
Bottom: Slim-fit jeans keep the outline clean, contrasting with the layered top and creating a modern, street-ready vibe.
3. Sherpa Jacket + Cargo Pants
A cozy sherpa jacket adds texture and warmth, perfect for winter streetwear. Match it with cargo pants for a rugged, utilitarian vibe. The multiple pockets and relaxed fit of the pants bring functionality, while chunky boots or sneakers complete the look.
Top: A sherpa jacket adds warmth and texture, perfect for cold winter days while maintaining street style appeal.
Bottom: Cargo pants bring a rugged, utilitarian feel with their multiple pockets and relaxed fit, adding functionality to the outfit.
4. Turtleneck Sweater + Bomber Jacket
A turtleneck sweater is a winter essential, offering both warmth and a polished look. Layer it under a bomber jacket for a streetwear edge that adds dimension to your outfit. Pair with slim-fit trousers or jeans to maintain a clean silhouette, finished with sneakers or boots.
Top: A cozy turtleneck sweater offers warmth and sophistication when layered under a bomber jacket for a modern twist.
Bottom: Slim-fit trousers or jeans create a clean silhouette, ensuring the look remains stylish and well-balanced.
5. Fleece Pullover + Tech Pants
Stay warm and stylish with a fleece pullover, a streetwear favorite for winter. Its relaxed fit and cozy fabric are ideal for colder months. Pair it with tech pants—modern, functional trousers designed for comfort and style. Add chunky sneakers to complete the tech-inspired look.
Top: A fleece pullover is soft and warm, offering comfort with a casual streetwear vibe that’s ideal for winter layering.
Bottom: Tech pants add a modern, functional edge with sleek, tailored lines, making them perfect for active urban environments.
6. Down Vest + Hoodie + Joggers
For days when you don’t need a full coat, a down vest over a hoodie provides the perfect layering option. The vest keeps your core warm, while the hoodie adds comfort and a laid-back vibe. Tapered joggers and sneakers keep the look streamlined yet relaxed.
Top: A down vest layered over a hoodie keeps your core warm while offering a stylish, casual streetwear look.
Bottom: Tapered joggers provide comfort and flexibility while maintaining a sleek look, balancing the more relaxed fit of the hoodie.
7. Overcoat + Sweater + Ripped Jeans
An overcoat is a classic winter piece that can be styled with a streetwear twist. Layer it over a thick sweater for warmth, and pair it with ripped jeans to add a rebellious, edgy touch. Finish the look with combat boots or chunky sneakers for a complete winter ensemble.
Top: A thick sweater layered under a structured overcoat offers warmth with a touch of refinement, making it perfect for colder days.
Bottom: Ripped jeans add a casual, edgy touch to the more formal top half, creating a balanced, street-ready outfit.
8. Plaid Shacket + Hoodie + Slim Jeans
A plaid shacket (shirt-jacket) is a great layering piece for winter. Worn over a hoodie, it combines warmth and style. Pair with slim-fit jeans to balance the oversized top and finish with sneakers or boots for a laid-back yet polished winter look.
Top: A plaid shacket layered over a hoodie creates texture and warmth while adding a relaxed, laid-back style.
Bottom: Slim jeans provide a streamlined fit that contrasts with the oversized top, keeping the look clean and stylish.
9. Parkas + Turtleneck + Jogger Pants
A parka is essential for extreme winter weather. Layer it over a turtleneck for a touch of sophistication. Pair with jogger pants for a functional yet stylish look that works for both streetwear and comfort. Finish with winter boots for practicality.
Top: A parka offers both warmth and functionality, while a turtleneck adds a sophisticated touch to the casual streetwear style.
Bottom: Jogger pants balance the volume of the parka, offering comfort and a contemporary fit perfect for winter.
10. Denim Jacket + Puffer Vest
Layer a denim jacket under a puffer vest for a casual, streetwear-ready winter look. The denim adds structure, while the puffer vest offers warmth without bulk. A beanie adds the final touch of winter readiness, and slim jeans with sneakers or boots round out the outfit.
Top: A denim jacket layered under a puffer vest combines classic street style with practical warmth. The beanie adds a winter-ready vibe.
Bottom: Slim jeans or joggers keep the look sleek and casual, complementing the layered top without overwhelming the outfit.
11. Puffer Coat + Utility Pants
For a functional and stylish winter outfit, pair a puffer coat with utility pants. The puffer coat offers warmth, while the utility pants bring a practical, rugged aesthetic with multiple pockets and a relaxed fit. Finish with combat boots or chunky sneakers for a full streetwear vibe.
