Skip to main content

The Manual may earn a commission when you buy through links on our site.

Decoding Men’s Streetwear and Street Style

So, just what is streetwear?

Honestly, even as an editor who has been covering this industry for decades, it’s a little hard for me to pin down some days. Let’s just say that for a long time the fashion system was all about designers telling people what to wear and now the roles have reversed. People find things they think are cool in off-beat surf/skate shops, in thrift stores, or from some internet start-up and then trends develop organically from there. Certain brands, styles, or silhouettes are discovered by normal, everyday people who share them across social media. 

Recommended Videos

Thus, these days the savvy shopper (and retailer) has to keep a sharp eye on the street to see what the coolest kids are wearing, knowing that the cool-ish kids will be coming for it next week. Of course, celebrities still wear the flashiest (or trashiest) outfits, but they also have a team of stylists at hand 24/7. How can a regular guy wear the chillest ‘fits without looking like a dad who just raided his teenage son’s closet? Stick with us, bro. We got you. 

There are a couple of key things to keep in mind. For right now, the bigger the logo, the better. (In the age of Instagram, that brand has got to show up), but that could all change. Have some fun with it, but don’t be a tool. Watch for your favorite, comfortable track pants and joggers, for camouflage prints and military looks, as well as workwear and sports inspirations. We like bold color…but remember you’re looking to project some swagger…so don’t pick hues that make you feel like a clown. 

Here are a few of our favorite brands and pieces that fit into that oh-so-finicky and ephemeral classification of “streetwear.”

Streetwear and Street Style Picks to Get You Started

Filling Pieces Iceman Trimix Sneakers – $180
Image used with permission by copyright holder

Let’s be honest. Doesn’t it always start with the shoes? Here Filling Pieces, based in Amsterdam, brings a Dutch sense of high design to your kicks: The oxblood, burgundy, and purple color combo is key for the season, while the suede and nubuck materials and paracord laces create an outdoorsy vibe. 

Shop Now

Mitchell & Ness 24K CXC No 1 Snapback – $40
Mitchell & Ness 24K CXC No 1 Snapback
Image used with permission by copyright holder

Bruno Mars fan or no, the bold graphic of this snapback is made by heritage brand Mitchell & Ness. It commemorates Mars’s 24 Karat Magic tour with bold Roman numerals. You’ll be a dangerous man with this cap on your head. 

Shop Now

Oyster Holdings Oyster Neck Layering Tee – $85
Oyster Holdings Oyster Neck Layering Tee
Image used with permission by copyright holder

The team at Oyster Holdings’ motto is “Traveling is a Sport,” and they design their collection of streetwear must-haves for optimal style and comfort whether dashing to the airport, the office, or out with the boys. While the brand also offers some sick hoodies and track jackets, the designers have elevated this basic T-shirt with a simple origami-like neckline treatment that makes each one into a real statement piece. 

Shop Now

The Hundreds Polar Button-up – $69
The Hundreds Polar Button-up
Image used with permission by copyright holder

You need a shirt jacket to layer over T-shirts and under jackets for the season. This one from The Hundreds’ version is extra-chill in that it’s extra warm — made from micro-fleece — and features a snap closure. The nylon contrast collar pops the brand logo while the eggplant color lends a regal hue to the season’s activities. 

Shop Now

ONS Issa Sweatshirt – $188
ONS Issa Sweatshirt
Image used with permission by copyright holder

Collaborations are the DNA of the streetwear world. ONS did this one with designer Niyi Okuboyejo of NYC-based Post-Imperial. Okuboyejo took inspiration from the Senegalese polymath artist, Issa Samb. We love the comfortable minimalism of this piece. It makes a great layer over a T-shirt or woven shirt. 

Shop Now

Stüssy Reversible Micro Fleece Jacket – $180
Stüssy Reversible Micro Fleece Jacket
Image used with permission by copyright holder

As noted above, this jacket offers you bold color in abundance, but sometimes we like to have the option to be a little more understated. Here, surfwear legend Stüssy offers a great combination of vibrant lime fleece that reverses to a handy rain- or snow-resistant — and understated — purple nylon. 

Shop Now

Willem Judd Cardigan – $268
Willem Judd Cardigan
Image used with permission by copyright holder

Sometimes a little goes a long way. Willem, a new collection from NYC, created this classic shawl collar cardigan in a wool/cashmere blend, adding a simple Jasper Johns flag patch that offers some art house posturing and street cred. Best of all, it pairs as nicely with a pair of joggers as it does a pair of dress flannels. 

