In most areas of life, I tend to be risk averse. I drive the speed limit, I arrive at the airport hours early (just in case), and I’ve never seen a skydiving video and thought, “oh, that looks fun.” Even with fashion, my riskiest looks rarely make it out of the home. As my boyfriend has previously advised: If you’re overthinking it now, it’s not going to get better once you’re out and don’t have the option to change (he’s right). But sometimes I see an outfit that, despite being out of my comfort zone, I feel compelled to try. And spoiler alert: it’s almost always on Hailey Bieber.

The Rhode Skin founder has found a way to make risk-taking seem not-so-risky by pairing styles teetering on controversial with classics. When the model wore a dress so micro it might be a skirt, she paired it with sheer tights, simple black heels, and a timeless wrist watch. And when she opted for a Michelin Man-inspired, marshmallowy puffer, she wore it with a simple pair of blue jeans. And just this week she made me want to throw caution to the wind when she paired a simple cropped-tee with not one, but two controversial denim styles at once.

Low-rise and ultra-baggy jeans have, on their own, both been hotly debated though emerging styles, and Bieber just put the two together. While she rocked a $564 pair from Martine Rose, you can get a similar look for less. I found nine low-waisted, roomy styles from retailers including Amazon, Nordstrom, Madewell, and more, with prices starting at just $59.

I’ve always had a soft spot for Gap’s jeans (I worked at Old Navy in high school and used that employee discount to raid Gap’s denim section). The brand’s denim is soft, flattering, and not overly restive, and I love that the lower price points allow me to test out different styles that I wouldn’t typically reach for. Shoppers describe its Low-Rise Stride Jeans, whose 10-inch rise sits below the natural waist, as “so flattering,” “comfortable, and true to size.” Another explained that they loved how the loose leg is “wide but…fits through the hips” while being “just fitted enough not to make them look too baggy.” Plus, they’re currently on sale.

Now that Madewell’s Slouchy Boyjeans — which I’ve been eyeing since their arrival — are finally on sale, I think it’s officially time to add them to my cart. This vintage-inspired style is crafted out of 100-percent cotton. While the non-stretch nature of this denim might be intimidating, it should be noted that the jeans do give over time, adjusting to your specific body type and relaxing in areas where it’s needed most (TLDR; after a few wears, they’ll perfectly fit you). One shopper called the best-selling style “on trend and very comfortable,” with another adding that they felt so good while they’re on, they didn’t want to take them off.

And at Nordstrom, you can grab a similar style to Bieber’s for just $59 with Hint of Blu’s Raw Hem Wide-Leg Jeans. By pairing a roomy leg with a raw hem, Hint of Blu created a jean with a lived-in look from the first moment you put them on. One customer wrote that the “best part is the stretch,” noting that it helps them “fit so well.” Others, of course, loved the style, with one writing, “I think they look so cool,” adding that they’re “comfortable,” “cute,” “soft,” and “true to size.”