40 Coolest Streetwear Men Outfits

Streetwear is a global fashion movement that combines luxurious clothing with comfortable, casual elements. It started out as a small subculture. Men’s streetwear is all about showcasing their uniqueness, fusing well-known labels with eye-catching patterns, and skillfully combining ease of wear with fashion. Streetwear ensembles offer for endless creativity and individual flare, from striking accessories and elegant sneakers to oversized sweatshirts and graphic tees. The greatest of modern urban style is showcased in these 40 of the trendiest streetwear looks for men.

1. Classic Logo Hoodie + Slim Fit Joggers

Stylish oversized hoodie with slim joggers.
@imgur

A timeless streetwear combo, the oversized logo hoodie adds a relaxed vibe, while slim-fit joggers keep it sharp. Choose neutral or monochrome colors for a minimalist touch, or go bold with vibrant, branded hoodies. Pair with classic sneakers for that effortlessly cool look.

Top: A classic oversized logo hoodie, featuring bold branding or minimal design. Opt for neutral colors for a versatile look or go bold with vibrant hues.

Bottom: Slim-fit joggers balance the oversized hoodie, offering a sleek outline. Choose tapered joggers in neutral shades like black or grey.

2. Graphic Tee + Cargo Pants

Bold graphic tee paired with cargo pants.
@thedripmanual

A graphic tee speaks to your personality and is a streetwear essential. Match it with cargo pants for an edgy, utilitarian look. The multiple pockets add functionality, while high-top sneakers or chunky boots keep it grounded.

Top: A bold graphic tee, showcasing artwork, logos, or street culture designs. Go oversized for a relaxed fit or fitted for a sleeker look.

Bottom: Utility-style cargo pants, with multiple pockets for a rugged, functional aesthetic. Opt for neutral tones or camo for added edge.

3. Denim Jacket + Hoodie Layer

Distressed denim jacket layered over hoodie.
@mister3523

Streetwear thrives on layering. Pair a distressed denim jacket over a hoodie for a casual, yet impactful style. Light-washed denim contrasts nicely with darker hoodies. Complete the look with slim jeans and low-top sneakers.

Top: A distressed or classic denim jacket layered over a basic or graphic hoodie. The hoodie adds comfort, while the denim jacket brings structure.

Bottom: Slim-fit jeans or tapered joggers that streamline the look. Ripped or distressed details can enhance the streetwear vibe.

4. Varsity Jacket + Ripped Jeans

Retro varsity jacket complemented by ripped jeans.
@whatsonthestar

For a retro street vibe, throw on a varsity jacket with ripped skinny jeans. The jacket brings in that old-school cool, while the distressed jeans add a modern twist. Finish it with a fitted beanie and clean kicks for an effortless, urban feel.

Top: A varsity jacket featuring bold patches and colors that offer a retro, athletic feel. The jacket is both stylish and functional for cooler weather.

Bottom: Skinny or slim-fit ripped jeans that create a modern, rebellious contrast to the jacket. Opt for a light or mid-wash for the best look.

5. Monochrome Tracksuit

Chic monochrome tracksuit for a sleek look.
@deomayocs

Nothing screams streetwear quite like a matching tracksuit. A monochrome tracksuit in neutral tones like grey or black creates a sleek outline. Top it off with a cap and stylish sneakers for that polished, athleisure vibe.

Top: A matching monochrome hoodie or track jacket, designed for a sleek, unified look. Minimalist logos or designs help keep the outfit polished.

Bottom: Slim-fit track pants that match the top, creating a streamlined outline. Keep the fit snug for a modern, sporty vibe.

6. Overcoat + Hoodie + Joggers

Layered overcoat over hoodie with joggers.
@society19

Blend smart and street by layering a long overcoat over a hoodie. Pair it with joggers for a juxtaposition of formal and casual. The mix of textures adds depth, while simple white sneakers keep the look grounded.

