This Jeans War (or The Fight To Find Jeans that Fit)

Buying jeans can be a challenge. Jeans occupy a special place in our wardrobe; they’re the go-to pants for work and play. They conform, over time, to your body and soften with wear. They’re a quintessentially American clothing item: tough, rugged, and devoid of pretentiousness. No wonder there is a thriving foreign market for blue jeans. How many times have we heard the following:

“Just throw on some jeans, no need to get dressed up!”

“Those are my favorite pair of jeans!”

“It fit like an old pair of jeans!”

There’s nothing quite like them, which is why it’s important to find the right pair for you. As a big man, this present a special challenge. Many of us are not shaped quite like jean designers imagine we should be, and that’s okay. With that in mind, here’s your guide to buying jeans as a big man.

Decide Over or Below the Belly

This is a trick question; the correct answer is over your belly. The reasons are many; let’s go over a few here.

No more hitching up your pants constantly.

Wearing your pants at your natural waist (the area between the top of your hip bones and the bottom of your rib cage) allows for free movement of your legs (from upper buttocks to the soles of your feet) without interfering with the waistband of your pants. If you find that you need to constantly hike your pants up throughout the day, the reason is that your pants are not sitting high enough on your body.

No more battling against physics.

When you wear your pants over your belly, you are no longer attempting to defy the laws of physics by attaching a looped cinch of material to the underside of a sphere. Imagine a basketball and you’re putting a belt around it. Any person, after giving it a moment of thought, would put the belt around the middle, right? Or, they would put it above the middle, no? You wouldn’t try to put it 1/3rd of the way up from the bottom. Putting it there would make the belt constantly slip down. You’d want it smack at the middle or a little above the middle, so if gravity pulls the belt down it will be unable to get past the largest part. It’s a logical physics-based solution.

It cuts your overall shape into two relatively equal parts.

You’ve got two halves to your body: a top half and a bottom half. We call these “halves” because they should be relatively equal in proportion. Not everyone is made from the same mold, but most outfits benefit from having the top (the shirt/jacket/hat part) make up roughly half of your overall shape. It’s the same with the bottoms (the pants/shoes bit); they should take up half of your shape. By wearing your waistband below your belly, you are grouping your hips, upper buttocks, and the lower half of your abdomen into the top half. This throws off the overall balance of your proportions.

Pants are not designed to be worn under your belly.

Yes, even large, plus-size pants are not meant to be worn under your belly; they aren’t cut for it. This is why your pants are baggy in the crotch, and why the crotch hangs halfway down your thighs. It’s why the pant legs are too long, and why the thighs are so baggy even with a slim cut. And it’s why you don’t have full range of motion when wearing your jeans; it’s hobbling you.

If you aren’t wearing properly fitting pants, what will you do in case of emergency? What will you do if you need to run for your life or save a child from speeding traffic? In the Dungeons & Dragons game of life, if your pants don’t fit properly, you are constantly rolling disadvantage.

To Cuff or Not to Cuff

Cuffing your denim jeans is a great style choice. I tend to wear all of my denim jeans cuffed for several reasons.

  • It looks sharp. The contrast of the lighter colored inner material against the darker (my preference) outer denim is visually interesting.
  • I don’t need a perfect hem, since I’m cuffing anyway.
  • It’s easier to find long inseam jeans than short (my size) inseam jeans. Buying longer inseam jeans is easier because more places carry 30-34 inseam jeans than carry 27″ inseam (my measurement).

On the other hand, cuffing your jeans visually shortens your legs when seen in terms of overall outfit balance. It also doesn’t look so great when paired with some sock/shoe combinations. So make the choice when wearing your favorite shoes and, if you aim to look taller, eschew cuffing for now.

A Guide to Buying Jeans in the Correct Size

Measure Your Waist

  1. Find the bottom of your ribs and the top of your hips.
  2. Place a tape measure around your middle at a point halfway between them (just above the belly button).
  3. Make sure it’s pulled tight, but isn’t digging into your skin or cutting off circulation.
  4. Breathe out, relaxing your stomach muscles while standing straight, and take your measurement.

Measure Your Inseam

  1. Stand up straight with your feet together and the tape measure held in your hand.
  2. Stick the starting end of the tape measure under your heel, with the tape sticking out on the inside of your foot.
  3. Pull the tape measure upward, taut, and make a note of where the tape measure comes up to the bottom of your ankle. This is going to be your offset, “X”. It may be around 2 or 3 inches. Doesn’t matter, just make a note of it.
  4. Continue pulling the tape measure taut and run it up the inside of your leg until it reaches the bottom of your crotch. Make a note of this measurement, “Y”.
  5. Subtract X from Y to get your inseam measurement, “Z”.
  6. If you plan on cuffing your jeans, add 2 inches to measurement “Z”.

Find Jeans that Match Your Measurements

Jeans are typically made in measurement increments of 2 inches. If, for example, your waist measurement is 57 inches and your inseam measurement is 29, you will likely not find jeans in that exact size. My recommendation is to round up in size instead of down. You can always get jeans “taken in” (reduced in size) through a tailor but it’s much more difficult to get them “let out” (increased in size). So, for our example, you’d need to find jeans in a 58 waist, 30 inseam or, as it’s more likely to be presented, a “58×30”.

