A Gentleman’s Guide to Fitting Trousers

01 selectionLet’s face it, most men don’t know how to buy or fit their trousers.

Properly fitted trousers will allow you to sit, stand, and walk without the material falling down, shifting, or becoming uncomfortable.
When purchasing ready-made off the rack trousers in a store, there are two measurements, the waist and the inseam.

It seems that many men don’t know where their waist is, or how to measure it.

The Waist

Stand in from of a mirror and bend sideways. You should see a noticeable bend between your hips and the bottom of your rib cage; normally this is just above your navel. This is your waist. Stand straight, and using a cloth tape measure, measure your waist just above your navel.

waistIn general, your waist measurement should be 95% of your hip measurement or less. If it is more than 95% than the hips, you are probably not physically fit, there is too much fat in your mid section, and you might be a good candidate for a heart attack. Go see a doctor.

Assuming your waist measurement is smaller than your hips, this creates the perfect spot from which your trousers should hang; that is, properly sized trousers can stay in place without the use of a belt or suspenders. The waist measurement should not be too tight or too loose. This will comfortably keep your trousers at the right spot on your body without a belt or suspenders. Your trousers will not slip down and you will be comfortable sitting, walking, or standing. Plus you will look good.

When being fitted by a tailor, all measurements begin with the waist and move down. A properly fitted pair of trousers is fitted from the top down. The construction of trousers begin with the waist, which is the proper location for wearing trousers.

From here, the tailor will measure for the rise (waist downwards) to a point, which is sometimes called the crotch or the “T.” Properly fitted trousers will have a long rise; meaning the top of your trousers should hang from the waist. Most men today, wear their trousers the same way they wear a pair of off-the-rack jeans. Most jeans have a low rise, and men wear such jeans hanging from their hips, which is not how a gentleman wears his trousers. But hey, if you like the plumber’s crack look, common jeans are for you. Remember that trousers with a low rise do not move with your body. They are not fitted correctly. The good news is that you can purchase jeans with the proper proportions.

02 jeansAbove (l to r): Calvin Klein jeans with a long (proper) rise, Wrangler jeans with a mid rise, and Levis 501 jeans with a low hip huger rise.

Now I don’t when the waist headed south and men started pulling their waist band towards their crotch, but it looks awful and is not as comfortable as properly fitted trousers.

The waist band should hang from the waist and the crotch of the trousers should be at the actual crotch of the body.

Many people cannot find the perfect size trousers to match their body shape. When buying trousers, purchase quality garments that can be fitted by a tailor.

03 jeans and dress pantsAbove: Wrangler jeans next to Ralph Lauren suit trousers that were custom fitted by a tailor.

Dress left, or dress right?

When you are properly fitted by a tailor, he or she will ask you if you dress “right or left.” This means, does your appendage naturally hang to the left or right of the center line of your trouser’s crotch? Most men dress left – or so I am told. The reason the tailor will ask, is to make the dressed side of the trousers a little wider, and a with a well fitted pair of trousers no one should be able to see if you are dressed to either side.

Today I see many men wear properly sized rise with the waist band around their hips and the crotch hanging too low on their body. And they complain their trousers are not sized properly, when in fact they don’t know how to wear their trousers. These are probably the same individuals who complain about chaffing on their inner thighs when hiking. If they would wear properly size trousers of the appropriate material, wear the waist at the waist, perspiration on the inner thighs would be wicked away from their skin, eliminating the fungus that causes this rash.

The best hiking trousers I have found for hiking and backpacking are made by RailRiders. They rise is proper and the material breathes well.

02a railriderss and tux

Above: These RailRiders Eco-Mesh Trousers (left) have the same rise as my tuxedo trousers.

04 jeans and rail riders

Above: Wrangler jeans (mid rise) next to a pair of RailRiders Eco-Mesh (proper rise)


The inseam on hiking trousers will not be the same as one would have on a pair of dress trousers (the should be shorter). However, lets discuss the proper inseam length on dress trousers, or even casual wear.

If you like plain bottoms, they should touch your shoes in front and be one-half to three-quarters of an inch longer in the back. If you prefer cuffs, they should be tailored so they hang horizontal to the ground and there are no wrinkles or gathering of the material where the cuff is made.

Are they Trousers or Pants?

Simple, gentlemen wear trousers and women wear pants. Seems that in Australia they have kept their civility when it comes to trousers. Seems even the slang men’s pants have crept into the language on Savile Row in central London.


Properly fitted trousers are are comfortable and functional whether you are walking, standing or sitting. Additionally you will look good on the trail, at social events, in a corporate boardroom, or a black tie event.

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