How to Wear Workwear Pants

Illustrations by Naomi Otsu

One of the best things about workwear pants is that there are lots of styles to choose from. Not only can you decide your color of choice, there is also a vast array of looks and materials at your disposal. Khaki, black, or olive green variations are probably the most common options people gravitate toward, but there are also more lifestyle-oriented styles coming in colors like orange and purple. Striped painter pants from brands like Stan Ray are another more unconventional option worth exploring if you are looking for something a bit different. Then, there’s the style. The trend right now seems to be the double-knee carpenter pant noted for its additional panels on the front of each leg. There’s also nothing wrong with some cargo pants covered in pockets, or classic, pleated Dickies. Be mindful of materials too. Dickies 874 are made of a heavier and more durable material to perform on the work site, but there are also ripstop options that offer a bit of a lighter weight and looser fit that might be ideal for warmer weather. Putting together a good looking fit means nothing if you feel stiff, hot, and uncomfortable. 

The best part is, there isn’t really a “right” or “wrong” answer when it comes to which style and color you choose. Experiment a bit. These pants are so affordable that you can even keep multiple pairs in your closet at once. Maybe you like how double-knee pants look in tan, but prefer a straight-legged pair of Dickies in black. Have them both on deck. If you are someone trying to stick to one pair and one pair only, some khaki Dickies 874s are probably the way to go. For $25, how can you go wrong?

Like a good pair of blue jeans, workwear pants are a worthy addition to your closet because of their versatility. You can dress them up or dress them down. Running out for some errands on a sunny day? Toss them on with a simple white T-shirt to keep it casual. Have a date or a dinner with friends later in the day? Toss on a button-up flannel or a chore coat to dress it up just a bit. In the wintertime, they will pair great with any hoodie or sweater in your closet too. Quite frankly, the only top that might NOT work with your Dickies is a blazer or a dress shirt. But hopefully you have a proper pair of dress pants or chinos for that occasion and that wasn’t even a consideration. 

Another thing worth considering is whether you are going to keep your pants draped over your shoes or cuff them up a bit. Like most of these things, it all comes down to personal preference. Try both out in a mirror and see what fits your style. It’s likely that you will find yourself doing both depending on your fit. Some outfits and footwear choices lend themselves to a cuffed look, while others will look better with a more relaxed fit. As a general rule of thumb, don’t go crazy on the cuff though. One, maybe two, small cuffs will suffice. Some people you saw on Instagram might have been able to pull off a 6-inch cuff on their pants, but chances are you won’t have the same result. If you do decide to cuff your pants though, it opens up an entirely new layer of decision making to guarantee you look as put together as possible. But more on that in a second. 

So you decided you preferred the look of cuffed pants. Maybe you even got them tailored to look cropped. Now, you need to make sure you’ve got the right socks on. People are going to see them, especially when you sit down and your pant leg hikes up that extra inch or two, so wearing the stained white socks or black crew socks covered in tiny holes that have been occupying your underwear drawer for far too long is probably not ideal. The best bet is to keep it neutral. White, black, or even grey crew socks will work here. If you are someone that likes an extra splash of color or a bolder pattern, at least make sure they match the rest of the outfit you have on that day. 

The masses seem to finally be accepting baggy pants again after years of skinny silhouettes running the show. But if you prefer a slimmer shape, there are plenty of tapered workwear pant options on the market. They give the same overall look of a classic workwear style with some upgraded details like more premium materials, custom logo hardware, and more. After all, while many people have adopted workwear pants from the likes of Carhartt or Ben Davis into their everyday wardrobe, they are still made for, well, working. The materials can be more stiff and rugged and they are much roomier. If you’re someone who has been rocking skinny or slim jeans for the past few years, it might take a bit to get used to just how baggy some of these styles can be. But once you realize how much more comfortable that extra bit of room between your legs and pants are, you will understand it’s worth it. Also worth noting, no matter how you prefer your pants to fit, keep them presentable. Not everyone is busting out the ironing board before they get dressed, but just make sure you aren’t walking around in pants covered in wrinkles because they were balled up in a corner for a few days.

