10 Underrated New York Menswear Brands We Wish Still Existed

Approximate lifespan: 2006-2010

Harry McNally, Bobby Waltzer, and Nick Poe formed PegLeg straight out of high school. Their passion project hit all the marks on what the market was really feeling at the time (and wouldn't look out of place now, either): all-over print gear, colorblocked shirts and shorts, and even floral print sweatsuits. The mid-2000s brand was one of the first convergence streetwear brands blurring the lines between fashion subculture and street culture, looking completely at home in both worlds, and collaborating with the likes of Opening Ceremony and G-SHOCK. Purportedly the PegLeg story even helped influence the short-lived HBO series How to Make It In America. These days brand founder Harry McNally can be found taking photos more than designing gear, while Bobby Waltzer is still flexing his design muscles, most recently for a new art/fashion venture known as 212.

Approximate Lifespan: 1871-1968

Hometown: Wappingers Falls, NY

Sweet-Orr was the East Coast's answer to Levi's and Carhartt. In its heyday, the workwear manufacturer made pants so strong that there are eyewitness accounts of real-life tug o' war contests where they were used in place of a rope. Under the guidance of Clayton E. Sweet, Sweet-Orr outgrew its hometown of Wappingers Falls and moved to a larger facility and factory in Newburgh in 1887. At its peak, Sweet-Orr was making jeans, chore coats, and other workwear that vintage heads still freak out about. Unfortunately, as manufacturing costs rose, more clothing was made overseas, and the public's tastes changed, Sweet-Orr became a victim of the times. By the 1980s Sweet-Orr had become more of a regional denim brand, providing colored jeans, worker stripe chinos, and painter's pants to upstate NY teens. While there have been some attempts to revive the brand via licensing, it hasn't really reclaimed its former glory, and besides, you can't really beat the O.G. stuff. The old Sweet-Orr factory became something of a historical landmark until it burned down in the 1990s.

Approximate lifespan: 2010-2013

Cutting his teeth as one of the design dudes behind hickey, another label on this list, Ian Velardi's debut collection came out swinging. Velardi's strength has always been mixing the utilitarian with the flourish, and items like a down-filled robe and camouflage prints with animals hidden in the pattern add an extra layer of detail and ingenuity to his garments. He did get some notable nods during his eponymous brand's lifespan, like being named one of GQ's 2012 Best New Menswear Designers in America, but in the end the line unfortunately buckled after just four seasons. Currently, Velardi is utilizing his talents as the design director at Bonobos, where he helped transform the bro-brand into a full-fledged purveyor of lifestyle, beefing up the in-house line with suiting, denim, and even a specialized line of non-garish, slim-fitting golf apparel.

Approximate lifespan: 2002-2007

Everyone knows Brendon Babenzien as the man behind Supreme's menswear-meets-streetwear sensibilities, but he spread his design wings long before that. Growing up in East Islip in Long Island, Babenzien may have been enamored by skating and surfing, but definitely grew up around northern prep staples. His dad was a lacrosse coach, for crying out loud. Cutting his teeth in the streetwear world at PERVERT with Don Busweiler and then Supreme, in 2002 he started a line called Noah, a line that flipped prep staples on their head and rendered them with extremely high quality. The stuff wasn't cheap, but it was good. Noah was a pioneer in the "rebel prep" aesthetic touted by brands like Rogues Gallery and Band of Outsiders and taken mainstream by Rugby Ralph Lauren, and it was sold in "if you know it, you know it" shops like Nom de Guerre. Though Noah is no longer, its legacy lives on in pieces like Supreme's LoroPiana trench coat and nautical block stripe basics.

Approximate lifespan: 1993-2009

Long before street art was a genre you could find on a Chipotle paper cup, prominent names like Futura and Stash were early adopters of the idea of clothing as a branding tool and canvas. Sure, nowadays the likes of Shepard Fairey and Uniqlo have the fusion of art and fashion down to a science, but in NORT/RECON's heyday, it was the perfect confluence of style, street culture, and sneakerheads. Stash's Subware brand was one of his many undertakings—RECON had its own label, and the obscure Project Dragon is held in high regard by some heads—and the one most people remember. It was a pioneer in co-opting elements of graffiti and street art and rendering it onto clothing. It also evolved the idea of the brand, dropping some fire collaborations with cult labels like Acronym, resulting in awesome military jackets that would still kill today.

