Now is the perfect opportunity to raise your street style game with ensembles that mix comfort, functionality, and unquestionable style when the weather drops and the leaves start to fall. There is something for every style, whether you like rough, casual looks or sleek, minimalist feelings. Here are 37 incredible fall street style looks for men to get you inspired for your next seasonal look, ranging from fitted pants and edgy boots to warm sweaters and bold coats.
1. Casual Denim on Denim
Pair a classic blue denim jacket with dark-wash jeans for a casual, rugged look. Layer a white tee underneath and finish with tan leather boots for a balanced outfit. This classic double-denim style is great for casual outings or weekend wear. Keep accessories minimal for a clean, timeless appearance.
Top: A classic blue denim jacket provides a rugged, casual vibe. Pair it with a simple white tee for a clean look.
Bottom: Dark-wash jeans complement the jacket and maintain a balanced appearance. Tan leather boots finish off the outfit.
2. Layered Hoodie and Overcoat
For a stylish blend of casual and formal, layer a hoodie under a wool overcoat. This look gives the perfect balance of streetwear cool and sophistication. Choose neutral tones like gray, navy, or black for the hoodie, and complement it with slim jeans and sneakers. It’s ideal for city strolls on chilly days.
Top: Layer a hoodie under a wool overcoat for a stylish blend of casual and formal. Opt for neutral tones for versatility.
Bottom: Slim jeans or chinos work well to balance the outfit. Complete with sneakers or boots for an urban look.
3. Flannel Shirt and Jeans
Channel laid-back fall vibes with a cozy flannel shirt in plaid patterns. Pair it with dark jeans and boots for a rugged, outdoorsy look. For added warmth, layer a plain tee underneath or throw on a denim jacket. This outfit works well for casual weekends or outdoor gatherings.
Top: A cozy plaid flannel shirt adds a laid-back fall vibe. Layer it over a tee for extra warmth.
Bottom: Dark jeans and work boots create a rugged, outdoorsy style. Ideal for casual activities or relaxed weekends.
4. Leather Jacket and Skinny Jeans
A black leather jacket paired with skinny jeans is the ultimate cool-guy look for fall. Add a simple white or black tee underneath for a minimalist touch. Finish the outfit with Chelsea boots or sneakers for a sleek, edgy vibe. Perfect for a night out or casual daytime wear.
Top: A black leather jacket delivers a sleek, edgy appearance. Pair it with a simple white or black tee underneath.
Bottom: Skinny jeans add to the modern, minimalist look. Finish with Chelsea boots or sneakers for an effortlessly cool style.
5. Trench Coat and Turtleneck
For a more refined look, layer a beige trench coat over a fitted turtleneck. This combination creates a sophisticated, polished appearance while keeping you warm. Pair with tailored trousers and loafers for a smart-casual look or with dark jeans and boots for a more relaxed vibe.
Top: A beige trench coat layered over a fitted turtleneck offers sophistication and warmth. Choose classic colors for versatility.
Bottom: Tailored trousers or dark jeans complement the top. Leather shoes or boots complete the smart-casual look.
6. Bomber Jacket and Joggers
For a sporty streetwear look, pair a bomber jacket with slim-fit joggers. A black or olive bomber works great for fall, and joggers in neutral tones keep the look sleek. Complete the outfit with high-top sneakers and a cap for an athleisure-inspired style that’s comfortable and trendy.
Top: A bomber jacket adds sporty flair to the outfit. Choose a black or olive color for fall.
Bottom: Slim-fit joggers keep the look comfortable and trendy. High-top sneakers and a cap finish off this athleisure-inspired outfit.
7. Puffer Vest and Flannel
Layer a puffer vest over a flannel shirt for a casual, cozy fall outfit. The puffer vest adds warmth without the bulk of a full coat. Pair with jeans and work boots for an outdoorsy, practical look. This outfit is perfect for apple picking or weekend hikes.
Top: A puffer vest layered over a flannel shirt provides warmth and style. Ideal for crisp fall weather.
Bottom: Jeans and work boots give the outfit an outdoorsy, practical edge. Great for casual outings and weekend adventures.
8. Cardigan and Chinos
A chunky knit cardigan layered over a crewneck tee or shirt is a great way to stay warm and stylish. Pair it with slim-fit chinos and leather sneakers or boots for a clean, casual look. This outfit balances comfort and style, perfect for coffee runs or casual workdays.
Top: A chunky knit cardigan layered over a crewneck tee adds comfort and style. Opt for neutral or earthy tones.
Bottom: Slim-fit chinos balance the relaxed top with a clean, polished look. Pair with leather sneakers or boots for a refined touch.
