Maybe it’s the fact that jeans are a casual style, but when jeans don’t fit right you end up looking extra sloppy.

I’ve always preached that getting clothes that fit properly will solve 90% of your style problems.

Today we’re going to go over how your jeans should fit. Here’s a bit of a bonus, you can apply these tips to any other type of pants, like chinos. 

What Most Guys Get Wrong: Going Too Big

After helping thousands of guys with their style, I’ve come to the conclusion that most guys are afraid of wearing clothes that are too tight.

They don’t want to be “uncomfortable”, so they overcompensate by wearing clothes that are too large because it’s not “constricting.”  

Why is this a bad look? Because you lose the shape of your body in that volume of fabric. It makes your legs look bigger and fatter than they actually are. That’s never a good look.  What you end up with is the dreaded dad jean look that even George Clooney can’t pull off. 

Think “Fitted”, Not “Skin Tight”

For some of you, wearing clothes that fit you properly might feel a little alien. I think it will help by debunking the myth that roomier clothes are more comfortable.

Clothes that actually fit you are going to feel more comfortable they’re so much more functional. When clothes properly fit your body, it’s easier to move. You’re not fighting all that fabric.

Think about it this way, if you put on a pair of boots that are 2 sizes too big, you could call it “roomy” and not constricting. But how well do think you can run in them?

I don’t like to use the words “skinny fit” or “tight” because it comes with certain connotations. I prefer to use the words fitted or tailored. But even that can be a little confusing.

So I have a few rules of thumb when it comes to jeans.

  1. If you need a belt to hold up your jeans, it’s too big. This goes for all pants.
  2. If you can trace the outline of your leg shape and butt (see right), it’s too tight. If your jeans look like denim printed yoga tights, they’re way too tight. 

Those are some solid rules of thumbs. Now let’s get into the details.

How Your Jeans Should Fit: Point by Point

Overall fit: Your jeans should fit your waist without needing a belt. It should fit close to your body but not be skin tight. For most guys, you want to go with a slight taper in the leg, which helps prevent a bell-bottom look. The image above left is a great standard to go by, even if you don’t have the same body type as him. It’s not too tight where you can see the outline of his leg shape. It’s not too baggy where his pants are falling, or his legs are unusually wide looking. It’s just right. 

Waist: Should comfortably sit on your waist without needing a belt. If you need a belt, it’s too big. If you can’t button it up, it’s obviously too tight.

Butt/Seat: It should hug your butt slightly without feeling constricting. (Image above, right) If you can’t lift up your legs or squat without feeling like your jeans might rip, it’s too tight.

If you can grab a handful of denim from butt area, or confidently smuggle a football thanks to the extra room, it’s too big/baggy.

Thigh: The trickiest part for a lot of guys.

For this, I recommend “The Pinch Test”

Stand relaxed and pinch the fabric around your thigh horizontally between your thumb and forefinger. You want to pinch around a finger tip worth (.5”-1”) of fabric.

Any less, it’s too tight. Anymore, it’s a bit too baggy.

Calves: Use “The Pinch Test” the same way you did on your thighs.

Length/Inseam: You want a bit of a break when it comes to your jeans, like the image above. Some men like to wear jeans super straight with no break. I think this looks strange for the most part. Too much stacking looks sloppy and is best avoided. 

Also, keep in mind you might want to allow a bit of extra length if you want to cuff them and show off some selvedge. Anywhere from .25-1”.

It’s all personal preference, but I go for more subtley. I like no cuff to a small, .25″ cuff. Anything more can start looking ridiculous. 

Don’t Forget: Not All Cuts Are Created Equal

The guidelines above apply to all men, regardless if you’re 5’6” and 230lbs or 6’ with a 28” waist.

In order to get that kind of fit though, you have to make sure you’re buying the right cut for your body type.

You don’t know how many guys I’ve worked with who complain that jeans never fit when they go shopping, and I find out that they’re shopping in the skinny fit section when they look like they should be over at the big and tall.

And while everything seems to be “skinny fit” these days, there’s actually a method to the madness. Here’s how to decode your local denim section:

Skinny fit: For guys with skinny thighs and skinny calves. True skinny fit jeans are meant for guys who basically have pencils for legs, they’re roughly the same straight, slim shape from their thighs to their calves.
Best for: Guys who have really skinny legs all the way through.

Tapered fit: For guys with a bit of thigh and butt muscle, but calves smaller than their thighs, hence the tapering of the cut.
Best for: Average to Fit guys that don’t have big thighs.

Straight fit: For your average guy that has a bit of muscle in him all around.
Best for: Average guys with a bit more size in their butt, thighs, and calves.

Athletic Cut: This is a relatively new cut. Basically, it’s a nicely tapered fit with a lot more room in the thigh and butt area. Great for guys that don’t skip leg day or larger guys who’ve always found that when they went up a waist size in, they were left with bell bottoms.
Best for: Athletic guys with large thighs, or larger guys in general

Boot cut: Jeans that have more room below the knee/calf area to accommodate cowboy boots. Unless you’re rocking jeans in Texas, you don’t need to be concerned with these.
Best for: Cowboys

Relaxed cut: From my experience, relaxed cut is what athletic cut used to be, but without as much taper. I generally prefer going for athletic cuts over relaxed now, and lot of brands have phased “relaxed” out in favor of the term “athletic”.
Best for: Athletic guys with large thighs, or larger guys in general

Final Thoughts: Finding Your Perfect Pair

Even with these guidelines, keep in mind that each brand has their own in-house definitions. Just look at Levi’s, who has a “Regular Straight”, “Original Straight”, and “Slim Straight”!

I don’t recommend just purely going off the sizing tags or labels like “skinny” or “straight”. They’re good starting points, but it’s going to take some trial and error.

Some final recommendations:

  1. Use sizing and labels as a starting point.
  2. Use the “Pull 3” Trick: When shopping in person, grab your size, then one size up and one size down. This will save you a lot of time going in and out of dressing rooms.
  3. When shopping online, you can do something similar. Order your size, one size up, one size down. Make sure you read the stores return policy. (Also keep in mind that many online stores do not accept returns on sale items, so I don’t recommend doing this on sale items.)
  4. Use the tips I listed above as well as the “Pinch Trick” to find the right size. 
peter@theessentialman.com'
Author

Hi, I'm Peter. I spent 11 years as a menswear designer here in NYC. Now, I help some of the most successful men look really good as a Private Personal Stylist and writer of The Essential Man. You can learn more about what I do by clicking here

  • Gopi

    This is a great article Peter! I used the pinch test this weekend when I was buying new jeans. Very helpful!

    • Peter Nguyen

      Awesome Gopi, glad it helped!