Top: A long, structured overcoat layered over an oversized hoodie. The hoodie brings streetwear flair, while the overcoat adds a sophisticated touch.

Bottom: Tapered joggers or slim-fit pants for a laid-back yet refined contrast to the overcoat. Stick to neutral tones for an effortless look.

7. Flannel Shirt + Baggy Jeans

Relaxed flannel shirt matched with baggy jeans.
@aestheticfashionofficial

A flannel shirt worn over a basic tee, paired with loose, baggy jeans, is a throwback to the 90s grunge aesthetic. Roll up the sleeves for a laid-back vibe, and finish with skate sneakers like Converse or Vans.

Top: A flannel shirt worn open over a basic tee, offering a relaxed, 90s-inspired look. Opt for bold plaid patterns for maximum impact.

Bottom: Baggy, relaxed-fit jeans add to the 90s streetwear vibe. Darker washes or distressed denim work best for a rugged feel.

8. Windbreaker + Cargo Joggers

Colorful windbreaker with tapered cargo joggers.
@lookastic

A retro windbreaker instantly adds color and movement to your outfit. Wear it with tapered cargo joggers for a balanced outline. Opt for vibrant or patterned windbreakers to create an eye-catching contrast.

Top: A retro windbreaker with vibrant colors or patterns, giving off a sporty, vintage vibe. Opt for lightweight, weather-resistant fabrics.

Bottom: Tapered cargo joggers in neutral tones that offer a sleek yet functional look. Pockets add a tactical edge to the outfit.

9. All-Black Street Ninja Look

All-black outfit featuring slim hoodie and jeans.
@cbyloredanapinascostudio

Opt for an all-black outfit, combining a hooded sweatshirt with skinny black jeans or joggers. The secret is in the fit keeping it slim and sleek. Add black high-tops or combat boots to complete the urban ninja aesthetic.

Top: A black hooded sweatshirt or tee, keeping the outline slim and sleek. Opt for a minimalist design or subtle branding.

Bottom: Skinny black jeans or joggers maintain the all-black, street ninja aesthetic. Go for fitted styles to keep the outfit streamlined.

10. Layered Longline Tee + Biker Jeans

Longline tee layered with biker jeans
@prttyboyproblms

For a more dynamic street style, layer a longline tee under a bomber jacket or flannel shirt. Pair with ribbed biker jeans for texture and add high-top sneakers for a coordinated look.

Top: A longline tee layered under a bomber jacket or flannel, adding depth and dimension to the outfit. The longer fit adds a modern streetwear twist.

Bottom: Ribbed biker jeans with a slim fit, adding texture and edge to the overall look. Dark washes or black denim work best.

11. Puffer Jacket + Slim Jeans

Bold puffer jacket paired with slim jeans.
@AndresNavaT

Puffer jackets are both functional and stylish. Opt for one in a bold color and balance the bulk with slim-fit jeans. This mix of oversized outerwear and tailored bottoms creates a stylish contrast perfect for colder weather.

Top: A puffer jacket in a bold color or neutral tone, offering warmth and an oversized, street-smart aesthetic. The puffy texture adds volume.

Bottom: Slim-fit or skinny jeans to balance the bulk of the puffer jacket. Keep it sleek with dark-wash denim or black jeans.

12. Boxy Tee + Wide-Leg Trousers

Boxy tee combined with wide-leg trousers.
@slingbagco

Wide-leg trousers are making a comeback in streetwear. Pair them with a boxy, oversized tee for a outline that’s both relaxed and on-trend. Choose neutral tones or minimal prints for a clean, polished look.

Top: A boxy, oversized tee, creating a loose, relaxed outline. Minimalist prints or logos keep it modern and versatile.

Bottom: Wide-leg trousers that create contrast with the top. Opt for neutral or earthy tones for a contemporary, polished look.

13. Utility Vest + Oversized Hoodie

Tactical utility vest over oversized hoodie.
@modesens

A utility vest worn over an oversized hoodie adds a tactical, street-savvy edge. Pair it with slim cargo pants and sturdy sneakers or boots for a functional yet fashionable outfit.

