Men’s Streetwear Outfits: 16 Looks That Aren’t Try Hard
How to wear streetwear in a way that looks cool and authentic, and not like a try hard.
Streetwear has become big business. What started out as an underground movement born out of skate and surf culture in the 90s soon developed into a global trend, with every high-fashion and luxury label in the world wanting to get in on the action.
Of course, going mainstream is the antithesis of what streetwear is all about, but that hasn’t stopped stylish men across the globe wanting to get in on the look, too. However, there’s a fine line between genuinely looking cool and authentic, and like a ‘How do you do, fellow kids?’ meme.
To help you stay the right side, we’re going to showcase a number of contemporary streetwear fits that range from classic skatewear to high-end designer looks, as well as a few tips you need to bear in mind when pulling together your own getups.
How to wear streetwear
Literally and figuratively. Streetwear is about loose, relaxed shapes and comfort above all else. But that doesn’t just mean the cut of your clothing. If you don’t feel comfortable wearing something (genuinely comfortable, not putting on an act), don’t wear it. Do you think the same skaters that the streetwear trend derived from were sitting there every day picking out their outfits and worrying about the logo on their chest? No, they simply needed clothes that performed and could stand up to a beating. Skating was a way of life and that sense of authenticity is the reason this look became so desirable.
So, forget about whether other people think that heavily branded, oversized Off-White hoodie is ‘cool’ – can you actually make it work with your wardrobe? If you typically dress a little smarter with your day to day attire then it’s going to be a hard ‘no’. Instead, you could lean into the Prep/Streetwear 2.0 aesthetic that the likes of Aime Leon Dore and Noah are pushing right now.
It doesn’t matter what your style is, you can make streetwear work for you, but it’s got to feel congruent with who you are and what you’re all about.
Act your age
If you’re a 40-year-old accountant from Denver then you’re not likely going to be able to pull off some of streetwear’s more out-there pieces. Relaxed-leg pants, logo hoodies, limited edition kicks and worker pants are all still fair game, but make it age appropriate: stick to muted tones, go for elevated versions in quality materials, pick fits that complement your body type and buy into streetwear brands you actually like rather than what’s being hyped.
Likewise, if you’re young and at the other end of the scale, get experimenting – with silhouette, fits, logos/graphics, colours and patterns – to see what feels right on you.
Pay attention to silhouette
Streetwear is full of relaxed shapes, whether it’s baggy jeans or a drop-shouldered hoodie. And while these looser fits look effortlessly cool and feel supremely comfortable, there can be too much of a good thing.
The key when pulling together any outfit is balance, particularly between the top and bottom half. Going for wide-leg jeans down below and an oversized puffer jacket on top can quickly drown your frame, making it look like a little boy playing dress up in his dad’s closet.
Instead, counteract any wide or loose pieces with something closer fitting. That doesn’t mean you have to go skinny or even slim cut, but you’ll find that a neat, cropped bomber jacket works a lot better with the aforementioned wide-leg denim.
Don’t be a hypebeast
There’s nothing more cringe than looking like a walking billboard for the current hottest designer(s). Yes, in some circles a logo brings clout, but dressing well is much more important. Plus, trying keeping up with the Joneses can quickly be damaging to your bank account.
Yes, it’s possible to pull off streetwear fits on a budget. No matter what anyone says, you don’t need to be decked head to toe in AMIRI and Palm Angels to look cool. The OGs of the industry remain some of the best and most authentic you can buy into, so look to the likes of Dickies, Stussy and Carhartt WIP to build the foundation of your wardrobe and then round it out with a few key designer pieces that will last the long haul.
16 streetwear outfits for men
The streetwear industry changes rapidly, with new labels and trends falling in and out of fashion quickly. Therefore the below looks are quite classic and designed to be able to transcend time and seasons. Use them as a foundation and adapt as you see fit.
