25 Cool Street Style Outfits for Men
Street style outfits for men have become the go-to choice for modern fashion, blending comfort with confidence and creativity. In this guide, we break down 25 cool street style outfits for men that showcase layered fits, bold accessories, clean sneakers, and effortlessly stylish looks inspired by real city fashion. These street style outfits for men are perfect for casual days, travel, hangouts, or any moment you want to stand out without trying too hard.
If you enjoy bold, expressive fashion, make sure to check out our guide on Eboy Outfit Ideas , where you’ll find unique aesthetic looks inspired by modern streetwear, grunge vibes, and TikTok trends.
Oversized Hoodie + Slim Denim
An oversized grey hoodie paired with slim-fit blue denim is one of the simplest yet most reliable street style outfits you can wear. The relaxed hoodie contrasts perfectly with the fitted jeans, creating that effortlessly cool city vibe seen in many modern street style outfits. White sneakers keep the look clean and fresh, elevating it into one of the easiest street style outfits for everyday wear. Add a crossbody bag for extra flair, and you’ve got a versatile look that fits perfectly into today’s trending street style outfits.
Streetwear All-Black Fit
Go full monochrome with an oversized black tee and cargo pants. The look is sleek, minimal, and confident. High-top sneakers complete the vibe, while a chain necklace or rings add subtle detail without breaking the aesthetic.
Flannel Layered Street Look
A white tee layered with a red flannel gives you that laid-back street touch. Pair it with distressed jeans and chunky sneakers for a balanced mix of rugged and modern. Perfect for everyday wear with zero effort.
Bomber Jacket Vibes
The bomber jacket is a streetwear staple. Keep it simple underneath with a black tee and comfortable joggers. The mix of structure (jacket) and relaxed fit (joggers) creates a stylish, confident look.
Graphic Tee + Ripped Jeans
A bold graphic tee adds instant personality to your outfit. Combine it with ripped skinny jeans and Vans for a straight-up street vibe. It’s youthful, expressive, and great for casual hangs.
Denim Jacket Fit
Layering a denim jacket over a hoodie brings depth and warmth. Black jeans and sneakers keep it grounded and wearable. A go-to look for fall and winter street style.
Tracksuit Street Look
A matching tracksuit is cozy yet stylish. Choose a clean color like grey or navy and finish with minimal sneakers. Comfortable enough for daily wear but stylish enough for street fashion.
Street Style With Varsity Jacket
Varsity jackets bring that cool collegiate vibe. Combine with black jeans and high-tops for a fresh, youthful street look with retro energy.
Baggy Pants + Fitted Tee
Baggy cargos paired with a fitted tee create the perfect silhouette contrast. Add a crossbody bag to make the outfit more street-approved. Great for summer or casual city days.
Techwear Street Style
For a bold statement, go techwear. Tactical jacket, cargo pants with straps, and high-tech fabrics give you a futuristic edge. Works best in dark neutral colors.
Hoodie + Shorts Street Fit
A hoodie with shorts gives a relaxed yet modern aesthetic. Combine with mid-high socks and sporty sneakers for full street appeal.
Color Pop Windbreaker
A windbreaker with bold colors instantly stands out. Keep the bottom neutral with joggers, letting the jacket remain the focal point.
Oversized Tee + Wide-Leg Pants
This outfit gives off clean, aesthetic street vibes. The oversized tee sits loosely over wide-leg trousers, offering comfort and style. Minimal accessories complete the outfit.
Leather Jacket Street Style
The leather jacket is timeless. Paired with a white tee and slim jeans, it turns into an effortless street statement. Boots elevate the overall appearance.
Street Style With Puffer Vest
A puffer vest adds warmth without bulk. Layer over a hoodie with joggers for a cozy and functional street fit.
Minimal Monochrome Fit
Monochrome always looks clean. Choose any color—grey, beige, or black—and stick to it from top to bottom for a very aesthetic street look.
Street Skater Outfit
Loose-fitting jeans, relaxed tees, and skate sneakers make this a comfortable and classic street style rooted in skate culture.
Hoodie + Denim Shorts
Denim shorts bring a laid-back feel to the hoodie combo. Works great for warm climates while still maintaining a street vibe.
Trench Coat Street Style
A trench coat adds sophistication to streetwear. Keep the rest casual—tee, pants, and sneakers—to balance the look.
Printed Shirt + Cropped Pants
A printed shirt brings color and energy. Cropped pants modernize the silhouette, giving a stylish yet street-ready appearance.
Hoodie + Leather Crossbody Bag
Adding a crossbody bag takes a simple hoodie outfit to the next level. Functional, stylish, and ideal for daily city movement.
Tactical Vest Layering
Sweater + Loose Denim
An oversized sweater with loose denim creates a cozy yet fashionable outfit—perfect for cooler weather while maintaining street aesthetics.
