Men’s winter street style is all about layering, keeping warmth without sacrificing style, and selecting materials that are both warm and fashionable. This season, the secret is to combine timeless items with cutting-edge styles to create ensembles that are both stylish and practical. You can dress up your winter clothing in a variety of ways, from classic outerwear like parkas and wool overcoats to adaptable shoes like Chelsea boots and combat boots. These 40 street fashion ideas can help you effortlessly traverse the chilly months with elegance.
1. Layered Hoodie with Overcoat
Go with the look that blends streetwear and classic fashion. The hoodie adds a laid-back vibe, while the overcoat gives it a refined, polished touch. Perfect for casual outings when you want comfort with style.
Top: Layer a grey hoodie under a camel overcoat for a smart-casual look.
Bottom: Pair with the slim-fit dark jeans.
Shoes: Pair with white sneakers for a sleek yet relaxed finish.
2. Puffer Jacket and Cargo Pants
Ideal for colder days, this combination offers both warmth and utility. The puffer jacket provides insulation, while cargo pants add a functional and rugged feel, making this look both practical and trendy.
Top: A black puffer jacket offers warmth and urban style, layered over a casual crew-neck sweater for a laid-back yet functional look.
Bottom: The relaxed-fit cargo pants in beige or cream colour add utility and a rugged vibe
Shoes: Chunky white boots or sneaker adding a touch of toughness to the overall outfit.
3. Turtleneck and Trench Coat
A sophisticated and sleek winter look. The turtleneck provides warmth and a polished base, while the trench coat adds a layer of elegance. Perfect for semi-formal or business-casual settings.
Top: The black turtleneck offers a sleek, sophisticated base, while the beige trench coat adds timeless elegance and structure to the look.
Bottom: Black tailored trousers.
Shoes: Black leather Chelsea boots complete the outfit with a minimalist yet classy touch.
4. Plaid Shirt with Denim Jacket
A timeless casual combination that never goes out of style. The plaid shirt brings a rugged, outdoorsy feel, and the denim jacket adds a layer of cool. Great for laid-back weekends or casual hangouts.
Top: The plaid flannel shirt adds a bold, casual touch, while the classic denim jacket layers over it for a timeless, rugged appeal.
Bottom: Black skinny jeans.
Shoes: White high-top sneakers bring a fresh, contemporary element to the outfit.
5. Wool Coat and Tapered Pants
A refined and tailored outfit, the wool coat exudes sophistication, while tapered pants offer a streamlined outfit. Ideal for more formal occasions or a stylish day out in the city.
Top: Cream wool coat over a sweater or long-sleeve shirt combines elegance with warmth
Bottom: Tapered trousers.
Shoes: Brown leather brogues or loafers.
6. Bomber Jacket and Joggers
This sporty yet stylish combo is perfect for the man on the go. The bomber jacket offers a contemporary edge, while joggers provide comfort and an athletic vibe. Great for casual, everyday wear.
Top: Classic bomber jacket with a crew-neck sweatshirt underneath.
Bottom: Black or grey joggers.
Shoes: Casual sneakers or slip-on shoes.
7. Sweater with Leather Jacket
Mixing rugged and comfortable elements, this look pairs the edginess of a leather jacket with the warmth of a knit sweater. It’s a versatile outfit that can transition from day to night.
Top: Chunky knit sweater under a black leather jacket.
Bottom: Dark wash jeans.
Shoes: Black combat boots.
8. Parka with Knit Beanie
A functional and stylish choice for colder months. The insulated parka provides warmth and protection, while the knit beanie adds a casual, urban touch. Great for outdoor adventures or city life.
Top: Insulated parka with a thick knit beanie.
Bottom: Slim-fit jeans or chinos.
Shoes: Waterproof boots or rugged sneakers.
9. Double-Breasted Peacoat and Chinos
A classic winter ensemble that combines timeless tailoring with modern style. The double-breasted peacoat adds a sharp, structured look, while chinos keep it relaxed but refined.
Top: Gray double-breasted peacoat over a turtleneck.
Bottom: Black chinos.
Shoes: Black leather dress boots.
10. Fleece Lined Jacket with Jeans
This combination is all about warmth and comfort. A fleece-lined jacket provides extra insulation, while jeans keep it casual and versatile. Ideal for chilly weekends or outdoor activities.
Top: Fleece-lined bomber or utility jacket.
Bottom: Blue jeans.
Shoes: Casual sneakers or hiking boots.
11. Chesterfield Coat and Dress Pants
A sophisticated outfit for formal or business settings. The Chesterfield coat adds elegance and formality, while dress pants complete the look. Perfect for professional environments or special events.
Top: Classic chesterfield coat over a sweater or dress shirt.
Bottom: Gray or navy dress pants.
Shoes: Black or brown leather dress shoes.
12. Zip-Up Hoodie with Ripped jeans
A mix of streetwear and classic tailoring. The zip-up hoodie adds a relaxed vibe, while wool blend trousers offer a refined, stylish contrast. Great for casual yet polished looks.
Top: Zip-up hoodie layered with a denim jacket for elegant and classy look.