Flannel streetwear outfit
Here we take a classic flannel shirt, which has its roots firmly in workwear, and give it a contemporary spin. The key is the surrounding pieces: a technical windbreaker brings the fashion forward element while the slim grey cargo pants and tonal New Balance kicks add a modern streetwear vibe.
The (slightly oversized) overshirt offers ballast on cold days while the logo beanie (by Kith) is another warm, practical element that allows you to show your brand allegiance.
Baseball jacket streetwear outfit
In 2023, preppy style has evolved to incorporate a number of streetwear elements, thanks to the likes of Teddy Santis, founder of Aimé Leon Dore, and Brendon Babenzien, founder of Noah NY and current Creative Director at J.Crew, which have both seen major success off the back of their 90s New York aesthetic.
It’s led to a number of key Ivy League pieces going mainstream, including baseball and Letterman jackets, as shown above.
This outfit is the perfect prep-streetwear crossover, utilising pieces from both sides – an Oxford shirt and baseball jacket from the former; loose pants, hoodie and limited edition kicks from the latter – to create an elevated casual fit that still looks put together.
The 90s is a key trend within streetwear circles, so we’re seeing a number of bold jackets and loose, light-wash jeans coming to the fore. This outfit incorporates both of those elements to great effect with the bright orange down jacket contrasting perfectly against the pale denim below.
This is anchored by layering the dark navy parka over the top (constraining the burst of orange), while the grey beanie and retro cream Asics runners reinforce just what decade this look is referencing.
Fall streetwear outfit
This is an ideal getup for fall, incorporating seasonally-appropriate textures and colours in equal measure. The loose navy pants have a depth and richness to them due to the material choice (likely moleskin or similar), while the wool worker jacket introduces another tactile element and visual point of interest due to its autumnal check.
Meanwhile the white hoodie and beanie offer the perfect neutral base for these pieces to shine against.
Note how the pants break perfectly over the chunky white kicks – there is a big difference between baggy and ill-fitting, and comfortable and stylish. Make sure you get it right.
Streetwear typically revolves around thicker garments such as loopback cotton sweats and heavy twill pants, but you can still make the look work in the summer. Here we stay cool and comfortable with an athleisure-inspired fit of jersey shorts, white tee and branded streetwear hoodie, finished with white tube socks, baseball cap and on-trend runners from New Balance.
It’s an easy outfit to make your own by playing with the individual elements, but whether you’re hitting the gym or running errands at the weekend it’s a foolproof getup to add to your rotation.
Technical fabrics streetwear outfit
With more than a little Japanese streetwear feel to it, this outfit is defined by technical fabrics and futuristic design – but what would you expect from Stone Island Shadow Project? With both the combat pants and MA-1 bomber jacket coming in a proprietary nylon fabric, it brings a sheen and natural texture to what is otherwise a basic combination, creating something that looks extremely slick and contemporary. Of course, those oversized, sculpted pockets help, too.
The technical sliders are another subtle touch that reinforces the from-the-future aesthetic, giving the look a springtime on Mars feel.
Carpenter pants streetwear outfit
Carpenter pants are having a moment right now, and make an excellent alternative to the traditional double knee or worker pants that skaters default to. Here we take a classic khaki pair and team them with a drop-shouldered logo sweatshirt in bottle green for an effective contrast that just works.
Again, we use a plain white tee (poking out the bottom of the sweat for a clever break point) and chunky white sneakers to create a neutral foundation for which the other pieces can shine.
The accessories are just as subtle but even more important, with the transparent shades and pendant necklace bringing personality and detailing to such a pared-back look.
All-black skater outfit
All-black outfits always look effortlessly cool, as proven here. An excellent option for older guys, a dark palette will conceal a lot of body flaws while keeping things the right side of sophisticated (there’s a reason stylish Parisians default to it).
The base of this look is clearly skate-inspired – chunky black skate shoes, wide black pants with wallet chain, dark green hoodie and beanie – but it’s given an upscale prep feel with the introduction of the Letterman jacket and subtle pleats on the trousers. A nice balance of high and low.
