The look · 2 streetwear fits

Styling tips for the streetwear look

Written by DJ from StyleUp ·

A lot of guys think streetwear means hype brands, long lines and a logo on everything. I get why, since that’s most of what shows up online, but I don’t think it’s true, and it’s the main reason people never try it.

For me, styling streetwear comes down to clothes you’re comfortable in, the right proportions and a bit of your own personality on top. That’s been the idea since it came out of skate, surf and hip-hop culture. It isn’t a uniform either. Streetwear started as DIY and counterculture, so keep the parts you like and skip the rest.

The short answerHow to style streetwear in five steps
  1. Go baggy on the bottom. Cargos or wide-leg jeans give the fit its shape.
  2. Keep the colors simple. Two or three is plenty. Black and white with one contrast is the easiest start.
  3. Let the hem stack. Pants should bunch a little on your sneakers, not drag on the ground.
  4. Keep the sneakers clean. White low-tops go with almost everything, as long as they stay white.
  5. Add one detail. A chain, a few rings or one loud piece. One is enough.

What is streetwear?

Streetwear is casual clothing built around comfort: tees, hoodies, baggy pants, sneakers and simple accessories. Skaters and surfers in California and the hip-hop scene in New York pushed it into the mainstream, starting around the 80s.

Compared with a suit, the point was always that you could move in it and still look like yourself. Today it goes all the way up to luxury (Louis Vuitton did a collab with Supreme back in 2017), but you don’t need any of that to get the look.

The key streetwear pieces

You don’t need all of these. Most fits use four or five, and it helps to know what each one does before you buy.

TeesThe base of almost every fit

A plain heavyweight tee is the easiest place to start, since it holds its shape and doesn’t cling. Graphic tees work too, but let the graphic be the only loud thing in the fit.

Hoodies, sweatshirts and sweatersYour layer when it's cold

After sneakers, hoodies are probably the most worn streetwear piece. Zip-up or pullover both work, and they layer well under a puffer or a bomber. A sweater with some color does the same job and looks a bit more put together.

Baggy pantsCargos and wide-leg jeans

Pants give the fit its shape. Cargo pants are the piece most people picture when they think of streetwear, and wide-leg jeans cover the days you want something plainer. One pair of each gets you through most of the week.

SneakersThe piece people notice first

Sneakers are a big part of the look, so a worn-out pair drags the whole fit down. Clean white low-tops are the safest pick because they go with almost everything.

JacketsVarsity, bomber or puffer

A jacket can be the loud piece. Varsity jackets come from American school sports teams, and bombers and puffers are just as common in streetwear. If the jacket makes a statement, keep everything under it simple, like dark jeans and white sneakers.

AccessoriesChains, rings and beanies

This is usually where the one detail comes from. One chain, a couple of rings, or a beanie when it’s cold.

Two streetwear fits to copy

Both fits use budget finds. Open one to see every piece and the job it does in the fit.

All black, plus one contrast

This is the one I’d start with if you’ve never tried streetwear. Black tee, black parachute cargos, white sneakers and silver on top. All black only looks boring when it’s flat, so this fit mixes cotton, nylon and metal to keep it interesting.

Monochrome cargo fit with silver chainsSee all 6 pieces and what each one does
Illustration of the monochrome cargo fit with silver chains on a white mannequin

Illustration of the fit on the mannequin. Open the full fit

One loud piece, everything else quiet

Here the patchwork sweater is the only color, and the black jeans, black beanie and white sneakers stay out of its way. A thin silver chain over the collar keeps the sweater from looking like something your aunt gave you.

Color-block sweater fitSee all 5 pieces and what each one does
Illustration of the color-block sweater fit on a white mannequin

Illustration of the fit on the mannequin. Open the full fit

How to get the proportions right

Proportion is just where the volume goes. If the pants are wide, the top can be boxy but should end around the hip. If you go oversized on top, pull the pants back to a straight or relaxed fit so you can still see your shape.

Length matters too. Pants should stack a little on your sneakers instead of pooling on the floor, and keeping one thing crisp, like clean sneakers, stops a loose fit from looking sloppy.

Dress for where you’re going

Streetwear works for most days, but not everywhere. A hoodie with a big graphic is fine for school or a concert, and it’s the wrong call for a wedding or a job interview. The way I think about it, if you’d feel weird being the most casual person in the room, swap the hoodie for a plain sweater and the cargos for dark jeans.

Dress for the weather

It’s hard to look good when you’re freezing, and just as hard when you’re sweating. When it’s cold, a chunky knit and a beanie do most of the work, and the sweater fit above is already a full fall fit. When it’s warm, drop to one layer in a lighter fabric.

Streetwear on a budget

Shape and color do most of the work, and neither one depends on the brand. Every piece on this page is a budget find on Amazon, picked for the look and the price. If you’re going to be picky anywhere, be picky about how heavy the tee is and how clean the sneakers look, since those are what people notice up close.

Common streetwear mistakesFive things that make a fit look off
  • Too many loud pieces. One looks styled, but three looks like you’re wearing everything at once.
  • Logos everywhere. A big logo is fine, as long as it’s the only one.
  • Dragging hems. Stack them, cuff them or use the ankle toggles.
  • Dirty sneakers. Nothing makes a clean fit look tired faster.
  • Too much jewelry. One chain and a couple of rings is plenty.

Make it your own

Once the basics feel normal, the fun part is changing things up. You can stick to one brand or mix a few, but if a piece has a big logo, keep it to one per fit so they don’t fight. One example of this would be the sweater fit above: keep the black jeans and white sneakers, and swap the sweater for whatever loud piece you like.

If you’re not sure where to start, copy the all-black fit exactly. Once that feels normal, swap the tee for a sweater with some color and you’ve got the second fit.

Every fit

All streetwear fits

Build your own

Streetwear pieces

All streetwear pieces