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In my short life, I've gone through numerous denim philosophies. There was a time when I only wore light blue Gap jeans, which I would "French roll" so the cuffs were about two inches above my socks. Then came Farlo's, stretchy legging jeans—some with zippers at the bottoms. When I could, I stole my older sister's perfectly shredded, tapered Levi's, long and bunched at the ankles. Later, I gave up on flattering my figure altogether (a form of rebellion?) and wore, exclusively, men's Lee's in a 40-inch waist, synched with a belt around my hips. Though, according to my mom, I was free to express myself however I wanted, on one occasion, she blurted out a distraught "Why are your pants like that?!" A more lady-like version emerged from this trend: Sailor jeans, which were a must-have in high school. They were cut low on the hips, wide in the legs, and flared to cover almost your entire shoe.

We all know what happened next: thong-flaunting boot-cut jeans captured the hearts of Americans in the late 90s. The amazing thing about this trend was the way it was hyped to flatter any figure. The slight flare in the legs balances and minimizes big hips, jeans pushers said. Yet, if a lack of hips is your problem, it will somehow enhance them. The low waist elongates the torso! The boot-cut lengthens the legs! Apparently, these were miracle jeans. But in the last couple of years, with an alarming number of new designer denim brands flooding boutiques and department stores, young women have been altering their Paper Denims, their Joes, and their Ernest Sewns to fit tight around the knees and stay slim through the ankles, which none of them did. Just as retro slouchy bell bottoms in the early 90s gave way to the "hipster flare", a return to Rock 'n' Roll has finally destroyed the boot-cut.

Today's denim craze is still, for the most part, low on the hip, though there are always rumblings that this is about to change. Denim designers have finally caught on to hipster boys and girls and are pushing "Drainpipes" or "Cigarette" jeans. Sometimes, they're simply called "skinny jeans"—but what if you're not skinny? Sure, these things look great on Kate Moss, but how much coke does one have to snort to fit into them? Being un-skinny myself, I took to the streets to try on pair after pair, and didn't stop until a lump began to form in my throat. Here's what I learned:

Dark and Lovely, and Simple No one should be subjected to the sight of herself in a light colored version of anything skin-tight—trust me. Even Scarlett and Sienna wear their drainpipes in dark blue or black. But a lot of black jeans have contrast stitching, which can be tacky (Diesel makes a pair for $140 that would be great if there were less back-pocket embroidery). Earl Jeans' "Sienna" ($160) are very dark blue and pleasantly plain. X-Girl, despite a penchant for giddily ornamented clothing, makes simple stretch jeans in dark or faded black for $118. They come in sizes zero, one, two, and three. If you wear a waist size bigger than 30 or 31, don't torture yourself—move on.

Like it Raw Thick, stiff, "raw" denim will keep you cozy, if constricted, all through the winter months. I was pleased to see a longer, leaner version of my legs in a pair of Denim Bird jeans, but when I turned, I realized I had traded in my butt for these new limbs. Word on the street is that these jeans are never to be washed and should be purchased very tight. Apparently, they will expand where they need to as they wear in.

Cheap and Chic If you feel like a sucker lusting after—or actually purchasing—$200 jeans, you should. There's nothing less Rock 'n' Roll than that. Do like the punk kids have for decades and head to Trash & Vaudeville for a pair of "Stretch Fucking Jeans" (from a company called Lip Service) in black. A return to simpler times, they come in small, medium, and large, and cost $53.