Top: A puffer coat offers maximum warmth and comfort, with its oversized silhouette making it a winter streetwear must-have.
Bottom: Utility pants add practicality and a rugged aesthetic, offering pockets and a relaxed fit that balances the heavy coat.
12. Knitted Sweater + Wide-Leg Trousers
A knitted sweater in neutral tones is a cozy winter streetwear staple. Pair it with wide-leg trousers to add volume and balance. The relaxed fit keeps the outfit casual yet stylish, and pairing it with chunky sneakers or boots gives it a modern edge.
Top: A knitted sweater in neutral tones provides warmth and coziness, adding a classic touch to the streetwear look.
Bottom: Wide-leg trousers create a voluminous silhouette, making the outfit feel relaxed yet polished for the winter season.
13. Varsity Jacket + Hoodie + Cargo Pants
Layering a hoodie under a varsity jacket offers both warmth and style. The varsity jacket’s structured design contrasts well with the relaxed fit of cargo pants. Complete the look with sneakers for a sporty, street-ready vibe that’s perfect for winter.
Top: The varsity jacket layered over a hoodie adds a sporty and retro vibe, perfect for casual streetwear in winter.
Bottom: Cargo pants offer a relaxed fit with functional pockets, adding practicality and an urban edge to the look.
14. Peacoat + Hoodie + Distressed Jeans
A classic peacoat brings a touch of sophistication to streetwear when layered over a hoodie. The contrasting textures create a dynamic winter look, while distressed jeans add an edgy, casual touch. Complete the outfit with high-top sneakers or boots.
Top: A peacoat layered over a hoodie blends classic outerwear with a casual, laid-back streetwear aesthetic.
Bottom: Distressed jeans add a rugged and rebellious touch, contrasting with the formal tone of the peacoat for a balanced outfit.
15. Fur-Lined Coat + Skinny Jeans
For a luxurious take on streetwear, opt for a fur-lined coat paired with skinny jeans. The coat offers warmth and texture, while the fitted jeans create a sleek silhouette. Pair with leather boots or sneakers for a stylish, winter-ready outfit.
Top: A fur-lined coat provides luxurious warmth and texture, making it a standout piece in winter streetwear.
Bottom: Skinny jeans create a sleek, fitted silhouette that contrasts with the bulk of the coat, ensuring a balanced and polished look.
16. Layered Bomber Jacket + Hoodie + Joggers
Layer a bomber jacket over a hoodie for a casual, street-savvy look that’s perfect for winter. The bomber’s sleek design contrasts well with the hoodie’s laid-back vibe, while joggers keep the outfit comfortable and relaxed. Finish with high-top sneakers.
Top: A bomber jacket layered over a hoodie creates a stylish, casual look with streetwear appeal, ideal for winter layering.
Bottom: Joggers keep the outfit comfortable and laid-back while maintaining a slim, tapered fit that complements the relaxed top.
17. Hooded Parka + Layered Turtleneck
A hooded parka is perfect for staying warm in style. Layer it over a turtleneck for a sophisticated twist. Pair it with slim or straight-leg trousers for a balanced look, and finish with boots or sneakers to keep the streetwear edge intact.
Top: A hooded parka offers ultimate protection from the cold, while a turtleneck underneath adds a sophisticated element.
Bottom: Slim or straight-leg trousers balance the bulk of the parka, creating a clean, stylish winter look.
18. Flannel Shirt + Puffer Vest + Slim Jeans
A flannel shirt layered under a puffer vest offers both warmth and style for winter. The mix of textures creates visual interest, while slim jeans keep the silhouette clean. Add sneakers or boots to complete this laid-back streetwear look.
Top: A flannel shirt layered under a puffer vest brings texture and warmth, perfect for creating a layered streetwear outfit.
Bottom: Slim jeans keep the look clean and modern, balancing the volume of the upper layers for a more tailored appearance.
19. Chunky Knit Sweater + Jogger Pants
A chunky knit sweater provides warmth and texture, making it a perfect winter streetwear piece. Pair it with jogger pants for a casual yet stylish outfit. Sneakers or winter boots keep the look functional and on-trend.
Top: A chunky knit sweater provides both warmth and style, making it a winter staple for casual streetwear looks.
Bottom: Jogger pants add comfort and a relaxed fit, ensuring the outfit stays casual and street-ready for everyday wear.
