Josh's ideas about fashion are somewhat incoherent, but follow some generally consistent themes. He frequently describes himself as a sexy goth bad boy, but on other occasions, has referred to himself as a hippie, a cowboy, and a dark wizard. He is often seen wearing his iconic black cowboy hat and spiked bracelets or chokers. His fashion could reasonably be summed up as “mall goth”, primarily consisting of the sort of things that Hot Topic and Spencer's sells.

Josh's fashion follows a distinct trend, easily separated into various costumes based on era, interests, and autistic hyperfixations. This is made easier by the fact that Josh showers once a week, and wears the same clothes for weeks at a time.

In the formative years of the channel, Josh can be seen wearing a wide collection of various gothic and metal-themed T-shirts. Between this, his eyeliner and black nail polish, and the full head of hair, many regard this as Josh's “Lesbian Aunt” era.

Some well-known apparel from this time includes:

• The Zombie T-shirt of a rotting corpse wearing a tie
• The skeleton arm playing a bass

Josh's first major forays into questionable fashion territory by entering his Goth Biker phase. First, Josh would start covering his head with a black bandanna in order to hide his receding hairline, and debuting The Camouflage Vest. This style would gradually include other gothic accessories over time, but Josh's Tough Guy appearance was the most important thing during this saga.

There's something about cowboys. Maybe it's the style. Maybe it's what they stand for. Maybe it's because Wyoming never left the 1800s. Maybe it's just that Josh really likes Tombstone. Whatever it is, towards the end of the Ellen Saga, Josh would receive a new hat he would declare was Most Definitely What's Up. Gaining a second, wider one in later months known as the Pie High Hat, Josh would tear the sleeves off his Camouflage Vest and turn it into a true man's vest, as his hat continued to degrade. It is unconfirmed, but rumors persist that Josh sleeps in his hats, causing the additional damage.

Tied into the most famous of all outfits, Josh would debut an olive drab-esque jacket with The Rolling Stones' logo emblazoned on its back. Between the admission of baldness, the larger spectacles, and his overall wrecked appearance, Josh would best resemble a homeless Vietnam veteran. Clint always wanted a US Marine as a son, but this is the best he could manage.

With the appearance of NakedAndLaughing, Josh's style has deteriorated heavily over time. Fluctuating heavily, Josh can be seen in multiple various styles during this time, past and present, while also showing off a new wide-brim hat and his black jacket.

Josh's history with hats is long and varied, especially given his huge gourd-shaped head and proclivity to wear hats while he's asleep, as well as to hide his balding head.

Josh has a long-lasting history with bandannas, although he wears them with the corners splayed out like dog ears. Among other patterns shown, he has worn:

• A black skull-and-crossbones pattern
• Another black one with numerous skulls on it
• A black one with a gigantic skull and crossbones on it
• The generic pattern for bandanas
• A number of generic graphic patterns, usually involving skulls

Most infamous of all headgear, the Pie High Hat is a custom hat sent to Josh by a fan. Of all hats, it has remained the longest and has been the victim of the most abuse from Josh in recent years, most notably taking abuse during The broken cigarette incident when Josh smacked it numerous times against the arm of his chair. After thoroughly destroying it, Josh would sell the Pie High Hat for a puzzling $834 dollars, a figure that was in no way the exact amount he needed to pay for something else. Due to a lack of buyers, Josh would grumpily take the hat off the market, saying that he'd “stick to making wands”.

During The Ellen Saga. Josh would receive a low-quality plastic cowboy hat not unlike one would wear for a Halloween costume of imitation black leather, with a silver skull. This cowboy hat would barely fit Josh, and would quickly be destroyed through nonstop wear and tear.

Josh would receive a more traditional black cowboy hat as well, but one day would “break it” off-camera.

To bravely go where no Boy has gone before - On March 16 2022, Josh would debut a new hat for his collection: A black Stetson akin to the hat worn by Indianna Jones, but goth as fuck, 'toobz.

Closely associated with The Bike, Josh's venom-green bike helmet is a great favorite among Cobra's fans, as it was usually associated with his Ride Bike content alongside his more autistic spergouts.

Josh would receive a custom ball park cap emblazoned with the phrase “Cookin with Cobra” and an upside-down pentagram during his Cooking With Cobra phase. Eventually, Josh would also receive a black hat with the word “Unholy” written in gothic script as well, much to the enjoyment of the Boy. This ensemble would also be joined by a hat with a similar design to the Cooking With Cobra hat, with a logo for Cobra Malt Liquor instead.
These hats also make Josh look the most normal out of all of his headgear, so naturally they have extremely limited screen time.

During The Conquistador Age, Josh would receive a gray, conical wizard's hat which he would wear extensively. It appears to be made from felt, and was not seen much after Josh received it(Presumably due to the material simply giving out one day).

At some point during The Wandmaker Saga Josh would start wearing a leather biker hat. This style of cap was closely associated with “Leather Daddies”, a gay male subculture of homosexual motorbikers. Josh would be clued into this fact after a few weeks(But not before attempting to combine it with a do-rag like it was a new style), and we would never see the leather daddy cap again.

Another infamous piece of fan mail, Josh would be gifted a black fedora with a marijuanna pattern on its band. As a pro-cannabis person, Josh would attempt to wear it, only to realize it was too small for his gargantuan, oddly-shaped head after attempting to force it on his head, causing him great distress and pain. After attempting to stretch it out using the vice on his wandmaking bench and nearly destroying the rickety table in the process, Josh would never show this hat off again.

Four score and seven sagas ago, Josh would obtain an oddly tall stovepipe cap, reminiscent of the hat worn by 15th president of the United States of America, Abraham Lincoln. Despite being Josh's worst/best look when combined with his paintbrush goatee, it was seldom seen after he was gifted it.

Josh has an inordinate amount of jewelry, namely in the form of rings. Typically he'll wear:

• An iron or steel pentagram ring
• Several skull rings
• Various rings engraved with goth AF designs

As of 2025, Josh has taken to wearing many of his rings on a chain around his neck, as his fingers have bloated outwards.

Josh can also sometimes be seen inexplicably wearing a small cowbell around his neck, sometimes dubbed “Satan's cowbell” by Cobra fans.