STARTED FROM THE BOTTOM
It's time to give your pants the break they so desperately need.
Whether you have a personal tailor or not, you still need to have your clothes tailored (at least your dress clothes). The best place to start is your dress shirts and suits, but an overlooked place to start is at the bottom, as in the bottom of your pants. If your pants are puddling all over your shoes, then that's not a good look bro. Get them hemmed (aka adjusting the length) at your tailor. This is step 1 of 2 in regards to tailoring pants. The other step is getting them tapered (aka shortening the width especially below the knees). Cuffing your pants is a personal preference, but you can take that up with your tailor (or ask me).
Anyway, we'll focus on the first step. Let's go through the various types of breaks which, by the way, are where the bottom of your pants rest on your shoes. Think of it as cropping your pants. That sounds weird... so here are some pictures for a visual stimulus.
Full break: Don't wear these pants this way if you're under the age of 74. It basically says you don't care about anything in life. It's a look we industry folks like to describe as 'puddling' or 'pooling', as mentioned earlier. This look is toxic and can damage your shoes from its toxicity. Don't damage your shoes man. Hopefully you get the idea with this pic, but I couldn't find any pants in my wardrobe where it shows the toxic pooling... this is bad enough to need some tailoring though. Notice the unevenness of the fabric and how it overflows.
Medium break: This is for the conservatives out there. You don't want to flash your cool socks, most likely because your socks aren't cool. But still, it's a personal preference. At least you show that you care. It's slightly better, but still not very modern.
Slight break: This may be where most find their comfort zone. You get that sock flash, but you don't feel like you're wearing high waters. This may be the crossroads of professionalism and style. Here's where you can start to see the pants straight out more. This may also be your best bet if you prefer to cuff them, but again take that up with your tailor and comfort level.
No break: This is my personal choice. I'll feel good knowing that if I had to ford a river in a real life Oregon Trail situation, my pants may not even get wet. I like how that feels. Anyway, it's the most fashion forward, so you have to be comfortable when you tell your tailor that you want no break. Much older gentlemen may give you a strange look, but that may have nothing to do with your pants.
Here's a side view of no break. Check those socks out! Keep in mind that when you sit, your pants tend to rise up even more. That's perfectly normal and expected. Just make sure you wear appropriate dress socks whenever a more formal attire is adorned. Back in the day, we used to make fun of kids with pants that look too short, calling them high waters. Now it's a fashion statement. Shame on me for not seeing that trend in the '90s.