Top: A tactical utility vest worn over an oversized hoodie, adding a functional, layered element. The vest’s pockets offer both style and practicality.

Bottom: Slim cargo pants or joggers to maintain a streamlined look. The contrast between the oversized hoodie and slim pants adds visual balance.

14. Cropped Hoodie + High-Waisted Pants

Trendy cropped hoodie matched with high-waisted pants.
@glorywrldwide

Cropped hoodies give a playful, modern twist to traditional streetwear. Match them with high-waisted pants for a balanced look that plays with proportions. Add some sleek sneakers to keep it fresh and simple.

Top: A cropped hoodie, offering a playful and modern streetwear vibe. Opt for bright or neutral colors depending on the desired impact.

Bottom: High-waisted trousers or jeans to balance out the cropped top. Choose a slim or straight fit for a sharp, modern look.

15. Retro Athletic Jacket + Jogger Shorts

Retro athletic jacket paired with jogger shorts.
@nadiagorg_

Channel vintage sports vibes with a retro athletic jacket paired with jogger shorts. This look is perfect for warmer weather, and pairing it with low-top sneakers keeps the style streamlined and casual.

Top: A vintage-style athletic jacket, zipped up or left open over a simple tee. Bright colors or retro patterns work well for a sporty vibe.

Bottom: Jogger shorts in neutral tones or matching colors. Keep the fit relaxed but not too loose for a clean, athletic look.

16. Oversized Graphic Hoodie + Layered Necklace

Bold graphic hoodie accented with layered necklaces.
@FashionFusion321

A big, bold hoodie with an eye-catching graphic is a staple. Layer necklaces over the hoodie for a subtle street-glam touch. Keep the rest of the outfit low-key with black joggers and minimal sneakers.

Top: A bold, oversized graphic hoodie with eye-catching designs or logos. The larger fit adds a streetwear edge, while the graphic speaks to personal style.

Bottom: Black joggers or skinny jeans to balance out the oversized hoodie. The simple bottom allows the top to stand out.

17. Plaid Pants + Oversized Sweater

Plaid pants styled with an oversized sweater.
@lookastic

Plaid pants offer a punk-inspired edge to streetwear. Match with an oversized, slouchy sweater for a cool contrast between structured and relaxed elements. Keep the shoes classic with Converse or Vans.

Top: An oversized sweater with a relaxed fit, offering comfort and casual style. Neutral or muted tones work well to let the pants pop.

Bottom: Plaid pants add a punk-inspired edge to the outfit. The bold pattern contrasts with the simplicity of the top.

18. Bomber Jacket + Track Pants

Sleek bomber jacket complemented by track pants.
@urbanmenoutfits

A bomber jacket always delivers that sleek, effortless cool. Wear it with track pants and a graphic tee for a casual yet put-together look. High-tops or sleek trainers finish the ensemble.

Top: A bomber jacket, sleek and minimal or decorated with patches for added flair. It brings a polished but casual streetwear vibe.

Bottom: Track pants with tapered legs, creating a sporty yet refined look. Choose solid colors or subtle stripes for a cohesive outfit.

19. Turtleneck + Denim Jacket

Chic turtleneck layered under denim jacket.
@lookastic

A turtleneck paired with a denim jacket blends sophistication with casual vibes. Keep the turtleneck in a neutral tone like black, white, or beige, and wear slim or skinny jeans to keep it contemporary.

Top: A turtleneck in a neutral tone, adding a sophisticated yet casual touch to the outfit. Layer it under a denim jacket for warmth and structure.

Bottom: Slim or skinny jeans to maintain a sleek outline. Dark-wash or black denim works best with the turtleneck’s clean lines.

20. Oversized Blazer + Hoodie

Stylish oversized blazer worn over a hoodie.
@fibucca

Streetwear meets high fashion when an oversized blazer is layered over a hoodie. This mix of smart and casual is great for making a statement while maintaining comfort. Pair with tapered pants and minimal sneakers.