Get Jeans With Stretch Or Nah?

In the past decade, stretch fabrics have come a long way. You can get 100% pure cotton denim jeans with no stretch, or you can get jeans with 2% Spandex that have a bit of stretch (my preference). You can even get 96-98% cotton-polyester blend denim jeans with 2-4% Spandex, which will stretch and accommodate your body like a pair of leggings. Heavier non-stretch denim has a more robust look, it breaks in over time better, it will last longer, and it drapes better in general. Stretchier denim wears out faster, it doesn’t look as nice, and it tends to drape in less flattering ways (think a balloon that’s had the air let out; it wrinkles instead of folding into waves).

So, given these drawbacks, why would someone ever buy the stretchier denim? Well, they require virtually no break-in period, they feel like an old pair of sweats right from the first wear, and they look, most of the time, like regular jeans. I could do yoga in some of the stretchier jeans I’ve had, or the splits, without fear of splitting my jeans. They also accommodate many different body styles, they tend to look slimmer on your legs, and they are (usually) pretty cheap.

I would recommend, based on the above reasons, that you go with as little stretch as possible based on how your jeans fit you. I personally prefer jeans with less stretch, but that still have some stretch. Levi’s tend to hit this balance well for me, as do Amazon Essentials denim jeans.

Pro Tip: Sit Down When You Try On Your Jeans

Many big men, including myself, are larger around the middle when they sit down. Your legs press upward on your belly and your midsection bulges out in front and on the sides, and it may increase your size by several inches. If you measure and purchase denim jeans in your exact standing size, you may feel uncomfortable when you sit down. And you may feel VERY uncomfortable when you have to sit down, like many of us do, at work for several hours a day with the waistband digging in to your stomach.

You can fight this in two ways: buy a larger size and/or buy denim with some stretch to it. Personally, I do both; I buy denim that has mid-level stretch to it and I also buy one size larger than I measure when standing up straight. Remember, it is better to err on the side of comfort than to get a clothing item that only fits when you are in a specific position.

Choose Dark Denim

Person holding a stack of denim jeans.
Choose from the bottom half of this stack.

Nothing screams “I buy my jeans the same place I buy chicken wings and Christmas decorations” like medium-wash blue jeans. Dark denim looks crisp, clean, and it wears better, revealing lighter-colored creases over time that show where you bend and move. They display, over time, that you are a do-er, you live and work in your jeans, and that’s pretty cool. (By the way, light wash blue jeans have a place in very specific outfits, which we’ll discuss in a later article.)

Dark denim looks good especially on big men. They don’t draw quite as much attention to your midsection as light or medium-wash denim. They help to balance out your frame, making your upper body and head the focal point of your outfit. The dark color also tends to blend with creases in areas that you may not wish to show to the world.

Are you limited to dark blue? No! Along with the classic indigo there is black, black wash, chocolate brown, charcoal… I’ve even worn a pair of dark red denim jeans that I really loved with several outfits. Branch out within reason but stay away from medium-wash blue jeans unless you’re going for a purposeful “dadcore” vibe, which is hard to pull off if you’re (a) dad age and (b) already kind of dad-like overall.

Try (Many) Before You Buy

Once you have your measurements, take several pairs of jeans with you into the fitting room. (Or, if ordering online, order several pairs in varying sizes, stretch levels, dark colors, and lengths that you can return easily.) The idea here is that, not only does fit differ between cuts of jeans (loose versus slim), but I find that many colors have different stretch levels and over several years even identically-sized jeans in the same style and color will vary in actual size. My indigo Levi’s are slightly less stretchy than my black Levi’s, though the cut and material are EXACTLY the same. I also have a pair of size 54 waist jeans from several years ago that fit looser on my waist than a size 56 waist jeans that I bought recently.

How can this be? Because every time the giant denim-cutting machines cut that jeans component parts out of a roll of fabric, they cut it slightly different. Every time the machine sews those jeans together, it sews them with slightly different overlap, or slightly tighter or looser. Over time, the same exact pair of jeans will differ in waist measurement, length, cut, etc, so depending on where and when your jeans were manufactured, on what machine, how they were dyed and dried, the fit might be ever-so-slightly off. This makes that magical pair of jeans that fit you great even more magical. They could truly be one-of-a-kind.

So take your time. If nothing fits right, try a different store, or a different brand, or a different cut. Don’t settle for something that doesn’t make you feel and look good.

Snap Judgements

As always, I have extensive personal experience with all of the below jeans and with jeans in general in this guide to buying jeans. I can especially recommend the Levi’s 541 Tapered in Rigid Dragon (last in the “Wear This” section). They have a bit of stretch and develop great fades, and they taper at the bottom below the knee. Unfortunately, sizing is limited on Amazon, so check the Levi’s website as well. Let me know if you have any questions by posting a comment below.

Wear This

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