streetwear for the office

Streetwear (aka athleisure to fashion types) has made its way into the office. And why shouldn’t it? Though your grandpa may be clutching his tie at the loss of stiff three-piece suits, nobody else is. Streetwear is comfy! Who wouldn’t want to wear more of it? Long live streetwear!

In fact, streetwear has been around for at least fifty years, thanks to those scions of relaxed culture, California surfers. And while you probably can’t wear flip-flops to the office (if you can, please tell us where you work), you can certainly wear a few easy pieces.
You just have to make sure your streetwear veers more on the side of “I just walked out of a Ralph Lauren ad” rather than “I just rolled off my couch after a Thanksgiving nap.” Luckily, it’s easy to style streetwear to be office-ready if you plan it out beforehand and consider some easy tips.

streetwear for the office

Start with Casual Friday

Obviously, step one is to take a hawk-like look around your office. How are people dressed? Maybe HR told you the dress code was formal, business casual, or elegant casual, or casual, but who knows what those mean?

The key is to see what other people are actually wearing – especially your bosses. If everyone in there is dressed in formal suits with matching pocket squares like they wish it was still 1950, you might want to ease into this style during casual Fridays only.

Even then, don’t just go full-blast with a head-to-toe sweats look. Pick just one piece such as a stylish sweatshirt and wear it with some well-cut jeans or casual slacks. This keeps the look neat and professional. No track suits, no jeans and baggy T-shirts. Just one.

Pair Street with Tailored

While we’re talking about neatness, one way to mix things up without too much forethought is to always pair a streetwear piece with a tailored one. Otherwise, in a casual office, an all-tailored look will feel as stuffy as those Buckingham Palace guards who aren’t allowed to talk.


What is formal? A button-up with a blazer is formal. Try a button-up with a zippered hoodie. Or wear your navy blazer with a nice pair of jeans. Instead of a plain button-up shirt, choose one with a pattern.

Many streetwear pieces come in nicer fabrics, too. That hoodie can be cashmere, for example, to elevate the look but still be super comfortable.

streetwear for the office

Make Sure It Fits

Streetwear doesn’t equal sloppy. It’s not an excuse to buy sweats that are two sizes too big or wear an ill-fitted shirt.

How do you know if your new paisley button-up shirt fits well? Raise your left or right arm and grab the fabric by your ribs. More than a couple of inches and you, my friend, should try out a smaller size or a slim-cut. You can then try rolling up your sleeves and experiment with a French tuck (which sounds like it should be more exciting than it is, but it’s just where you tuck in half the front of the shirt).

Make sure your pants fit, too. Look for:
• No weird wrinkling on your thighs or around the crotch. That means they’re too tight.
• A fit around your natural waist for the neatest look.
• Legs that are the right length. That thing where the legs wrinkle as they hit your shoe is called a “break” in tailoring terms. If your pants are bunched up like a Sharpei around your ankles, they’re too long. Try the next length down or get them hemmed, which is usually inexpensive.

Try out a few different styles of cuts, like slim fit and wide cut, to see which ones you like.

Express Your Personality

Clothing is one easy way you can distinguish yourself in the office. But just because everyone dresses a certain way doesn’t mean you have to. Determine what you like.

Maybe you work in an office with millennials who wear nothing but ironic T-shirts, but you’re a Gen Xer who personally still enjoys dressing like an 80s villain with a flipped collar Polo shirt. Own it. Wear your Polo shirt, but don’t pair it with khakis, or you really will look like you’re in costume. Try a slim-cut pair of pants and a sweatshirt thrown around your shoulders instead of an argyle sweater.
Jackets are another way you can amp up your style. Go ahead and wear your old letterman’s jacket, but wear it with modern-cut dark jeans. Break out your Mr. Rogers sweater – remember he had to change out of his “work clothes” when he got home – he’d be so stoked that you’re allowed to wear that at work, don’t you think?

streetwear for the office

Paint it Black

Or if not black, then dark. One of the things that make streetwear seem too casual is brighter colors. So when in doubt, reach for darker hues.

Shoes and Socks

But what about shoes? If your office is casual, go for a sneaker. But not the roughed-up ones you wear while you’re jogging through the mud – go for a “dress pair” that you’ll keep clean, made out of high-quality material like leather. Converse is another good option.

As for socks, repeat after me. “I solemnly swear to only wear white tube socks when I’m working out. Never at the office.” Okay? Good.

Other than that, socks have a lot of leeway. You can choose a sock with a fun print. You match the sock color to your shoes or your pants or choose a complementary color or neutral. Experiment with brighter colors and prints, or, if your pants are shorter, try a no-show sockless look.

The only hard and fast sock rule is to not wear the same pattern on your feet that you’re already wearing someplace else on your person. So no argyle sweater plus argyle socks. You’ll look like a toddler. If you’re feeling extra bold, mix your patterns – stay in the same color family and choose prints that are different sizes.

streetwear for the office

Mix Up Designers

Remember the Ed Hardy phase? The early aughts, when young men like Nick Jonas dressed head to toe in Ed Hardy, terrorizing everyone’s eyeballs by dressing solidly in one brand. We don’t want a repeat.

Dressing all in one popular designer is an amateur, youthful move. If you’re over the age of twenty-five and do this, you might as well be carrying a sign that says, “I am trying way too hard to look younger.”

Here’s the deal. You’re at your favorite store. You stop in the “young men’s section” and notice a display of popular clothing items. You grab ONE piece – and only one – and try that on. Boom. Done. Cheaper, too.

So, now that you know some simple ways to work streetwear into your office look, give it a try. If you’re feeling unsure, start small, with some unusual socks. If you’re not even sure about that, at least get some unique cufflinks. Above all, remember the keys are to have a good fit and be reflective of your personality. And have fun!

Author Bio:
Alex DeMarzo is a passionate writer who has published numerous articles for various industries such as fashion & lifestyle, green energy/sustainability, sports/outdoors, real estate, organizational, public education, and public affairs.