Fit Lesson 2: Pants.

Posted on July 22, 2009 in Basic Fit Lessons, Casual, Denim, Dress, Fit Lesson, How to Wear a Sport Coat with Jeans., Pants, Popular, Tailoring, Tips.

I’m consistently amazed as to how often guys neglect to wear pants that fit them properly. Ill-fitting pants may even beat out ugly shoes as the most common mistake made by guys. I’m curious as to if this is because most guys don’t own a full-length mirror and rely upon their bathroom mirror that only shows from waist up.

By and large, creating hard and fast rules for pants is more difficult than for shirts. This is because there are so many different types of pants, each with subtly different valid style points. Shirts, generally, have the same rules for a casual shirt as for a dress shirt. However, there are some general rules to help you achieve cleaner lines.

Here are some counterexamples with pictures so you can get a feel for what I’m talking about. Notice the size of the pant leg relative to the model, the way the pants sit on the waist, and the length of the pants.



(CC) Photo credit: CharlesFred



Photo credit: Lucky Brand Jeans


Photo credit:

Photo credit: Eddie Bauer



Photo credit: Urban Outfitters

Contrast the above pants to the following, while noticing the same things: width of pant leg, inseam length and position on waist.



Photo credit: Gap



Photo credit: Banana Republic



Photo credit: Banana Republic



Photo credit: Banana Republic

Now for the rules.

Pant Leg

Just about every guy can get away with a little bit of a slimmer pant leg. This is a very common problem. Slim does not equal skinny. Just more trim. None of the pants in pictures #6-9 could be considered as skinny. This works even if you have large legs; it’s all about proportion. Odds are you can still maintain sufficient room to be comfortable while trimming a decent amount of fabric off.

Compare the jean width of pictures #1 & 2 to that of #6. All three are denim, yet notice how #6 immediately sets itself apart as clean and precise (apart from the more modern wash)?

The same is true for #3 & 8. Both are essentially chinos, but #3 looks like a kid threw on his dad’s pair of Dockers. In stark contrast, the pants in #8 looks like something a modern man would wear.

Inseam (the length of your pants)

This one is for my sanity. I have a visceral reaction when I see somebody in flip-flops with about 7 inches of pant leg under their foot. How is this even comfortable? If you’re wearing casual shoes you typically want a shorter inseam pant so that the cuffs aren’t dragging. I repeat. Do not let your cuffs drag. If your pants begin to fray at the back of your cuff, go to a tailor and get them shortened.

There can be variations in the leg size depending on what type of pants you’re wearing, but when it comes to your inseam the rule is pretty consistent: you typically want a single break in your pants. Envision a break as just a slight interruption of fabric from the otherwise clean lines of the pants. This keeps a simple straight line, with just a hint of excess fabric for comfort. You do not want that huge bundle of fabric hanging around your calves.

Check out picture #1. There’s a ton of fabric bunching on top of his sneakers. Some people like this look, I personally think it looks bad. It’s got all the negatives of a disheveled style, without any of the positives. Contrast this to all of the pants in #6-9. Notice how none of these pants bunch around the shoes, all with a subtle break right before you encounter the top of the shoe.

Here’s how these combinations work together, notice how #3 has a similar relative break in the pant length to that of #7 but #3 looks more sloppy. It’s because of the combination of the right length of pant with the wrong size pant leg (too big). #7 is the right combination.

Leg opening

Steer away from tapered leg pants. Moving on…

I know skinny jeans, and straight leg jeans are in, but I think for most guys they look incredibly stupid. Allow me to present exhibit A: Picture #5. I dare you to tell me that that looks good.

Skinny (and even some straight leg jeans) cause your shoes to look HUGELY disproportionate to the rest of your body. Like flippers. It creates a very odd silhouette.

So the lesson is wear the right type of pants for your shoes. For the most part, you want your pants to slightly cover whatever shoes you’re wearing. Don’t completely cover them, but also don’t expose too much of your shoe (as in #5).

You probably want your pant leg to cover enough of your shoes that about 45% of the total shoe is visible. This can be accomplished by pairing the correct leg opening with the correct type of shoe. For instance, if you’re wearing boots, wear boot-cut pants that have a slightly larger leg opening (as in #9).