20. Down Parka + Cargo Pants
A down parka provides maximum warmth for winter, while cargo pants offer a practical, rugged touch. Pair them together for a functional streetwear look that’s both stylish and weather-ready. Add boots to complete the ensemble.
Top: A down parka offers insulation and warmth, making it essential for cold-weather streetwear.
Bottom: Cargo pants add a practical, functional touch, with multiple pockets and a loose fit that complements the heavy parka.
21. Hoodie + Quilted Jacket + Ripped Jeans
A quilted jacket layered over a hoodie is a stylish way to stay warm. Pair it with ripped jeans for a rebellious edge, and finish the look with sneakers or winter boots. This outfit blends comfort, style, and functionality.
Top: A quilted jacket layered over a hoodie provides warmth while maintaining a sleek, urban aesthetic for winter.
Bottom: Ripped jeans add a casual, edgy element, balancing the more structured top for a streetwear-approved look.
22. Trench Coat + Beanie + Slim Jeans
A trench coat brings a sleek, sophisticated element to streetwear. Pair it with slim jeans and a beanie for a casual winter look that’s both warm and stylish. Add boots or sneakers for a balanced, urban-ready outfit.
Top: A trench coat adds elegance to streetwear, while the beanie brings in casual comfort, perfect for cold winter days.
Bottom: Slim jeans create a sleek silhouette that contrasts with the voluminous coat, keeping the outfit modern and urban.
23. Oversized Hoodie + Puffer Vest + Joggers
An oversized hoodie paired with a puffer vest creates a warm, layered look. Joggers add a casual, relaxed feel to the outfit. Complete the look with chunky sneakers for a sporty, streetwear-inspired winter outfit.
Top: An oversized hoodie provides warmth and comfort, while the puffer vest adds another layer of insulation without bulk.
Bottom: Joggers keep the outfit relaxed yet stylish, with a tapered fit that balances the oversized hoodie and vest.
24. Leather Jacket + Hoodie + Cargo Pants
A leather jacket layered over a hoodie brings a rebellious, edgy vibe to winter streetwear. Pair it with cargo pants for a functional yet stylish look. Finish the outfit with boots or sneakers to keep the street-ready aesthetic intact.
Top: A leather jacket layered over a hoodie brings a rebellious, rugged streetwear vibe to the winter season.
Bottom: Cargo pants offer a functional and relaxed fit, adding practicality to the look while maintaining a stylish streetwear edge.
25. Sherpa-Lined Jacket + Distressed Denim
A sherpa-lined jacket adds warmth and texture, making it ideal for cold weather. Pair it with distressed denim jeans for a rugged, casual streetwear look. Add boots or chunky sneakers to complete the outfit.
Top: A sherpa-lined jacket offers both warmth and texture, making it ideal for colder months in streetwear fashion.
Bottom: Distressed denim adds a rugged, casual touch to the outfit, providing contrast to the cozy, sherpa-lined top.
26. Puffer Jacket + Wide-Leg Trousers
A puffer jacket offers warmth and a voluminous silhouette, while wide-leg trousers bring a relaxed yet stylish element to the outfit. This combination is perfect for winter streetwear enthusiasts looking to stay cozy and fashionable.
Top: A puffer jacket brings volume and warmth, offering protection from the cold while making a bold streetwear statement.
Bottom: Wide-leg trousers add a relaxed, modern silhouette, ensuring the outfit remains comfortable and stylish.
27. Bomber Jacket + Hoodie + Tech Pants
Layering a bomber jacket over a hoodie is a streetwear classic. Pair it with tech pants for a modern, functional twist. The tech pants’ slim, sleek design contrasts well with the relaxed fit of the hoodie, creating a balanced winter outfit.
Top: A bomber jacket layered over a hoodie combines classic streetwear pieces with modern functionality, perfect for winter layering.
Bottom: Tech pants offer a slim, tailored look with modern materials, adding a sleek contrast to the relaxed top.
28. Wool Coat + Turtleneck + Skinny Jeans
A wool coat layered over a turtleneck offers warmth and sophistication. Pair it with skinny jeans for a streamlined silhouette. This blend of streetwear and refinement is perfect for urban winter fashion.
Top: A wool coat layered over a turtleneck brings a refined, polished element to streetwear, perfect for colder weather.
Bottom: Skinny jeans maintain a streamlined silhouette, balancing the heavier wool coat with a fitted lower half.
29. Oversized Puffer Coat + Cargo Pants
An oversized puffer coat makes a bold statement, while cargo pants add functionality and a streetwear edge. This combination ensures warmth and style throughout the winter season.