All-white streetwear outfit
Staying on the monochrome theme, this is how you pull off an all-white outfit. The key is to vary the shades to create contrast and ensure it doesn’t appear too stark, which is why the tonal retro runners, off-white jeans and ecru/black overshirt works so well together.
Layering a hoodie over a flannel is a go-to combo for skaters and here we use it to inject a welcome shot of colour in the form of a bold blue pullover.
Everyday streetwear outfit
This is an easy everyday look that any guy can pull off. Straight black cargo pants set the foundation and are slightly cropped to show off the chunky sneakers and ensure the bottom half isn’t swarmed in fabric.
Meanwhile, up top, a classic heavyweight loopback hoodie from the inventors of the garment, Champion USA, brings the authentic branding that any street- or skatewear look should have.
Streetwear vest outfit
The tactical and utility vest played a major part in the streetwear aesthetic for a number of years, after being pushed by rappers like Stormzy and Drake. However, all those pockets and clear military references made it feel a little over the top for day-to-day wear, and a bit like playing soldiers, which is why the humble worker or down vest has now taken its place.
Offering the same layering benefits – use it as a top layer or slot it underneath a jacket – without the overt connotations, a vest brings something different to any basic look, as shown above.
The black combat boots, black twill pants and white hoodie is a combo every man will feel comfortable in, while the thick cotton vest gives it a streetwear twist and keeps you ready for urban warfare.
Summer streetwear outfit
The current marriage of streetwear and prep means there are a lot of sports references in 2023, which work particularly well in the warmer months. Athletic pieces like running shoes, tube socks, tank tops and lightweight cotton/nylon shorts are great in the heat, offering a comfortable and cool base to work from, as shown above.
Throw a patterned Cuban collar shirt over the top and you have a look that cherry picks the best elements from both worlds.
Simple streetwear outfit
As we mentioned at the start, streetwear is all about the fit and attitude. And this is why something as simple as a cargo pants and T-shirt combo can look so effortlessly cool.
Here, the dark green cargos come in a relaxed fit and heavyweight material that drapes perfectly, finishing at the top of the sneakers so you can show off your latest cop.
Up top, a dark graphic tee with subtle branding brings the clout without trying too hard, while the masculine silver chain adds a nice point of interest.
Modern Ivy League streetwear
This outfit ratchets up the 90s prep aesthetic that has become so popular in streetwear circles, combining light blue jeans (complete with an Ivy League-approved pleat) with a marine blue rugby shirt for a look that would have been common place on East Coat campuses back in the day.
Finished with tonal navy suede sneakers, it manages to simultaneously have one foot in the past and the other in the present.
Classic skatewear outfit
This look hits all the classic skatewear touch points – black canvas skate shoes, cropped wide-leg twill pants, cotton loopback hoodie and thick plaid flannel shirt – yet elevates the aesthetic through the relaxed yet tailored cuts and quality materials.
Setting an entirely black base allows you to introduce a shot of colour via the overshirt, which has an element of black running through it to tie everything together.
With a look like this you can play with the colour of the beanie – any shade would work, from neutral greys and greens through to bright yellow or cobalt blue.
Winter streetwear outfit
Traditional outdoor brands like The North Face, Patagonia and Canada Goose have become extremely popular in streetwear circles over the past few years, which is not surprising considering this type of clothing has a lot in common with skatewear: practical, built for purpose and full of bright colours.
It’s primarily the outerwear that has made the crossover from hiking trails to the city, with fleeces, technical anoraks and puffer jackets the key silhouettes you should be looking to introduce to your wardrobe. A bold puffer is ideal for winter and makes a statement on its own, which means you should keep the surrounding pieces restrained, as shown here.
The khaki carpenter pants and white hoodie allow the jacket to take centre stage, while the multipaneled kicks and striking yellow beanie give the look an extra punch.