Men’s Streetwear Pants: The Key Styles & Hottest Brands For 2023
These are the pants that will anchor all your streetwear fits in 2023 and the brands that do them best.
If you’re looking for a killer pair of streetwear pants then you’ve landed on the right page. This diverse breed of loose-fitting legwear (and everything else that accompanies it under the general ‘streetwear’ banner) has taken the world by storm. So much so that streetwear and high-fashion have become intertwined to the point of almost disappearing into one another. Some would even say the term ‘streetwear’ has lost its relevance – it’s just the way people dress now.
Either way, you know exactly what we mean when we talk about streetwear pants. This is the type of legwear that has its roots in street and skate culture, workwear, sportswear and 90s/00s fashion. They’re loose fitting, roomy, wide in the leg and go great with a pair of chunky sneakers.
You know it when you see it, but if you’re thinking about adding a pair of streetwear pants to your legwear lineup, it’s worth understanding the finer points. There are lots of styles that fall under the umbrella, and picking the right pair is a hell of a lot easier when you know the subcategories and the brands making the best versions.
In this guide, we’ll explain it all, so keep scrolling to find out everything you need to know.
Key types of streetwear pants
Cargo pants have long been a staple of the streetwear scene. They’re usually worn in a straight or relaxed fit, and feature at least one side pocket to each outside leg, sometimes more.
There was a time when these pocketed pants were seen as uncool, but these days they’re anything but. Wear them with chunky sneakers, work boots or high tops.
As the line between smart and casual continues to blur, sweatpants are becoming more and more acceptable as everyday wear with each passing year.
We’d suggest going for a classic plain grey pair in fleece-backed jersey cotton fabric. This is the most classic version of the sweatpant, it goes with almost any type of sneaker, and you can even dress it up to an extent with some nice formal-ish outerwear.
If skateboard fashion of the 00s is remembered for baggy jeans, then skateboard fashion of the 2010s will surely be remembered for wide-leg chinos.
These loose-fitting, smart-casual pants – combined with a tucked white tee, a beanie and a pair of Vans or Converse – were (and still are, albeit to a lesser extent) the unofficial uniform of a certain breed of skatepark dweller.
The most popular brand for this style is Dickies, which makes some super-durable and versatile options at extremely competitive prices.
Baggy jeans have been on their way back in for a while now. They’re comfortable, roomy and relaxed, and they’re the perfect accompaniment to the ongoing chunky sneaker trend as they help to balance out proportions.
If you’re still trying to peel yourself out of skinny- and slim-fit jeans then going baggy straight off the bat might feel a little daunting. If that’s the case, a pair of straight-leg jeans might be a better option.
Again, this cut of denim has long been popular in the streetwear world. In fact, it’s probably the most consistently popular fit there is. While other denim trends come and go, straight leg remains consistent.
Check out Supreme for some of the best streetwear-leaning straight-leg jeans.
Double-knee work pants
Double-knee work pants have enjoyed a serious surge in popularity over the last few years. They’re straight or loose-fitting in the leg, with utility pockets and large reinforcement patches to the front of the knees.
They were originally popularised by brands like Carhartt as rough-and-ready workwear, but these days you’re just as likely to spot a pair hanging out in your local trendy coffee shop as you are on the job site.
Carpenter pants are similar to double-knee pants in the sense that they’re made for manual labour. The key difference is the lack of reinforced knees, more utility pockets and often a hammer loop to the side.
Granted, most of us will never be using any of those things for their intended purposes, but hey, they look good.
The best streetwear pants for 2023
British luxury streetwear at its best, Represent started life as a student side-hustle but bloomed into a respected and boundary-pushing label. Its collection is vast but considered and walks a line between minimalist styles and loud-and-proud urban fashion.
The brand’s streetwear pants sum up the ethos. There’s a broad range of colourful joggers, utility and cargo pants, denim and tailored trousers. Aside from a few prints and patterns, the collection is relatively pared back, with a lot of stone and off-white colours that work to set off Represent’s louder range of streetwear tees and sweats.
Fusing Swedish and Japanese approaches to minimalist style, Axel Arigato is the sneaker designer that grew into an all-singing streetwear brand. It’s modern streetwear, but with a pared-back, luxury aesthetic.
Its mix of east and west comes through in the brand’s well-considered trouser collection. Think loose and floaty carpenter pants that look like tailored trousers or mid-wash jeans perked up with floral embroidery.
With Brendan Babenzien (former creative director at Supreme) at the helm, Noah is a streetwear label with royal blood. Taking an environmentally-conscious approach to streetwear, the brand mixes skate and surf culture with music and preppy fashion to land on something that feels both youthful and established.
The pants go wide. Double-pleated twill chinos and wide-fit jeans are key parts of the look, while corduroy trousers and worker pants with double knees show how broad a church streetwear is today. Pair any of them with one of Noah’s throwback rugby shirts to nail the look.
Aime Leon Dore
Another label that brings preppy staples into its take on streetwear, Aime Leon Dore is one of the most hyped brands in menswear right now. Eclectic and nostalgic, it’s one of the few labels that can put richly patterned silk trousers next to denim carpenter pants and somehow they look like they’re part of the same collection.
Throw in some throwback sweatpants, tapered chinos and even some compression pants (in its ultra-hyped collab with New Balance) and you get a sense of how broad the label’s influences are. Its lookbooks are all about mashing together sporty and refined pieces, and styling them with surgical precision.