Approximate lifespan: 2006-2012

Simon Spurr is a British-born designer who learned the biz under several of the GOATs. Plucked straight from college in London, Spurr worked at Yves Saint Laurent under Hedi Slimane, then did a short stint at Calvin Klein before working for none other than Ralph Lauren, where he was the design director for the label's tony Purple Label and Black Label. Establishing a reputation as a master of all things luxe, SPURR was launched in 2006 as a line of ultra-premium raw selvedge jeans that combined a minimal design with great fits and top-class materials. The following season it became a full line, developing notoriety for being as expensive as it was eye-poppingly good.

Everything from exploded houndstooth suits to buttery oxblood moto jackets was executed at a superb level, which is why it was totally surprising when Spurr left his own brand in 2012 (it shuttered shortly after). For a time, Spurr took his talents as a design consultant for Tommy Hilfiger, but has recently returned to the game in full force. As the creative director of storied English brand Kent and Curwen, Spurr's debut collection for the brand proved he's still got his menswear chops intact.

Approximate lifespan: 1976-1990

Like the other famous Will Smith, designer Willi Smith also hailed from Philadelphia. That's about where the similarities end. Founded in 1976, WilliWear and its designer quickly became one of the most successful fashion brands by a black designer, selling about $25 million worth of clothing in the mid-80s. His collections were known for being as bold as they were affordable (uncharacteristic of a high fashion designer at the time), and he was a pioneer in experimenting with pattern and color in menswear. In 1985, he earned a Cutty Sark award for his men's designs, and shortly before his untimely death in 1987, his work was cemented in pop culture history when he designed Mary Jane Watson's wedding dress for the Spider-Man comic books.

Approximate lifespan: 1987-2004

PNB Nation started as a brand that took the old "Post No Bills" abbreviation prevalent on New York City construction sites and flipped it into terms like "Proud Nubian Brothers," "People Never Believe," and "Puerto Ricans 'N Blacks." In doing so, it embraced and promoted multiculturalism in a way that seemed more inclusive than exclusive, like those "It's A Black Thing... You Wouldn't Understand" tees. Founded in '87 by a group of high school graffiti writers, Roger "Brue" McHayle, James "Bluster" Alicea, and Sung Choi. The crew was rounded out by Isaac "West" Rubinstein and Kahlil "Zulu" Williams, himself of mixed Japanese and black ancestry.

"The vision and intention was to be socially relevant for our people, outside of race," Brue told LTD. PNB's "it ain't where you're from, it's where you're at" approach ascribed fans of the brand that aligning with its values didn't make you a poser like if you were a non-skater who wore skate labels. As the brand grew, its original founders eventually sold the company, and its clothes lost a certain sense of authenticity—and profitability. The founders would go on to run shit in different ways. Brue worked for Nike, West worked for Supreme, Bluster designed for Rocawear, Zulu became the design director for American Rag, and Choi founded sneaker brand CLAE.

Approximate lifespan: 2005-2010

Love Club Monaco's current menswear? Thank hickey for it. The younger offshoot of storied NY clothier Hickey Freeman, hickey's take on American sportswear was trad minus the t. Designers Aaron Levine and Ian Velardi really let their freak flag fly with the label, introducing bananas pieces like rubberized raincoat yellow harrington jackets, blackwatch toggle jackets, and Donegal tweed tuxedos. They even used a marijuana leaf as their logo on items like polo shirts, adopting a subversive attitude and aesthetic into their clothes that channeled the best parts of DickieGreenleaf and Mr. Ripley.

For the burgeoning #menswear scene, hickey was a gamechanger, one of the first brands that encouraged dudes like Lawrence Schlossman that it was totally cool to have fun with your clothes. Post-hickey, Levine and Velardi both dipped their design toes into new endeavors, but most visibly, Levine can be seen bringing that same "choose your own menswear adventure" sensibility into Club Monaco's consistently envelope-pushing offerings.

Approximate lifespan: 2003-2010

Nom de Guerre opened as a shop that was its own best-kept secret. Located in a multi-level basement across from Atrium, its wares were the kind that dudes would look at and ask "Yo, where did you GET that?" to which you were supposed to shrug and say "I forget." What started as a line of minimal slogan T-shirts evolved into a collection that took military-inspired clothing to new levels of fire flames. M-65s were rendered in water-resistant blackwatch plaid fabrics from the British Millerain Company. Cotton peacoats were cropped, slimmed down, and painstakingly made in Japan. The brand's luxe take on mil-spec paratrooper pants have become a cult item amongst menswear nerds. So much so that when the second A.P.C. Kanye collaboration dropped, many aficionados were quick to point out the similarities between the NDG joints and the collection's Army Pants.