Drew Jessup for Levi’s® SecondHand
Campaigns /
July 2024
Model, creative director, and thrift store cowboy Drew Jessup knows a keeper when he sees it. An ever-evolving style fueled by modern trends, eras past, and really great hair – he brings an unmistakable uniqueness to our latest collection at Levi’s® Williamsburg.
Drew Jessup for Levi’s® SecondHand
Launching July 15th, this hand-selected capsule of vintage Levi’s® bottoms, Truckers and shorts from the 80s, 90s, and early 2000s will be featured exclusively at Levi’s® Williamsburg. Don’t miss your chance to strike vintage gold.
Levi’s® Williamsburg
120 N 4th St
Williamsburg, NY 11249
We sat down with Drew to get his take on how thrifting and repurposing elements from the past helps to shape his style today.
Tell us about your journey to living in NYC
My story mirrors that of many NYC transplants who arrived with a dream, no money, and no plan. In 2012, during my first semester of college in Maine, I realized my passion for clothing went far beyond what I initially thought, leading me to leave school after a semester eager to explore the ‘real world’. By 2014, after working various odd jobs, I landed my dream internship with the fashion brand KJP in Rhode Island. There, I was first introduced to modeling, styling, photography, and building editorial concepts. My intermittent work with KJP garnered interest from a NYC modeling agency. After couch surfing with friends, I eventually found an apartment in Chelsea, marking the beginning of my new life.
How did you get into thrifting?
My father laid the foundation for my thrifting journey through his love for high-quality, durable, and timeless items. Growing up in Maine, with the nearest department stores an hour away, I found myself gravitating towards my local Salvation Army and Goodwill. Finding a one-of-a-kind worn-in treasure always excited me more than buying something new.
How would you describe your style?
My style is ever-evolving, influenced by modern trends and my latest inspirations from different eras, music, films, literature, and hairstyles. For me, everything starts with my hairstyle, which is tailored to the baby-mullet and dirty mustache I've been rocking for over two years. Ultimately, I aim for a cohesive look that balances silhouettes, incorporates muted tones with a pop of color, combines complementary textures, and doesn’t include statements that speak louder than their counterparts. It’s classic and creative, masculine and feminine, and always trying to make it feel personal.
Where do you get your style inspiration?
Pinpointing my style inspiration is challenging, but living in NYC is likely the overarching influence. I'm a sponge, absorbing daily influences from the city's large-range of street style, my friends creating their own personal-style, and uncovering the timeless looks of old artists.
Do you have a favorite fit?
Occasion aside, I feel most like myself in a vintage pair of flared denim, cowboy boots or loafers, a tank top, a vintage leather blazer, dainty jewelry, and a great hair day.
What do you look for in a vintage piece?
Firstly, I never buy unused vintage—I'm drawn to pieces with quality and character. The distress and stains tell an untold story, creating a connection to history and heritage while breathing new life into the past. Dramatically speaking, finding a perfectly worn-in ripped T-shirt, aged denim, or a weathered leather jacket with its unique marks is exhilarating.
What stands out about fashion from each era in the collection: 80s, 90s and early 2000s?
The 80s, 90s, and 2000s eras all present stand out styles with their own individual flavors. I love the 80s straight-leg 501’s, distressed by wear, and accompanied by a slightly oversized trucker jacket. The 90s grunge scene also remains relevant, with stone-washed 550’s or cut-off baggy denim shorts and a larger oversized Trucker. For the 2000s, the bootcuts are a staple, but the low-rise baggy women’s jeans and skirts stand out the most.
