Poorly fitted bottoms (jeans, pants, skirts) are a distraction, to say the least. Think of it this way, the bottom half of your body represents 50% of your exterior, physical self (because half is equal to 50%). That's a lot of you that should look as good as possible. This means that saggy butts, dangerous amounts of thigh exposure, and unintentionally visible ankles are not casualties of your style.
Jeans:
I worked at Gap for about 2 years while I was in college. I absolutely loved my job there (really). Every day I worked I got to sift through new product, organize clothes, and fold things. Those are things I (oddly?) enjoy. If you spend enough time at Gap, you become quite talented at being able to fit people visually, especially when it comes to jeans. So, as always, I'm the self-proclaimed expert.
Step one, tell yourself what your favorite part of your lower half is (mind out of the gutters, please). This serves a two fold purpose: you deserve to compliment yourself and it gives you some direction where to start. My favorite part of my lower body is the sheer length of my legs. I'm about 6 feet tall and don't shy away from that fact. When I am in search of jeans I look for something that shows off this attribute. Identify what this attribute is for yourself. Maybe it's your bum, or maybe it's shapely calves. Once you have identified your best assets, you can then narrow which jeans are probably going to work the best with your body. Using myself and my legs as an example, I go for trouser and curvy fits.
Step two, find your length. I personally believe that all women's bottoms should be sized like men's. I am not a "long," "average," or "short" individual. I need a 36 inch inseam (the length from your crotch to your feet), not whatever the arbitrary "long" means. Regardless of my preferences, not many brands measure women's inseams as such, so you will have some try-al (see what I did there) and error ahead of you. It is important to remember several things when considering length. Exactly what types of shoes are you most commonly going to wear your jeans with? Flats? Sneakers? Heels? Each of those shoe types comes with a need for a different length. Additionally, what is the fabric makeup of your denim purchase? This will affect about how much they shrink if you chose to dry them at any time. The rule of thumb I operate on is that jeans will shrink about a half inch when washed and dried mechanically. This doesn't mean you should just go with the longest pair you can find and hope for the best. As previously posted, it is easier to fix a something that is longer than it should be, than something that is shorter than it should be. No one enjoys the ratty look of jeans or pants that have been drug across the pavement a few too many times.
Step three, pay attention to petite and tall. This step may not apply to everyone. Tall is not the same as long, and petite is not the same as short. Long and short, when referring to length, are sort of like the "extra helpers." They provide, or take away, a few extra inches from the regular length in the inseam alone. These sizes make no proportional changes to the waist, hips, or crotch. This means, that is you need more than about one to two inches of extra or less length, you should be looking at tall or petite sizes. Tall and petite sizes take in to account that when you were growing, your femur was not acting alone. These sizes have made adjustments to how the overall garment fits in areas other than length. This also applies to other clothing items such as jackets or dresses.
Step four, get those jeans on and try them out. Walk around. Sit down. Do some lunges. Twerk. Do whatever it is that you need to do to make sure they fit in all the right places. If you can't walk, sit, or stand comfortably in your jeans before you have purchased them, nothing is going to change later.
Pants:
Pants follow the same rules as jeans but with a few other areas worth noting.
Camel toe isn't a good thing. It's a fun thing to joke about, but nothing worth committing to yourself. Unlike jeans, pants more frequently find themselves in professional or work settings. As a result, shirts tend to be tucked in, which adds an area of visibility that you may not have considered otherwise. Make it a priority to be very aware of how your pants fit in the crotch when you are in-store. Additionally, the fabric in pants tends to be less discriminating than denim, which means they may be more apt to cling to you in a way that makes you uncomfortable.
Skirts:
I would argue that skirts have infinitely more versatility now than they ever have. They work for every season and every outing. This, of course, means you should pay attention to proper fit.
The biggest lesson I can provide you regarding wearing a skirt that fits correctly, is pay attention to two things: your hips and your height.
Most skirts, unless high waisted, are intended to sit on your hips. If there is a substantial disparity in the size of your hips and waist (hourglass figures) you will likely run in to the problem of having skirts slowly ride up to your natural waist. Losing three inches of a skirt in an upward direction is a guaranteed disaster.
Similarly, your height with play with the perceived proportion of a skirt to your body. For example, if my friend is 5'5 and I am 6'0, identical skirts will not look identical on either of us. Her skirt may rest naturally three inches above her knee, while mine is exactly two inches below my butt. Unfortunately, I'm not going for this look. If you are plagued by a similar situation, this is a good time to educate yourself on the perks of sizes in tall and petite (as mentioned above).
Follow this guide and you may save yourself from certain fashion disaster. Hopefully, you can also save yourself some green by purchasing clothes that look good and fit, instead of opting for one over the other in a fit of exasperation.