Streetwear has taken the fashion world by storm. What began as an underground movement rooted in skate and surf culture has now become a global trend, attracting high-fashion and luxury brands from all corners of the globe. However, there is a fine line between looking effortlessly cool and like a walking fashion meme. In this article, we will showcase a range of contemporary streetwear looks that strike the perfect balance, along with some key tips to keep in mind when creating your own outfits.
How to Wear Streetwear
Be Comfortable
Streetwear is all about embracing loose, relaxed shapes and prioritizing comfort above all else. But comfort goes beyond just the fit of your clothing. It's about wearing something that truly feels authentic to you, not putting on an act. The skaters who pioneered the streetwear trend didn't spend their days fretting over logos and outfit choices - they needed clothes that could endure the demands of their lifestyle . So, when considering a streetwear piece, ask yourself if it aligns with your personal style. If you typically dress on the smarter side, explore the intersection of prep and streetwear, championed by brands like Aime Leon Dore and Noah.
No matter your style, streetwear can work for you as long as it feels congruent with who you are and what you stand for.
Act Your Age
While streetwear can be worn by anyone, it's important to adapt it to suit your age and personal style. If you're a 40-year-old accountant, some of the more avant-garde streetwear pieces might not be the best fit. Stick to more age-appropriate choices like relaxed-leg pants, logo hoodies, limited edition sneakers, and worker pants. Opt for quality materials and muted tones, and choose brands that resonate with you rather than chasing the latest hype.
Conversely, if you're a young and adventurous fashion enthusiast, don't be afraid to experiment with different silhouettes, logos, colors, and patterns to find what feels right for you.
Pay Attention to Silhouette
Streetwear is all about relaxed shapes, but it's essential to balance your outfit's proportions. If you're sporting wide-leg jeans, pair them with a more fitted jacket or top to avoid looking overwhelmed. For example, a neat, cropped bomber jacket complements wide-leg denim beautifully. The key is to strike a balance between wide and loose pieces and something closer-fitting to create a cohesive and stylish ensemble.
Don't Be a Hypebeast
While logos may carry clout in some circles, true style is about more than flaunting the latest designer trends. Dressing well and showcasing your personal style are far more important than being a walking billboard for a particular brand. The streetwear aesthetic can be achieved on any budget, with authenticity and quality being the true markers of style. Opt for OG streetwear brands like Dickies, Stussy, and Carhartt WIP as the foundation of your wardrobe, adding a few key designer pieces to enhance its longevity.
16 Streetwear Outfits for Men
The streetwear industry is constantly evolving, with new labels and trends emerging and fading quickly. The following looks offer a timeless foundation that can be adapted to suit your personal style.
Flannel Streetwear Outfit
Man wearing loose streetwear sweatshirt by Represent and black pants.
This outfit takes the classic flannel shirt, rooted in workwear, and gives it a contemporary twist. The key lies in the accompanying pieces: a technical windbreaker adds a fashion-forward touch, while slim grey cargo pants and tonal New Balance kicks bring a modern streetwear vibe. Layer a slightly oversized overshirt for colder days, and don't forget a logo beanie to showcase your brand allegiance.
Baseball Jacket Streetwear Outfit
Man wearing Oxford shirt and baseball jacket.
This outfit captures the perfect prep-streetwear fusion, incorporating elements from both styles. An Oxford shirt and baseball jacket form the foundation, while loose pants, a hoodie, and limited edition sneakers contribute to the streetwear aesthetic. This combination creates an elevated casual look that exudes sophistication.
90s-Inspired Streetwear
The 90s remain a dominant influence in streetwear fashion, with bold jackets and loose, light-wash jeans making a comeback. This outfit combines these elements effortlessly, contrasting a bright orange down jacket with pale denim. Layering a dark navy parka over the top tempers the burst of orange, while a grey beanie and retro cream Asics runners complete the 90s-inspired look.
Fall Streetwear Outfit
Man wearing loose navy pants and wool worker jacket.
For a stylish fall ensemble, combine seasonally-appropriate textures and colors. Opt for loose navy pants made from materials like moleskin, which offer depth and richness. Pair them with a wool worker jacket in an autumnal check pattern. Complete the outfit with a white hoodie and beanie to create a neutral base that allows the pants and jacket to shine.
Athleisure-Inspired Streetwear
Man wearing jersey shorts, white tee, and branded streetwear hoodie.
Who says streetwear is only for colder months? This outfit demonstrates how to rock the streetwear aesthetic in summer. Embrace an athleisure-inspired look with jersey shorts, a white tee, and a branded streetwear hoodie. Finish the ensemble with white tube socks, a baseball cap, and trendy runners from New Balance. This versatile outfit is perfect for hitting the gym or running weekend errands.
Technical Fabrics Streetwear Outfit
Man wearing combat pants, bomber jacket, and technical sliders.