Shop Now

Alpha Industries NASA MA-1 Flight Jacket – $165
Alpha Industries NASA MA-1 Flight Jacket
Image used with permission by copyright holder

Boldly go with this great layering piece from Alpha Industries. It ticks the military box — a must have for your streetwear wardrobe — plus it’s got a cool, techie, but slightly retro vibe from its tie-in to the space shuttle program. With it’s simple, short silhouette, think of this jacket as a substitute for a navy blazer. It can be either your top layer or worn under another longer jacket. 

Shop Now

Perry Ellis America Relaxed Bleached Jeans – $225
Perry Ellis America Relaxed Bleached Jeans
Image used with permission by copyright holder

Because, yeah … just when you were getting used to how your legs looked in skinny stretch jeans, it’s time to bust out a pair of Dad jeans you haven’t seen since, well, since your Dad wore them in the 1990s. Only now they’re cool. Like SERIOUSLY cool. These will be your foundation, the go-to of your streetwear wardrobe. Wear ‘em just high enough to show off those carefully curated kicks and some novelty socks. 

Shop Now

Brooklyn Cloth Wine Cozy Knit Jogger Pants – $42
Brooklyn Cloth Wine Cozy Knit Jogger Pants
Image used with permission by copyright holder

You’ll be wishing you’d spotted these even earlier in the season because the wine color is a perfect complement for fall palettes. These are great for casual dressing during the holiday season, but can easily be dressed up with a soft sport coat or sweater. They are super-soft and comfy, and the marled finish adds some visual texture. 

Shop Now

Looking for other streetwear resources? Look no further than Stadium Goods.

John Jones
John Jones is a Jersey City, New Jersey-based writer who enjoys covering design in all its forms, from fashion to…
1920s Men’s Fashion: The Ultimate Roaring 20s Style Guide
Great Gatsby Still

The 1920s and the 2020s share a number of things. Sure, there’s the Spanish Flu pandemic and our current COVID crisis. There was a time of surging economic prosperity countered by The Great Depression, which mirrors our current financial story. There are also some interesting sartorial parallels between the two decades. 

“Not unlike today, men of the 1920s looked to movie stars as their fashion icons, including Rudolph Valentino and Douglas Fairbanks,” says costume designer and fashion historian David Zyla. “But an even bigger influencer of the period was the Prince of Wales, who put a sporty spin to classic menswear, introducing brown shoes worn with a suit and other trends such as red ties, knickers, and Argyle socks.”

Read more
Parmigiani’s new Toric redefines modern dress watch elegance
The new Parmigiani Toric offers a fresh perspective on elegance
The TORIC Petite Seconde

Parmigiani Fleurier, a respected Swiss manufacturer celebrated for an authoritative voice and unrelenting dedication to premium craftsmanship, has once again etched its signature upon time itself. Innovation thrives here as the brand releases its latest piece de resistance: two new iterations of the Toric Petite Seconde — each one a testament to visionary execution primed for the wrists of the discerning world.

Launching in September 2025, these timepieces represent a conscientious evolution of the dress watch, skillfully merging the Parmigiani’s dedication to heritage with a refined and modern sensibility. This is not a watch designed for a boisterous display, but rather a quiet yet assured elegance intended for those who value subtlety over mere appearance.

Read more
Aminé’s New Balance Biblioteca 2000 shines with glow-in-the-dark soles
Aminé and New Balance reveal their newest sneaker that glows in the dark
amine new balance sneaker

A giant in the retro sneaker game, New Balance has become the go-to brand for unveiling archival silhouettes for the modern era. While the vault is full of designs that can easily be redesigned, the brand’s latest collaboration takes a look at the ABZORB 2000 sneaker. Joining forces with American rapper Aminé, New Balance’s most recent partnership is far beyond just another retro revival. Equipped with a glow-in-the-dark detail, the new sneaker is one of the brightest designs in the brand’s collection. Inspired by libraries, the sneaker also holds a motivating message that goes beyond footwear. Combined with the uniqueness of the sneaker, this New Balance x Aminé design is poised to become a favorite among collectors seeking the ultimate item. 

Aminé and New Balance bring a new glow to this retro sneaker

Read more