Pleats v. Plain front

File this under “Brooks Brothers is not always right.” As a general rule, I really really really discourage pleats. For the majority of guys, flat front pants just look better. It’s cleaner and more modern. However, I do realize that larger guys MAY look a bit funny in flat front pants (the front-butt effect). So, I will say this: if you go with pleats, go with a bit more modern of a label. Think less so of the pants in #3 and more like #8. And if you do go with pleats, it is doubly more important to ensure that the pants aren’t tapered, just to keep the look modern.


You’re a man now. Do not sag.

However, that doesn’t mean embrace the high-waisted pants of the 90’s as in #2. Notice how the waist in #2 creates a silhouette of the jean that looks like a (  ), whereas the pants in #6-9 look more like |  |.

So, go with pants with a low-rise waist.  Some may feel this contradicts the no sagging rule, but low-rise does not equal sagging. All of the pants from 6-9 are types of low-rise pants. They sit comfortably below your waist, not falling off it (#1), and not riding up to your midsection (#2). They should do this without the aid of a belt.


Most modern trends dictate that cuffs are out. Though top-end designers like Thome Browne use cuffs. However, for most guys I think it’s best to steer clear from cuffs. Mostly because the bigger clothing brands that are on trend with the way pants should fit leave cuffs out of their modern pants. So, in some ways, cuffs can be a harbinger of an ill-fitting pant.

7 Responses to “Fit Lesson 2: Pants.”

  1. […] any of these shoes with a pair of dark, modern jeans, and a perfectly-fitted shirt for a great going out outfit. Or for a more dressy occasion, […]

  2. Zach says:

    I love the looks of the latter dressed men and am trying to update my style. my problem is finding a pair of pants that fit right. Even if they are tailored they just dont look right. Im a 33-34 waist but my butt and thighs are real thick and muscular. Is there any way around this?

  3. CYH says:

    @Zach- It depends on what you mean by doesn’t look right. It may be better (depending on your height) to have a pant that does not have any tapering at the ankles. As with everything, it really depends on proportion. You’ll have to be conscious of the relationship between your waist, rear and ankles. If you’ve got a large rear, sometimes it can be better if you have a more straight to moderate boot leg in your pants. I’ll DM you for more details.

  4. trendy says:

    Except Picture 1 & 2, I liked all….dress as per the situation..not always the standard sizes/rules works..

  5. Rani says:

    Your blog is a godsend! I’ve got to style a client, he has a large stomach and is a short, plus size, with bald head. I’m thinking of going with your sports jacket, plaid shirt look, but with slacks instead of jeans to stay on the smart side? Or should he steer clear of jeans altogether? In summary of your excellent blog post, would you recommend low rise, regular fit, flat fronted trousers with the shirt always untucked? For warmth, a cardigan worn underneath the sports jacket to give vertical layering.

    For suits where shirt need to be tucked in, should he wear braces instead of a belt? Thankyou!

  6. CYH says:


    Thank you for your compliment!

    How old is your client? I would say instead of the slacks with sport coat look, he could just go with a suit. I find that matching fabrics and colors between sport coat and trousers can be complicated and ends up not looking put together. I do acknowledge that it can be done well, it’s just a bit more difficult.

    For larger guys, I typically recommend a straight fit jean. The modern labels typically have these cut very nicely and walk the line between slim and relaxed. I recommend untucking the shirt only for very casual settings (unless it is a t-shirt or polo shirt). The length of the shirt should not extend past about halfway down the rear pocket of the jeans.

    Definitely love the look of layering for guys of all sizes. Cardigans immediately add a lot of style.

    The braces question is interesting. I would defer to the formality of the setting and his age. If he is older (45+) and typically engages in formal settings, then braces are acceptable. Otherwise, just go with a belt.

  7. Jean says:

    nag-shopping pud ko sa kohls momi Jess, sa clearance setcion pud for triz and tiara’s clothes. and with the deals i got, i guess i can always get great finds at kohls!

What do you think?