High Waisted: Trouser Silhouette – How A Trouser Should Fit & Getting It To Fit Right

There are three main components when it comes to dressing: top, bottom and feet. The goal – to look presentable, stylish, masculine and all the other fun synonyms, is achieved by a cohesiveness between the three proportions.

You need a balance between everything. However, out of the three sections, I pay the closest attention to the “bottom”. Although not by a substantial margin, the trouser holds the biggest weightage in maintaining this cohesiveness, or the balance. However, fret not, unlike a jacket it is a lot easier to nail the fit of a trouser.

For a trouser to fit correctly you need to keep a few things in mind, 1) rise, 2) length and 3) slimness.



I am an advocate for wearing one’s trousers at the natural waist. The natural waist can be determined by tilting your upper body to either side, the point that causes a crease or fold is an indicator of where your natural waist is. Most people’s natural waist is located near the belly button.

Wearing your trousers higher allows you to keep your shirt tucked in, make your legs appear longer (subsequently you taller) and prevents you from committing the awfully dreaded shirt triangle (showing shirt when the jacket is buttoned).

If you are uncomfortable with wearing your trousers that high due to social conformity then I suggest a upper mid rise. Some brands to consider: EpauletImperial Shearer (Denim)Rota or Last & Lapel. Unfortunately some of these brands are on the pricer end of things. If you are not willing to drop that kind of $$$, I recommend made-to-measure companies that offer more casual friendly fabrics, such as: Knot StandardIndoChino or Black Lapel.


This is short and simple. Rule of thumb, if you are below 6″ consider a quarter or half break, if you are after 6″ consider a quarter or no break. Note: a no break trouser shortens the user’s legs, hence only recommended on someone above 6″.


You probably already have an image in your mind of how slim your trousers should be. Well, unfortunately you have to take that image out of your mind because how slim your trousers can go is solely dependent on how slim your legs are.

I always get asked “what’s your trouser opening?”. I could tell you but its rather irrelevant. I have small legs, so unless you have the same leg size as me, which is highly unlikely, my trouser opening will not fit yours.


The opening of these bespoke denim trousers are actually at 15.5″. This is a rather big difference in comparison to my old opening of 13.5″ to 14″. That’s more than an 1″ wider but yet it still looks slim. How is that so? Well have a really good tailor for one and two its all perception.

If you look down (from your perspective), you will have the tendency to think that your trousers are wider than they really are, especially from the sides. Best way to judge? Take trousies (trouser-selfie) in front of the mirror. Never go too slim on your trousers as it restricts it from draping naturally, which can cause stacking at the knees and a magnitude of effort to sleep your ankle through its opening.


Go with a slightly higher rise on your trousers, keep your height to trouser length in mind and go slim, but not too slim, to nail the fit of your trousers.

4 thoughts on “High Waisted: Trouser Silhouette – How A Trouser Should Fit & Getting It To Fit Right

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