Top: An oversized blazer layered over a hoodie for a smart-casual blend of street and formal wear. Choose neutral tones for a balanced look.

Bottom: Tapered pants or slim-fit jeans to create contrast with the oversized blazer. Dark colors keep the outfit streamlined and modern.

21. Tie-Dye Tee + Skinny Jeans

Vibrant tie-dye tee paired with skinny jeans.
@stylegirlfriend

A tie-dye tee gives off carefree, artistic vibes. Pair it with skinny jeans to keep the outfit sleek, while the bold colors of the tee shine. Complete the look with skate-inspired sneakers or combat boots.

Top: A vibrant tie-dye tee, bringing a carefree and colorful element to the outfit. Opt for oversized fits for a more relaxed street look.

Bottom: Skinny jeans, either ripped or plain, to balance the boldness of the tie-dye. Black or dark-wash jeans work best.

22. Boxy Hoodie + Straight-Leg Jeans

Boxy hoodie styled with straight-leg jeans.
@presotn

Boxy hoodies paired with straight-leg jeans are all about comfort with an edge. Keep the jeans slightly cropped for a modern twist, and finish off the look with retro sneakers.

Top: A boxy, oversized hoodie, providing comfort and a relaxed outline. Stick to simple designs or solid colors for versatility.

Bottom: Straight-leg jeans for a vintage-inspired fit. Go for mid-wash or light-wash denim to keep the outfit casual.

23. Varsity Jacket + Joggers

Classic varsity jacket complemented by joggers.
@0v0_J

Varsity jackets bring that old-school athletic feel, while joggers keep it contemporary and relaxed. Opt for contrasting colors and throw on a pair of high-tops to complete the sporty street look.

Top: A classic varsity jacket with bold colors, patches, and details. This athletic-inspired piece adds structure and flair to any look.

Bottom: Joggers with a slim or tapered fit to contrast the structured top. Opt for neutral tones like black or grey for balance.

24. Denim on Denim

Contrasting denim jacket worn with jeans.
@imgur

Denim on denim can be tricky, but when done right, it’s the perfect streetwear combo. Choose two different shades of denim (e.g., light jeans with a dark jacket), and finish the look with fresh sneakers.

Top: A denim jacket in a contrasting shade to your jeans. Lighter jackets work well with darker jeans for a balanced look.

Bottom: Slim or straight-fit jeans in a different wash from the jacket. Darker tones are ideal to offset a lighter top.

25. Band Tee + Ripped Jeans

Vintage band tee paired with ripped jeans.
@lookastic

A band tee paired with distressed jeans offers that grunge-inspired, rock-and-roll street style. It’s a simple yet iconic combo, best complemented with leather boots or classic Converse.

Top: A vintage or graphic band tee, bringing a rock-and-roll edge to the outfit. Oversized or fitted styles both work, depending on your vibe.

Bottom: Ripped skinny jeans for a rebellious touch. Opt for dark or mid-wash denim to keep the focus on the distressed details.

26. Leather Jacket + Slim Cargo Pants

Rugged leather jacket matched with cargo pants.
@hagenrichter

A leather jacket is timeless, and paired with slim cargo pants, it brings a rugged edge to streetwear. Add black combat boots or sneakers to maintain the tough-guy aesthetic.

Top: A leather jacket adds a timeless, rugged edge to any streetwear look. Opt for a black or dark brown one with minimal embellishments for a sleek, rebellious style.

Bottom: Slim cargo pants in neutral tones like olive or black provide both functionality and a slim silhouette, contrasting well with the structured jacket.

27. Oversized Sweatshirt + Fitted Shorts

Relaxed oversized sweatshirt styled with fitted shorts.
@lookastic

For a laid-back street vibe, an oversized sweatshirt with fitted shorts works perfectly. The loose-on-top, tight-on-bottom outline keeps things balanced. Add low-top kicks for a casual finish.

