Kelsey Ashley, The Stylist Behind Jayda Cheaves' NYFW Slay

She’s A Trailblazer: Meet Kelsey Ashley, The Stylist Behind Jayda Cheaves’ 2023 NYFW Slay

For Women’s History Month 2023, The Shade Room’s “She’s A Trailblazer” series celebrates women who have shattered glass ceilings and made groundbreaking contributions to creative lanes across social media. Join us to celebrate these inspiring trailblazers who empower future generations.

If you ask Kelsey Ashley about her earliest fashion memory, she’ll tell you it stems from her parents. Since the age of two, Ashley’s parents — her dad a photographer and her mother his muse — would dress her up in all kinds of extravagant furs and she would eventually grow up falling in love with the world of style through the pages of Vogue, Teen Vogue, and Seventeen magazine.

Years later, Ashley would find herself at the fashion capital of all HBCUs — and colleges — around the nation, Howard University. And would even go viral for her eclectic take on collegiate apparel. It was there that Ashley realized she wanted to pursue a career in styling.

[At Howard] there was this great experience of Black people really dressing up and expressing themselves through clothing… So that’s part of what drew me in.

From there, the public relations major took up a few internships in the field. But soon transitioned to her first fashion internship, assisting and styling professional athletes.

During this apprenticeship is when I realized I could have a career in something that I had been passionate about my whole life. I took what I learned through interning, and the skills that I gained in college, and I applied both to studying and breaking into the fashion industry.

Kelsey Ashley’s Rise To Teen Vogue

Between the years of 2014-2017, Ashley would lay the groundwork for her celebrity-studded stylist career with a strenuous schedule as an intern. “It was basically like a 25/8 job,” she recalls. “I, literally, was on call at all times.” Her days would consist of pulling clothes, prepping for fittings, packing suitcases for clients, cleaning out closets, email outreach, traveling, and more.

I remember my first time on the job I had to get a car and like three Ubers to fit all the bags that I had for this fitting [laughs]. It was so hard, and I was doing all this by myself.

However, Ashley’s hard work and diligence rewarded her with her very first job as a stylist — working at Teen Vogue in New York for the publication’s digital series Teen Vogue Take.

This was like a dream come true because Teen Vogue, Vogue, and Seventeen Magazine were publications that I had been inspired by, and created mood boards and scrapbooks ever since I was little. So to be in that space and to be working on a show the very first year that Teen Vogue went digital definitely gave me a push and motivation with my career. It gave me the confidence to put myself out there as a wardrobe stylist, and on social media.

Kelsey Ashley’s Iconic Roster

Kelsey Ashley’s iconic roster has consisted of — but is not limited to — the likes of rapper Lady London, singer Keyshia Cole, NBA player Ziaire Williams, and more!

But most recently added social media’s favorite “it-girl” Jayda Cheaves to her star-studded list of clientele.

Jayda, obviously, is an amazing client of mine. We actually just started working together, almost two months ago, but the experience feels like it’s something that’s definitely been aligned because we understand each other so much and she gives me the freedom to create however I want.

Kelsey Ashley & Jayda Cheaves Take NYFW 2023

When Ashley styles her clients she always reminds them that with every garment they wear, they are stepping into their “limitless power.” She’s successfully translated that intention through her meticulous work with Cheaves, as the pair slayed NYFW with back-to-back ensembles which were stylish yet fresh and unique.

Fashion today can be repetitive. I’m someone that likes to take risks and create that perpendicular lines through parallel fashion… I like to play with colors, layering, and mixing multiple textures… I like to convey a message through the things that I and my clients wear and not follow trends.

Ashley explained the concept behind two of Cheave’s NYFW 2023 looks.

For this look, Jayda was going to the Heron Preston show and when you go to these designer’s fashion shows, you want to incorporate the brand within the look. So Jayda has on a Heron Preston corset and featured is the brand’s signature orange tag. So I knew I wanted to incorporate orange into the look but still keep it elevated and streetwear. And a blazer is something that people have seen before, it’s classic but can be worn with denim, baggy pants, or a pencil skirt. And I personally loved that I’d never seen a skirt like this before — it was just something that was very different. Then, I incorporated the orange shoes to bring this whole look together. It was just very cohesive.

This was a look that Jayda and I collaborated on. The message on the shirt is so strong and as I said, fashion should be a way to express yourself. So, when you think about fentanyl, you think of a euphoric world in a sense. This is why we went the spunky route. What I also love about this look is that we mixed a lot of different textures.


You have a latex boot and a fur coat. The bag is a custom Oliver Prime and it features a gummy texture with spikes. The skirt is fuzzy and there are holes in the entire bodysuit. So bringing the look together was definitely a play on self-expression, portraying a message, and mixing different prints and layering… Both of these looks were like my favorites, for sure.

Kelsey Ashley’s “It-Girl” Fashion Advice & Where She Sees Herself Next

Kelsey Ashley’s biggest piece of styling advice for those looking to make an “it-girl” impression every time they leave their house is to never dim your light.

There’s a quote from the poem called ‘Our Deepest Fear’ by Marianne Williamson and it says ‘there is nothing enlightening about shrinking so that other people won’t feel insecure around you.’ And that’s always been an important piece of advice for me because sometimes it feels like we have to dim it down depending on where we live or where we’re going and who’s going to be there.


But it’s so important to just be yourself. Be bold and take risks but also don’t be afraid to shine. Sometimes people get dressed and question if others are going to judge them. But don’t dim your light for other people.

The star-studded stylist may be working with some big names currently, but she still has big dreams — one that includes working as a creative director in Rihanna’s fashion house, Savage X Fenty. Another involves working as a costume designer on the big screen. And her final goal is to elevate her brand, Beyond Measure, to become a well-respected fashion house.


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