9. Hoodie and Denim Jacket
For a relaxed street style look, layer a hoodie under a denim jacket. Choose a neutral-colored hoodie like gray or black and pair it with slim jeans. Finish with sneakers or boots for an easygoing, urban vibe. It’s an ideal choice for a day of errands or casual hangouts.
Top: Layer a hoodie under a denim jacket for a relaxed street style. Choose a neutral hoodie for versatility.
Bottom: Slim jeans maintain a sleek silhouette. Sneakers or boots complete this easygoing, urban look.
10. Tweed Blazer and Jeans
Mix casual and formal by wearing a tweed blazer over a simple T-shirt and dark jeans. The blazer adds structure to your outfit, while the jeans keep it casual. Complete the look with leather boots or brogues for a smart-casual style that’s great for date nights or weekend brunches.
Top: A tweed blazer adds sophistication to a casual outfit. Layer it over a simple tee or shirt.
Bottom: Dark jeans keep the look casual and balanced. Leather boots or brogues complete this smart-casual ensemble.
11. Military Jacket and Cargo Pants
For a rugged, utility-inspired look, pair a military-style jacket with cargo pants. The earthy tones of the jacket complement the casual vibe of the cargo pants. Add a simple tee and boots for an effortlessly cool street style look that’s functional and stylish.
Top: A military-style jacket offers a rugged, utilitarian look. Earthy tones complement the casual vibe.
Bottom: Cargo pants add functionality and style. Pair with a simple tee and boots for a cool, street-ready outfit.
12. Varsity Jacket and Ripped Jeans
Channel vintage street style with a varsity jacket layered over a hoodie or tee. Pair it with ripped skinny jeans for an edgy contrast. Complete the look with sneakers or combat boots for a bold, youthful appearance that works for casual outings.
Top: A varsity jacket layered over a hoodie or tee delivers a vintage street style. Opt for bold or classic colors.
Bottom: Ripped skinny jeans add an edgy contrast. Finish with sneakers or combat boots for a youthful, dynamic look.
13. Suede Jacket and Sweater
A suede jacket paired with a chunky knit sweater creates a rich, textured look perfect for fall. Opt for earthy tones like tan or brown for the jacket and a neutral sweater underneath. Pair with slim jeans and Chelsea boots for a refined yet relaxed look.
Top: A suede jacket adds a touch of luxury and texture. Layer it over a chunky knit sweater.
Bottom: Slim jeans or chinos complete the look. Chelsea boots or casual loafers add a polished touch.
14. Plaid Shirt Jacket and Trousers
A plaid shirt jacket (or shacket) adds both warmth and style to your fall outfit. Layer it over a simple tee or sweater, and pair with tapered trousers. Sneakers or casual loafers complete this street-ready look, ideal for transitioning from work to weekend.
Top: A plaid shirt jacket (shacket) offers both style and warmth. Layer over a tee or sweater for added comfort.
Bottom: Tapered trousers keep the look clean and versatile. Sneakers or casual loafers complete the outfit.
15. Parka and Knit Beanie
Stay warm and stylish by layering a parka over a hoodie or sweater. Add a knit beanie to keep things cozy while maintaining street style credibility. Pair with slim-fit jeans and sneakers or boots for a laid-back, functional look perfect for colder days.
Top: A parka provides protection from the cold while maintaining style. Layer it over a hoodie or sweater.
Bottom: Slim-fit jeans and sneakers or boots keep the look practical and casual. A knit beanie adds extra warmth.
16. Rollneck Sweater and Trench Coat
Elevate your fall street style with a rollneck (turtleneck) sweater layered under a trench coat. This combination is sleek and sophisticated, perfect for chilly days. Pair with tailored trousers or dark jeans and finish with leather shoes for a refined, urban look.
Top: A rollneck sweater paired with a trench coat creates a sleek, sophisticated look. Opt for classic tones.
Bottom: Tailored trousers or dark jeans balance the refined top. Leather shoes or boots complete the elegant outfit.
17. Sherpa-Lined Denim Jacket and Jeans
For extra warmth, opt for a sherpa-lined denim jacket paired with jeans. This rugged look is great for casual street style, especially when paired with a flannel shirt or hoodie underneath. Boots complete this outdoorsy, comfortable look.
Top: A sherpa-lined denim jacket adds warmth and texture. Ideal for cooler fall days.
Bottom: Pair with jeans and work boots for a rugged, outdoorsy style. This outfit is great for casual or outdoor activities.
18. Chunky Knit Sweater and Wool Coat
A chunky knit sweater layered under a wool coat is a cozy yet polished look. Choose neutral or earthy tones for the sweater, and pair with dress pant and boots. This outfit is perfect for everything from coffee runs to casual office days.