Featuring technical fabrics and futuristic design, this outfit exudes a Japanese streetwear feel. The combat pants and MA-1 bomber jacket, both made from proprietary nylon, create a slick and contemporary look. The oversized, sculpted pockets and technical sliders add subtle touches that reinforce the futuristic aesthetic, making you feel like you're on a springtime mission on Mars.
Carpenter Pants Streetwear Outfit
Man wearing khaki carpenter pants and logo sweatshirt in bottle green.
Carpenter pants have become a popular alternative to traditional skater attire. This outfit pairs classic khaki carpenter pants with a drop-shouldered logo sweatshirt in bottle green, creating an effective contrast that just works. Layer a plain white tee under the sweatshirt for a clever break point, and finish the look with chunky white sneakers. Subtle accessories like transparent shades and a pendant necklace add personality and detail to this pared-back ensemble.
All-Black Skater Outfit
Man wearing all-black skater outfit with Letterman jacket.
An all-black outfit always exudes effortless coolness. This look, suitable for older individuals, conceals body flaws while maintaining a sophisticated edge. The skate-inspired elements, including chunky black skate shoes, wide black pants, a dark green hoodie, and a beanie, are elevated with the addition of a Letterman jacket and subtle pleats on the trousers. The combination of high and low pieces strikes the perfect balance.
All-White Streetwear Outfit
Man wearing all-white streetwear outfit with tonal retro runners.
Pulling off an all-white outfit requires careful attention to detail. Vary the shades to create contrast and prevent the look from appearing too stark. Combine tonal retro runners, off-white jeans, and an ecru/black overshirt to achieve balance and visual interest. Layer a hoodie over a flannel shirt to inject a bold blue pullover, adding a welcome pop of color.
Everyday Streetwear Outfit
Man wearing straight black cargo pants and heavyweight loopback hoodie.
This easy everyday look can be effortlessly pulled off by any guy. Opt for straight black cargo pants, slightly cropped to showcase your chunky sneakers and ensure a well-proportioned silhouette. Pair them with a classic heavyweight loopback hoodie from Champion USA to infuse an authentic streetwear vibe. This outfit strikes the perfect balance between comfort and style.
Streetwear Vest Outfit
Man wearing worker pants, thick cotton vest, and black combat boots.
The tactical and utility vest was once a staple of streetwear, but its overt military connotations have given way to the more versatile worker or down vest. This outfit showcases how a vest can add a unique twist to a basic look. Layer a black vest over black combat boots, black twill pants, and a white hoodie for a streetwear edge. The combination of these pieces creates a versatile outfit that's ready for any urban adventure.
Summer Streetwear Outfit
Man wearing running shoes, tank top, and lightweight cotton/nylon shorts.
The marriage of streetwear and prep has resulted in a plethora of sports-inspired outfits, particularly suitable for warmer months. Embrace athletic pieces like running shoes, tube socks, tank tops, and lightweight cotton or nylon shorts. Layer a patterned Cuban collar shirt over the ensemble for a look that combines the best of both worlds.
Simple Streetwear Outfit
Man wearing cargo pants and graphic tee.
Streetwear is all about fit and attitude, and this simple outfit exemplifies that. Embrace the effortless coolness of a cargo pants and T-shirt combination. Opt for relaxed-fit, heavyweight fabric cargo pants in dark green, allowing them to drape perfectly. Pair them with a dark graphic tee that subtly showcases branding and a masculine silver chain for a touch of detail.
Modern Ivy League Streetwear
Man wearing light blue jeans and marine blue rugby shirt.
This outfit takes the popular 90s prep aesthetic to the next level, combining light blue jeans with an Ivy League-inspired pleat with a marine blue rugby shirt. Together, these pieces seamlessly bridge the gap between the past and the present. Complete the look with tonal navy suede sneakers for a touch of sophistication.
Classic Skatewear Outfit
Man wearing wide-leg twill pants and plaid flannel shirt.
This look captures the essence of classic skatewear while elevating it with relaxed yet tailored cuts and quality materials. The outfit includes black canvas skate shoes, cropped wide-leg twill pants, a cotton loopback hoodie, and a thick plaid flannel shirt. Opt for an entirely black base to allow the overshirt, available in various colors, to become the focal point. Complete the look with a beanie in a shade that suits your style.
Winter Streetwear Outfit
Man wearing puffer jacket, khaki carpenter pants, and white hoodie.
Traditional outdoor brands like The North Face and Patagonia have found their place in streetwear fashion, especially during winter. This outfit embraces practical yet stylish pieces, with a bold puffer jacket as the centerpiece. Pair it with khaki carpenter pants and a white hoodie to maintain balance. Finish the look with multipaneled kicks and a striking yellow beanie for an extra punch.
With these 16 streetwear outfits, you have the foundation to create unique and authentic looks that suit your personal style. Remember to stay true to yourself, prioritize comfort, and experiment with different silhouettes, colors, and brands. Streetwear is all about self-expression, so have fun exploring this fashion trend and find the perfect balance between cool and effortless style.
