Alright. So I admit it. Buying jeans can be pretty stressful, or at least, tedious. You walk into a store, and it seems as though an infinite combination of colors, rises, and sizes, await you. Even for the most adept shopper, this sight can be overwhelming. You have probably read, or at least seen, countless magazine articles attempting to solve this dilemma by matching a specific style of jeans to a body type. But I don't agree with that method. Shopping for jeans should not be approached as if it were a math problem. Unfortunately, no magic formula for finding the perfect pair of jeans exists. So here's an alternate method.
The first step in the process: forget about the size. It truly does not matter. Additionally, buying jeans and assuming they are going to stretch just leaves you doing a little jean dance every morning. Yes, maybe they will stretch a little, but then you wash them. And you are back to wiggling your butt into those jeans all over again. Don't pretend you've never done it.
Once, I was absolutely convinced that I found the perfect pair of jeans, but they were a size too small -- I know. My logic was slightly flawed. Instead of accepting the fact that they just did not fit, I convinced mom that they would stretch and purchased them anyway. Well, they didn't stretch. The only thing I dreaded more than wearing them was admitting to my mom that they didn't fit. So I wore them. They were so tight that the waistband bruised my hips. So please, avoid the bruises and buy the jeans that fit you, not the jeans that you wish would fit.
Before embarking on the search, you need know what style you are looking for. There are four basic decisions: baggy or loose, long or cropped, high-rise or low-rise, and flared or straight.
When considering how tight you would like your jeans to be, remember that tighter is not always better. Jeans don't need to be skin tight to accentuate your figure; similarly, baggy jeans do not ensure comfort or concealment. If jeans are too fitted, they tend to have unflattering effects and may even cause your skin (yes, skin not fat) to fold over the waistband, which is not ideal and can be easily prevented with a larger size. Furthermore, although baggy jeans have a reputation of hiding everything, they don't. I think the most flattering jeans are ones that accentuate your figure without being too form fitting.
Two effective ways of testing whether jeans are too tight or just right are the waistband and knee tests. You should be able to comfortably fit one hand (unclenched) under the waistband, and you should be able to see that your knee exists, but not be able to point out the different bones in your knee.
In terms of the length, the longer, the better. Longer jeans create an illusion of an elongated leg while cropped jeans tend to awkwardly shorten the leg. Granted, your jeans shouldn't be dragging on the floor either. But, whether they fall just above your ankles or just graze the floor is up to you.
In terms of the rise, I have a general rule: no thong, no camel toe. Low rise jeans may be the trend, but come on, how trendy do you think it is to display your lacy thong to the world? If the waistband does not comfortably fit over your hips, I recommend investing in some cute underwear. It's important to note, however, that really-high-rise jeans that may make your waist look really small also have a tendency to make other features look, well, not so small. The rise that hits right in the middle of the hipbone tends to look most flattering.
Lastly, you need to decide on the leg width. The most basic options are wide, straight, or pencil. Although you may have heard that wide leg jeans are more visually balancing and skinny jeans are only for skinny people, I beg to differ. I think it depends on your outfit and how you balance the pair of jeans with the rest of your ensemble. If you wear skinny jeans, then wear a loose top, and if you wear flared jeans, wear a more fitted top. If you don't want to think about "balancing" your outfit, then I would recommend straight leg jeans.
Once you have your four aspects of fit chosen, you can choose a color. If you are looking for a "go-to" pair of jeans, choose a neutral color such as blue, black, or gray. I think dark washes are generally more flattering and are more versatile in terms of dressy to casual wear, but choose a color that you love and feel comfortable in.
One last tip. When looking at pockets, just keep these two aspects in mind: simple and full-coverage. The best pockets are the ones that have nothing on them. Furthermore, pockets are most flattering when they fully cover your lower butt and even extend a little below it. When the pockets go slightly past your lower butt, the delineation between your butt and your leg goes through the pocket and creates the impression of a smaller butt.
Although some of these suggestions may seem technical and hard to follow, they are quite simple. First forget about the size and then make the four decisions about the fit. Then, choose a color. Use the waistband, knee, and pocket tests if you are having trouble deciding if a pair fits. This is just my philosophy; hopefully it helps.