Millennial Men: The Proper Fitting of Suit & Dress Pants

Millennial Men: The Proper Fitting of Suit & Dress Pants

Once again, this post is long overdue! Sorry about that gents. Life can get busy, but hey, no complaints.

Previously, we went over the proper fitting of suit jackets, blazers, and sport coats, but now it’s time to cover our other half! Since most people don’t look down majority of the time, they don’t notice men’s lower proportions as often as their upper torso. Unfortunately, this means that men typically ignore their pants’ fittings. Proper fitted pants can take your look from average to another level!

There’s a fine difference between skinny pants, baggy pants, high waters (some exceptions), and properly fitted dress pants. You want your pants to follow the proportions of YOUR body. And fortunately for us, getting the correct fit for dress pants is cheaper and easier than our upper counterpart, but will require a tailor’s touch to accomplish this.

Time to dive in!




If you’ve wondered why some trousers, suit pants, and dress pants come in a very long length with no cuffs, no worries, it’s typical. Most dressier pants are unhemmed and are usually a 38” in length. This isn’t necessarily a bad thing but will force you to go to a tailor.

My #1 pet peeve is men’s dress pants that drag on the floor. This should never happen. Promise me that if this is you, it stops today.

Well, how long should they be then? This is where a pants hem comes into play.

First off, you want to decide if your pants will be cuffed or uncuffed (cuffed pants are more traditional and what most of my pants have). Next, you need to decide which pant break you like:

  • No Break: (a.k.a high waters) Definitely not a classic style, and in my opinion, only looks good with loafers with no-show socks or socks that go with the outfit and formality. There’s a fine line between looking dumb and looking sharp with this look, but in my honest opinion, most look dumb.
  • Half Break: This is my go-to pant length. There is a slight fold after the pant barely touches your shoe while standing straight up. The pant length typically stops around ½-3/4 of the way down the back of your shoe. And yes, your socks will show when moving around, but not all the time.
  • Full Break: With the most classic break, you don’t have to worry about socks showing, except when sitting. In a full break, the pant length will extend to the top of your heel when standing straight up and should neatly fold ONCE at the top of your dress shoe.

And lastly, when you do take your pants to the tailor for hem alterations, make sure you bring your dress shoes with you! It makes it so much more difficult to hem pants without them.




Any issues with a pants waist really aren’t that big of an issue at all. Any skilled tailor can fix this quickly and it won’t break the bank.

Most men have upper legs/quad areas that are wider than their hips, causing issues with waist fit. The trick here is to size up your pants in order for your legs to have breathing room, then have a tailor take in the waist.

A quick trick to see if your waist sits correctly is if they stay up on their own, meaning you shouldn’t need to wear a belt. Your pants should sit around your upper hip bone without any support from a belt or suspenders. Another good measure of how your dress pants/trousers sit is to see how your butt looks. If you’ve noticed that your butt stands out more than normal, allows you to move, and stays up on their own, then your pants fit properly at the waist.

Remember that dress pants or trousers do not sit the same as chinos or jeans. Chinos/jeans are more casual and typically sit lower on one’s hips. AND FOR EVERYONE’S SAKE, these are not skinny pants. If you’re dress pants or trousers are too tight, “X” shaped wrinkles will appear at the zipper and pockets and you will be very uncomfortable, especially when sitting down.




The proper rise differentiates between having a permanent wedgie or drop cotch dress pants or trousers. The rise is the distance between the middle of the crotch seam to the top of your pants waistband.

A perfect pants rise elongates a man’s body, making him look more masculine.

A rise too high will throw off the proportions of your body, but a rise too low doesn’t have the formal look that you’re going for, and both are uncomfortable. Personally, I suggest getting a rather higher rise, compared to the standard rise of around 11 inches. A high, but acceptable pant rise should have your waistband at, or right below your navel.

The fit of your rise varies from person to person, but I recommend making sure this area of your dress pant is comfortable and looks right before purchasing. This is a very tough and expensive fix for tailors.




In my opinion, a pants taper sets an entire outfit, whether a suit or just dress shirt and slacks, apart from what other men are wearing. The taper is pretty much how loose or tight your dress pants fit along your legs. REMEMBER, these are not skinny jeans, and you want to be comfortable.

For guys that have worked extremely hard to get the physique they wanted, tapering your pants will make you stand out from a far. But, they aren’t for everyone. Men with larger upper bodies, compared to their lower halves will look oddly disproportionate. For me, tapering my pants makes me look much slimmer and elongates my entire body, which is what I and most men want.

This can be costly, depending on how much pant leg needs to be taken out. Most alterations for tapering a pants legs are from the knee down, so if you get pants that fit in the quad regions, you shouldn’t have any issues at all when tapering the rest of your pants legs.


And that’s all folks! If anyone, male or female, has any questions regarding men’s dress attire, don’t hesitate to reach out! And if you’ve missed last week’s post on minimalism for beginners, click here!

As always, don’t forget to like, comment, share, and subscribe!


“A man in a well-tailored suit will always shine brighter than a guy in the off-the-rack suit.”


Book of the Month:     “The Little Book of Common Sense Investing: The Only Way to Guarantee Your Fair Share of Stock Market Returns” by John C. Bogel


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