Founded in California in 1990 by Erik Brunetti with the help of street skater Natas Kaupas, FUCT is arguably the first streetwear brand to present social and political commentary through satirical graphics. Brunetti—who came up as a graffiti artist under the name of Den One in 1980s New Jersey—funded FUCT with his own money and no game plan. It is this DIY attitude that has helped keep FUCT unique despite the proliferation of streetwear brands over the past twenty years. Brunetti’s brand has developed a cult following for tongue-in-cheek, hand-drawn graphics that appropriate pop-culture logos and characters, such as Pepé Le Pew holding a joint, a camel with a missile strapped to its hump labeled “Air Jordan,” and—most famously—a riff on the Ford logo featuring FUCT’s name, which Brunetti received a cease-and-desist letter for in the early ‘90s.

Despite a 2005 sabbatical, FUCT is still going strong, as demonstrated by the relatively recent introduction of the SSDD (Same Shit Different Day) line, which pairs Brunetti’s singular graphics with a subtler design ethos and higher-quality production. The brand counts HBX and End Clothing among its current stockists, and even released a twenty-year retrospective in collaboration with Rizzoli in 2013; the book offers an in-depth look at many of Brunetti’s graphics, which helped pave the way for artists like Shephard Fairey, even if FUCT isn’t as big of a name as OBEY.

Rhode Island School of Design roommates Adam Silverman and Eli Bonerz (along with Eli’s brother Adam) opened the original X-Large shop on Vermont Street in Los Feliz, Los Angeles in 1991. In the beginning, the store carried mostly workwear and vintage clothing, along with deadstock adidas and Puma sneakers, while blending hip-hop, skate, and club aesthetics. However, with funding and free promotion from the Beastie Boys’ Mike D, the Bonerz brothers and Silverman quickly shifted their focus to their in-house line, featuring the now famous gorilla logo (which debuted a year before Nigo’s A Bathing Ape).

X-Large grew rapidly, opening shops in Chicago, Seattle, Toronto, and Tokyo and topping 1 million in sales by 1993—the same year the brand introduced its women’s line, X-Girl. Designed by Sonic Youth bassist Kim Gordon and stylist Daisy von Furth, X-Girl channeled skater girl and riot grrrl aesthetics while creating clothes for “women curves up and down.” With on-trend advertising, such as X-Girl’s 1995 film directed by Phil Morrison and co-written by Chloë Sevigny, and X-Large’s “Action Suit” campaign starring John C. Reilly, the brand seemed destined to continue its dominance.

Yet, despite arguably being one of the first true streetwear brands and developing a cult following (especially in Japan) X-Large—much like Stüssy—lost some of its original crew and struggled to maintain sales in the late ’90s and much of the 2000s. However, with the current crop of high-end, graphic-based streetwear brands, such as Gosha Rubchinskiy and Cav Empt, X-Large has reestablished itself in the market, boasting stints in stock at stores like Notre, V-Files and (the now-defunct) Reed Space.

Opened in 1998 as a small record store on Lower Haight in San Francisco by visual artist Matt Revelli with the help of college friends, Matt Yep and Dennis Kennedy, Upper Playground has grown into a hundred-plus artist collaborative and multi-million dollar clothing brand over the past twenty years. Recognizable for its walrus head logo, Upper Playground has been at the forefront of recontexualizing fine art by taking it out galleries and screen-printing it on T-shirts. Ironically, the brand also has its own gallery, FIFTY24SF, which stands adjacent to the main shop in San Francisco and features work from many of the artists Upper Playground collaborates with on clothing. The brand also produces accessories, fine art prints, books, DVDs, toys and home goods, and has helped expand the reach of artists like Sam Flores and Jeremy Fish, who have established sub-brands under Upper Playground’s umbrella.

In 2001, Adam Krohn joined the company as a partial-owner, a move that proved instrumental for the brand’s subsequent growth. Between 2006 and 2008, Upper Playground opened shops in Berkley, Sacramento, Portland, London and Taichung, Taiwan and in 2007, moved into a 6,600-square-foot warehouse in Hunters Point, California. Revelli’s company has expanded into womens and baby clothing over the years and, although the brand doesn’t produce a fully conceptualized fashion line, has been instrumental in developing the dialogue between fashion and art.

