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. 

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
decoding mens streetwear street style filling pieces sneaker

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

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

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

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

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

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

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

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

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

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.

Grooming

Juniper Ridge Founder Hall Newbegin Talks Sustainability in Men’s Grooming and the Search for Natural Scents

We caught up with the lightning-tongued Mr. Newbegin for a quick and dirty interview about what sustainability really means in the context of fashion and grooming.
Living

The Best Pillows Designed With Stomach Sleepers In Mind

Pillows designed for stomach sleepers are distinguished by their thin yet supportive design, which allows the head to sink into the pillow to promote spinal alignment.
Fashion & Style

Our Favorite Sustainable Styles in Honor of Earth Day

Earth Day is a reminder to consider more than just how your clothes look or fit, but where they come from and how they're made.
Living

Fender Custom Shop Unleashes Game of Thrones Guitars

Put these axes in the hands of Jon Snow, Jaime Lannister, and Arya Stark, give the Mountain a double-necked bass and Cersei a mic and a tambourine, and you’d have a stadium rock concert for the ages.
Fashion & Style

The Coolest Watches We Wanted (and Wore) at Baselworld 2019

Every so often, one would jump out at us and scream, "Put me on your wrist!"
Fashion & Style

Baselworld 2019: 6 Insane Watches that Made Our Heart Skip a Beat

The crazier corners of Baselworld 2019 are where the real gems can be found.
Fashion & Style

Grovemade’s Newest Timepiece Features a Bold Colorway and Watch Face

his handsome, rugged, and seriously cool take on an everyday watch joins the rest of the brand’s stylish timepieces.
Living

Dodge the Drizzle with the 7 Best Umbrellas of 2019

Our picks for the best umbrellas this rainy season include simple, strong travel accessories and big, beautiful, windproof protection.
Travel

5 Best Travel Clothes Brands You Can Get Away with Not Washing

These high-tech, premium pieces are comfortable, quick-drying, odor-resistant, and infinitely wearable.
Fashion & Style

6 Lightweight Men’s Dress Shoes to Wear When the Weather Is Warm

You can finally free your feet from the weight of winter boots.
Fashion & Style

You Don’t Need to Play the Game to Wear One of these Awesome Polo Shirts

You don't actually have to play polo to rock this classic style. It's an essential piece of any warm-weather wardrobe.
Fashion & Style

The Gerber Fastball Knife Should Be Your New EDC Knife

There are those who carry a pocket knife and there are those who carry a Gerber.
Fashion & Style

Timex is Bringing Watch-Making Back to the U.S. with Its American Documents Collection

With Minnesota leather straps, Massachusetts-made glass, and New England-forged bronze, these watches are as American as apple pie (and maybe more so).
Fashion & Style

What’s in Our Weekender Bag: Everything to Pack for a Weekend Away this Summer

We’ve assembled our favorite weekender essentials, which can be mixed and matched for a ton of different looks, vibes, and situations.