9 Best Men’s High-Waisted Pants & High Rise Trousers For 2023

Fashion is a fickle old game, eh? One minute you’re getting ridiculed for having your pants too high (alright, grandpa), the next, everyone’s doing it.

It can be difficult to keep up. So, let me help: men’s high-waisted pants are going to be sticking around for a while. And to ensure you’re investing in the right pair(s), I’ve highlighted every modern style worthy of your consideration.

But before I go diving in above the hip, I should make something crystal clear. While some of the pants included are high-rise by design, others simply require a little hiking up to achieve the desired look.

Understood? Get comfortable and continue reading for your free ticket to high-waisted heaven.

Key Takeaways

Many moons ago, men’s high-waisted pants were the norm. Until guys started wearing jeans at their ankles (slight exaggeration) and ruined it all. Thankfully, we’ve started to pull them back up to a more sensible level. And now, men are even starting to revert back to the ways of our grandparents. Good thing for you, I looked high and low across dozens and dozens of sites to find the true gems.

In this article I’m going to be taking you through a selection of belly-level beauties that deserve a place in your wardrobe. Whether you’re dressing for a wedding or days in the office, designs like Casatlantic’s Mogador pants and Haversack’s army-inspired pair are now a must-have for every fashion-forward fella.

Why it’s great: If you asked me for my favorite men’s high-waisted pants, I’d point proudly towards this military-inspired pair from Casatlantic. Comfortable, versatile, and available in three lengths, they’re an excellent everyday option that team well with a wide range of smart and casual staples. Not just easy on the eye, the side adjusters help to achieve the perfect fit, while the high rise allows them to sit sweetly on the top of your choice of sneakers or shoes.

How to wear them: They can be styled in many different ways, but I think they work best with a mesh-knit polo and canvas sneakers. If you find yourself in a spot of bad weather, a denim or Harrington jacket is a convenient and stylish addition.

Flaws but not dealbreakers: If you are usually between two sizes, you should probably size up. Don’t worry if they feel a touch too big, by using the side-adjusters you can tighten them by 1.5 inches.

Material: 100% Cotton | Sizes Available: 28-38” | Colors Available: 5 | Style: Chinos

Why it’s great: Made from a lightweight whipcord cotton, these chinos are durable as well as seriously soft. There’s a hint of stretch for added comfort, plus an internal waistband that helps to keep your shirts neatly tucked in. The mid-rise design isn’t quite as high as some of the other styles on this list, but that’s what makes them the perfect option for every day.

How to wear them: Comfortable enough for long commutes and days full with meetings, they look particularly smart with a button-down shirt and loafers. At the weekend, I’m wearing mine with a crew neck sweater and high-top Chucks.

Flaws but not dealbreakers: The light material makes them particularly suited to the warmer months and a great alternative to shorts. As it gets super chilly, you may want to think about something slightly cozier.

Material: 97% Cotton, 3% Elastane | Sizes Available: 28-40” | Colors Available: 7 | Style: Chinos

Why it’s great: An absolute dream for lovers of vintage gear, these roomy, relaxed pants are heavily inspired by 1940s British Army trousers. Similar to those that would have been worn by Gurkha’s (Nepalese soldiers recruited by the Brits), they’re defined by a double-pleated front and high, cummerbund-style waistband. As comfortable as they are cool, they’ll give your looks a unique twist that even your grandpa will love.

How to wear them: A surprisingly versatile pair of pants, they’re the ideal for those after something a bit different from the regular chino. They pair perfectly with Oxford shirts and suede loafers, but look just as good with a chunky sweater and high-tops.

Flaws but not dealbreakers: Small and stocky guys should be cautious, as these pants are on the wider side. This can sometimes visually shorten your legs, making them appear even shorter.

Material: 100% Cotton | Sizes Available: S-XL | Colors Available: 2 | Style: Chino

Why it’s great: It can be hard to find the kind of pants you can wear with both formal shirts and slouchy tees, but Closed appears to have aced it. The Blomberg is a wide-fitting trouser that’s suitable for work or the weekend. It’s made from a stretch-cotton twill fabric that boasts a beautiful texture and superior softness.

How to wear them: Dress them up or down, the decision is yours. I find they work particularly well with a plain white tee, bomber jacket, and Derby shoes.

Flaws but not dealbreakers: You’ll need to be working with a pretty big budget to be at peace with the price tag.

Material: 97% Cotton, 3% Elastane | Sizes Available: 27-38” | Colors Available: 2 | Style: Trousers

Why it’s great: Regular fit with an elasticated waist, these ultra-comfy casual pants will soon become a mainstay in your everyday rotation. There’s much to love about them, but the standout feature is the organic cotton fabric that’s super soft as well as durable.

