I Conquered My Fear of Low-Rise Jeans With These Elevated Outfits

I’m a millennial, so I was young when the first low-rise jeans came along. Well, not the first, but you know what I mean. I remember the 2001 Levi’s commercial where computer-generated belly buttons sang Diana Ross’s “I’m Coming Out” (IYKYK).

Intrigued by the Y2K-era denim trend, I enthusiastically purchased several pairs of low-rise jeans. But truth be told, they ended up making me feel extremely uncomfortable. The low-slung silhouette never fit my proportions, and while some people were excited to show off a “whale tail” (an exposed thong), I was self-conscious about baring skin down there.

Several years later, when American Apparel said let’s go high and skinny, I was totally on board. I even remember saying that I wanted my denim to double as a bra—that’s how high I liked to wear my pants. And for quite some time, I remained committed to the high-rise look.

However, everything changed when I got diagnosed with uterine fibroids, and very suddenly, I couldn’t pull my pants up above the equivalent of a 20-week-pregnant belly. In desperate need of a quick fix, I reluctantly returned to low-rise jeans.

At first, the hip-skimming style served as a solution to my health condition. But even after I had a myomectomy to get the fibroids removed, I kept wearing low-rise jeans because I learned how to style them comfortably. I felt silly for having such stringent policies on the cut of jeans that I was willing to wear. So, nowadays, I’m open to whatever fit feels right.

If you’ve carried around some early-aughts trauma surrounding low-rise jeans, I’m here to ease your anxieties with some tips on how to wear them.

While some low-rise jeans are fitted, this style is considerably baggy. These pants are so spacious, they make me feel like I’m wearing a pair of cozy denim sweatpants. Here, I paired them with an oversized rugby sweater for an ultra comfortable feel. Not to mention, the length of this top prevents me from possibly showing off a whale tail.

This kind of roomy look is a great way to soft launch yourself into wearing low-rise jeans. Plus, it's the perfect outfit for those days when you want to feel like you’re wrapped up in a plush blanket.

Look at how low these pants are! Absurd! I never thought I would be wearing jeans like this and yet, here we are! These bottoms are made from recycled denim, so they're more accommodating than the low-rise jeans of yesteryear. They don't pinch or squeeze me in the wrong places and I feel okay with having more midriff exposed than I normally would.

Since these low-rise baggy jeans can drift toward the “boyish” end of the style spectrum, I like to balance them out with feminine pieces that show more skin. For this reason, I chose a cropped bandeau top and a matching shrug, both cut from a soft knit fabric. It’s quite cold where I live, so the shrug is not just stylish, but also very necessary.

These jeans are a little more fitted than the rest, but still incredibly comfortable. Paired with kitten heels, a designer bag, and a slim cardigan, this outfit works well for those moments when I want to feel more put-together—whether I’m running errands or hitting the town for a weekend outing.