Top: An oversized sweatshirt creates a relaxed, comfortable vibe. Choose neutral colors or subtle graphics to keep the look casual and laid-back.

Bottom: Fitted shorts in black or grey balance the loose top, offering a contemporary twist. Opt for above-the-knee length for a more modern feel.

28. Fleece Pullover + Joggers

Cozy fleece pullover paired with joggers.
@maybedrip

Fleece pullovers are both practical and stylish, especially in colder weather. Pair with matching joggers for a cozy, laid-back look. Add a beanie and high-top sneakers to round out the outfit.

Top: A cozy fleece pullover, perfect for colder weather, brings texture and warmth to the outfit. Stick to neutral tones like beige, grey, or black for a refined look.

Bottom: Joggers in a matching or complementary color. Choose a slim fit to avoid overwhelming the outfit, making it both stylish and practical.

29. Track Jacket + Ripped Jeans

Retro track jacket complemented by ripped jeans.
@jleconteberlin

A retro track jacket combined with ripped jeans is the ultimate street-sporty look. Keep the jacket zipped halfway for a clean, layered appearance, and finish with some classic trainers.

Top: A retro-inspired track jacket, either zipped up or open over a plain tee. Opt for bold colors and stripes to emphasize its sporty origins.

Bottom: Ripped skinny or slim-fit jeans add an edgy contrast to the track jacket’s athletic vibe. Dark denim or black jeans work best with this look.

30. Logo Tee + Distressed Denim Jacket

Logo tee layered under distressed denim jacket.
@lookastic

A logo tee tucked under a distressed denim jacket gives a laid-back but styled feel. The simplicity of the logo shirt contrasts nicely with the worn-in denim look, finished with a clean pair of sneakers.

Top: A logo tee, either oversized or fitted, adds a touch of branding to your look. Keep the tee simple to let the logo or graphic be the focal point.

Bottom: A distressed denim jacket over the tee adds texture and a vintage feel. Pair it with ripped skinny jeans or slim-fit pants to maintain the street style edge.

31. Sweatshirt + Corduroy Pants

Comfortable sweatshirt paired with corduroy pants.
@menstyle11

Mix textures with a simple sweatshirt paired with corduroy pants. The softness of the cords adds a rich, retro vibe, while the sweatshirt keeps things casual and cool.

Top: A comfortable, oversized sweatshirt, perfect for casual streetwear. Keep the colors neutral or muted to complement the corduroy.

Bottom: Corduroy pants in earthy tones like brown, mustard, or green, offering texture and a subtle retro vibe. The relaxed fit pairs well with the loose sweatshirt.

32. Trucker Hat + Hoodie + Ripped Jeans

Trucker hat worn with hoodie and ripped jeans.
@Holtthegreat

A trucker hat adds a laid-back, classic touch to any streetwear outfit. Combine it with an oversized hoodie and ripped jeans for a chilled, easy-going vibe that’s perfect for any casual day out.

Top: A trucker hat paired with an oversized hoodie brings a relaxed, street-smart edge. Opt for a hoodie with minimal branding for a casual, laid-back vibe.

Bottom: Ripped skinny jeans create a sleek, modern contrast with the oversized hoodie. Go for dark or mid-wash denim for the best effect.

33. Parka + Skinny Jeans

Functional parka layered over skinny jeans.
@beeinspired1

A parka jacket is perfect for colder weather, and pairing it with skinny jeans creates a balanced look. Add some combat boots for a tough, street-ready aesthetic.

Top: A parka jacket, perfect for layering in colder weather, adds a functional, streetwear-ready vibe. Choose neutral or army green for a classic look.

Bottom: Skinny jeans to balance out the bulk of the parka. Darker denim or black jeans work best, maintaining the sleek outline.

