What Should You Wear With A Denim Jacket?
So, you’ve got yourself a denim jacket. Congratulations! You’re now the proud owner of one of the most versatile, fundamental pieces a man can own. And if you’re not quite sure what to do with a piece that offers so many options, then you’ve come to the right place.
If you haven’t noticed already, Westernwear is major this year—a denim jacket fits right into the trend, so just by wearing one, you’re pretty much bound to look stylish. But there are definitely some ways to make it look really great, even if cowboy-core isn’t your thing.
A denim jacket is more wearable than you might think. It’s not formal, but in 2025 you can dress one up for formal events and evening wear. Of course it can dress down for casual, daytime vibes and even turn it into a standout, timeless fit without putting much effort in at all. How, you ask? I’ve got some tips for you below. Welcome to the wide, wide world of the denim jacket.
Don’t Overthink It
Denim jackets have been cool since the dawn of time (also known as the 1950s). In the style’s heyday, it was all about keeping things casual—and over the years, handfuls of indie rockers, hipsters, and, yes, even cool fashion guys have kept that trend alive. Chances are, if you have a denim jacket, you bought it for its wearability. It’s inherently an easy garment, one you don’t have to put too much thought into—and it looks best when you do just that.
Don’t overthink it. A classic tee is always a great match for a denim jacket, whether you go for a vintage band shirt, a funky graphic, or your favorite plain white T-shirt (or one of ours). What you’re going to want to pay most attention to is the way everything fits; if your jacket is cropped and boxy, don’t get a tee that has a longer hem, or your proportions will look a bit wonky. Your tee should be the same length, if not slightly shorter, than your jacket; if it’s longer, tuck the tee into your pants.
And speaking of pants—jeans are a great bet, but more on that later. Everything from trackies and joggers to pleated pants is a safe bet for your denim jacket. And if you want to add some more personality, accessorizing is the way; throw on a baseball cap, a pair of cool socks, a tote bag, whatever. The options are, quite literally, endless—but keeping your silhouette and proportions in mind while you get dressed is going to make the difference between looking effortlessly put together and looking slightly sloppy.
Dress It Up
Personally, my favorite way of styling a denim jacket is to elevate it. It’s way easier than it sounds—throw your jacket over a white (or striped) Oxford shirt with a tie (bonus points if you lean into the Western trend and go for a bolo) and see for yourself. As for pants, something classic and pleated with leather loafers will do the trick.
Essentially, you can treat your denim jacket like it’s a blazer. Wear it with whatever you’d throw one over, whether it’s an OCBD or a tee with a nice sweater vest. Accessorize the same, too; keep your leather belt, your nice watch, your leathershoes. It has the effect of modernizing your look a little bit, even if you’re going for business casual.