A Bathing Ape
Some streetwear labels let the top half do all the talking, keeping the trouser department restrained to let graphic tees and logo sweats shine. No danger of that at Bape. The Japanese brand, beloved among streetwear diehards, brings many of its trademarks – camo prints, animal prints, cartoon shark motifs – to legwear.
We’re talking sweatpants adorned with red, white and blue camo; tie-dye track pants; trousers with the aforementioned shark logo biting your backside. There are quieter styles, such as simple workwear trousers and monochrome sweats but honestly, where’s the fun in that?
If wide-leg pants feel like a recent fashion trend, know that Maharishi has been doing it since 1994. The label blends eastern and western design codes, with floaty legwear that’s part yoga guru, part urban hypebeast.
If it feels a little bit hippy, know that the brand takes a nerdy, utilitarian approach to the construction of its trousers. There are luxurious Italian fabrics, thoughtful design touches (like hidden pockets for your phone) and upcycled military pieces reimagined through a pacifist lens.
Styles include track pants, utility designs and traditional Hakama trousers inspired by the Japanese Edo period.
The late Virgil Abloh is rightly beatified as a streetwear pioneer, and before he was poached to run menswear at Louis Vuitton his legacy was already being forged at his own label.
Off-White takes a luxury approach to sportswear, and its signature style brings in influences from music and wider culture, too.
A mix of skinny- and wide-leg fits mark an eclectic trouser collection. There are high-end streetwear staples, like cashmere joggers, track pants and carpenter styles, but there are others influenced by everything from sci-fi to disco.
If you want to push the envelope, how about a pair of purple, flared leather trousers?
Carhartt is one of the best known and most respected workwear brands on the planet. Its hard-wearing duck-canvas pants and jackets have a long-earned reputation for reliability and durability, and from a style standpoint, they look pretty cool too.
Pants wise, the iconic US label has a number of options that fit the bill – perhaps more than anyone else. Across the workwear range and the streetwear-influenced Carhartt WIP line, there are a number of styles that stand out.
The Double-Knee Pant is a big hitter, as is the Aviation Cargo and the Single-Knee carpenter pant. There’s also a huge range of denim, including baggy and straight-leg options.
If you’re looking for a pair of classic wide-leg chinos, American workwear brand Dickies should be your first port of call.
The Dickies 874 is one of the label’s best-selling styles, and is extremely popular in the skateboarding and alternative music scenes. It features a straight wide leg and a mid rise. It’s the baggiest style Dickies offers, so it fits the streetwear bill perfectly.
For those looking for something a little more fitted, there’s the 873, which is a slightly slimmer (but by no means ‘slim’) alternative. Or there’s also the 872, which has a classic slim cut.
Stan Ray is another American workwear brand that has become popular in the streetwear world thanks to its trademark mix of durability and style.
The label’s pants are some of its best-selling products, particularly the iconic Painter Pants, which are available in a couple of different fit options. They’re basically a carpenter pant, with a roomy cut and lots of utility pockets to the legs.
If you’d prefer something with fewer pockets, Stan Ray has plenty of other legwear options. The military fatigues are great too, and then there’s the aptly named ‘Fat Pants’, which feature a super-wide and roomy cut.
From New York via Japan, Engineered Garments is a solid choice for all sorts of casual wear and even soft tailoring. However, the area in which it really excels is legwear.
The brand is well known for its gung ho approach to putting pockets on stuff, which is a blessing where cargo pants are concerned and has become something of a visual signature.
In addition to cargos, check out the fatigues. Expect loose fits and utilitarian styling across the board.
California’s Stussy is better equipped than most to deliver the perfect pair of streetwear pants. After all, the surf-brand-turned-clothing-label pretty much singlehandedly gave rise to what we now call ‘streetwear’. Its graphic tees, sweats and pants paved the way for everything that followed, including streetwear’s high-fashion takeover.
The label’s collections vary from season to season and year to year, but you can usually expect to find legwear along the lines of cargos, jeans and sweats.
Expect loose fits, logos and the odd quirky print or pattern to boot.
New York’s premier skate brand and the label that gave rise to drop-based hype is a great choice if you’re shopping for a pair of streetwear pants.
The hype has died down a little in recent years, which makes it much easier to cop on a drop day, and even if you miss out on the hot-ticket items, classic core staples like the brand’s straight-leg jeans tend to be available most of the time.
For the uninitiated, gorpcore is a subgenre of men’s fashion that’s heavy on outdoorsy, sporty, technical details, utility and functionality. It’s been huge over the last few years, but Nike ACG was doing it long before the term was coined.
The brand changes its legwear lineup from season to season, but you can usually find some sort of baggy cargo pant, often with quirky technical details like zip-off legs, performance fabrics or built-in belts.
Japan’s Needles is known for its unusual silhouettes, patterns and aesthetic blend of sportswear, streetwear and casual wear. It puts its own unique spiny on modern classic pieces, most notably cardigans and track suits.
The brand’s track pants are one of the things it’s best known for. They feature a wide leg, webbed stripes to the sides and the Needles’ iconic butterfly branding.
Not the easiest to style, but a streetwear favourite all the same.
It also makes some fantastic sweatpants using heavyweight, fleece-backed jersey cotton. They’re warm, cosy, comfortable and perfect for styling with casual outfits and sneakers.
Trendy skate brand Dime has become one of the stand-out names in the baggy jeans revival. It makes a number of loose-fitting styles in classic shades of blue, with understated branding and mid-range price points.
If you ask us, they’re some of the best baggy jeans you can buy.