Top: A chunky knit sweater layered under a wool coat provides both comfort and sophistication. Choose neutral colors.
Bottom: Dress pant and boots complement the top. This outfit is perfect for both casual and smart-casual settings.
19. Graphic Tee and Overshirt
Layer a graphic tee under an overshirt for an easy, laid-back look. Pair with slim jeans and sneakers for a casual streetwear vibe. The overshirt adds a touch of warmth and style, making it perfect for fall’s cooler temperatures.
Top: A graphic tee layered under an overshirt creates a relaxed, street-ready look. Opt for bold prints or designs.
Bottom: Slim jeans and sneakers keep the look casual and cool. This combination works well for everyday wear.
20. Corduroy Jacket and Black Jeans
A corduroy jacket adds texture and warmth to your outfit, while black jeans keep the look edgy and clean. Pair with a simple T-shirt or sweater underneath and finish with boots or sneakers for a stylish, fall-ready outfit.
Top: A corduroy jacket adds texture and warmth. Pair it with a simple tee or sweater for a cozy look.
Bottom: Black jeans maintain a sleek, modern appearance. Boots or sneakers complete the outfit for a stylish edge.
21. Double-Breasted Coat and Scarf
Add a touch of class to your fall wardrobe with a double-breasted wool coat paired with a scarf. This look is polished yet cozy, perfect for urban strolls or evenings out. Pair with dark jeans and boots for a refined yet approachable outfit.
Top: A double-breasted wool coat paired with a scarf creates a polished, warm look. Opt for classic colors.
Bottom: Dark jeans or tailored trousers keep the outfit refined. Finish with leather shoes or boots.
22. Down Jacket and Track Pants
For a sporty street style look, pair a lightweight down jacket with slim track pants. Complete the look with high-top sneakers or trainers for a functional, comfortable vibe. This outfit is perfect for running errands or casual weekend wear.
Top: A lightweight down jacket offers warmth and style. Pair with track pants for a sporty edge.
Bottom: Slim track pants maintain a comfortable, athletic look. Complete with high-top sneakers for a dynamic outfit.
23. Blazer and Hoodie
Mix smart and casual by layering a hoodie under a structured blazer. This unexpected combo works well with slim jeans or chinos and can be dressed up or down depending on your footwear. Opt for sneakers for a casual look or boots for a more refined appearance.
Top: Layer a hoodie under a blazer for a mix of smart and casual. Choose a neutral hoodie for versatility.
Bottom: Slim jeans or chinos keep the look balanced. Sneakers or boots add a touch of modern street style.
24. Oversized Sweater and Slim Jeans
An oversized sweater paired with slim jeans creates a balanced, relaxed look. The loose fit of the sweater contrasts nicely with the fitted jeans. Finish with casual sneakers or boots for a laid-back, cozy outfit that’s great for casual outings.
Top: An oversized sweater provides a relaxed, cozy vibe. Pair it with slim jeans to balance the proportions.
Bottom: Slim jeans maintain a clean, sleek appearance. Sneakers or boots complete the laid-back look.
25. Quilted Jacket and Beanie
A quilted jacket paired with a knit beanie creates a casual, layered look perfect for chilly fall days. Pair with dark jeans and sneakers for a comfortable yet stylish street style outfit. This combo works well for outdoor activities or city walks.
Top: A quilted jacket offers warmth and style. Layer it over a tee or sweater for added comfort.
Bottom: Jeans and casual boots or sneakers keep the look practical and stylish. A knit beanie adds extra coziness.
26. Fleece Jacket and Joggers
A fleece jacket is a comfortable, warm option for fall street style. Pair it with joggers for a casual, sporty look. Finish with sneakers and a baseball cap for a laid-back, athletic vibe that’s perfect for relaxed weekend wear.
Top: A fleece jacket provides warmth and a sporty touch. Pair with joggers for a casual, athletic look.
Bottom: Joggers offer comfort and a modern style. Sneakers complete the outfit for a relaxed, street-ready appearance.
27. Harrington Jacket and Chinos
The classic Harrington jacket adds a touch of British style to your fall outfit. Pair it with chinos and a simple crewneck tee for a clean, casual look. Finish with loafers or sneakers for a polished yet relaxed outfit perfect for everyday wear.
Top: A Harrington jacket adds classic style to your outfit. Layer it over a tee or shirt for a refined look.
Bottom: Chinos keep the outfit polished and casual. Loafers or sneakers complete the look for a versatile, urban style.