Top: An oversized puffer coat offers warmth and a bold silhouette, perfect for staying stylish in the winter months.
Bottom: Cargo pants add functionality and a streetwear edge, with multiple pockets and a relaxed fit that balances the coat.
30. Quilted Jacket + Track Pants
A quilted jacket creates a comfortable and stylish winter look. Track pants add a sporty element, perfect for casual streetwear. Complete the outfit with sneakers for a modern, laid-back vibe.
Top: A quilted jacket layered over a shirt creates warmth and texture, perfect for casual winter streetwear.
Bottom: Track pants offer a sporty, laid-back feel, ensuring the outfit remains comfortable and effortlessly stylish.
31. Longline Puffer + Beanie + Slim Jeans
A longline puffer coat is ideal for colder days, offering maximum warmth and style. Pair it with slim jeans and a beanie for a clean, minimalist streetwear look. Finish with boots or sneakers for a balanced outfit.
Top: A longline puffer coat provides extra warmth and a sleek silhouette, perfect for colder winter days.
Bottom: Slim jeans keep the look sleek and clean, contrasting with the oversized coat for a balanced, stylish look.
32. Varsity Jacket + Beanie + Cargo Pants
A varsity jacket layered over a hoodie or tee brings a retro-inspired look to winter streetwear. Pair it with cargo pants for a functional yet stylish twist. A beanie adds warmth and a casual touch to the ensemble.
Top: A varsity jacket layered over a hoodie or tee brings a retro touch to streetwear, while a beanie adds casual warmth.
Bottom: Cargo pants provide a functional, relaxed fit, perfect for adding an urban edge to the sporty top half.
33. Wool Overcoat + Hoodie + Slim Pants
Layer a wool overcoat over a hoodie for a refined yet casual winter streetwear outfit. Slim-fit pants balance the volume of the coat, while sneakers or boots complete the look for a modern street vibe.
Top: A wool overcoat layered over a hoodie offers both refinement and casual comfort, creating a versatile winter streetwear look.
Bottom: Slim-fit pants balance the volume of the overcoat, keeping the silhouette sleek and stylish.
34. Hooded Down Jacket + Joggers
A hooded down jacket offers unbeatable warmth and comfort, perfect for cold winter days. Pair it with joggers for a laid-back, street-ready look. Complete the outfit with chunky sneakers for added flair.
Top: A hooded down jacket offers excellent insulation and warmth, perfect for braving the cold in streetwear style.
Bottom: Joggers add comfort and flexibility, keeping the outfit relaxed yet street-ready for everyday winter wear.
35. Teddy Coat + Slim Jeans
A teddy coat brings warmth and texture to your winter streetwear look. Pair it with slim jeans for a sleek silhouette that balances the oversized outerwear. Add boots or sneakers for a complete outfit.
Top: A teddy coat brings texture and warmth, creating a cozy and fashionable top layer for winter streetwear.
Bottom: Slim jeans ensure the outfit remains sleek and balanced, providing contrast to the oversized, voluminous coat.
36. Layered Hoodie + Peacoat + Cargo Pants
Layering a hoodie under a peacoat combines casual streetwear with a polished, winter-ready look. Cargo pants add a practical, utilitarian touch to the outfit, while boots or high-top sneakers keep the style grounded.
Top: A peacoat layered over a hoodie blends formal outerwear with streetwear essentials, creating a stylish winter look.
Bottom: Cargo pants bring a utilitarian, relaxed fit to the outfit, adding practicality and a casual edge to the refined top.
37. Fleece Jacket + Utility Pants
A fleece jacket offers warmth and softness, perfect for winter streetwear. Pair it with utility pants for a functional yet stylish vibe. Add sneakers or winter boots to round out the look.
Top: A fleece jacket provides warmth and a soft texture, making it a perfect winter streetwear piece.
Bottom: Utility pants add function and rugged style, with multiple pockets and a relaxed fit ideal for street-ready looks.
38. Sherpa-Lined Parka + Tapered Pants
A sherpa-lined parka provides unbeatable warmth and style for winter. Pair it with tapered pants for a clean, modern silhouette. This outfit combines functionality and fashion, ideal for the colder months.
Top: A sherpa-lined parka offers excellent warmth and style, making it a must-have for cold winter days.
Bottom: Tapered pants maintain a streamlined silhouette, balancing the bulkiness of the top and ensuring a modern, polished look.