Bottom: Black ripped jeans
Shoes: Casual loafers or stylish sneakers.
13. Down Vest and Long Sleeve Tee
A casual but smart outfit for cooler weather. The down vest adds warmth without bulk, while the Henley shirt keeps it simple and stylish. Ideal for layering on chilly fall or winter days.
Top: Down vest over a long-sleeve Henley shirt.
Bottom: Slim-fit jeans or chinos.
Shoes: Casual boots or sneakers.
14. Sherpa Jacket and Corduroy Pants
This outfit blends cozy textures with winter style. A sherpa-lined jacket adds a warm, rustic feel, while corduroy pants introduce vintage-inspired texture. Perfect for outdoor winter activities.
Top: Sherpa-lined jacket with a thermal shirt.
Bottom: Corduroy pants.
Shoes: Ankle boots or casual sneakers.
15. Military Jacket and Slim Fit Jeans
This look gives off a rugged and masculine vibe. The military jacket brings utility and structure, while slim-fit jeans add a modern, clean-cut look. Great for everyday casual wear.
Top: Military-style jacket with a graphic tee or sweater.
Bottom: Slim-fit jeans.
Shoes: Combat boots or rugged sneakers.
16. Tech Fleece Jacket and Track Pants
A sporty, athleisure style that focuses on comfort and performance. The tech fleece jacket keeps you warm, and the track pants provide flexibility and ease. Ideal for active days or casual weekends.
Top: Tech fleece jacket with a moisture-wicking base layer.
Bottom: Matching tech fleece track pants.
Shoes: Athletic sneakers or trainers.
17. Cable Knit Sweater and Wool Overcoat
A classic, sophisticated winter look. The cable-knit sweater adds texture and warmth, while the wool overcoat offers a timeless, elegant layer. Perfect for more formal winter settings.
Top: Cable knit sweater layered under a wool overcoat.
Bottom: Dark jeans or tailored trousers.
Shoes: Leather loafers or boots.
18. Quilted Vest and Henley Shirt
This casual look is all about layering and comfort. A quilted vest provides lightweight warmth, and a Henley shirt gives it a relaxed, easy-going vibe. Great for casual outings or layering in winter.
Top: Quilted vest over a long-sleeve Henley shirt.
Bottom: Casual jeans or chinos.
Shoes: Casual boots or sneakers
19. Checker Wool Jacket and Black Skinnies
A sharp, urban look that combines patterns and slim fits. The checker wool jacket adds visual interest, while black skinny jeans give a sleek and modern edge. Perfect for a night out.
Top: Checker wool jacket with a simple tee or turtleneck.
Bottom: A skinny jeans.
Shoes: Chelsea boots or sleek sneakers.
20. Varsity Jacket with Relaxed Fit Jeans
A sporty, retro-inspired outfit. The varsity jacket brings a youthful, collegiate vibe, while relaxed-fit jeans add comfort and casual style. A great look for laid-back weekends.
Top: Classic varsity jacket over a hoodie or sweater.
Bottom: Relaxed fit jeans.
Shoes: High-top sneakers or casual loafers.
21. Faux Fur Lined Parka and Denim
This combination balances warmth and style. The faux fur-lined parka is a winter essential, and denim keeps it casual and versatile. Ideal for cold, urban environments.
Top: Faux fur-lined parka with a crew-neck sweatshirt.
Bottom: Dark denim jeans.
Shoes: Insulated boots or rugged sneakers.
22. Peacoat with Button-Up Shirt and Pants
A clean, sophisticated winter look. The peacoat adds structure and warmth, while a button-up shirt and pants create a polished base. Perfect for business casual or semi-formal occasions.
Top: Navy peacoat over a button-up shirt.
Bottom: Dark dress pants.
Shoes: Leather dress shoes or boots.
23. Leather Bomber with Chino Shorts
This edgy, transitional outfit combines a leather bomber with chinos for a mix of cool and casual. Ideal for mild winter days when you want to stay stylish without overheating.
Top: Leather bomber jacket with a simple tee or sweater.
Bottom: Casual chino shorts.
Shoes: Casual loafers or sneakers.
24. Insulated Puffer and Thermal Leggings
A performance-focused winter look that prioritizes warmth. The insulated puffer offers excellent protection, while thermal leggings provide flexibility and warmth. Ideal for outdoor activities.
Top: Insulated puffer jacket over a thermal shirt.
Bottom: Thermal leggings or skinny jeans.
Shoes: Winter boots or high-top sneakers.
25. Wool Blend Blazer and Casual Pants
A smart-casual outfit with a refined edge. The wool blend blazer adds a touch of formality, while casual pants keep it relaxed. Great for a casual office environment or a date night.
Top: Wool blend blazer over a casual sweater or shirt.
Bottom: Casual trousers or chinos.
Shoes: Leather loafers or casual boots.
26. Oversized Hoodie with Straight-Leg Jeans
A relaxed, streetwear-inspired look. The oversized hoodie offers comfort and a laid-back aesthetic, while straight-leg jeans maintain a balanced, casual outline
Top: Oversized hoodie for a relaxed, casual look.
