LOST SHDWS is dressing Offset and Kai Cenat in handmade workwear

When Ship Skylark launched his streetwear brand in 2020, it came with a tide of setbacks. Not only was he running the company by himself — from processing shipments to designing jeans by hand — but a former collaborator tried to steal his designs. The betrayal was one of many roadblocks that the now 29-year-old Skylark had to set straight. “Let’s just say, I went on Instagram Live [about it], and he no longer has a social media presence,” he says.

Five years later, Skylark is miles removed from that situation which for some would’ve been a major career disruptor. When we hop on a video call for this interview, he’s just returned home from his third ComplexCon where strangers came up to him dressed in his clothes. That brand he started in 2020 was renamed LOST SHDWS (née Lost Angels) in 2021 and is now experiencing a rapid, celebrity-assisted expansion. Over the past month alone, its array of sleek bombers and utilitarian cargo pants has been spotted on rappers like Offset and NBA Youngboy and Twitch star Kai Cenat, among others.

LOST SHDWS initially formed as a joint partnership with Rickey Bowen Jr., a designer behind a now-defunct label called Hidden Shadow. It allowed Skylark to merge his affinity for the streetwear giants (Supreme, BAPE, Virgil Abloh’s OFF-WHITE) with Bowen’s high-fashion sensibilities (Rick Owens, Dior). (The LOST SHDWS name was an amalgam of their two brands.) “I wanted to expand my mind more,” Skylark says of the endeavor. In 2021, Bowen departed the project and the two-person team dwindled to one, with Skylark again being the sole front-runner. Since then, he’s turned LOST SHDWS into fashion’s newest home for workwear with a distinct street sensibility.

Skylark’s journey into fashion stemmed from humble beginnings in Nashville, Tennessee, where he “never did an internship, never had any of those things. I had to figure things out on my own,” he says. Without the big-city resources or typical credentials — a fashion school degree or high-fashion connections — Skylark had only what a designer truly needs to inspire creation: the world around him, his Brooklyn-bred father’s sartorial influence inspired by New York hip-hop artists such as Nas and Jay-Z, and his favorite film icons like Dame Dash.

“I always say the TV raised me,” he says. “I was watching everything happen, but I knew there was much more out there for me. But no matter what, I feel like my greatest asset is being from Tennessee. I couldn’t afford things that I really wanted, but I went to my school’s design lab and taught myself how to sew, screen print, and embroider. I always asked myself: ‘How can I be fly and make pieces on my own?’”

His hobby eventually turned into a side hustle that captured the attention of his followers on Instagram. He’d post ‘fit pics on the platform pre-pandemic, and people would DM him about them. But things only truly began gaining momentum when custom sneaker pioneer John Geiger, a leading designer in the custom footwear space, reached out. “He saw some of my clothes, loved what I was doing, and wanted a pair of pants for Art Basel,” he says. After that, Skylark went from waking up to zero orders to 500 orders. “I was like, ‘Oh snap, my life is changing.’”

Today, LOST SHDWS represents the endless possibilities Skylark has created for himself despite the odds. His signature pieces include sun-painted denim, hoodies, and sweat sets that are shaped by his experiences with family, grief, perseverance, and purpose. “Even in the darkest moments, the sun is still on you. Your shadow is always with you, no matter what,” he says of the brand’s design philosophy.

His Fall 2025 workwear-inspired capsule collection is filled with Easter eggs that recall adversities and life events experienced during his journey: a Nokia T9 phone that was a gift from his late grandfather many years ago; a 1-800 number etched into a hoodie that translates to “you fuck,” an homage to a friend who passed away.

Skylark is now on a mission to take LOST SHDWS from emerging name to household status. In January, he attended his first-ever runway show at Paris Fashion Week; in September, he held an intimate dinner with Mass Appeal during New York Fashion Week. He’s been pouring into his ever-growing vision, setting his eyes on bigger and better goals: events, consistent drops, and, maybe, a spot on the fashion week calendar?

It’s not something he ever thought he’d do as a young boy growing up in Tennessee, but now, as a rising creative, he sees his chance to claim a seat at the table. “I didn’t want to follow the calendar. I didn’t ever want to have a brick-and-mortar, but I’ve changed my mind as I’ve evolved,” he says. “I can’t wait to be a part of the new vanguard of designers on the pulse of culture and creativity.”