It's no secret that the worlds of fashion and hip-hop are intertwined, from artists setting some of our favorite trends [1] like LL Cool J and Dapper Dan's logomania, to rappers actively working with design houses, like Kendrick Lamar's ambassadorship with Chanel. Women rappers are taking up this mantle as well: think Megan Thee Stallion and Glorilla's partnerships with Coach or Cardi B gracing the front rows [2] of Paris Fashion Week. Rapper Destiny "Dess Dior" Bailey [3] is likewise cementing herself as one to watch for her distinct personal style, which she describes as "expressive, bold, and a little unexpected."
Outside of her confidence-boosting hits like "Favourite Girl" and her upcoming single "IDC," the 26-year-old artist is known for her outfit posts on Instagram, where she's often seen sporting archive designer looks, from rare Chanel finds to Hermes Birkin bags. And her presence at Fashion Week [4] feels natural. "Fashion has always been one of the main ways I express myself outside of music, so being at [New York Fashion Week] feels really special," she tells Popsugar. "I'm incredibly honored to be here, to take it all in, and just live in the moment."
While Bailey appeared at some of the most major designer presentations this season, her attendance at Kim Shui's Spring 2026 show is especially referential. The New York-based brand took attendees to the top of the One World Trade Center, for a collection that emphasized the founder's Roman upbringing and "tailoring, traditions and texture" and Bailey's look for the show echoed those themes. With the help of stylist Alex Battant [5], the star wore a white blouse complete with a floor-kissing train from Front Row and various Dior pieces: an oriental midi skirt, orange wedges, and a fur-trimmed clutch. It's a look that perfectly fuses Shui's unapologetic approach to design and Bailey's unique, luxe taste.
Ahead, the St. Louis native gives us a closer look at how she got ready for the show, and the beauty must haves she can't live without, including a viral mascara from Too Faced.
On Her Skin-Care Routine Before the Show
Two products for that are must haves in Bailey's skin-care routine? The Laneige Water Bank Gentle Gel Cleanser [6] ($29) and the Caudalie Deep Exfoliating Cleanser [7] ($38). "That combo keeps my skin flawless all day," she says.
On Her Hair Essential For the Show
The star relies on the tried-and-true BaBylissPRO Nano Titanium 1" Digital Hair Straightener Flat Iron [8] ($110) to achieve her signature, sleek look, and on-the-go touch-ups.
On Her Makeup Essentials For the Show
"Concealer is my holy grail, and though placement is everything, I love a bright under-eye," she says of her favorite Fenty Beauty Pro Filt'r Instant Retouch Longwear Liquid Concealer [9] ($30). "It's my go-to hack for keeping my glam fresh and camera ready."
She also loves the Too Faced Better Than Sex Volumizing Mascara [10] ($29) for the perfect finishing touch to her makeup.
On Her Travel Essential For the Show
On the travel front, Bailey keeps the Dove Advanced Care Cool Essentials Deodorant Stick [11] ($9) on hand, especially for Fashion Week. "It's honestly a non-negotiable — if you forget it, you're definitely in trouble," she says.
On Unwinding After the Show
The rapper recently incorporated eye masks into her sleep regimen, namely the TheSleepGuard Pure Silk Sleep Mask [12] ($30, originally $40), which she describes as a "game changer" during such a hectic week.
Naomi Parris [13] is an assistant shopping editor at Popsugar, based in New York. With over eight years of experience and previous roles held on the brand's Beauty and Operations teams, she enjoys telling stories that merge fashion, beauty, and Black culture. Naomi has also lent her skillful pen to Essence Girls United, Elle, Bustle, and Elite Daily. When she's not crafting shopping roundups, high-profile features, beauty op-eds, or trend guides, you can find Naomi behind her blog "Eli-Nay," where she inspires readers through style guides, cultural pieces, and innovative content on her Instagram.