What Pants Should You Wear With a Denim Shirt? [Men's Fashion Guide]

You just couldn’t resist its charm. Whether it’s your first denim shirt or you’re adding another to your wardrobe, you’re now the proud owner‌ — ‌or soon will be‌ — ‌of this timeless piece.

The question is, what are you going to wear with it?

For many of us, denim feels like dangerous territory when it comes to fashion. Get it right and you look like the new Johnny Cash. Make a misstep and you end up more like a tumbleweed cowboy or a washed-up member of the Backstreet Boys. 

We’re not sure which is worse.

To help you avoid that fate and find your perfect style, we’ve compiled this handy guide to denim shirt wearing. 

What pants to wear with your denim shirt

One of the best things about denim is that it's super versatile. When you put on a denim shirt, you have a wide range of combinations to choose from. The decision is more about what look you're trying to create.

Jetsetter Straight Fit pants

I mean, duh. Our Straight Fit pants go perfectly with denim shirts, creating a smart-casual look that's ideal for date night, drinks at the golf club, and the office party.

They're smart enough for work, as well — so you can just wear the Jetsetters all day (thank you, anti-odor fabric) and swap out your shirt.

In terms of color combinations, Deep Blue, Charcoal Gray, and Sand Stone all create a really pleasing contrast. If your shirt is darker, you can try Oak Khaki or Ice Gray.

Jetsetter Slim Fit pants

Prefer to show off that toned derrière? You could sling on a pair of Jetsetter Slim Fit pants instead.

Much like their straight-legged kin, these pants look neat and tidy in formal settings. But when it’s time to crack open the beers, you’re still going to feel comfortable. Tuck your denim if you want that “I go to the gym” silhouette. Leave it loose if you’re not into flexing.

Pretty much every color in the range can work. We particularly like the contrast of Sand Stone and Deep Blue.

Dark chinos

Chinos deliver some of the same aesthetic as the Jetsetter pants — just without the butt-lifting, ball-freeing, non-wrinkling style. 

If you're going this route, we recommend pairing your blue denim shirt with black or dark gray pants.

Choose leather dress shoes if you want to look truly smart-casual, or put on clean white sneakers for a more relaxed, modern look.

Olive green pants

If you like the cargo pants look, but need something more refined, our Olive Green Slim Fit or Straight Fit pants should do the trick. There's a military vibe here, but the muted green creates a harmonious, understated outfit that works brilliantly for fall and spring.

The overall style with this pairing is definitely laid back. That said, the color combination is intentional enough to impress on a coffee date or in casual offices. 

Navy dress pants

Here's the bad news: You probably can't get away with wearing a denim shirt as part of a tuxedo. But that doesn't mean you can't dress up a little.

Wearing light blue denim with navy dress pants is a creative way to look sharp. The deeper blue provides a refined backdrop that makes the denim shirt look intentional and stylish rather than too casual.

This outfit idea is perfect for workplaces with flexible dress codes, and folks who work in creative industries.

Tan corduroy pants

Think corduroy belongs in thrift stores? Think again. Corduroy pants have made a serious fashion comeback in the past couple of years.

Tan cords bring some textural complexity and vintage-inspired charm to your denim shirt outfit. The soft ribs really complement the stiffer denim, creating a layered, autumnal look.

Go for slim, tailored pants for a crisp, modern look — or opt for something baggy if you prefer a bit of a hippy style.

Gray wool pants

If you want to look good when the winter chill really hits, consider matching your denim shirt with a pair of gray wool pants.

This sophisticated look bridges casual and formal wear. The soft, refined texture of wool trousers really elevates the denim shirt to look smarter than you might expect. 

Jetsetter shorts

What about the other end of the seasonal scale?

If you’re still wearing denim, you could pair it with Jetsetter Tech Shorts. They have all the same butt-lifting, anti-ball-crushing features — you just get to feel the wind on your knees.

For summer evenings, try wearing our Anytime Tee underneath an unbuttoned denim shirt. White and Charcoal Gray are likely your best options.

And now, for the elephant in the room…

Can you wear a denim shirt with jeans?

Yes, you can. But tread carefully. The key here is to create contrast. Wearing matching double denim is dangerously close to ‘90s boy band territory.

If you're going with classic blue jeans, try to make sure they're a different shade than your shirt. 

You could also try:

• White slim jeans: Combining white with blue denim creates a clean, modern look that's perfect for backyard summer parties. It's casual, bold, and relaxed.

• Black jeans: Another option for creating contrast is pairing your denim shirt with black jeans. This tried-and-tested casual look is perfect for rocking up to your local sports bar, or just for running errands around town.

What type of denim shirt do you own?

Not sure which pants to choose? It's worth taking a moment to ID your denim shirt.

We know this sounds like a group activity for the Dull Men's Club, but it does actually matter. Denim shirts come in many different styles, and that affects your overall look.