Bottom: Straight-leg jeans.
Shoes: High-top sneakers or chunky boots.
27. Trucker Jacket and Thermal Turtleneck
A stylish layering option for colder days. The trucker jacket provides a rugged outer layer, while a thermal turtleneck adds warmth and a chic touch. Ideal for casual winter outings.
Top: Trucker jacket over a thermal turtleneck.
Bottom: Slim jeans or chinos.
Shoes: Casual boots or sneakers.
28. Gore-Tex Jacket with Cargo Pants
A functional, weather-resistant outfit. The Gore-Tex jacket keeps you dry, while cargo pants offer utility and style. Perfect for outdoor activities or unpredictable weather.
Top: Gore-Tex jacket with a moisture-wicking base layer.
Bottom: Cargo pants for a rugged look.
Shoes: Waterproof boots or sturdy sneakers.
29. Teddy Coat with Slim Fit Joggers
This cozy, trendy look combines the warmth of a teddy coat with the relaxed fit of joggers. It’s the perfect blend of comfort and style for casual winter days.
Top: Teddy coat over a casual sweater or hoodie.
Bottom: Slim fit joggers.
Shoes: Casual sneakers or slip-on shoes.
30. Houndstooth Overcoat and Dress Shoes
A sharp, classic look. The houndstooth overcoat adds pattern and sophistication, while dress shoes keep it polished. Ideal for formal or business occasions during the colder months.
Top: Houndstooth patterned overcoat over a sweater or shirt.
Bottom: Tailored dress pants.
Shoes: Polished dress shoes.
31. Puffer Vest and Layered Long Sleeve
A great option for layering. The puffer vest offers lightweight warmth, while the long sleeve adds comfort. Perfect for mild winter days or layering under a heavier coat.
Top: Puffer vest layered over a long-sleeve tee or shirt.
Bottom: Casual jeans or chinos.
Shoes: Casual boots or sneakers.
32. Winter Parka with Utility Pants
A rugged, practical winter outfit. The parka provides excellent insulation, and utility pants add functionality. Ideal for cold outdoor adventures or casual winter days.
Top: Winter parka over a thermal or sweater.
Bottom: Utility pants for a rugged look.
Shoes: Insulated boots or heavy-duty sneakers.
33. Peacoat with Crew Neck Sweater
A timeless, polished look. The peacoat adds structure, and the crew neck sweater provides a comfortable, stylish base. Suitable for both casual and semi-formal winter events.
Top: Classic peacoat over a crew neck sweater.
Bottom: Dark jeans or trousers.
Shoes: Brown or black leather boots.
34. Knit Jacket with Casual Chinos
This smart-casual look is perfect for colder days. The knit jacket offers warmth and texture, while casual chinos keep it relaxed. Great for casual office settings or dinners.
Top: Knit jacket over a casual shirt or sweater.
Bottom: Casual chinos.
Shoes: Loafers or casual sneakers.
35. Wool Blend Blazer with Denim
A stylish blend of casual and formal. The wool blend blazer elevates the look, while denim keeps it grounded and versatile. Ideal for casual business meetings or date nights.
Top: Wool blend blazer over a sweater or button-up shirt.
Bottom: Dark denim jeans.
Shoes: Leather boots or loafers.
36. Track Suit and Puffer Jacket
A sporty, comfortable winter outfit. The track suit offers a relaxed fit, and the puffer jacket adds warmth. Ideal for casual outings or athleisure-inspired looks.
Top: Matching track suit with a puffer jacket on top.
Bottom: Coordinated track pants.
Shoes: Athletic sneakers or trainers.
37. Over-sized Cardigan with Dress Pants
This look mixes comfort with sophistication. The oversized cardigan adds a cozy feel, while dress pants keep the outfit structured. Perfect for a casual office or stylish winter outings.
Top: Oversized cardigan over a dress shirt or turtleneck.
Bottom: Dress pants
Shoes: Leather loafers or dress boots.
38. Field Jacket with Wool Sweater
A rugged, outdoorsy outfit. The field jacket provides structure, and the wool sweater offers warmth and texture. Ideal for casual winter days or outdoor activities.
Top: Field jacket layered over a wool sweater.
Bottom: Casual jeans or chinos.
Shoes: Casual boots or rugged sneakers.
39. Faux Leather Jacket and Jogger Pants
A laid-back, streetwear-inspired look. The faux leather jacket adds edge, while jogger pants keep it casual and comfortable. Perfect for casual weekends or nights out.
Top: Faux leather jacket over a simple tee or hoodie.
Bottom: Jogger pants for a relaxed fit.
Shoes: Casual sneakers or boots.
40. Longline Wool Coat and Slim Fit Jeans
A modern, sleek winter outfit. The longline wool coat adds sophistication, and slim-fit jeans offer a streamlined outline. Great for formal occasions or stylish city outings.
Top: Longline wool coat over a sweater or turtleneck.
Bottom: Slim fit jeans.
Shoes: Leather Chelsea boots or dress shoes.