How to wear them: Suitable for your daily errands as well as weekend meet-ups with friends, they work well with your classic casual staples such as crew neck tees, zip-up hoodies, and sweaters.

Flaws but not dealbreakers: They’re designed to be unisex, so you may want to keep them out of your girlfriend’s grasp. Failure to do so and you’ll probably never see them again.

Material: 100% Cotton | Sizes Available: XS-XL | Colors Available: 3 | Style: Chinos

Why it’s great: Roomy through the hip and thigh with a universally flattering straight leg, these Amazon pants are a real winner. Perfectly combining form with function, they come with belt loops but also have an expandable waist that gives you an extra 2 inches should you need them.

How to wear them: Working in the office? They’ll look the part with a crisp formal shirt and shoes. For something a little more relaxed, I find a slim-fitting tee and smart sneakers works best.

Flaws but not dealbreakers: A few reviewers say that they found them to run slightly large. Something to bear in mind before you choose your size.

Material: 100% Wool | Sizes Available: 28-60” | Colors Available: 6 | Style: Trousers

Why it’s great: 90s-style jeans are big news right now and this pair from Suitsupply (available in regular and long) are as close to perfect as you’re going to get. Made from pure cotton denim using a robust twill weave, the high-rise design is tailored to a regular fit and cut straight through the leg and hem—making them an excellent option for pretty much all builds.

How to wear them: Keep it classic with a plain white T-shirt and sneakers or dress them up slightly with penny loafers and a knitted polo shirt. When it’s cold, throw on a cropped jacket and complete the ensemble with a baseball cap.

Flaws but not dealbreakers: As far as jeans go, they’re quite expensive. But they’ll last—so well worth the splurge if you ask me.

Material: 100% Cotton | Sizes Available: 28-36” | Colors Available: 1 | Style: Jeans

Why it’s great: More 70s-style icon than Simon Cowell, these wide-legged wonders are going to quickly cement your status as the best-dressed guy around. The baggy silhouette and lightweight construction ensure optimum comfort, while the elasticated waistband means you don’t have to worry about a belt.

How to wear them: Whether you’re on a first date or hanging with friends at the weekend, they’ll look great with a crew neck tee, bomber jacket, and boots. Alternatively, for an effortless everyday look, you can try them with some sneakers and an untucked Oxford shirt.

Flaws but not dealbreakers: The price tag is enough to put a lot of people off and they’re probably going to appeal most to the more sartorially daring.

Material: 100% Wool | Sizes Available: S-XXL | Colors Available: 1 | Style: Trousers

Why it’s great: Inspired by the kind of comfy bottoms worn in the kitchen (yes, seriously), these garment-dyed chef pants will help you cook up a storm in the style department. They’re made from a heavyweight organic cotton and feature an elasticated drawstring waist that can be pulled tight to keep them high.

How to wear them: As long as you keep it fairly casual, you have endless options when it comes to styling. From oversized tees to hoodies and flannel shirts, Service Works’ pants pair well with just about anything.

Flaws but not dealbreakers: Sizes are pretty limited, so you’ll need to grab these quickly.

Material: 100% Cotton | Sizes Available: S-L | Colors Available: 1 | Style: Casual Pants

Buying Considerations for Men’s High-Waisted Pants

Size

To ensure the perfect fit, accurately measure your waist at its narrowest point and choose high-waisted pants that match this measurement. Proper sizing is essential for a comfortable fit that sits at or slightly above your natural waistline.

Style

Consider the style and occasion for which you intend to wear your new purchase. Men’s high-rise pants are available in a range of styles, from jeans to smart slacks. Therefore you should select a pair that suits your needs and personal fashion preferences.

Fabric

Evaluate the fabric of the pants for comfort and season-appropriateness. Lightweight cotton or linen may be ideal for summer, but wool or heavier materials are better suited for the colder months.

Why You Should Trust Us

Believe it or not, I didn’t just throw the names of random men’s high-waisted pants into a hat and pull them out one at a time. C’mon, guys. I’m a really experienced fashion writer. I actually started with a list of 30 styles and narrowed it down to just nine—each offering the ultimate blend of style, function, and affordability.

Final Verdict

As we bid adieu to the era of low-slung jeans (warning: probably not for long), it’s time you introduced some men’s high-rise pants to your roster. More specifically, one of the seriously stylish options featured in this list.

Still contemplating whether they’re your cup of tea? May I remind you of Casatlantic’s pair? Versatile, charming, and eternally timeless, they’re a fine everyday option that’ll quickly become the kind of reliable garment you’ll never want to take off.