28. Denim Jacket and Cargo Pants
For a rugged street style look, pair a denim jacket with cargo pants. This combo is both functional and stylish, with the denim jacket adding structure and the cargo pants providing utility. Finish with boots or sneakers for a tough, casual outfit.
Top: A denim jacket provides a rugged, casual look. Pair with a simple tee for a laid-back appearance.
Bottom: Cargo pants add functionality and style. Finish with boots or sneakers for a cool, practical outfit.
29. Varsity Bomber and Jeans
Combine the sporty look of a varsity jacket with the sleek fit of a bomber. This hybrid jacket pairs perfectly with jeans for a bold, street-ready outfit. Finish the look with sneakers or boots, depending on your mood.
Top: A varsity bomber jacket combines sporty and street style elements. Choose bold or classic colors.
Bottom: Jeans keep the outfit casual and balanced. Sneakers or boots add a modern touch to the look.
30. Chore Coat and Slim Jeans
A chore coat adds a workwear-inspired touch to your fall street style. Layer it over a tee or sweater and pair with slim jeans for a clean, utilitarian look. Finish with boots for a rugged, outdoorsy vibe perfect for everyday wear.
Top: A chore coat offers a workwear-inspired style. Layer it over a tee or sweater for a practical look.
Bottom: Slim jeans maintain a clean silhouette. Boots or sneakers complete this functional and stylish outfit.
31. Hooded Puffer Jacket and Jeans
For colder days, layer a hooded puffer jacket over a hoodie or sweater. Pair with slim jeans and sneakers for a casual, laid-back look that’s both warm and stylish. The puffer jacket adds volume while keeping you comfortable in cooler temperatures.
Top: A hooded puffer jacket adds warmth and style. Layer over a hoodie or sweater for extra comfort.
Bottom: Slim jeans and sneakers or boots complete the look. This outfit is ideal for cold days and casual outings.
32. Peacoat and Skinny Jeans
A tailored peacoat pairs perfectly with skinny jeans for a sleek, structured look. The coat adds polish to your outfit, while the skinny jeans keep it casual and modern. Finish with boots or loafers for a refined yet approachable street style outfit.
Top: A tailored peacoat provides a sleek, structured look. Layer it over a simple shirt or sweater.
Bottom: Skinny jeans add to the modern, minimalist style. Finish with boots or loafers for a refined appearance.
33. Turtleneck and Military Jacket
Layer a turtleneck sweater under a military-style jacket for a rugged yet refined fall look. Pair with dark jeans and boots for a clean, masculine outfit. This combination is perfect for chilly days when you want to stay warm and stylish.
Top: A turtleneck sweater under a military jacket offers a rugged yet refined look. Opt for classic tones.
Bottom: Dark jeans and boots complete the outfit. This combination is great for staying warm and stylish.
34. Wool Blazer and Ripped Jeans
Pair a wool blazer with ripped jeans for a mix of formal and edgy street style. The blazer adds structure, while the ripped jeans keep the look casual and cool. Finish with boots or loafers for a bold, modern outfit that works for casual outings or evening events.
Top: A wool blazer adds sophistication to a casual outfit. Layer it over a simple shirt or sweater.
Bottom: Ripped jeans provide an edgy contrast. Boots or loafers complete the look for a bold, modern appearance.
35. Plaid Shirt and Quilted Vest
A plaid shirt layered under a quilted vest creates a comfortable yet stylish fall look. Pair with jeans and work boots for a rugged, outdoorsy vibe. This combo is perfect for casual weekend wear or outdoor activities.
Top: A plaid shirt layered under a quilted vest offers warmth and style. Choose earthy tones for fall.
Bottom: Jeans and work boots enhance the outdoorsy vibe. This outfit is great for casual wear and outdoor activities.
36. Rollneck Sweater and Leather Jacket
A rollneck sweater layered under a leather jacket creates a sleek, refined look with an edge. Pair with slim-fit jeans and Chelsea boots for a sharp, modern outfit that’s perfect for a night out or weekend adventures.
Top: A rollneck sweater paired with a leather jacket creates a sleek, refined look. Opt for neutral or classic colors.
Bottom: Slim-fit jeans and Chelsea boots complete the outfit. This combination is perfect for a night out or weekend adventures.
37. Graphic Sweatshirt and Bomber Jacket
For an urban street style look, layer a graphic sweatshirt under a bomber jacket. Pair with ripped jeans and sneakers for an edgy, laid-back vibe. This combination is perfect for casual outings or a day in the city.
Top: A graphic sweatshirt layered under a bomber jacket creates an urban, street-ready look. Choose bold designs.
Bottom: Ripped jeans and sneakers keep the look casual and cool. This outfit is ideal for everyday wear and casual hangouts.