Here's a quick spotter’s guide:

• The fitted denim shirt: More slim-cut, modern styling. Can be dressed up or down. Pairs with navy dress pants and Deep Blue Jetsetter Pants.

• The oversized denim shirt: Relaxed, loose fit for streetwear style. Works as a denim jacket or layering. Pairs with tan corduroys and gray wool pants.

• The raw/selvedge denim shirt: Unwashed, stiff denim — usually high-quality material. Develops unique wear patterns over time. Pairs with black jeans, and black or dark gray chinos.

• The classic western shirt: Typically pearl snap buttons, two chest pockets with pointed flaps — a traditional ranch-style design. Pairs with cargo pants and dark brown leather chinos.

• The workwear denim shirt: Heavyweight, durable construction with reinforced stitching, designed for manual labor and rugged use. Pairs with cargo pants and dark chinos.

How to style your denim shirt outfit

Of course, a shirt and pants aren’t a complete outfit. If you're wondering how to style a denim shirt, we have you covered.

How to “dress up” with a denim shirt

Oh, so you're dressing to impress! No problem.

To dress up a denim shirt, start by choosing a fitted or slim-cut shirt. Light-wash denim is a good option for this.

Pair your shirt with tailored navy dress pants or dark chinos, and elevate the look with leather dress shoes or sleek Chelsea boots.

You can layer with a well-fitted blazer in navy or charcoal for a sophisticated touch (our Legacy Jacket would fit the bill). Make sure your shirt is neatly pressed and tucked in. Add a leather belt to match your shoes. 

For a refined finish, add some simple accessories like a classic watch or simple cufflinks.

How to “dress down” with a denim shirt

If you're the kinda guy who focuses on the casual part of smart-casual, we'd recommend choosing a denim shirt with an oversized or relaxed-fit style in a darker wash.

You can pair this with cargo pants, distressed jeans, or even joggers if you're really hanging loose.

For your feet, choose comfortable canvas sneakers or rugged boots. Leave the shirt untucked and consider rolling up your sleeves for a more relaxed vibe.

You can complete the look with a watch or simple leather bracelet. The key is to embrace the relaxed vibe while still looking intentional.

How to layer a denim shirt

When the temperature calls for a little more insulation, you have loads of options for layering when you wear denim.

In the fall, you could keep out the breeze with a slim-fit sweater or cardigan over the shirt. Pull out the shirt collar so it stays visible. In winter, layer up with a tailored wool blazer or a leather jacket.

For outdoor activities, a quilted vest or lightweight down jacket works well. As always, be mindful with your color choices — you don't want a blue that matches your shirt too closely. And if you want to avoid an overly bulky look, make sure your layers are fitted and proportional to your shirt.

How to accessorize a denim shirt

No matter how you wear it, denim always has that timeless look. So, we'd recommend using accessories with a similar vibe.

Leather is a great option. The brown goes nicely with different shades of denim, without detracting from the main event. You can choose a watch with a brown or black leather band, or a quality leather belt. Leather shoes and bags generally work well, too.

If you're not a leather person, try putting a canvas bag on your shoulder and a minimalist silver bracelet on your wrist. Classic sunglasses also look ridiculously cool with denim — try aviators or wayfarers.

Dos and don’ts of denim shirts

We can't cover every denim-related possibility in this guide. But we can give you the tools to make good decisions before you leave the house.

Do…

• Choose the right fit: Different cuts work well for different body types. If you're going down the fitted route, avoid buying anything too tight.

• Match the wash to the occasion: As a general rule, light washes are better suited to casual outfits, while dark denim is more formal.

• Choose complementary colors: Color contrast is a big factor when you wear denim. If in doubt, choose something neutral like black, gray, or white.

• Iron or steam for crisp appearance: If you want your denim outfit to look really sharp, it's worth taking the time to get rid of the creases.

Don't…

• Wear matching denim: Please, please, PLEASE don't try to pull off the Canadian Tuxedo. It's not the double denim that's the problem, it's the matching colors top and bottom that'll really put people off their food.

• Wear oversized shirts in formal settings: It's almost impossible to look smart in a chunky denim shirt. 

• Pair your shirt with clashing patterns: If your denim shirt has a subtle pattern in the fabric, try to pair it with something plain. Otherwise, your style is going to be way too busy.

• Neglect shirt maintenance: Denim can last for decades if you treat it right. But, it can look pretty rough if you don't clean it regularly and address minor damage promptly.

Don't get your threads in a twist

As you might have learned by now, styling a denim shirt isn't rocket science. If you can avoid the fashion faux pas of double denim and find the right fit, there's a fair chance you're well on your way to a winning look.

If you're looking for a guaranteed match, be sure to pick up a pair of Jetsetter pants. Pretty much all the colors work with denim, and they come in both straight and slim cuts.