34. Sweatpants + Denim Jacket

Casual sweatpants styled with denim jacket.
@cdna.tid.al

Elevate basic sweatpants with a denim jacket. The combo of structured denim with casual sweats keeps things balanced, while sneakers tie the outfit together for that off-duty model look.

Top: A relaxed-fit denim jacket adds structure to the otherwise casual vibe. Go for light or mid-wash denim to contrast with the sporty bottoms.

Bottom: Sweatpants in a neutral tone for maximum comfort. Opt for slim-fit joggers to avoid an overly baggy look, keeping the outfit balanced.

35. Hawaiian Shirt + Shorts

Bold Hawaiian shirt paired with stylish shorts.
@SHEINofficial

A bold Hawaiian shirt paired with shorts is ideal for warmer days. Keep it open over a plain tee for a laid-back beachy vibe, and finish off with classic skate sneakers.

Top: A Hawaiian shirt in bold patterns and colors adds a laid-back, vacation-inspired feel to your outfit. Keep it open over a plain tee for added style points.

Bottom: Simple, well-fitted shorts in neutral colors like black, beige, or khaki balance out the vibrant top. Go for above-the-knee length for a modern, street-ready look.

36. Track Jacket + Cargo Shorts

Sporty track jacket worn with cargo shorts.
@mrigendrabhanu

For a sportier vibe, pair a lightweight track jacket with cargo shorts. The shorts add function, while the track jacket brings a touch of athleticism. Stick to neutral sneakers to let the outfit shine.

Top: A lightweight track jacket with athletic stripes or bold colors. Wear it zipped or unzipped over a plain tee for an easy, sporty style.

Bottom: Cargo shorts in neutral tones like olive or tan. Their relaxed fit and functional pockets offer a streetwear edge that complements the jacket.

37. Oversized Flannel + Skinny Jeans

Relaxed flannel shirt styled with skinny jeans.v
@imgur

A large flannel shirt layered over a tee and paired with skinny jeans balances volume on top and sleekness on the bottom. Opt for sneakers or boots, depending on the vibe you’re going for.

Top: An oversized flannel shirt in bold plaid patterns, perfect for layering over a plain tee or hoodie. Roll up the sleeves for a more laid-back, casual feel.

Bottom: Skinny jeans in black or dark wash create contrast with the oversized top. The slim fit ensures a clean, modern look, balancing the volume of the shirt

38. Sweater + Wool Trousers

Cozy sweater matched with sophisticated wool trousers.
@lookastic

Mixing a cozy sweater with wool trousers is a great blend of smart and casual. The relaxed fit of the trousers offers comfort, while the sweater adds texture and warmth.

Top: A cozy, oversized sweater for a warm, casual look. Opt for neutral or earthy tones like beige, brown, or grey to complement the trousers.

Bottom: Wool trousers in a relaxed fit add a sophisticated, smart-casual element to the outfit. Stick to neutral colors for a polished look.

39. Hoodie + Overalls

Casual hoodie layered under playful overalls.
@pandcretailuk

Overalls are making a streetwear comeback. Layer them over a hoodie for a relaxed, practical outfit. Sneakers complete the laid-back vibe, but you can also swap them for boots for an edgier look.

Top: A basic hoodie worn under overalls for a comfortable, street-ready outfit. Choose an oversized hoodie for a more relaxed vibe.

Bottom: Overalls in black or dark denim add a playful yet functional layer to the look. Go for a slightly loose fit for an effortless streetwear style.

40. Utility Jacket + Jogger Pants

Rugged utility jacket paired with jogger pants.
@manieredevoir

A utility jacket is the ultimate blend of style and function. Pair it with jogger pants for a military-inspired streetwear aesthetic, and complete the look with combat boots or chunky sneakers.

Top: A utility jacket with multiple pockets and zippers for a rugged, functional streetwear aesthetic. Opt for muted colors like olive, black, or tan.

Bottom: Jogger pants in a slim or tapered fit, adding a sleek contrast to the more structured utility jacket. Neutral tones work best for a cohesive look.

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