Since workwear pants have become a trend, you will likely see plenty of people rocking some tan dungarees or cream double-knee pants up and down your IG Explore page or out and about on the weekend. They are such a staple item that quite honestly, that isn’t a bad thing at all. It isn’t the same as everyone rocking the same graphic T-shirt or pair of new Air Jordans 1s. However, if you want to get creative and make something one-of-a-kind, workwear pants can also be a fun DIY project. Buy a white pair to dye or bleach. Adept with a sewing machine? Hit up a local fabric store and find some colorful patterns you can sew on to make a unique patchwork styling. Artistic? Sketch some subtle illustrations on the pockets. If you aren’t exactly the most crafty person, there are also plenty of amazing people doing great DIY work right now that are worth exploring too. Small Talk Studio can create a one-of-one pair covered in detailed sketches of your favorite interests. RHEE and Juliet Johnstone are two other DIY designers who have become known for using workwear as a canvas for their own unique art. And those are just a few examples. Do some exploring on social media, or maybe even hit up your artsy friend and see if they would want to customize something for you. The results will be worth it. Just expect some stares and “where did you get those?” questions from strangers when you walk outside. 

The best part about workwear pants is how affordable they are. Dickies 874s hover around $25. A pair from Carhartt or Ben Davis is $40-$50. There really isn’t any reason to explore beyond the classic workwear brands if you are on a budget, but we know that some people like to go above and beyond. Well, there’s options to satisfy those shoppers too. Brands like Darryl Brown or Stüssy offer solid options that are more focused on style and fit than traditional workwear brands. The price creeps up to the $150-$200 range though. Hayato and Tombogo are some other up-and-coming designers in the same price range who have gotten attention recently for their unique takes on the classic style. Hayato remixes his styles with details like colorful contrast stitching or patterns covering the panels on double-knee pants inspired by designer furniture, while Tombogo has created the Convertible Double-Knee Pant, a double-knee style on steroids with ample pockets that can be customized with removable and reversible panels. Have a bit more money in your budget? Reese Cooper has great cargos on his site hovering in the $400-$700 range. If Japanese fashion is more your thing, there’s always Visvim too. Just expect to shell out $1,000 and up to own something from the iconic Japanese brand. There are options for any budget. Just don’t feel like you have to shell out designer money for an item like this if you aren’t able to.

This isn’t an outfit choice that everyone will necessarily agree with, or be able to pull off, but there is definitely a place in the workwear discussion for going all out and deciding to rock the head-to-toe ensemble. The look is perhaps most connected to West Coast rap legends like N.W.A. or Snoop Dogg who helped popularize the look on a more mainstream level in the late ‘80s and early ‘90s. Dickies, Carhartt, your favorite designer; the brand isn’t too important here. But someone out there is going to want to rock the full Dickies suit trying to replicate Kanye’s 2019 Met Gala look. Some people might think you’re fresh off of a construction site, but who cares? If you are one of the few who can pull it off, go for it. They make the jackets and short sleeve button-ups for a reason. Worst case scenario if you end up not feeling the whole look together, you can always pair them with other stuff. A workwear jacket is still a solid staple piece to add to your wardrobe, too.

If it wasn’t apparent yet, workwear pants are super versatile. That means that you can pretty much wear whatever style of footwear you like. A pair of Nike Dunks or Air Jordan 1s looks just as good as a pair of Vans or Chucks. Not feeling sneakers on a particular day? Throw on some loafers and dress it up a bit. You can even toss on some boots in the wintertime. They will all look good. Each presents its own styling opportunities too. For instance, a high-top sneaker might look better if you let your pants drape over top of them, but if you opt for a dressier shoe like a pair of loafers you may prefer to cuff them and show off a little bit of your sock. At the end of the day, it all depends on your personal taste, but it’s also nice to know if you want to experiment with some new footwear that it doesn’t mean you need to worry about also buying an entirely new style of pants to guarantee you can pull them off.