Founded in 2002 by professional skateboarder Keith Hufnagel—who cut his teeth in 1980s NYC before moving to San Francisco in 1992—HUF began as a shop meant to bring skateboarding, streetwear, and sneaker cultures together. Hufnagel christened his store after the nickname he developed while skating around New York, tagging “HUF ONE” throughout the city and—despite its growth during its decade-and-a-half existence—the brand has maintained its skateboarding roots. HUF originally stocked a small range of in-house shirts and hats, along with an array of sneakers from other brands, but now produces a full line of clothing, sneakers, and accessories, some of which are made locally in LA.

In 2011, HUF closed its original location on Hayes Street in San Francisco, but Hufnagel’s brand is hardly hurting. On the back of its own box logo and Plantlife (see: weed) socks, its become a go-to for skaters and streetwear fans alike. Since it’s also opened shops in Los Angeles, New York, Tokyo, Osaka and Nagoya over the years, its footprint is bigger than ever. If anything, the 2011 store closing mainly represents Hufnagel’s increased focus on refining and expanding his brand’s own line of offerings; the original location was predominantly known as a sneaker store and, in the years since it closed, HUF has successfully solidified a space for itself within the skateboarding market, while producing products of increasing quality. This includes the Classic Hi sneaker, which is entirely made in Japan.

Opened in 2002 in Los Angeles as a sneaker and clothing boutique by art director James Bond and Union and Stüssy alumni Eddie Cruz, Undefeated (often stylized as UNDFTD) has been an influential force in sneaker culture and streetwear since its inception. Bond first conceptualized the shop after quitting his job and travelling throughout the South Pacific with his wife; their trip convinced Bond that there was a dearth of local men’s lifestyle stores throughout the world and that starting his own shop in his hometown was the first step in solving the problem.

Similar to its predecessors like Supreme and X-Large, Undefeated introduced its own in-house line not long after opening. The clothing features athletic-inspired garments, many of which bear the brand’s unmistakable “five-strike” logo, designed by heavy-hitting graphic designer Adam Levite. The brand has grown rapidly over its fifteen years and now boasts four flagship stores in California, one in Las Vegas, and another two in Japan. Throughout its history, Undefeated has collaborated with all the biggest sneaker brands (Nike, Jordan Brand, Converse, Adidas, New Balance, Puma, and Reebok to name a few), as well as the likes of A Bathing Ape, Visvim, and Timberland. Without question, Undefeated consistently generates a level of hype that is nearly unparalleled for a brand of its size, and has remained as one of the most well-established fixtures within—not just the California streetwear scene—but the global streetwear conversation.

Founded in Los Angeles 2003 by law school classmates Bobby Kim and Ben Shenassfar, The Hundreds began as a humble T-shirt operation inspired by skate, sneaker and street culture. Kim (aka Bobby Hundreds) and Shenassfar (aka Ben Hundreds) paid a friend with a 2-color press in his backyard a few hundred dollars to screen-print a small line of T-shirts for them, but after numerous excuses and months without contact the friend delivered only a small quantity of usable shirts. Kim and Shenassfar managed to sell a handful of the tees and used the proceeds to source a reliable print shop. Although initially put off by The Hundreds’ small orders, the print shop grew to value the relationship as Kim and Shenassfar returned again and again, each time with larger orders. Eventually, the owners of the shop offered to sell their operation to Kim and Shenassfar, which allowed The Hundreds to quickly and efficiently print collections—even while providing screen-printing for competing brands.

The Hundreds’ early collections consisted of T-shirts printed with ironic graphics and characters (the most famous being “Adam Bomb”), but the brand has expanded into a fully-fledged collection over the past ten-plus years, and now offers everything from denim and outerwear, to socks and sunglasses. The Hundreds presented its first lookbook in 2005 and opened its first shop on Fairfax Ave in 2007, just down the street from Brooklyn Projects—which served as the brand’s first collaborator. By 2008, The Hundreds reputation had grown large enough to collaborate on limited-edition T-shirts with Disney and, by 2011, the brand had opened additional shops in San Francisco and New York—simultaneously boasting over 400 stockists worldwide. The Hundreds has closed a couple of flagships over the past few years, but the brand still has a significant following and will always hold a place in the hearts of many West Coast sneakerheads who came up in the early and mid-2000s.